# How to Scale Into Enterprise Effectively and the Biggest Mistakes Made When Making the Move From PLG to Enterprise

Why Discovery Today is F***** & The Biggest Lessons on How to Do Sales Team Compensation with Sean Murray, CRO @ Greenhouse

20Sales · Jan 24, 2024 · 70 min · 13,786 words
Speakers: Sean Murray, Harry Stebbings
Source: https://www.996.fm/episodes/20vc--ep-465bcf0e/

## Cold open

**Sean Murray** [0:00]:

The worst deal is the one that takes too long. Half the sales leaders probably are not gonna make it in the next year or two. The three biggest hurdles in taking that holy grail of moving up into the enterprise. First, the credibility. No one knows who you are. The second is do you have real product market fit for those big companies? And third, your financial and your financials because as you move upmarket, they don't trust that you

**Harry Stebbings** [0:25]:

can survive as a startup for that long. This is 20 sales

## Intro

**Harry Stebbings** [0:28]:

with me, Harry Stebbings. And the single biggest problem I see founders struggle with today is how to move into enterprise effectively. Today, we sit down with a sales leader who's done it not once, but four times with immense success. And so with that, I'm thrilled to welcome Sean Murray, CRO at Greenhouse. But before we move into the show with Sean today,

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**Harry Stebbings** [0:49]:

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## Conversation

**Harry Stebbings** [4:03]:

Sean, I am so excited for this. I heard so many good things from Maggie beforehand. So thank you so much for joining me today.

**Sean Murray** [4:10]:

Harry, it's such a treat to finally meet you and have this conversation. I've been looking forward to this conversation for the entire week. And before we get started, I have to thank you for what you're doing to our overall craft of selling in 20 sales. I'm learning so much. I've been listening to the conversations, and we are accelerating the craft. So thank you for all that you do.

**Harry Stebbings** [4:29]:

I can't believe I get paid for this, Sean. I'm waiting for someone to catch me, but I wanna start with your falling in love with sales. I I often find that there's a moment. When did you fall in love with sales? And when was that like, uh-huh. I really wanna do this as a career.

**Sean Murray** [4:42]:

I wish I had a really elegant answer. I listened to Egan's conversation. Was like very intentional. And similar to say Mark, from Grammarly, I'm an accidental salesperson. Now I'm a son of a salesperson. My father, my late father, was a dedicated salesperson, so I was never gonna get into sales. So through undergrad and uni and graduate school, I was a bartender. But when all of my smarter friends were taking on internships, I was slinging cocktails. So I got my first assignment at the corporate executive board, CEB, and my job title was marketing associate. Well, it turns out that I was making 300 cold calls a day to c suite executives in the Fortune one thousand. I was what's now called a sales development rep, an SDR. And that's when I fell in love with sales. I had this moment where I said, wait a minute. If I make more phone calls and book more meetings for my account executive, you'll just give me more money. Yeah. Okay. This is amazing. And it tapped into my competitive spirit, trying to be on top of the stack rankings. And I've been basically at SDR ever since. It's, like, twenty two, twenty three years later. But that's when I fell in love with sales.

**Harry Stebbings** [5:49]:

Can I ask you and I'm just excited to be conversational? I just think so much about the blurring between marketing and sales today. Because I think if people don't know your brand when you first speak to them, really it's on the fold of marketing and brand awareness. How do you think about the blending of sales and marketing in that way? And actually, there is a chasm between the two today almost.

**Sean Murray** [6:09]:

Yes. Well, the blend couldn't be more relevant today. I view my role right now as the head of selling when I used to be the head of sellers. The CMO, the marketer, must be very effective at selling, and the head of sales must be very effective in marketing. And the primary reason why is because of the buyer. On an inbound lead to your business, the seller now gets 9% of that buyer's time to evaluate whether they're gonna go with you or not. And, Harry, in that 9%, this is according to Gartner, you must split that time with the other partners or vendors in that process for the buyer. So the reason why this is such a great question is that how do you grab their attention, their buyer attention? How do you teach them about your product? How do you teach them about what you do when they're not talking with you? So there's much more of a blend today than ever before.

**Harry Stebbings** [7:01]:

Okay. Let's unpack that. There's two sides there. CMOs that need to be good sellers and, yeah, heads of sales or CROs that need to be good marketers. What does it mean to be a good marketer coming from the sales side with that hat on first?

**Sean Murray** [7:14]:

Yeah. There are two big elements pop out to me. The most important is messaging. What problem are we solving? And what's the problem behind that problem that we're solving? Many sellers, you're just deployed, go and produce more revenue, and then come back with all of the revenue. But now we must think differently about demand generation. The second being branding. How do we attract more people into our sales process? So that demand generation piece is what's most relevant to me right now.

**Harry Stebbings** [7:41]:

But is that not marketers? Like, as a sales rep and as a SDR on your team, do I not go to you, my boss, Sean? But that's their job. Don't look at me for that. I'm here to make the calls to the leads that come in.

**Sean Murray** [7:54]:

Yes. And and that model has long been gone. Right? Where my role right now is to make those SDR conversations much easier. And how do I generate more inbound demand for what we do rather than having just to completely go outbound? Now I grew up Harry, and 98% of my pipeline was completely outbound, creating the category, creating the demand. But now there's a much smarter way to do it. And there's really cool technologies that's available to enable those SDRs or those account executives to have those better conversations.

**Harry Stebbings** [8:26]:

Okay. Sorry. I'm this is great. But if if SDRs and sales teams are doing messaging and brand, well, what the fuck are marketing doing?

**Sean Murray** [8:36]:

Well, marketing is holding our hand throughout the entire process. So marketing, looking at our digital spend, the brand excellence, making sure we show up where our buyers hang out, whether it be at events or online or through social. We're all one big team. I'm not just talking shit about this either. Like, the sales and marketing organization is very, very tight, And that's how you enjoy the most success

**Harry Stebbings** [8:59]:

today when that is one whole unit. And if we put the other hat on, I'm just gonna I'm getting in so much trouble for this. I mean, dude, there are so few good marketers who are good at marketing. I mean, the CMO generation is one dearth and like yeah. Very few talented people. Sorry. Jesus. If we're expecting them to be good at selling as well, we're in the real minutiae. I mean, so what does it mean for a CMO to be a good seller on the flip side?

**Sean Murray** [9:25]:

So Karen Van Vuren is a CMO I get to work with. What Karen or what the best CMOs do, they know our buyer better than anyone else. They spend time with our customers. CMOs don't spend time with the customers. Right? That's just kinda like a head fake. But the best CMOs understand deeply the pains of the buyer, what makes them tick, what drives business value and personal value for the buyer. And that's what makes the best CMOs today. Because when you know that, then you become a great seller. Right? Because people, they don't wanna be

**Harry Stebbings** [9:52]:

sold to, but they do want to buy. Do you combine those meetings? Because you can't spend too much time with the customer. If I'm your customer, I'm like, oh, Jesus. I've gotta spend time as a CMO, the the CRO. But I just want your But, like, my question is, like, do you combine them together? Do you join calls together? What's the right way for you? Because you both need to have that interaction with customer.

**Sean Murray** [10:14]:

Yeah. Yeah. It's a great question, and it's probably a sense of all of the above. So for example, our marketing organization, they run our customer advisory board. So our core key customers that help drive our product and drive our innovation, that's a marketing generated event. And so that's one example of how they spend time with our customers. And we invest heavily in conversation intelligence as a technology. And so our marketers, they're frequently listening to our customer calls, listening to our prospect calls. They're very in touch with what's going on and the personas of who we are engaging with.

