Why the Founder Should Not Be the One to Create the Sales Playbook

Well, thank you, Harry. I really appreciate you having me on. It’s it’s an honor.

Yeah. So I’m a little bit of an accidental sales leader. After graduating college, I didn’t know what to do, so I went and backpacked through South America. And along the way, I decided to go to law school because I figured you could always make a living as a lawyer. That is a very bad reason to go to law school, turns out. So after graduating law school, I became a lawyer and not a very good one at that. And it was there that I said, I need to do something else with my life.

I need to actually have impact. And so this was the late nineteen nineties. The first dot com boom was happening out in California. I was a lawyer in Chicago sitting in a very large office building wearing a suit in a very large office, and I was lonely and my soul was dying. And I thought to myself, boy, if I just move out to California and join a startup, everything will take care of itself. So I remember telling my parents, I’m moving to California. I’m gonna take a pay cut of about two thirds, I’m and to join a startup.

And they said, are you out of your mind? And that’s what I did. I moved to California. I joined a startup as the second employee. And along the way, I joined them as their head of business development. They were raising money. I knew how to fundraise. I knew how to structure contracts. I knew how to structure core partnerships. So they hired me to be their head of BD. And along the way, we had multiple pivots. The business, like most startups, failed a number of times. And we kept pivoting our way into a new market.

And I was the one that helped the company figure it out and sell the first big solution. And then I fell in love with sales. The intellectual aspect of it, the emotional aspect of it, all of it. And that’s how I ended up in in sales and as a sales leader.

Well, I grew up in a family of professionals. Right? When you grow up in the middle of the country, you do a job and you typically do it for life. Like, that is what you are and that is what you do. My father, I think, has had one job his whole career. So for me, it was always about you have to earn a living. And so being a lawyer, you could always earn a living. The irony of all of that is when you get into sales, you’re probably in the least secure profession because it really is a performance oriented profession.

But I found that much more suited to my temperament and personality. It sort of struck me in ways that that law didn’t. But I think that was the original thesis was you just have to earn a living. And then I found by trying to earn a living, being a lawyer, it just didn’t comport with my personality, with my sense of what I wanted to do, and that led me in a very different direction.

Yeah, well, I think as you heard in my narrative of going from lawyer to sales leader, it just takes a lot of courage and conviction. One of the big lessons is when you make that pivot, just remember why you made it. Like, remember what drove you to make it in the first place, and that is an anchor for you because there are all sorts of moments of insecurity and doubt and fear. And I think the more you have that reminder of the conviction of why you made it, I think ultimately the more successful you’ll be.

And then along the way, it really is about momentum. I think as you move into something new, there are little wins along the way. There are lots of defeats, but it’s those little wins that you have to focus on and celebrate because win begets win. And I just think that momentum really helps you get through all the inevitable challenge that you have as you as you make that pivot.

When you think about early, early days, momentum could be the first time you pick up the phone. Momentum could be the first meeting that you’re able to secure. Momentum could be you have a first meeting, you actually get a second meeting. Momentum could be you have a first meeting and you’re able to translate that meeting back to the product team to help them understand what it is you heard.

There are lots of little ways to do it in sales that doesn’t have to manifest in the win because the win is a byproduct of lots of little things that you do along the way, and you sort of have to study each one of those things that got you to the next thing that then gets you to the next thing that gets you to the next thing. Each one of those things, it’s actually a win along the way. It may not feel like it because you feel the overwhelming stress of the organization having to build and go out and win and place and all that stuff, but those little wins actually add up to the ultimate win, which is you can win your first customer.

Absolutely. And confidence is is really everything because it’s such a hard job. You’re listening and you’re processing and you’re trying to figure it out, and there is this actual overwhelming pressure if you let it overwhelm you because the company rests on your shoulders. You’re brought in to figure all this out, and the the reality is nothing’s been figured out. And as much as the founder who sells you into the job says, there’s product market fit. We figured it out. It’s to be glorious. All you have to do is walk into the market and it’ll sell itself.

