How to Layer Enterprise Sales on PLG

I learned so much from your shows, Harry. I’m excited to be here.

Well, the interesting thing about my first sales role is I didn’t realize it was a sales role until I accepted the job and was in the role. I would say my first customer facing role was at my mom’s beauty salon where I was picking up the phone, talking to customers, answering their questions, and booking appointments. And I went to university for marketing. I landed my first job outside of school at a tech startup in a marketing role. And it was there that I started hearing whispers about a local founder in Vancouver who was starting his next gig.

And that was Stewart Butterfield and he was starting Slack. And I became obsessed. I read everything about Slack. I read all of their customer tweets. I read all of their blog posts. I saw on their website that they were hiring their first account manager. Now I didn’t know what an account manager was, but I saw they were looking for someone with great communication skills, and I figured I’ve got that. So I threw my application in cold on their careers page. I went through a few interviews and I got the job.

And it was in the job that I realized that the account manager role was an account executive, a solutions engineer, and a customer success manager all in one helping our customers. From that point forward, I’ve been in sales ever since. Now I lead our go to market team across The Americas at Notion.

I would tell myself be confident. I would say that especially in getting into the customer calls and when the customer calls got hard. Because it was easy enough to talk to someone who loved using Slack, loved the product, but then as soon as they asked for a discount or they had an objection, like they were evaluating Slack with a competitor, I started to feel a little bit more insecure. I would say to myself, you’ve got this. Like it’s all in confidence in like in how you present yourself and just be confident.

You got this role for a reason and, like, learn as much as you can.

Yes.

My advice is don’t treat it as awkward. Treat it as any other conversation that you’re having with the customer. Early stages of a deal, you lean into discovery and that’s where you’re learning about them, asking questions, and things typically seem very friendly. As soon as you get to the negotiation stage, instead of thinking about it as a tense conversation, think about it as another conversation because your customer is going to feel your energy. So if your energy is, oof, I don’t know if they’re gonna like this price or this this is expensive.

I’m scared what they’re gonna say. They’re gonna feel that energy. Whereas if you just go in and you say, hey, so we’ve been talking for a while. Here’s the value that I’m hearing that we can bring to you and here are the problems that we’re solving. This is what it’s gonna cost and pause and just see what they say. Because they’re probably gonna say something like, woah, this is expensive. And instead of going into defending your product and why the price is the price, go back into question asking.

Go into like, okay, tell me more. Why do you think it’s expensive? What do you think is the right price to pay? And then just treat it as that conversation to understand, like, how can both parties seek mutual value here?

I was gonna add, and that that’s actually something that we’ve brought into our sales process here at Notion. So when you’re building a sales process, it’s very typical to think about the stages of the deal. Stage one, qualify the deal. Stage two, do discovery. Stage five is negotiation. Stage seven is closed one. Instead of calling it those stages, we actually think about the mindset in each of those stages because that’s what we want our sellers to embody. It makes for a much more adaptable mindset than just having the exit criteria or the checkboxes that a seller needs to do at each stage of the deal.

So as an example, at stage two, we call that the curious investigator. So we expect our sellers to embody being a curious investigator that researches the heck out of their customers, understands how they make money, ask questions from a place of genuine curiosity. And then just what we were saying about stage five negotiation, instead of calling it negotiation, we expect our sellers to embody the mindset of a value articulator. So how are you truly articulating the value of your product?

It’s a nuance, but I don’t know if you think about this even in podcast hosting where instead of thinking about the content that you’re going to ask, it’s actually thinking about what’s what’s the tone, the body language, the feeling that I wanna give off in this conversation? Because people often say they’ll remember how you made them feel versus what you actually said.

I agree. You need to create that psychological safety. If you’re creating a fear based environment or or you don’t have that safety, people are not gonna tell you the real answer. They’re gonna hold back.

This is what I found when you really love the product that you’re selling. This was the same at Slack and at Notion where we love selling the product and our customers who are using the product love hearing about the product and the features. What mistake sellers make early on is they’ll talk about the product. They’ll have premature pitching syndrome. And so it’s hard to stay in this zone of let’s just ask questions and let’s actually not even talk about the product.

We’re just gonna talk about the observations we’ve seen of what makes the company great, what makes that person great, what are their new challenges that they’re coming up against, what are the biggest risks that might prevent them from getting there, And just like really leaning into that conversation without talking about your product at

Yes. We record all of these calls. We have both Gong, which records the calls and the video, but we also use Notion AI internally to transcribe those calls. Okay. So we have that with this curious investigator. We ask loads of questions. What’s stage three? Stage three is solution design. This is when you start to talk about your solution and start to think through where can your solution help them based on the problems that you’ve heard. The key here is not taking all of that research and discovery that you’ve just done and then completely neglecting it and just talking about all of the wonderful problems that your solution solves for, it’s actually starting to connect the pieces.