**Harry Stebbings** [10:48]:

Can I ask you, as a CRO, how do you measure the effectiveness of a marketing team? Is it on numb because you can always gamify success, number of leads, converted pie. It can all be gamified to some extent. How do you measure success of marketing teams?

**Sean Murray** [11:03]:

We have a full dashboard on how we measure the success of marketing, and it's inbound generation, the demand. But it's also we go all the way down to our customer journey because our marketing organization is very heavily involved with our existing customers, NPS, gross retention, net retention. We do measure our marketers on the full suite of everything that I am measured with. Our marketing organization, we hold them as accountable to the revenue as I am. So for example, if you were to ask my marketers at the last two or three companies where I've engaged and helped build, they would know the revenue numbers as tight as I know. Wow.

**Harry Stebbings** [11:35]:

That's impressive. That's rare for marketing teams. I'm I'm really getting in trouble here. Now, I I I wanna start, you know, we mentioned kind of dialing for dollars and the outbound nature. Nature. I I speak to so many companies today and they're all going, it is so hard. Just to place this in context, are we in a recession from a sales environment, do you think? And how does it compare to prior environments you've sold through?

**Sean Murray** [11:58]:

Yeah. I don't know if it's a recession. However, we are rightsizing. Maybe that we all shouldn't have grown as fast as we did. Like, the valuations of businesses and companies, when we were raising, let's say, 2020, 2021, those valuations are they're beautiful. Don't get me wrong because I benefited from some of those valuations. However, they just were overinflated. No pun intended. So I do believe we're at a rightsizing type environment, but it does feel harder now than it has in the past.

**Harry Stebbings** [12:25]:

So is that rightsizing the reason why so many teams are struggling with new logos?

**Sean Murray** [12:31]:

No. Personally, I'm experiencing the opposite where new logo sales are actually fairly strong and, say, some customer churn might be a little bit more difficult. But new logo sales has always been hard. And the best sellers right now, they are adjusting. They're just changing how they go into the market. And yeah, don't get me wrong. I would prefer fish to jump in the boat with inbound leads. Yeah. That was a lot easier. But I don't think that's a primary reason why selling is hard right now.

**Harry Stebbings** [12:59]:

How are they adjusting? Everyone says all budgets are going back to CFOs, and CFOs aren't buying technology. That's what everyone says. How are they adjusting, and do you agree with that?

**Sean Murray** [13:08]:

I do agree with that. The CFO in different personas. There are functions people have never even heard of that are getting involved in the sale right now. Right? So I agree with that sentiment. And I also agree that it is hard hard stuff. But what the best sellers are doing now, and I geek out with a lot of other sellers, and what I'm finding with the best sellers are doing right now, they're revisiting their ideal customer profile. They're revisiting their target accounts, who they want to go and pursue and engage with. They're adjusting their messaging. You and I both know growing up that there there was a monster under the bed. Right? We both knew that. And that's how many sellers talk about their problem is like, oh, there's a monster under the bed. But you know what? The better sellers, they're talking about the monster that's down the hall through the other door and hiding in the closet. They're teaching their buyer about that monster, not about the obvious monster that's under the bed. So I think the better sellers are adjusting.

**Harry Stebbings** [13:59]:

That's really interesting. I always say when you have to educate your customer, it's so much harder. It's like when you're fundraising and your VC doesn't know anything about the space you're in. Good luck. Do you agree or not given the fact that the best educate?

**Sean Murray** [14:12]:

I do believe the best educate. And in fact, in my sales process internally, third company in a row, the first stage of the sales process is called teaching hypothesis based selling. If you are a seller today and you engage a potential buyer and you're wasting your time asking about what CRM that they use or where they're located or who they do business with or how they make money, just don't even call. So the first stage is teaching. If I can teach you more about your business, if I can teach you something about your business that you might not even be thinking about, you will engage with me. And so I agree to the to this to your sentiment of what you're saying, but that teaching component is critical.

**Harry Stebbings** [14:54]:

Has how you sell changed given the fact that, bluntly, bottoms up buying has now largely evaporated and CFO centralization of budget has largely taken place?

**Sean Murray** [15:06]:

Yes.

**Harry Stebbings** [15:06]:

But,

**Sean Murray** [15:07]:

Harry, what changed more than just selling is buying. Buying is changing. The comment I made earlier that if I'm gonna go buy something, literally, according to Gartner, 9% of that entire process is actually engaged with the seller. So what's changed more in selling is how people buy. And so how selling has changed here is my comment about marketing earlier, which is how can I teach the market, the shoppers about

**Harry Stebbings** [15:32]:

what I do and the value I create when I'm not even talking to them? And it's hard. Isn't that why content marketing is the most important thing that you can do today? And then should all sales teams not just be a team of content marketers? If you're the only final 9%, then surely you should just have a amazing content marketing team and fuck it. They'll tip over for the final 9%.

**Sean Murray** [15:50]:

Well, I've got good news for the sellers out there. I've got good news. Because according to Gartner, Harry, forty three percent of buyers that had a digital only experience in purchasing have a 1.65 x higher regret rate. So the best sales cycle is when it is rep enabled. Like, the rep is part of that process. In fact, you reduce buyer regret by her if the rep is involved in the process. So what the rep does so to your point, yeah, like, content marketing is super important. Teaching things when no one's around. Yeah. Yeah. Yeah. You gotta do that. But the good news for the sellers is that we get to be there to make sense, to bring the human context to what they're buying, and so they

**Harry Stebbings** [16:30]:

can ask actual questions. How do you think about what ACV is, the right level ACV for sales reps and teams to interject versus let them be self serve? Like, is it above 10 k? Is it above 50 k? But then, you know, someone from a huge company can come in and sign up for one seat. How do you determine?

**Sean Murray** [16:49]:

I have sellers where I prioritize the SMB segment. Those sexy startup companies that are in Silicon Valley or in London or in Paris, wherever they are, they grow up to be enterprise customers. So I still want human engagement. And that ACV is, say, $9.10 k US. That's not a big ticket, but those customers are still valuable. And if I just automate that whole process, which I think we're moving toward as a craft, I think we're moving there, but I'm not ready to concede to my competitors that have not automated that segment. But I am constantly looking at automation, different technology on how I make it easier for buyers to buy on their own and renew on their own and engage with our company on our on their own. There's a lot of innovation happening with that, like, fifteen, twenty k ish ACV.

**Harry Stebbings** [17:36]:

You said that about, like, constantly looking. I think another reason why so many are struggling with new logos is just the broken nature of Discovery. How do you think about Discovery today? What's your thoughts?

**Sean Murray** [17:47]:

I took out the word Discovery from the sales process, and I inserted the word teaching. And words matter. And what I would prefer my organization, what they do when they engage with a potential buyer is they teach them. Teach them about their company. Teach them about the category. Teach them about their craft instead of asking the lazy, dumb questions that they can find out on their own. Well, that's the discovery that is dead because technology allows you to understand so much about your buyer before you talk with them within minutes.

**Harry Stebbings** [18:17]:

Do you think you need specialization on a vertical playbook basis then? Because if you can teach me more about my business, Sean, I'm either incredibly stupid or you should be leading Microsoft. Right? So how are you gonna get smarter than me on my business?

**Sean Murray** [18:33]:

And it might not be about your specific business, but it could be about the investor world. And the keyword that we try and use is reframing the problem. Reframing. Right? So in your world, whether you're investing, you're looking for certain types of companies before you make an investment, whether it be LTV, CAC, whatever metrics that you're looking in. But we wanna reframe it to be about something different, something you might not be thinking And that could be your voice internal survey results from their employees. Do they have happy employees? It could be what their customers are saying about the company you might invest in. Now I'm not I'm not giving you an insight right now, but if I'm selling to VC firms, I talk to 30 VC firms in a month. And if I don't have some insight about the VC community that you might not be exposed to in the last month.