Well, it never does. It just never does. You

Matt? Yeah. mean, a playbook is simply a set of repeatable processes that lead to the best possible outcome.

Yeah. I’ve had a lot of debates with my colleagues around playbooks. A lot of my peers have their playbooks and they come into their business, they get a new job, they bring their playbooks, and that will somehow manifest victory. I am not a subscriber into here is my playbook. Hire me and I’ll run my play. Because I think every company is actually unique because every company has different product, sells into a different market, has a different position, has a different way of pricing, has a different way of thinking about it, has different culture.

All of these things ultimately are unique for a company. While certain processes may be repeatable, there’s 80% of commonality. It’s that 20% that actually is the difference between winning and losing. And that 20% of the playbook that you really have to build only once you get there and you understand the business deeply and you understand the process, that’s where the win happens. You can come with a set of ideas about how to run something based on stage, based on product, but it’ll all be upset once you get into the market.

It’s a little bit like the Tyson quote, everybody has a plan until they get punched in the face. Well, when you get into the market and you start to get punched, you then develop your playbook because you have to figure out how to get around the punches, how to move through and navigate the process. And that navigation, the nuance of it, when you start to start to crystallize that into a playbook, that’s where winning happens. That’s the difference between building a high performing team and a team that may win once or twice, but it’s not to win repeatedly because that’s the magic is gives them that 20%.

Yeah, I would encourage a lot more flexibility than rigidity. The great sales leader is able to deeply and uniquely understand the market they’re in, what they’re positioning, what the process needs to be to maximize the success of the team, and they’re able to build that. And And I’ve kind of lived this. Right? I’ve never worked in the same industry twice. I very rarely work in the same sales motion twice because I believe part of the the challenge and the joy is figuring out hard problems. And what I bring to companies is the unique perspective that is formed from lots of different experiences because you’re seeing sales models start to merge.

You’re seeing it used to be enterprise, then it’s SaaS. And now you’re seeing a lot of different motions all come together in unique ways. And I think sales leaders need to be flexible and understand that and be able to pick up different signals from different parts of the of the market and pull it together. Otherwise, you end up with a playbook that’s probably 80% right, but you need it to be a 100% right to actually build a motion that wins repeatedly.

Yeah. So, Harry, let’s call this our first point of divergence. I think founders, they have superpowers in lots of areas, but my point of view is building a playbook ain’t one of them. And let me explain. I think you need a level or a layer of abstraction to be great at building a playbook. Now founders are so close to their business. They’re so close to their product. Their language is the language of going out and talking to investors, of talking to pilot customers, and they hear things through that lens.

That’s not actually the lens through which I think you ought to build a playbook. Like, I’ve been I worked with some amazing founders, and their language, their narrative is always a little bit different than the customer. The challenge of sales is translation. Right? You have to translate what you do in a way that the buyer can hear it. And you need to take the buyer’s language and translate it back to the company in a way that company could hear it. That translation is what’s to ultimately lead, I think, the company to build to product market fit.

And founders sometimes hear things very differently based on the universe and world in which they live, because they’ve been told certain things from the investor community, from early employees, and it doesn’t really matter. What matters is how the customer hears them. And so I think that layer of abstraction actually is important. And I think sales leaders can hear things differently than the founder. Now the founder will be great at positioning, and they should be in the meeting because they understand the product deeply. But I think in terms of building that process, that abstraction actually is a benefit to the business.

So I think we diverge a little bit in in points of view there.

What do you think

Yeah, so I agree with you there. I think founders have a point of view around the type of leader they to hire based on the model they’re selling it. Right? That That to me is very different than a playbook, which I’m defining as a process by which to win an account. Now, what I will tell you in terms of your question around sales hire, this is again one where I may have a slightly different view than most, which is the mistake that I see founders make all the time is the hire for pedigree, where they try to match perfectly someone from the sales motion that they’re selling in.