Or if you’re hearing pieces that they’re actually not within your wheelhouse or like that’s not what you do best at, it’s also being honest and being the the challenging skeptic to say like, is this deal really gonna go anywhere or should we part ways?

So I’ve spent my career at PLG companies, Slack and Notion, which have great distribution across a whole host of different customers. You have students, you have communities, you have b to b companies across all industries, across all departments. The uniformity tends to start very general. But the key here is ensuring that your sales team is very focused so that you can build or bring in the most successful customers, and those customers tend to have patterns.

Not quite. And this is the common trap that PLG companies fall into because they’ll typically look at their data and look at product usage signals. And they’ll use that product signal to figure out where should they focus. And so at Slack, we saw that our biggest workspaces were actually communities. They were professional networks that were using Slack to trade best practices. There were student groups that were using Slack to work on projects. And the sales team was tempted to sell them because our sales team was using product led growth signals and seeing what are the biggest workspaces because lots of active members translated to lots of licenses.

And it was very important that we actually remained focused on the biggest customers that had the most value from the product. And so that wasn’t necessarily communities because when you think of communities, it’s a very different post sales motion. The values that you’re seeking are different than if you were selling to a company. It would have led your product roadmap in a very different direction because you would have had to invest in features like inappropriate message flagging within a community. Those groups also don’t have a lot of money.

And so while they might have had a lot of licenses, there’s not a lot of budget to unlock there. And so we made a very deliberate decision to not focus on communities. That was great if they were using Slack from a product like growth promotion, they were using our freemium product, But from a B2B sales motion, we were very focused on selling to B2B.

So if I was a Founder and I had a PLG motion, so I saw that customers are already using my product, I would start doing a lot of interviews. And I would interview all of those customers, and I would understand what motivated them to try the product. How are they using it today? How do they see it fitting into their business priorities and what they’re ultimately trying to drive as a business or if it’s a consumer as a consumer. I would start to put in the pieces of what do those customers look at.

And instead of looking at the product led growth signals, which is the common trap, I would actually look at the firmographic details. What’s a firmographic detail? It’s like what is the industry that they’re operating in? How big is their company? Where are they located? Are they located in major cities or are they located in a certain geographical area? Basically everything outside of your product that you could use to describe them. And then going even deeper inside of those companies, if you are b two b, who are the personas in those companies that are getting the most value?

And I would use that to work backwards to figure out who is getting the most value, that unlocks the most budget that we should be focusing on.

Well, I wouldn’t even call it this Well, I guess it is. It’s ICP. It’s figuring out who is your ideal customer profile, and I strongly believe it’s the founder. Because that’s not only gonna guide your go to market strategy, it’s also gonna guide your product roadmap and where do you continue to lean in. So back to my Slack example, like, we actually didn’t lean into community roadmap features. We leaned in to b to b specifically for our distribution as we went up market.

Yes. Exactly. Having the founder start to build sales initially that helps bring intuition into the product. It also helps to figure out who to hire for. Like, if you don’t know who your ideal customer profile is or what kind of sales motion is going to work for your company, how do you know who you’re gonna hire as a sales leader who will actually bring your business to the next level?

My biggest advice for the early stages of building a sales team is thinking through it as if you were thinking through a manufacturing supply chain. And this idea comes from the HBR article of the sales learning curve. Have you read it?

It’s a Harvard Business Review, but I highly recommend founders to read this article because it talks about the stages of building a sales team. And the earliest stage of building a sales team is not looking for traditional coin operated reps that are gonna come in and just build the sales playbook for you. The earliest stages are actually about learning. Similar to how if you were bringing a manufacturing product to market, like you were selling bathing suits. Your first 10 that you make are going to be really expensive, But you’re gonna learn a lot in making those first 10 bathing suits.

That’s like when you’re hiring sales. Your first few sales reps, say three to four sales reps, it’s gonna be very costly because you’re not gonna know what they’re exactly doing, but we call them the Renaissance Reps where they’re generalists, they’re adaptable, they’re highly skilled in communicating and collaborating with the internal stakeholders at your company, that being marketing, product, engineering, and talking to customers. And that’s where you learn the most.

I’ve found it’s a little bit of both and it’s not as a matter of like where they are in their career because I think you wanna build a diverse sales team. And so typically you hire three to four reps. Some could be earlier on their career, but I’ve shown a high aptitude for learning. And then others can be potentially making a career switch or they’re really excited about building. And that’s the thing. They’re not excited about just making a lot of money because that’s not the point in the first year of sales.

They’re actually really excited about learning and building something and bringing the mission forward.