**Harry Stebbings** [19:21]:

Do you know what the most interesting thing you could do actually? You could do an analysis of, like, talent churn within portfolio companies of a specific VC. You could say, hey, I took five of your outperformers. When I looked at head count variation across them, actually, these two have a much higher churn rate than these other three. Maybe it might be something to talk about. Do wanna hop on a ten minute call? If

**Sean Murray** [19:43]:

I can tell you a two minute story, I promise it's worth it.

**Harry Stebbings** [19:45]:

Yeah. Yeah.

**Sean Murray** [19:46]:

Okay. There's a company called Dentsply. This is from CEB now Gartner. Right? There's a company called Dentsply. Dentsply is located here in The United States. Like, $2,000,000,000 in revenue. Right? When you go to the dentist, they make all the tools and the drills and the things that you go to when you go to dentist. Right? I'll make this fast. They produce these drills, the most ergonomic light drills that were gonna take the world by storm. 500 sales reps go out and try and sell these drills to these dentist office. Right? They couldn't sell them. You know why? Because all the dentists were saying, no. No. No. You sold me these drills three years ago, and they worked just fine until one rep did something differently. That one rep did research. The rep found out that thirty percent of dental hygienists were out of work each year, thirty percent of the time, of absenteeism and found out they were out of work through absenteeism because of carpal tunnel. Because if you're, like, a dental hygienist, you're in these weird positions all day working on on people's mouths. Right? Anyway, that rep did the math and figured out because if you cancel your appointment to go to the dentist, family took the whole day off of work to go to the dentist. It's an expensive problem to the tune of a small business dentist shop to the tune of about $700,000 and a year of lost business. So this one sales rep goes back to the dentist office, explains this problem in a new way, the problem of absenteeism with these folks being out of office or being out of the dentist's office. And the dentist would just say, no. No. No. That's just part of doing business. That just costs doing business. How can I fix this? Well, the rep said, I gave you a way that you could avoid your hygienist to suffer from carpal tunnel absenteeism, would you buy these drills? Well, that he's like, that doesn't exist. Lo and behold, these most ergonomic drills that were the lightest ever that would prevent absenteeism. So you see what I'm doing here. Right? It's like reframing the problem that you think that you're solving. And that's what I mean about teaching

**Harry Stebbings** [21:33]:

your buyers something different about their business. I totally get you, and I I totally agree with you. How do you do that, though, when it's horizontal? Like, it's easy when you sell dentist drills. It's like, that's all you sell. Greenhouse, you sell talent. But when you sell Airtable, Notion Yeah. Could be anyone.

**Sean Murray** [21:49]:

Well, and that's just it because we are let let's just use hiring software as an example. It's persona based. I'll go sell to a retail manufacturer, tech company, and a biotech business. But many of the problems are still the same within talent acquisition. There are parallels that you can draw. And what many talent organizations, what they're thinking about differently right now is, let's say, DE and I, diversity, inclusion in their businesses, not just hiring. And so I can go in and teach different industries about how other industries are visualizing inclusion and diversity hiring in their business. Right? So it can be done in horizontal or vertical, but it's not easy.

**Harry Stebbings** [22:27]:

Okay. So if we have that on new logos, the one thing that is also very apparent is kind of renewals are harder than ever. Steve, your successor at Sales Loft, I guess, said that every renewal is a new deal. Do you agree? And a renewal's harder than ever.

**Sean Murray** [22:41]:

I do agree. Renewals are harder than they've been in the past. And what creates these renewals to be more difficult, there is a lack of consensus. There's dysfunctional consensus when new personas enter that renewal process. I do agree with the sentiment, Harry, that CFOs, IT, functions I've never even heard of show up in renewal conversations today. And we now must prove not just ROI anymore, but it's time to value what we're gonna do differently for them. And no one really feels comfortable making solid decisions right now, which creates this dysfunction within the consensus buying at the renewal point because budgets are tight.

**Harry Stebbings** [23:20]:

People aren't spending. What do you think if there's one or two things that you most need to prove, what do you think they are across the board? First is the data.

**Sean Murray** [23:28]:

Proof. You must prove that you are helping your customer measurably better at whatever is the problem that you are solving. So I would say data probably one and data probably number two. It's in that proof point. And what's the next problem that they have in the coming year that

**Harry Stebbings** [23:42]:

you can solve for? Do you have to change your team structure to accommodate the changing data requirements of your customers in order for them to upsell? Before, people just came back and said, Henry Schuck at ZoomInfo came on the show and said, before, everyone just came back and was like, yeah, sure, we'll take it again, and why not buy 10 more seats, 20 more seats, 30 more seats? Now it's like, they need so much more. He's like, we changed our whole customer success team to be like data first to prove upsells. Do you need to do that, or is that a step too far?

**Sean Murray** [24:12]:

I do not think that is a step that's too far at all. Our customers are leaving breadcrumbs throughout our product at all times, and making sure that we get the right sets of data in the right hands at the right moment is critical. I don't know if it requires a full restructure. However, what I do know today within customer success or account management, whatever the structure looks like, everyone should be in customer success and in sales at the same time.

**Harry Stebbings** [24:36]:

What does that mean? Like, how do you actually do that? Does that mean sales team spend time in CS and CS in sales? Like, just unpack that for me. And if I'm a founder listening, what should I do?

**Sean Murray** [24:45]:

No. It's a great equation to go and solve for. What I'm finding now is that in customer success, you have fewer touch points with your customer. And the product must sing for you at some point, of course. But when you're having those customer conversations, can you also weave in the commercial component of upsell and or cross sell? Because in customer success, you're building trust. You're building that relationship. And in some models, of one of which I'm part of and I've been part of, is you have this, like, awkward high tension moment where a salesperson comes on and is like, but wait. I got more things for you. But to have that process a bit more centralized is probably the best part. So if I'm a founder right now, you must find people that care greatly. I just saw a post by Jason Lemkin. It was spot on. Like, your first few CS hires, someone that cares greatly about your product. They're passionate. They're smart. And everything else will sort itself out. But if I'm a founder right now, I would think about combining those roles a bit within CS and account management. But separate that from your new logo hunters. Make sure that's separated.

**Harry Stebbings** [25:45]:

Okay. So how do you manage the challenging element of the handoff? Hey, Sean. I've sold you. And now you've just you've learned to love me. Meet my colleague, Sarah. And you're like, woah. What? How do you handle that?

**Sean Murray** [25:58]:

We handle that. How I'd handle the past is through technology. That handoff should be flawless. So to the founders that are listening, ensure that you should have a hunter organization that chases new logos. I firmly believe it. By the way, Harry, I was able to one of the highlights of my sales career is I was able to launch the sale of the Challenger sale. Have you heard of the Challenger sale?

**Harry Stebbings** [26:18]:

No.

**Sean Murray** [26:18]:

Oh, Harry, this is a must read for you. Brent Adams and Matt Dixon, they are the authors and the researchers behind a lot of the content. But the argument is, and I firmly believe this to this day, you have an organization that secures new logos so long as you have the runway and the TAM to support it, and then you have a customer facing organization. You separate those two. But to answer your question, the technology Well,

**Harry Stebbings** [26:39]:

that that's too good. So wait. Wait. You have someone to secure new logos. What does that mean? Like, they go out and they pull together a list of names that could be good targets? And just help me understand how that works.