So I have seen time and time again, I’m hiring someone from Google. Harry, don’t hire anybody from Google. Okay? Don’t hire anybody that says on their LinkedIn, x Google, x Amazon, x Facebook. Okay? When they put that on their LinkedIn, they’re associating themselves with the success of the business, and it is almost impossible to tell what contributions they actually made to the success of that business. But the founder sees it and says, wow, I’m hiring an executive for Google. They must know. The reality is they don’t.

What you’re looking for when hiring that sales executive is something very different. The first sales executive, you wanna hire an ex banker, an ex consultant, an ex lawyer. You don’t even necessarily want hire an ex sales leader, right, or a sales leader. You to hire someone that can radically listen, that can actively listen, that can ask probing questions, that is able to think critically, analytically and is able to figure out patterns based on a set of conversations to quickly hone in on, here’s actually where the market is. here’s actually where the ICP is. here’s the kind of things that the buyer is actually asking for.

Those types of folks are great active listeners. They ask incredible questions to get at the essence, the root of things. That is where you’re to build your playbook.

Yeah, I think you should be sales leader. I I really do. I mean, I think the the junior rep has a lot of success because they’re they’re figuring it out. They’re the first one on the ground. And so you to invest behind that person. The reality is you’re trying to build you’re trying to build for scale. The The problem is that junior rep then will ultimately be replaced, and it creates a whole bunch of challenge internally. I I just think you could avoid that because someone that has been there and seen that and has a little bit of maturity, you’re to be able to build around that person and scale that team a lot faster.

My point of view is why not just start there? Just start with someone that can see the patterns, that could ask the questions, that understand it. They’ll bring that junior rep along and train and develop them so that perhaps they could become a director of sales or run a team. You’re not to lose the junior person if you bring the right senior person in over them. You’re to give them actually a lot of headroom in which to grow their career. But junior folks will hit the ceiling, and then they’ll burn out and fall apart, and it just doesn’t end well for the business or the culture of the business.

My bias, if you’re a founder, is shoot above the junior mark because you want someone that you can scale with to the next level. You may have another decision to make, like that person you brought in, you have to scale above them, but I would start higher.

That’s how I started. So I have a particular bias. It’s not recency bias because I’m old, but they they figure it out. The first thing you’re doing for that first hire is you’re trying to figure out how you’re to sell this thing, right? Yes. How do you sell it? How do you build it? How do you ask the questions? How do you build discovery? And they may not think about it in terms of the traditional, well, here’s the discovery process. We’re to move from stage to stage to stage to stage But this is why I would say the second most important hire is get a great, great sales operations lead to partner with that person.

Everyone always neglects sales ops, but sales ops is sitting in the background figuring out the process, the motion, the stages. They’re very different skill sets, by the way. And if you separate the two skill sets, I think you end up with the best of both worlds. You end up with a documented process that’s following along with someone that understands how to actually figure out what the customer needs, what questions to ask, what product to build, and then you end up in a pretty good spot. Do you hire them both at the same time?

That would be ideal. Very hard to do because most companies at the very, very, startup stage don’t have the capital budget to do it. And typically sales ops will want have a little bit more certainty around what it is they’re building to. So it’s a hard thing to hire initially, but a fast follow for sure, if you can. I think that’s that’s the way to do it.

Yes. But did you say like a comparison mechanism?

same time. I definitely like the idea of two and support that. And I understand the value of comparison for sure. but I think it’s the collaboration value that actually outweighs the comparison value. Because, one, you’re doubling your conversations. Two, if you have two in a box that are really working together and not competing with each other, the the the challenge with two is you end up with two people competing they’re kind of racing and it’s like, who’s better than the other? Even the way you set up the question, felt like one’s going do better than the other and that’s gonna say something.

I actually think Is that not good?

Not with your first two sales hires. Not that early. You want collaboration, not competition. You want people to be able to experiment with each other and say, I asked this. This is the response I get. What do you think? This worked for me. Does it work for you? You’re essentially in a laboratory and you want scientists collaborating. You want people working together. That collaboration of idea and idea, what works, what doesn’t work is much more valuable than person against person. The market, it’s too small a sample size to be able to draw real conclusions from two people.