So if I’m a founder, I would make sure that I have some great go to market advisors on my board or in my arena. And I would talk to them and learn. What do they look for in hiring great early sellers? What are the key competencies that are important to look for? And knowing the business and the unique aspects of your business, what’s important to that business to double down on? So if it’s a certain industry that you’re selling into, perhaps it’s some industry knowledge. I can’t think of another example, but it’s like starting to define what that looks like because I think a common mistake is not knowing what you’re looking for and then just relying on heuristics that can lead you astray.

Heuristics like they come from a big flashy company, they must be a great seller. Or heuristics like they’re a great communicator and presenter. Customers are gonna love them. That surface level, like you really need to dig into what are the key competencies that you should be looking for. And when I’m talking to early stage founders, there’s three competencies that I think are really important. The first is high motivation. The second is effective at problem solving. And the third is a continuous learner. If you start to define what those competencies look like, then you can start figuring out what is your process, what are the questions that you can ask so that you can figure out whether that’s a great hire for your business.

This is where past behavior is the best predictor of future behavior. So asking for stories and examples of how they’ve solved problems in the past. Questions that I really like are, tell me about a time you weren’t set up for success. Because then you can also start to hear not only did they solve that problem, but did they take accountability or were they a victim in that scenario? Another line of question that I really like is tell me about a really big challenge that you had to overcome.

Great. Tell me another challenge that was really hard that you had to figure out the right path forward. And you’ll start to see, like, is there a pattern of them taking an ambiguous problem and just finding a way to persevere and get to a great outcome?

Because it will be everything from, I didn’t have enough inbound or my manager left and I didn’t know what to do. And so those are the places where you’re like, okay, so what did you do?

Yes. We do. Especially for our sellers in commercial and mid market, we expect them to be very well versed in the product. And so we’ll ask them to research our product and let’s do a case scenario where we’re going to be a customer. You’re going to pretend to be the account executive selling our product, and let’s go through a first call to see what that sounds like. What we’re looking for is what are the questions that they’re asking? Can they adapt and learn about what we’re selling and the actual problems that we’re solving?

And then without any training, how far can they get with our product? And that’s another example of assessing problem solving. Like, can they be resourceful and do this without a lot of guidance?

Few days. We because the other thing is, like, we need to move fast. We need to get hires, and so we can’t draw out our hiring process. We wanna get hires in fast. We give them a few days because we also wanna see how can they be a pacesetter, how can they deliver with short time deliverables because that’s gonna be the reality of the environment that they’re operating when they’re getting here.

I would say there are two ways. The first is a lack of preparation. A lack of preparation, research, and actually doing their homework to come up with a polished first meeting. And so I’m looking for, did they look at our customer stories and read through all of our customer stories? Did they watch all of the videos that we’ve published about what we’re trying to solve? Did they actually sign up for the product and start using it themselves to see what it feels like? And so you can see where someone put a lot of time, put a lot of effort in actually learning, or they sort of just winged it or relied on a playbook that they’ve used before.

And then I would say the second place that people mess up is thinking on their feed. That’s very important in sales. We say a seller needs to be audible ready. So if we throw them off, what do they do? If we, as an example, give an objection and we say, hey, do you offer discounts? And they just make something up and they’re like, yes, we offer a 40% discount and they like cave under pressure, then we’re like, ugh. Or if we ask them a technical question and they just make up an answer versus saying like, hey, let me get back to you.

Those are some areas where we’re like, Okay, there’s an integrity piece here, and can they really think on their feet and adapt?

Yes, do. Early stages, it’s a lot of cross functional partners, so it’s not just sellers on the team, but also looking at the partners that they would be working with most closely. It’s similar, but we have a few people on the panel and ensure that we have laid out what are the competencies that we’re looking for so that we all know what we’re looking for.

The expectations are set upfront. Especially in The US, you can see what the comp ranges are for all of our jobs. And so it’s important to also see as like a seller, okay, does that range meet what I’m looking for? And then what I would say at a company that’s a startup or scale up, if you’re just looking to maximize your OTE, that’s probably not the best place. Like, go to one of the large giants because that’s where you’re going to maximize your OTE. You also wanna think about the equity and the full package.

It depends on where you are in your career. Like early days, I actually think it’s a big miss to just focus on comp and to not focus on the bigger picture. Because if you’re at a fast growing company that is doing really well, your equity is going to be way

So my biggest advice is to think about the key outcomes that you’re looking for the seller to achieve in the early days. And oftentimes, it’s not like they make their first huge sale. It’s actually looking at the leading indicators before that. And we’re actually redesigning our onboarding program at Notion. And what I really like about it is we’re thinking about the key outcomes that we expect our sellers to learn in the first few weeks. As an example, one of the first key outcomes is learning how to prioritize their book of business.