**Sean Murray** [26:50]:

Okay. You have the new logo organization, and their only purpose in life is to go get more new customers. So when they get an an order for signed, you pass it off to a customer facing team, whether that be called account management, customer success, customer support, whatever you wanna call them. But these are two distinct different teams. Harry, when you have those roles combined, the research is profound. When you combine those roles, it doesn't work very well. So long as you have the TAM, the total addressable market, and you have the greenfield available where you can go and secure new logos, you've got that runway, those roles should be separated.

**Harry Stebbings** [27:27]:

Okay. So they're separated. And then we have the handoff where you bring in technology. How does technology help a handoff? Like, conversational intelligence. Help me understand how, you know, Gong will help our sales and CS teams make a seamless transition.

**Sean Murray** [27:44]:

So a big plug for Gong, but the AI that they are building within the conversation intelligence is remarkable. If I'm a customer success person and I'm inheriting a new customer, I can go into Gong and just look for quick highlights, quick moments that were important during the sales process on how I'm gonna absorb and learn about that customer. It's brilliant. And so that's how that transition now happens flawlessly.

**Harry Stebbings** [28:08]:

So you would then expect your CS person to come into the course, learn, and then me as a CS hop on that hand off call and say, Sean, you're the customer in this case. How are your daughters doing? I know that you're going to Taylor Swift. And you go, oh, wow. Like, they've got that relationship based sell already. Is that what you want?

**Sean Murray** [28:28]:

In the enterprise, the short answer is yes. The last three companies I've helped build, I pursue every segment from SMB startups all the way up to the 20,000 employee mega companies. And in the enterprise segment, that level of personalization makes a difference and very important. So to answer your question, yes. We expect our teams maybe not that I'm gonna go to a Taylor Swift concert in London with my daughter. Maybe not that far, but certainly, what my top three problems are that I must solve in this current year, that level of detail, yes. Now at scale, maybe in the SMB where it's a bit more automated, not as much personalization is required.

**Harry Stebbings** [29:06]:

Okay. So then we have that, and you're like, yeah, I like the CS person. That's good. That's good. And now I'm going, as the CS person, we can upsell him. How do I bring in the sales person back into the process when I've now built quite a good relationship with CS?

**Sean Murray** [29:23]:

Yes. You have account managers or salespeople that are also talking to your customers along with these customer success relationship builders that are typically measured on NPS, my argument is to combine those rules. Leverage technology, leverage the data on when you know customers should be up for expansion, should be up for cross selling. Your data should tell you that whether you're using Gainsight or Gong, whatever technology that you're using, you should be able to see that and allow that frictionless sales environment to happen within the customer organization.

**Harry Stebbings** [29:56]:

So CS is sales?

**Sean Murray** [29:58]:

Yes.

**Harry Stebbings** [29:59]:

Okay. If CS is sales, is there not a misalignment? Hear me out here. You're one of my customers. You know what? You may not quite be ready for our full Enterprise AI product yet, but I think you could be soon. And so why don't I sell it to you now because it's nearly the end of the quarter and I really want that bonus. So you know what, Sean? You need it now.

**Sean Murray** [30:21]:

But really, Harry, we're all in sales. Come on. We're all in sales, and we're serving our customer. We are. And I the good news, the customers expect it. Right? They expect it. They expect to be sold to.

**Harry Stebbings** [30:32]:

Do you think in CS, they don't feel like it's a safe space where you do just want them to be made as successful as possible? Maybe I'm ignorant and naive.

**Sean Murray** [30:41]:

No. You're not ignorant because my CS organization today, they are not in sales. They are not. I wanna make an argument that we should be. Today, they are not in sales. Many customer success organizations do not have a quota. Right? They sit in cost of revenue or COGS, and they do not have a quota. And they focus on adoption, using the product. That's very that's a classic model.

**Harry Stebbings** [31:01]:

If they're not, but you would want them to be, why are they not?

**Sean Murray** [31:06]:

That's the question.

**Harry Stebbings** [31:07]:

Can you not stomp your feet?

**Sean Murray** [31:08]:

Well, I I am, you know, banging my hand against the desk. I gotta be better at my persuasion. But it really also, Harry, it depends also on the product. Because if the product is easier to adopt, you probably need less customer success. Yeah. So the innovation of the product makes the difference. And if you have a heavy people or human oriented customer success organization, could be a red flag for the buyer.

**Harry Stebbings** [31:31]:

No. I get that. You said about kind of the range of customers you sell to and you have sold to over your career. I'm investing in many companies, kind of the holy grail is like, well, we're gonna scale into enterprise and then hundreds of thousands of dollars of ACVs will just magically open up. It doesn't happen like that. And there's this real naivety. What do you think customers or founders get wrong about moving into enterprise?

**Sean Murray** [31:54]:

A lot. Okay. There is a lot to get wrong. The three biggest hurdles in taking that holy grail of moving up into the enterprise, those massive ACBs, the sexy LTV to CAC, those sexy logos that you get to talk about. But the hardest problems. First, the credibility. No one knows who you are, especially in the enterprise. IT will destroy you. The second is do you have real product market fit for those big companies? Because those big companies, they all believe that they're special snowflakes. And so they need things that are just different because you've built an SMB or mid market platform that's there to scale. And third, it's somewhat related to both, but your financial and your financials because as you move upmarket, they just don't trust you. Very similar to credibility, but they just don't trust that you'll be around. They don't trust that you can survive as a as a startup for that long. So I think those are the three that I've experienced in my way up.

**Harry Stebbings** [32:49]:

Okay. So IT will kill you. Why? Why will IT kill me? What do we get wrong here?

**Sean Murray** [32:55]:

Because as you move upmarket, the IT organization gets more senior and more senior and more authority and more authority the higher you go up. And the worst thing that can happen to an enterprise is a data breach or security flaw. And many of startups, they don't have the proof points that they meet all the compliance requirements that the enterprise will demand of them. So to me, that's when IT really becomes difficult. So as you prepare to move upmarket, make sure that you can defend those arguments before we even try moving upmarket.

**Harry Stebbings** [33:28]:

That's one.

**Sean Murray** [33:29]:

Two,

**Harry Stebbings** [33:29]:

will you do customization for me to land my contract? How do you advise founders on the willingness to customize versus not in order to secure a contract?

**Sean Murray** [33:38]:

I love this, Harry. So this is the most friction a founder will experience in their life.

**Harry Stebbings** [33:44]:

Not not not marriage. No.

**Sean Murray** [33:46]:

Marriage is easy compared to this friction, but this is going to be the real friction is when they are moving up that market and how they're going to differentiate those two on the customization of sales debt. Because the sales organization is gonna say, hey. Look. We've gotta go create 15 different bells and 20 different whistles to make this company work for us. And I refer to that as sales debt. And so the lesson learned is how do you balance sales debt? Because every once in a while, you're gonna wanna take down Adobe as a customer so you can say you've got Adobe as a customer or the snowflakes with those sexy logos, Slack, Salesforce, whatever. But you must balance that sales debt and just know when to walk away from deals because the biggest pain point you move into the enterprise is they want you all to be special, and they want customization, and it's gnarly. So as one example, Harry, at Greenhouse, where where I'm building now, I really cap it at 10,000 employees that I try not to pursue much more above that. And it's mostly because it just gets so difficult above that threshold. And I don't think the the big money really isn't with those companies anyways. They actually there aren't many companies that have over 10,000 employees. But when you get to that level, it gets gnarly.

**Harry Stebbings** [34:58]:

Can I ask you, have you made any mistakes in terms of taking on sales debt too much with a specific customer? Yes. It's easy to.

**Sean Murray** [35:06]:

Yes. Many, many, many mistakes. And it's less about overpromising. It's being upfront about what we can and can't do or what we can try to do. But the biggest mistake is the time I can't get back. So I went to go after one of those sexy logos. I went back to my product and my engineers. They're like, look. Is gonna be easy. You gotta trust me. I've never been an engineer before, but this sounds really easy. And I had my product team and my engineering team invest a year of their time trying to make it work, and it didn't. And so I can't get that time back. And with founders, that time is too precious. And so those are the big mistakes. It's not about being false or lying to your customer, but it's the time that you can't get back.

**Harry Stebbings** [35:45]:

Yeah. I mean, that's a very accommodating product team, to be fair, to actually engage for that long and to let you roll with it. Yeah. No. I'm totally sure. You mentioned the sexy logos. Do they really make a difference? Like, when companies come and say, hey. We've got Slack and Dropbox and you name it. Do they make a difference or not when closing? It's a

**Sean Murray** [36:03]:

good question. The short answer is it does make a difference. Now every salesperson in the world pitches and they over pitch those enterprise logos. But the first problem that I mentioned when moving up market is you lack credibility. And the reason why those logos do matter is I need to show you so, Harry, you're my enterprise customer, you're and looking at me like, you can't do half the shit that you're talking about. But what I need to be able to say is like, Harry, look. I'm gonna set you up with the folks at Slack, DocuSign, and Snowflake, and they're gonna tell you a story of how they use my product. I need that. You need that.

**Harry Stebbings** [36:38]:

That's very impressive and different, though. There's a difference between, hey. Look at these sexy logos now buy. And, hey. Why didn't you speak to existing customers, and there'll be references for us? Do you see what I mean?

**Sean Murray** [36:49]:

Yes. Yes. But they're they're two in the same.

**Harry Stebbings** [36:51]:

Right? Which is the hurdle you're jumping over is the credibility hurdle. Do you worry about asking existing customers to sell for you? Do you worry that it's too much to ask, that they don't have time? It depends.

**Sean Murray** [37:02]:

Okay. Harry, we're role playing again. Harry, you as my enterprise customer, I'm not gonna ask you for your time to help me go sell to other big companies. But if you do, maybe I'll give you a little bit of a discount and renewal. I'll do something for you. So I do ask in advance. So when I'm moving upmarket, I make these concessions as part of my negotiation when I'm closing a deal, which is

**Harry Stebbings** [37:25]:

Okay. So you'll say, hey. If you can help on up to three different potential customers, we can have a wiggle room of 10% on a renewal. Correct. Right? So as I'm moving up

**Sean Murray** [37:35]:

market, so the founders that are listening that have aspirations to go be bold and move up into the enterprise, do it. But think very carefully on when you're negotiating these terms with your first 25, say, enterprise customers, give and gets. You're gonna need their help to get this going. So give them the concessions that they need. Make it worth their while, and get it in writing so that you can use it.

**Harry Stebbings** [37:57]:

Okay. Another area where they're like, not only yes. Everyone wants customization, especially now everyone wants a discount. And some are like, you know what? We don't discount. We know the value of our product. And others are like, of course, we discount. What's the right approach to discounting for founders listening, thinking about that scale into enterprise?

**Sean Murray** [38:16]:

Discounting is okay. It's fine. In different environments, it's important that you adjust when you need to. We all believe that our products are the best, especially those founders that are listening, I know. But there are moments that when everyone on the block is charging $80 for a beautiful steak, and then the market goes south, and then the rest of the street is selling those steaks for $20, you can't keep charging $80 for your steak. You can, but you're going to lose. The worst deal is the one that takes too long. Just move on. Go get the next deal. So I have been a big advocate of flexibility. Maybe not discount and reframing it a little bit. It's flexibility in negotiating terms. It's not necessarily just discounting a drop of your price, but go get something different. So as an example, if my price is 100 k, I will do this deal for 60. And then, Harry, what I expect from you is a story about how you love my product. Harry, I want you on the stage of my annual conference raving about my product, and I want two social posts from you raving about my product. And then we'll do the deal for 60. So it's not a discount. It's a trade.

**Harry Stebbings** [39:19]:

I like that. You said that I loved it. You said there about kind of the time is the biggest killer, and if it takes too long, move on. Do you think you know upfront if a deal will take a long time? And what are signals that a potential prospect is gonna be a slow mover?

**Sean Murray** [39:35]:

Yes. There are many indicators. And having a data driven process teaches you about what those clues are. Okay.

**Harry Stebbings** [39:44]:

What are they?

**Sean Murray** [39:45]:

There's probably a list of about 40. The level of consensus that's required. The level of approvals that are required.

**Harry Stebbings** [39:52]:

Okay. Okay. So let's just take those. Sorry. I'd like to go. Are people honest? Everyone likes to feel important when you say, hey. You know, who are you a decision maker for for buying Greenhouse? Of course, am. Yeah. Yeah. Yeah. Yeah. It's me. You're you're speaking to the right person. How do you know?

**Sean Murray** [40:08]:

That's a great call out, and you are right. That happens nine times out of 10. And frankly, they are not the person that can sign the order form. So you you are right. The question to ask maybe differently is who should I engage early? Because Harry, role play again. Okay? Harry, buyers like you, I have 7,000 customers. And buyers that look and feel just like you, what happens at the end of this process is the CFO will get involved. The head of procurement will get involved. IT will get involved. Harry, I don't think your company's gonna be any different. So in order to be a good steward of your time, let's get them involved now because then I can set you up for success. Harry, you want this product. I know you do. But in order for you to be successful, let's

**Harry Stebbings** [40:46]:

get these players involved. Do not damage their ego? I'm sitting here thinking, you don't believe that I'm the buyer.

**Sean Murray** [40:52]:

No. No. I don't. I have this credibility on my shoulder, Harry, because what I said to you, Harry, companies that look and feel just like you, some of your competitors, companies that are in your ecosystem, this is what happens at the end. My hypothesis is this is what's gonna happen to us at the end. These people are

**Harry Stebbings** [41:08]:

gonna wanna get involved. Does competitive selling work? Does saying I mean, I'm taking the most competitive industry, CRMs. You know, monday.com and Pipedrive. Does saying, hey, monday.com, we're actually working with Pipedrive and they're seeing incredible success. You don't wanna be left behind. Does competitive selling work in that respect? I value the question. The short

**Sean Murray** [41:29]:

answer, be yes. What I will say about with the competition and selling against your competition is when I'm directly the seller is to not belittle or throw mud at my competitors. It rarely works. If you roll around in the mud with pigs, you just get dirty. And so I teach my sales organizations as best I can to not speak ill of the competitors.

**Harry Stebbings** [41:51]:

I totally agree. I think it's the fastest way to lose credibility to chat shit about someone. I think it's you see it often with venture investors too, and it's just like, yeah. That's not a good way to do it. Okay. We missed one crucial thing which is like, for me, I think a lot of companies actually try and move into enterprise way too soon. A million in ARR? SMB market's a lot bigger than that. Okay? So if we wanna start that, let's start that proper. When's the right time to move into enterprise? You know, you've done three now. When are you like, okay, this is ready to ramp?

**Sean Murray** [42:20]:

Yes. I like this question. The first answer will be let the data teach you on when you're able to do it. So if you have inbound, if you have clues from companies as you start to move up ever so slightly, if you get those clues from you, again, the inbound or how your customer is using your products, let that data teach you if you can start creeping up market. And then the third would be to run a phase one. Try it. Try. If you want to go into the enterprise, yes, it's a full company effort, and that's what a lot of founders get wrong. What founders think is it's a sales and marketing go to market thing. It takes the whole company to rally around it. It's an entire company motion moving into the enterprise. It is ambitious, but try it.