What are the accounts that they’re gonna focus on that deserves the time and the attention to ensure that we’re focusing on the right accounts?

We say a $100,000 plus. And that’s actually a really good question because I think it’s important to have a dual focus as a seller. So you have your strategic deals that are a $100,000 and above, but you also have your velocity deals that are more tried and trued. So those are like your twenty, fifty k deals that you know you can win and that are less risky. And I’ve seen that where if you have a diversified portfolio, similar to financial advising, like, you don’t wanna just focus on the highest risk stock, like you wanna make sure you have a diversified portfolio.

I bring that mentality into sales to think about, okay, in your week, in your months, as you’re planning your path to target, what are the accounts that you should be focused on? You should have a few big bet accounts that are gonna get you the 100,000 or million dollar deals. And then you should have the tried and true accounts that you know that these are the customers that typically evaluate more quickly, you know you can win them, there are all the right signals here for you, and ensure that you’re not minimizing focus on those accounts and so that you build this pipeline that can reliably get you to your number.

That’s a good question. And no, I would say this is diversified within your portfolio of the segment that you’re selling into. So if you’re a commercial seller selling to SMB, your big accounts might actually be like the $50,000 accounts and above while still making sure that you’re knocking out the 10 to $20,000 deals. If you’re an enterprise seller, it’s most likely like your big accounts are those million dollar deals and the velocity accounts are like the 50, the 100 k deals that you’re bringing in.

So I have different answers depending on the stage of your company. Okay. Early days, like as the first account manager at Slack, I was on customer calls on day two. It was just like get in there, you’re adaptable, start talking to customers. Now at Notion, we think about like what are the checkpoints that we need them to meet before being in front of a customer. And I’m a big fan of mock scenarios. So instead of having your first discovery meeting or your first pitch in front of a real customer, you’re doing that with your manager or you’re doing that with your onboarding cohort so that you can practice it.

And then once your manager says, yes, you are ready, then you can start working with your customers directly.

Every sales team I’ve led, our account executives are responsible for their pipeline. And they’re responsible for their pipeline because they’re also responsible for their number. While they may have resources like a business development rep to help them build their pipeline, they are at the end of the day the ones that have to figure out what does that motion look like? How do I want to coach my BDR to be really effective in my book of business? Where do I see the accounts that we should prioritize?

Who are the key stakeholders that we need to map in order to build consensus? And what is the messaging that is tailored to that customer that we’re going after, for the big deals like personalization to the nth degree is really important. Otherwise, we’re not gonna get a meeting.

I agree. You can get very strategic in your outbound playbook, and it’s on the seller to really understand that. We’re also diversified in our channels. We’re not just emailing. We’re cold calling. We’re using LinkedIn. We’re using warm connections from LinkedIn Sales Navigator. And it’s on the sales it’s on the account executive to be that quarterback and understand, like, who do we need to get in front of? And then how do I divide and conquer with my BDR if you happen to have a BDR?

gonna say here, you are brilliant. The fact that on the fifty third email you got Mark Benioff to come on your show is so impressive because that’s the other trick with outbound pipelining. You just have to keep going. Just because you don’t get a response on your first, your second, your third, your seventh, you gotta keep going.

Totally. And you build empathy for the people around like, yes, exactly.

Yes. This is where I’d go back to the firmographic data points to figure out what are the firmographic data points that signal the best long term customers for your business. Those can be industry, company size, location, what their tech stack looks like, everything outside of your product. And then if you are a product led growth company, what are the other product signals that signal to you that you can accelerate this expansion, this upsell, or this deal, and then using those signals to figure out how do where do you focus your time?

Pretty fast. And I like this framework that I got from Winning by Design, the sales enablement program where they talk about REKS, r e k s, results, effort, knowledge, and skills. And it’s working through that to understand where are we going wrong with this rep. So if they’re not hitting the results, they’re not hitting the pipeline or revenue results, then we work backwards. Do we see the effort? Are they putting in the emails, the meetings in order to drive that pipeline? They could be high in volume and if that’s the case, then you look back further.

Okay. You look at skills. Are they prioritizing their accounts in the right way? So are they just completely prioritizing the wrong accounts? They’re hammering them with emails and meetings and they’re just not going anywhere? Or is it other sales skills like discovery? They’re not asking the right questions to compel the customer to move forward with the evaluation or the negotiation calls are falling flat. Or the last place to look is the knowledge. Are they not coming off as credible in front of their customers because they’re not speaking the customer language?

Or are they not knowledgeable enough in the product to really understand where to take the conversation? Because when you think about starting to piece together what the actual problem is, that will help you figure out, can you coach this rep on that specific area, or is this just not gonna work out?

Yeah. Well, I’d try and figure out, like, what is the negative consequence then? Is the negative consequence then that they are selling deals, but they’re not selling a high volume of deals? Because then I would argue that is a problem, and you need to look for a different skill set. Or it could be they’re selling a lot of deals, but they’re actually churn bombs. So they’re bringing in bad deals. They’re overselling. And when it gets to our customer success team, we’re realizing those are not the right customers that are gonna get long term value from our product, and we need to figure out how we can implement better qualification.

And so, like, those are a few of the nuances that we would also want to look out for.

It really depends. We keep track in our onboarding program. So like I said, we look at outcomes in the onboarding program like, okay, first check, did they prioritize their accounts correctly? Second check, how do they do in their mock call scenarios? And then you can tell pretty quickly of are we on the right path here or could this potentially be a mishire? And then depending on the ramping period, so for enterprise reps, the ramping is longer than commercial reps, but I would still look at indicators like what we just talked about to figure out is this gonna work.

Mhmm.

Honestly, I would say I actually saw it and I just felt the pressure of hiring quickly that I felt like I needed to hire the person.

No. Because that is a very costly mistake, and it’s way more costly to have a bad hire. What I would do in that scenario is I would say like, okay, instead of lowering my hiring bar, we need to change something else within our hiring process. And usually that’s we need to increase our hiring funnel and people coming in at the top of our funnel. And so I’d say if we’re seeing five candidates a week and none of them are working out, we need to see 10 candidates next week to make sure that we’re finding the right people.

And there’s a few ways to do that. I’ve seen us do hiring jams where even though you ask people in your company who are the best referrals, make sure to refer them. We actually make it fun. We all say we’re gonna do a hiring jam at 12:00 today. We’re gonna order in donuts. Everyone opens their laptop and on LinkedIn, here is the query that we want you to search. Everyone go through everyone in their network to figure out who meets that query and let’s start to strike a conversation with them.

It’s also tapping into your friendlies, tapping into your network to say like, can you please post this on LinkedIn? We’re looking for an amazing seller to widen that pipeline and try to get more candidates into your pipeline so you have more of a selection.

I agree. And our most successful hires are referred people.

It is difficult. Because when you have a product led growth motion, there’s often the perception of the product sells itself. We don’t need salespeople. It’s gonna be way more efficient for us to just focus on product led distribution. And this is the biggest mistake that PLG companies make. They are afraid to hire salespeople because they want to do it differently. And so if I think back to all of those founders, they eventually come around and realize that building sales is going to be vital to continue accelerating your company forward.

You shouldn’t try and reinvent the wheel when it comes to sales. And so it does require the first few sales leaders coming into the business to really educate the founders, the business around why sales is so important, and how we can work together to make sure it’s not product led growth or sales. The best companies I’ve seen layer sales on top of product led growth.

I would say it’s always earlier than you think because you think your sales team needs inbound leads, whereas there is going to be a point where as you go up market, those customers do not buy without talking to a human. And you need to figure out without a product led growth motion because executives of Fortune 100 companies aren’t typically tinkering with the latest technology. They’re focusing on their business priorities. They’re focusing on how to drive the business forward, and you don’t get in front of those people with a product led motion.

And so it’s earlier than you think. I would say it’s typically after your three or four Renaissance Reps that you’re bringing in just to learn about the business, then start building outbound because it takes a while. It’s going to take longer than you think. And when I think back on my experience, like it typically takes like a year to figure out who are the accounts that we’re outbounding, who within those accounts care about what we’re selling, what is the messaging that is gonna compel them to book a meeting with us?

Cold calling.

Yes.

I agree. Yes.

Because I see it working, and people don’t do it. Cold calling is hard. It’s way easier to send an email and get a rejection. That’s easy. When you cold call someone and you get a rejection, that hurts. And so when you think about the other sellers around you in this landscape, they are not cold calling. So if you are putting yourself out there and cold calling and oftentimes, it’s actually just leaving a message. Because a lot of people don’t answer their phone, and it’s just leaving a message.

So that audio memo also gets you top of mind for the people that you wanna get in front of.

Of course, we have to. And we actually did just did something at Notion where we hosted a global outbound day. And because cold calling is hard, no one wakes up and is like, I want a cold call. And I think it’s even harder if you’re sitting at home. So at Notion, we support a hybrid policy where we have our team coming in at least three days a week.

And so we use one of those in office days to say, we’re gonna make this fun, we’re gonna cold call, and every single person on this team, including your sales leaders, gonna get on these calls, and we’re gonna start practicing what that sounds like, and we’re gonna listen to the people who are actually able to book meetings. And it’s way easier to be around your colleagues in person and get rejected because then you’re like, ugh. And people will console you, but then when you actually get a win and you book a meeting, you are a hero.