**Harry Stebbings** [43:01]:

Is there a way to try it without huge resources? Is there a way to put your foot in the water of, like, enterprise with a couple of customers, see if it's what you need, or is it a full on budget reallocation?

**Sean Murray** [43:14]:

The hard truth is it's a full on budget allocation. It's a full on effort. However, you can test to see if your product will work with a few test cases, with some few customers. So for example, to the founders out there, try and engage an enterprise and maybe do it on the house. Engage a few customers and give them your product for a year and let them use it for a year. Find out where the mistakes are. Find out what goes wrong. Learn what's wrong with your product before you really go big. So there's probably a little bit of bold Harry, but the truth is, yeah, you need some capital to go into the enterprise. And you won't get that immediate love. It takes time. It doesn't have the same return and speed as the SMB

**Harry Stebbings** [43:55]:

or mid market will have. That's the truth. I always say enterprise is like content. It's way harder than people think, and it takes way longer. We did 300 shows before we got to a thousand plays per show. 300. You said there about kind of the speed and, like, obviously, small ACV, smaller companies, you know, kinda quicker. How do you know when a sales rep's not working out?

**Sean Murray** [44:15]:

It's a bit easier in sales to know when it's working or when it's not working. And

**Harry Stebbings** [44:19]:

But do think so in enterprise? Because it takes so long.

**Sean Murray** [44:21]:

I do. I do. And and the reason why is if you structure a data driven sales process, when you can see when deals fall off from, let's say, stage two to stage three, or in stage two, if that sales rep wasn't clicking off the right criteria to graduate from stage two into stage three, then you know that you've got a talent issue pretty quickly.

**Harry Stebbings** [44:43]:

What do you do then?

**Sean Murray** [44:44]:

What do you do with those reps?

**Harry Stebbings** [44:46]:

Yeah. Do you say, hey. Like, it's not working and just cut it? Like, how often are reps repairable versus just let them go?

**Sean Murray** [44:53]:

It's a great question. The right answer is you move on and you bring in new talent. That's the right answer.

**Harry Stebbings** [44:59]:

Do you think you're good at hiring sales reps?

**Sean Murray** [45:01]:

Yes. I'm the best. You know why? Why? Because I've got software. I don't worry about hiring because I've got great software.

**Harry Stebbings** [45:07]:

Okay. Well, help me understand that. I'm a founder. I'm hiring my sales team. How do I hire sales reps or sales teams with software?

**Sean Murray** [45:14]:

Okay. There's a lot to unpack here. But I've been leveraging software for many, many years in my hiring effort. And when I'm learning about hiring salespeople, the best people, there's a lot more data and science involved than one would think. So it really first starts with how you attract talent to your company. What are the words that you're using in your job description to ensure that you're creating a fair and equitable environment to motivate people to come and work for you. So that's like really where the process starts for me, is how I'm attracting talent.

**Harry Stebbings** [45:48]:

Can I be blunt? Yeah. Fair and accurate environment to encourage people to motivate. Do you know what honestly sales reps want, Sean? They want a company that's selling fast and easy, where you get high comp and you get good comms and the sales aren't that freaking hard. Doesn't that sound like a dream? That's what you got two job offers. One where you feel inclusive and you're empowered, and another where sales are easy and comms is high.

**Sean Murray** [46:12]:

I don't think so, Harry. Now here's what I've learned in my journey. Let's go back to that example of attracting talent to your company. Okay? According to Forbes Women, that in general neutral job posts, seventy four percent of women less likely to interview. Now hear me out. When in that same description, in the same source, if there are masculine related tasks or words, like you'll crush it, you'll dominate, like those types of words, only 55% of women will apply. Now hold on. According to Xactly Insights, those that identify as female outperform their male counterparts by 8%. If you, as a sales manager, have a certain profile that you're most attracted to, then that's probably who you're gonna go and hire. And so when I feel as though I've perfected sales hiring, it's because I eliminate bias from the process. It's very structured. It's driven by competencies.

**Harry Stebbings** [47:10]:

Okay. So we realized that the words matter in terms of how they impact our funnel of applicants on the talent side. So we use gender neutral words. We use personality neutral words. And then what? And then we have, like, a talent pool. How do we then hire?

**Sean Murray** [47:26]:

The next step, after you've attracted all this talent to your company, right, you're an advantage because you've got this massive pool to choose from. Right? Yeah. So then what happens next is your proper kickoff and agreeing on what are the right competencies that we are seeking? What are the right attributes that we are seeking? And then who is going to do what? So setting up the structured process to ensure you have consistency for the follow through in the interview process. So for example, the high performing reps, they have similar competencies: drive for results, persuasion, negotiation, intellectual curiosity. So you incorporate that in your structured process. And you only get so much time with a candidate. Candidate's only gonna give you, as a hirer, so much time. Let's say there are three or four people that interviewed that candidate. They all ask the same damn questions. So you're not getting enough data from that candidate in the short time

**Harry Stebbings** [48:21]:

allowance that you do have. So how do you get enough data? And how do you make it different where it's not like, oh, tell me about a time when you've persuaded someone to do something they wouldn't have otherwise done? Great question. The interview for each person,

**Sean Murray** [48:35]:

interviewee, is highly structured. So, Harry, you and I, we're on the same interview team. Okay. In our software, here's what I'm going to do. I'm seeking and checking out for negotiation competencies, persuasion competencies, and drive for results. Here are the questions I'm going to ask, and here how they will be assessed. Okay. Harry, you are going to test for these other competencies. Here are the questions you are going to ask, and here's how you will assess them. And so the interview is very structured, and I'm making this up. It's a three hour process for the candidate, and every candidate is also gonna have the same take home test. Every candidate is gonna go through the same personality test. There's no room for bias. There's no room for repetitive nature, and you follow that process. So you you can get the most data for your candidate in the that amount of

**Harry Stebbings** [49:24]:

time that you're allowed. Okay. So we have three different interviews over three hours. And how are they just divided up? Just so I understand. I'm I'm a founder literally hiring my first salespeople. One is, like, competencies. What's what are the other two?

**Sean Murray** [49:37]:

Yeah. So the competencies are your big buckets. Okay. Yep. So let's just use one big bucket as an example. Drive for results. Like, that that's the bucket that you're using. Then you have three questions that are related to drive for results, but you must ask each candidate the same exact questions so they have consistency across the board. Right? You don't tweak those questions at all. You wanna make sure that when you're testing for drive for results like, let me give you a specific question. Right? So the question that could be consistent is, tell me about a time when you were told to call me back in six months. What did you do? What was your action? And then what was the result? As an example.

**Harry Stebbings** [50:15]:

No. I've got an answer for you. I actually did this. I emailed Mark Benioff 52 times, once every single week, with a different email every time related to a tweet he sent in the prior week with, like, one of my comments on it.

**Sean Murray** [50:28]:

I saw that. That was, like, four months ago. Right?

**Harry Stebbings** [50:30]:

Yeah. It was a long sales cycle. Problem. But but yeah. Okay. And so you're looking for that story of persistence. Question for you. Yes. Do you feel you lose the art of someone's story and understanding them with the rigidity of a formula? I hear you, but it's like me saying I asked the same structured questions in 20 sales. Because your story is different, and I wanna understand the fabric of what makes you you, not a robot.