People are celebrating you. They’re asking how did you do it. We actually brought out prizes to make it even more fun. And so that’s an a way for us to, like, start building the momentum because it you can’t do this from scratch. Like, you really need to create that celebratory collaborative environment to actually start seeing what works and what doesn’t work. And you know what? It may not work, but you have to try it.

I think it’s so important too, and that’s why I’m so happy that we have a hybrid work environment here. I don’t think you can build the same type of collaborative dedicated sales team where everyone’s just working from home. I think there’s really something to that in person collaboration. And I will say the best sales team see celebration and collaboration as a competitive advantage.

The best sellers are extroverts. They’re great at messaging and pitching. Now I I don’t believe that. I think the best sellers are consultative, curious, and ask the best questions.

I would say both. And here’s why. I see AI taking on a lot of the transactional selling activities. And if you have a point solution or if it’s a small deal, I can see AI taking a lot of that down market selling motion. So sellers really have to focus on the complex strategic sales that require multiple stakeholders building consensus across the company, finding who the right people are that have influence. And then to your point, like, the technical aptitude to map their solution back to them.

Ugh. Okay. The area that I really hope that is completely fixed is data enrichment. And so what sellers dislike the most is when there is bad data within their Salesforce or their CRM. Bad data meaning the account has the wrong employee account, so they’re not able to prioritize them correctly or the territory is inequitable. I hate manual data entry, and I’m really excited to get more and more enriched data that doesn’t require that manual entry.

Well, internally, use Notion AI that’s powered by the best models like ChatGPT, Quad, and it is incredible. Like, just this week, we had our executives meet in front of customers, and they always ask for an executive briefing doc. And so before, the seller would have to aggregate all of this information from Slack and the customer’s website and Salesforce. Now we use Notion research mode that aggregates information from all of those different sources and then creates a polished briefing doc within seconds.

I think it’s figuring out what are the most impactful flows that they would benefit from using AI. So start with, like, what is the challenge that they’re trying to solve? If it is preparing research documents, like, let’s start there. I found that celebrating the people who are doing it best internally is the best way to actually get that behavior spread across your entire team. And that’s why I really like a culture of celebration because I think that’s the best way to lead. Instead of being like, you’re not using AI, bad.

Saying like, wow, these are the best sellers. They’re using AI. Here’s how they’re using it. Like, how can we incorporate this more into our process? And I also think it’s involving them into this exploration. So asking questions in our team meetings like how might we use AI with the bottleneck activities that we have today? What are some ideas that you’ve had? What are some things that you’ve looked out into the market and used recently that we should start trying? And honestly, it’s actually really helpful selling an AI product because with Notion AI, we can do all of that.

I like saying we’re constantly drinking our own champagne versus we’re dogfooding our own product. We’re constantly drinking our own champagne and trying to figure out what are the best use cases for Notion AI so that we can also speak intelligently about it when we’re going out to market and talking to our customers.

Why? Because selling in today’s environment is very complex. You have to figure out who are the stakeholders and you have to build relationships. It’s a complex product that you’re selling. I will say, I believe it would work if it’s a very transactional product. Like if you’re like, hey, we’re a conference and we are selling conference booths, This is the price. I think like an AI seller can actually probably sell that quite well. But when you’re selling solutions like Notion and Slack, like, we’re a long, long ways away to ever being able to take those sales roles.

I agree with that. I’ve been very impressed with the pace of AI innovation, but in terms of AI adoption, it’s actually been very slow. And the average enterprise company is still waiting and seeing what happens. And we actually just ran a survey and we see that. The biggest thing that’s top of mind for executives is how do they integrate AI into their existing workflows? And that makes sense to me because when you think of the average enterprise company, they have a lot of process. They’ve already built what that looks like internally.

There’s a lot of priorities across many individuals, so getting them aligned on what AI can look like for them can take a while. And so it’s our job to figure out how do we make that easier for them.

For enterprise, it’s security, legal, And some enterprises have policies where they just have a no AI policy right now because they’re worried about the legal aspects of AI. And so it’s trying to figure out how do we get around that.

It’s like picking up, and I see enterprises going from experimental AI budgets to looking at what are the outcomes that they’re trying to drive with AI because that’s where AI is going to be very sticky. Another thing I’ve heard recently is vibe revenue where there’s a lot of experimental budget with AI and companies are just trying things out. But the real winners will be the companies that have those renewals a year or two later because they’ve they’ve figured out how to drive business priorities with AI.

And I was actually thinking about this in my reflection of my performance review. So I had my performance review on Tuesday. My performance isn’t based on, like, how well am I using AI? How savvy am I? My performance review continues to be how do I drive revenue? How do I drive pipeline? How do I drive my people? So there I think through like, okay, how can I use AI to do that more effectively so I drive those results even further? And I think the companies that really figure out how to drive the ultimate bottom line are gonna be the ones that win.