**Sean Murray** [50:59]:

Sure. You can get those stories through that structured process. So for example, let's go back to that question that you shared about Marc Benioff. I just learned a lot about you and your craft in the elegance of your answer. You're still capturing a little bit of the art, but what I'm trying to avoid, Harry, is the unconscious bias that inevitably creeps in to every single interview that all human beings do. That's And okay. But if I can build in more science and more data driven results and the little amount of time that I do have, I'll take that every time other than the nuance that you're referring to, like the art side.

**Harry Stebbings** [51:36]:

Okay. I got you. And so the competencies are, like, the three equal buckets. It could be drive, another one persuasion, another one, whatever we wanna choose. And we then do three different interviews for each one. Correct?

**Sean Murray** [51:49]:

No. So the interview let's say the interview is one hour. Okay? You and I, before we start our process of interviewing in general, we're gonna have a kickoff meeting, and we're going to agree on these are the core competencies. There are probably I'm making this up. There are six to eight of them. On the first interview, I'm gonna interview for these three competencies across nine questions. It's gonna be in a scorecard, and then you're gonna be able to see it, the scorecard. Now you, Harry, you've got these three or four competencies, and here are the nine questions that you're gonna ask. And they're different from mine. They must be different. So we get as much data about this candidate as we possibly can.

**Harry Stebbings** [52:22]:

So we have that as that structure for those core pillars. You said about a sales task and a take home task. What do you ask them to do? Is it one on you? Is it one on another company? How do you structure that?

**Sean Murray** [52:35]:

Yeah. It really depends, Harry. It depends if it's my first sales rep or my first sales manager. If it's a first sales rep, it might not be a take home test. Instead, it could be a CCAT test that you would take. It could be a personality test that you could take. It could be different types of tests. But when I do take home tests, it could be something as simple as what would be your thirty, sixty, and ninety day plan when you start with me. That could be it. So then you can grasp their intellectual curiosity. You can grasp their drive, their passion about your product and the problem that you're solving. It can really be a choose your own adventure on what that take home test could be. Would you ever

**Harry Stebbings** [53:12]:

hire someone who hasn't done sales before?

**Sean Murray** [53:15]:

Yes.

**Harry Stebbings** [53:15]:

And I have many, many times. What's more important? Someone sold the ACV that you're selling or to the industry that you're selling to? I don't have a sexy answer, but what I

**Sean Murray** [53:25]:

can say is I've hired teachers before. School, educational teachers, professors into sales. Right. It goes back

**Harry Stebbings** [53:33]:

to the teaching element. Is there any big lessons for you on, like, negotiation on comp and what that tells you about people? I find, like, specifically, title and comp are two of the most revealing parts of a hiring process. Do you have any lessons on this?

**Sean Murray** [53:45]:

I have so many lessons on comp. So first, the biggest lessons I've learned on comp is transparency. My biggest lesson. For those that are up to negotiate at final offer, to me, that just creates a different economic bias that could come in into that process. So maybe someone's better at negotiating compensation than another. Right? So maybe that filters it. But with transparency, look. I'm never gonna be the highest paid shop in town. You can always go somewhere else to make more money. But I'm looking for transparency so everyone knows what they're walking into. Here's the variable pay. Here's the salary. And it's just very transparent. Everyone knows what it is. So I don't waste my time. I don't waste theirs. Transparent pay. The second lesson I've learned is I've moved to a national pay structure. If I live in London, if I live in New York City, if I live in Cleveland, Ohio, it's still the same job. Right? You're still performing the same tasks. So that transparent standard pay doesn't really matter where you live, and I pay on the higher end. I assume you live in London. I assume that you live in New York City, and I will pay you on that high end. Not the highest paid shop in New York City, but I'll pay you on that high end. So transparency and one pay structure. What are the biggest mistakes people make when they're negotiating comp? They underpay or they overpay. Those are the biggest mistakes. There's great data that exists about how much people are paid for certain roles. It's very transparent, but some people, they underpay in a startup, and they just try and overpay them, say, on the equity side. Right? I get that, but that's a mistake.

**Harry Stebbings** [55:19]:

Yeah. What's the right OTE level, do you think?

**Sean Murray** [55:21]:

So on the enterprise and national pay, depending on what your quota would be, is probably the right place to start. Right? So best practice is a five to one ratio. If I'm gonna pay someone £200 sterling, I want them to have a million quid as a as a goal or as a quota. Think about what that ratio that you're willing to pay. Now in a startup, you may have to sacrifice that a bit to maybe four to one based on what that quote is versus what you're willing to pay. But that's considered best practice to look at it in that type of way. Then depending on where you're hiring, you can get plenty of data on what, like, the averages are.

**Harry Stebbings** [55:55]:

How long does it take to ramp to get people to quota? Like, you bring me in. Like, second quarter, does Harry tend to hit quota? In third quarter, I know it depends on the ACV, but selling in Enterprise with large ACV's, how long does that take?

**Sean Murray** [56:08]:

Yeah. So if you're selling into the Enterprise, and let's just use an ACV of a 100 k, you wanna let that rep ramp for about six months, Move slow in order to move fast later. But don't wait those six months to measure their performance. Have stage gates along the way those six months. But an enterprise rep, it'll take a good year. Right? Because the next six months, you ease them into their quota. You want

**Harry Stebbings** [56:30]:

them to be successful at the end of the day. The thing that fucking kills companies is churn. When you look at the amount of sales reps that leave after two years, it's so high. And so you actually have, like, six months of productivity in '24 because it takes a year to ramp. The final six, they're thinking about, you know, how they're gonna leave. And so you've got six in the middle where they're productive. Doesn't this kill organizations? It does if you let it.

**Sean Murray** [56:53]:

And the conversation we're having a little bit earlier a piece of conversation we had earlier, which is in your sales process, you'll know within the first six months if this rep's gonna cut it in the enterprise or not. You should. And when I think founders make a mistake is they wait for how many deals that they get a year and a half later. There should

**Harry Stebbings** [57:10]:

be more stage gates. What are the stage gates in the first six months that should be had to understand the effectiveness of a rep in enterprise? Certification.

**Sean Murray** [57:18]:

So I've always embedded a certification culture within my revenue organization. And so you're testing these sales pros. You're having them test on your product. You're testing them on your narratives. You're testing them on whatever it is that you wanna test them on. And then when they get in sales cycles, are they graduating from stage two to stage three in the sales cycle or not? What's missing? Listening to the Gong conversations or Chorus or SalesLoft or wherever you use. But those first six months in the enterprise are very, very critical.

**Harry Stebbings** [57:47]:

How the fuck do I forecast in 2024, Sean? Like, you know, everyone's telling me it's harder than ever. Everyone's saying, oh, CFOs, they're not buying. And I'm sitting here today as a CRO or a CEO thinking, are we gonna two x last year? Are we gonna three x?

**Sean Murray** [58:02]:

The short answer is artificial intelligence. That's how you're gonna forecast in 2024. There's technology shout out to my friends at Clari. There's technology today that's putting a lot more science using the machine learning into what's gonna be the output ninety days out. And frankly, on my new Logos side, it's been within 5% accurate ninety days out. So that's how you should forecast in 2024. Use the technology. I have wasted years of my life trying to predict the future in forecasting. Years of my life, I'll never get back. And I still can't get it right. I still try so damn hard, but forecasting is very difficult.

**Harry Stebbings** [58:37]:

Do you think sales leaders are very good today on the whole? When you look across the sales leader landscape today, are you like, yeah, awesome set of sales leaders? Or are you like, I was quite rude about CMO as being useless? Do you feel that most heads of sales are pretty useless?