The other thing I will say is from selling AI, I think it’s also the company is making it easier for them to get started. And one solution would be how can you really easily integrate with their existing solution. So if they’re already using Salesforce, they’re already using Microsoft Teams or Slack or Google Drive, how can you start to integrate into those systems so you’re starting to change that AI behavior in processes that they’re already used to?

funny because, yeah, I go to events and I’m like, this can’t be an event if we don’t say AI. But the hype is real. I actually will say like the hype is real and executives genuinely wanna see and hear how other companies are leveraging AI. And so what I found to be most impactful is using customer stories. And so we’ll say here, like, the fastest growing companies like OpenAI, Vercel, Perplexity, they’re all relying on Notion. Their product and engineering teams are collaborating on everything from meeting notes to how they do their product planning to ensure that they’re staying ahead of innovation.

And it’s those stories that start to showcase like, okay, there’s real advantage here. Tell me, how do they do that?

I agree. I think it’s bad form for you to shit on your competitors. I like the phrase customer obsessed, competitor aware. So you should know what your competitors are doing. And I think it’s much better to have a factual perspective and have a conversation around it. And I’d probably go back to Discovery if this was a real conversation. I’d say, great. What do you like about granola? Okay. What does that help you do? And what we’re seeing in the market is there is a lot of SaaS sprawl.

And I think I actually heard this on your podcast recently where you’re like the average company uses over a 170 different software solutions and that’s real and my prediction is it’s gonna get a bit worse in the short term, but long term we are going to consolidation different because there’s no way an employee can learn 200 different tools and be effective in their day to day. It’s also extremely costly because all of those come with a price tag. So how much are you paying for software?

I will say, Harry, I’m not a gimmicky person. So I’m not the seller or sales leader who’s like, let’s send them a cake. And on the cake, we’re gonna say, will you sign our order form? That’s just not how I sell. Sometimes it works. I’m much more like how do we think strategically about this and get really creative in our strategic approach. So it’s figuring out how do we align to stakeholders at all levels and make sure that we bring them value.

And so the creativity that I would bring is like, okay, making sure that every important person in the deal is aligned to someone at my company, whether that’s a set subject matter expertise where they can get value from learning how, say, another product manager is using our software, what they’re seeing within their field and comparing notes so that we have that relationship, Or it’s a CFO to CFO relationship to ensure that they’re looking at the financials in the right way and they have that relationship. And then it’s using different touch points like workshops.

How can we bring in a workshop where we’re just jamming on what are the ideas that we can hack away at and implement in the next week? It’s also showing teachable moments in every part of the deal. So I wouldn’t say like there’s one really big moment where I’m like, this was it. I think it’s continuing to look at how are you getting in front of the right people and, like, surrounding them with your solution.

One that I’m thinking of right now is we were just in front of the wrong stakeholders, and the people that we were in front of didn’t have the influence to get the deal done. Did they say

No. They said they did. And that’s what you’ll hear. And the common mistake is that you’re single threaded, you’re with the wrong people, and you’re not multi threaded enough in the company in order to actually change the way that they’re doing something and bringing them your new solution. No matter how much this happens, it’s still common in losing deals where your champion will say like, I can get this done. Don’t worry. We’ve got this. And then you build this relationship where you trust them. And then they also say things like, we don’t need to bring anyone else into the deal, just trust me.

And then they’ll even give you a hand slap if you talk to anyone else in the company. And that’s a really big sign that you don’t have a real deal here. Like, you need to get multi threaded with different lines of business and who actually holds a budget.

My take here is that you start to use other people in your company to help doing the multithreading for you, and you make it easy for them. And so instead of that message coming from you directly, you ghostwrite messages for your manager or another person in the company that you see has a connection on Sales Navigator, and you start to build inroads with your team. I found that is the best way to start testing, do you have a real deal here? I’ve often sent a message to who we think is the exec executive sponsor to understand like, hey, we hear that you’re evaluating.

Is this on your radar? And oftentimes, I’ll be like, oh, never heard of it. Or like, yes, this actually is on my radar. And then you’ll start to see like, do you have a real deal here and is your champion actually selling internally? I would argue it’s not a real champion if they’re not willing to introduce you to more people because a real champion is putting you in front of the right people to get the deal done.

Status quo. We use a framework, why change, why your product, Why now? And it’s not a competitor. It’s the company isn’t stuck in their ways. They don’t see a big enough problem, and they don’t do anything. And so what that signals to us is we didn’t truly identify the real pain point or priority that we could tie to or we weren’t in front of the right person who could actually give us what those priorities are.

That’s looking at why companies do anything. They either do it to make more money, to save costs, or in your example, to mitigate risk. So what’s stopping them from making more money? Oftentimes, it’s the innovation and the pace of innovation, especially in this AI world. And so it’s trying to figure out how are they staying ahead and how can they look at a product like Notion to help them do that. The other is saving costs. As we spoke about, SaaS sprawl is real and they’re paying for a lot of different solutions that is adding up.

And so oftentimes, it’s looking at a compelling event, like when is that renewal, and let’s work backwards from that renewal to figure out how we can save you some money.

The easier one, I would say, is saving money because that is cut and dry. But the long term one and where we want our customer success to really help them see the value because otherwise, the risk is another competitor is gonna come along and do the exact same sell. And so it’s you can get them in the door, but ensure that they are seeing that value in their workflows.

I’ve been fortunate to work with a lot of great sales leaders. I would say the early mentor that stands out to me is Dannie Herzberg, and here’s why. Before meeting Dannie Herzberg, I always thought that sales was a stepping stone for me, and I didn’t know if it was going to be a long term career path. And what she taught me was one, the parts of my job that bring me the most joy all points back to sales. I love achieving wins. I love working collaboratively with a team.

I love figuring out go to market across sales, marketing product. And the other piece of it was also seeing how sales could be done differently. One, she was a very she’s a very successful female sales leader, and she taught me that sales can be very data driven. And sales is almost like being a therapist. Like, you’re asking a lot of questions and you’re truly trying to figure out where is the pain. And so those two things made me realize like, oh, I could do sales in a different way.

And that’s that’s a big part of why I continue to be in sales.

No. Title does not matter. The company matters way more than the title. Case in point, I was at Slack. I didn’t even know what an account manager was, but I was like, sure. I I really like this company and I see where this is going. And I got to help Slack grow from 6,000,000 to nearly 2,000,000,000 in revenue by the time I left. And if I cared about title, I don’t know if I would have joined, but I am sure as hell lucky and excited and fortunate that I did.

For me, it’s very personal. I actually think back to, like, the point where I didn’t know if I was gonna stick it out, And it was when my boss left, my boss’s boss left, and it felt like everything was crumbling around me. And I was working with a coach, which I highly encourage if you have the resources or the learning and development funds to work with a professional coach because she helped me reflect on what was actually happening. And she asked me questions like, okay, well, what’s the worst thing that can happen?

And when you actually put words to it, it’s never that bad. And she was like, okay, well, what what’s actually true? Because what I had said is like, oh, I don’t have my advocates, my leaders in my corner to really push me in my career forward. And she’s like, that’s not true. Like, you have a lot of advocates in this company. Like, who else can you look to? And you need to believe in yourself. And then she asked me, what’s the best thing that can happen?

Oftentimes, change leads to opportunity. And so the best thing is actually stepping up. And for me, it was like, how could I actually do my boss’s job and like use this as an opportunity versus a point of crumbling? And so that’s ultimately what I did. It felt at the time like I was at, like, a huge crossroads, but now looking back, I’m so happy I persevered and stayed.

When you’re looking for jobs, even if you meet 80%, go for it because the man beside you is going for it. And I would also say something I’ve learned in my career is just because you do hard work doesn’t mean it’s going to get noticed. That may work when you’re very junior, but as you go on in your career, you need to learn how to advocate for yourself and ask for it. Ask for the for the promotion.

Totally. That goes back full circle to the beginning of this podcast. Like, confidence and belief in yourself is going to go so far. I like that advice better. Just go for it. And the worst that can happen is you fail or they say no.

Focus less on doing and more on reflecting and zooming out. It is in my DNA to just do it, to build, to showcase that I can do it. And I think it’s being okay with not always having doing as the outcome like writing the next Slack message, creating the next Notion document, ensuring that I’m doing all of the things and actually zooming out as a sales leader and reflecting because that’s going to be what’s most impactful in seeing around corners and understanding what does the road need to look like ahead.

Enterprise sales.

Specifically at a scale up like Notion, you need to hire someone who is familiar with doing the big deals, but also scrappy enough that they’re willing to be resourceful and build from scratch.

In my job today, when I look ahead, it would be we built a world class enterprise strategic team. All of the companies around me, when I look at their laptops, they’re all working in Notion. I’ve been able to help and accelerate a lot of the people around me in their careers. We would have already rung the bell and made life changing money for our team. I think personally that that might be me moving from San Francisco to my hometown, Vancouver, and figuring out what a new career path could look like in Vancouver, I’ve always had an aspiration for teaching.

And so a part of me has always contemplated going back and being an adjunct professor and teaching about the lessons I’ve learned in sales from Slack, Salesforce, Notion, and the other great companies.

Thank you, Carrie.