**Sean Murray** [58:51]:

I think it's about half are useless, half are very good. I listened to a bit you did about playbooks. And first, I would refer to playbooks as sheet music. That's about playbooks. Fun fact for you, the term playbooks is a sports analogy based on American football. So I prefer, like I use, like, sheet music instead. Yeah. Why sheet music, not playbooks? Because I'm auditioning right now for candidates in the future that might come work for me. And I wanna make sure that I can attract the right people that work in my organization, because I'm not running an old school playbook. I wanna run sheet music and pattern recognition. It's a little bit different. And so the the sales leaders that are shit right now, Harry, they're running the old sheet music. They're trying to get people back into an office where there's high fives and kegs and ping pong, and they feel that that's like the culture that they need to be successful. Where today's salespeople, they're more interested in career pathing. They're more interested in learning and in development. I had one sales rep, one of the highest performers that we have. We're all getting together, those that live in the same city, and we're having a conversation about when the sales manager said we were talking about the year end close. And the sales manager said, oh, I missed the sales floor. You know, the gongs and all that low noise and the music. And one of the highest performing reps said this. He said, what's the sales floor? So to me, was the biggest, like, moment. Look. I miss I wanna lean in much harder to the future of sales, not to where we were in the past. And the bit that I heard about what you're saying about playbooks, I agree to a certain extent. There's 75% of key pillars that make up a sales craft that is the same no matter where you go. There's sales strategy. There's talent management. There's operations. That's the same that you pick up and you bring somewhere else. Right? But in every organization, it's different. There are probably 35 key attributes that make up those core four pillars that make up a sales organization, and those might vary from company to company. But to answer your question, Harry, half the sales leaders probably are not gonna make it in the next year or two.

**Harry Stebbings** [60:49]:

A final one, because I could talk to you all day. But on that sheet music versus playbook, should the founder be the one to create the first sheet music, or should it be an external head of sales, first sales hire? Founders

**Sean Murray** [61:03]:

are incredible salespeople. They are. They care greatly about the product. They built the product. They typically know everything about the product, which makes them great salespeople. I would argue that that sheet music get created by a professional that has the pattern recognition that has seen it before. So I do not believe a founder should build that sheet music or playbook for how we're gonna go to market. That's

**Harry Stebbings** [61:24]:

fascinating. I believe they should. If the founder doesn't know, then how are we gonna hire someone who's gonna do it? If I don't know the person that I'm selling to, the ACV that I'm selling, how I'm gonna reach them, the message that I'm gonna reach them. There's many different types of sales leaders. I don't know which one to hire if I don't have that playbook built out. That's not a wrong

**Sean Murray** [61:43]:

assessment that the founder should know all of those things. I agree with you. However, there are professionals that know exactly how to craft that message. Like, in the sales go to market motion, three common themes. You got a methodology, process, and behavior. Now you, as a founder, might not have that pattern recognition skill set built up enough to know what those behaviors are that you wanna incorporate or what the segmentation strategy should be or what methodology or process to use. Bring on someone that has that pattern recognition and that expertise that can do probably better than a founder that's never done it before.

**Harry Stebbings** [62:19]:

Yep. No. I get that. Right. Sean, I could talk to you all day, clearly. So I'm gonna pepper you with questions unlike the last hour and twenty minutes, and you're gonna give me an immediate thought. And we're gonna start with what single trait is most important for a sales rep to have? Intellectual curiosity. How do you test it? Like, what question?

**Sean Murray** [62:38]:

You test intellectual curiosity based on their questions that they ask of you, maybe at the end of your interview.

**Harry Stebbings** [62:45]:

I'm so with you. I always say to founders, also at the end, like, you know, do you have any questions to me on the process, on the firm, anything that and the best always do have many questions.

**Sean Murray** [62:53]:

Yes.

**Harry Stebbings** [62:54]:

What sales tactic has died a death?

**Sean Murray** [62:56]:

Discovery. There's too much information that we can extract on our own that we should know a lot about our buyer before we engage with them. What's your favorite question to ask in an interview process for a sales rep? Explain the time to me when you were asked to call back in six months. The reason why I love that question, Harry, is you will expose that person on how they operate pretty quickly.

**Harry Stebbings** [63:19]:

So the majority not just say, I haven't I haven't been asked to call back in six months.

**Sean Murray** [63:23]:

No. The majority say, oh, that's great. I'll make sure I put it on my calendar. Here's what I'm gonna do in the interim, and I'll call you in six months. I've had the majority say that. What's the best answer? The best answer to that question, They reframe the problem, and they teach me something that I didn't know about my business right now in that moment. That's the best answer.

**Harry Stebbings** [63:41]:

What other function does sales has have the most friction with?

**Sean Murray** [63:45]:

Sadly, it's product and marketing. Because salespeople, they want a product that's applicable for everyone. Right? So they complain about the product, which is wrong. And the second reason why sales are wrong is on marketing. They want a fat pipeline of buyers that are ready to buy, and they blame marketing for it, which is also wrong. So that's typically where the most conflict

**Harry Stebbings** [64:04]:

Take me to a

**Sean Murray** [64:04]:

deal you've had to get really creative to win. What did you do, Sean? Everest feature. What we're talking about earlier about discounting, it's just not about discounting. It's about give and get. And I've had some of the biggest companies that I must win, I and must have them as a customer, but they'll sit on my customer advisory board. We will promote them in different ways. We will use their product in new ways. There are ways to get creative to win the business. But, basically, people want to buy. They just don't want to be sold to. And so the way I get creative to win deals is to make it a no brainer for that buyer to trust me and to go with me.

**Harry Stebbings** [64:37]:

How do you maintain morale when missed goals happen? It always happens at some point. How do you maintain morale? It's goal visualization. Celebrating these

**Sean Murray** [64:47]:

small, quick wins is very important because there are small wins that happen throughout the day. And goal visualization, reminding the team of our purpose and our mission and why we do this every day. Reminding the team of the impact that we're having in the market. As an example, Harry, over this past year, when there's a very low hiring volume that's happening right now, Greenhouse, we have helped over a million people win the job of their dream by using a fair process leveraging Greenhouse software. So I remind people of really what we're building and what we're doing. We're 7,000 customers, and we've processed over a million offer letters through our software this year when no one's hiring. But to answer your question, don't forget the goal visualization. Yeah. We all wanna make money and hit our quota, all those things. But you gotta go deeper sometimes and get back to what really motivates people because not everyone's motivated by money, shockingly.

**Harry Stebbings** [65:39]:

Final one. What one company sales strategy has most impressed you recently when you look across the landscape?

**Sean Murray** [65:45]:

20 VC. You. I appreciate what you're building, and I now want to because you're creating value. You're drawing someone like me in, and you're offering this value to other people that are just like me. And then now I want to buy more of what the products that you have. I want my leaders to get exposed to what you're doing. You're not trying to sell me anything. But that gets back to the teaching and how buyers want to buy. So I'm impressed with the operation, whether you're meaning to do this or not. I'm impressed by it.

**Harry Stebbings** [66:12]:

I so appreciate that. I've loved this. As you can tell, for me, the best shows are when it's really very natural. I definitely feel that this was a natural conversation. Thank you so much, Sean. I've loved doing this.

**Sean Murray** [66:23]:

Harry, it's been a treat. This is such a fun conversation. When are we gonna have this conversation again?

**Harry Stebbings** [66:28]:

Taylor Swift.

**Sean Murray** [66:29]:

In London, Taylor Swift.

**Harry Stebbings** [66:32]:

And we'll be live streaming our excursions, Taylor Swift's live event in London. No. I'm obviously joking, but you can check out the full episode and the video of that show on YouTube by searching for 20. Sean was incredible there. I love the natural discussion. But before we leave you today,

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**Harry Stebbings** [66:47]:

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