What you want do is you to draw conclusions of what’s working and what’s not working. Two different styles. You wanna figure out your styles that are working and marry the two. That’s to give you, I think, a more positive outcome than a chaos. Because look, you could have a great salesperson and a bad salesperson and bad product market fit, and the great salesperson isn’t gonna sell anything either. And then what are you really told?

lessons? Yeah, I mean, early, early, days we’re talking like there is no reason every call shouldn’t be recorded. There is no reason that every call shouldn’t be listened to together. If it’s sales leader and two, three in a box in a room breaking down the call, it’s like any athlete breaks down tape and you’re listening and stopping and asking and probing what else could you do. And I think the three by three framework here works really well. You ask the person that did the call, are the three things that you felt went extremely well, and what are the three things you wish you did differently?

Capture that, calls played, ask the person listening to the call, what are the three things you went well? What are the three things that you would have done differently? And then sales leader, you go through the same process. You typically will have some pretty good alignment at the end of what’s good and what you need to tweak. This is why the laboratory and everybody in a room in a box is so important. You’re all trying to figure it out because at the end of the day, what you’re striving for is an optimal process that leads to a best practice.

Right? And that leads to pattern recognition. So when you’re starting to talk to a customer, it’s like, oh, I’ve heard this story before. We all agree. here’s the best way to approach it. That’s to give you a lot more scale early on than any other mechanism because it’s all about exposure and at bats. so I think that that really does help.

Yes, it does. It becomes more challenging because the level of conversation amongst your peers is just different.

Yeah, I mean, I’ve always if anyone that’s ever worked for me that happens to be listening to this will know, I say it always comes down to discovery and deals are won and lost in discovery. Right? I mean, it’s just it’s very simple. You win a deal in discovery or you lose your deal in discovery. Now, you may not realize you lost it because bad discovery leads to very long losses. Good discovery leads to very quick wins. It’s a truism in my world. Right? To your question, how do you do it?

What questions do you ask? Well, discovery starts way in front of that conversation with great research. Now, the person you’re talking to cares about certain things. They typically care about what their boss cares about. If you understand what their boss cares about, you probably understand what they care about. Now, what does their boss care about? If you do the research on the company, you could understand a lot about what the boss cares about. What are the core strategic objectives for the business? What are their priorities?

And a lot of this is very readily available. If it’s a public company, it’s all out there. Just read the filings. It’ll give you a pretty clear roadmap into what the business is trying to achieve. Once you understand that and then you ask, what is that person’s priorities? How does it map to what the business priorities are? Generally, find some pretty good alignment. The next set of questions is, how is your success measured? Like, what do you care most about? And how do you know whether you’re being successful or not?

Next set of questions, what are you doing very well? Always start with what’s going well because people will open up and they’ll talk about it. And then what could you improve? And And if it’s nothing, that’s fine. What are things that aren’t going so well and why? They’ll tell you that. And then that’s where you’re really listening. If you were to fix those things that aren’t going well, what impact would it have for you, for your business, or how you’re measured? That’s the question that’s always missed by salespeople.

They’re just so happy to hear something that they think they can sell against that they move too fast. Slow it down and ask that payoff question because if you truly understand what their value is of solving it, then you’ll have a business case, then you’ll reduce discounting in the end, then you’ll be able to build close plans and you’ll actually be able to close that customer quickly. And then at the end of it, you repeat back what you heard. How would you prioritize those issues? Because you need to know what they care most about.

One, two, three. And then you have the map to winning the account. You understand how to win it. If you don’t have that information, you don’t understand their biggest pain points, what it means to solve them, you’re probably gonna be on a slow road road to a to a closed loss in the end.

the truth? Well, people will feel comfortable expressing themselves more openly if they believe that you are a trusted partner and have some insight to share. Right? Like, are you worthy of getting the truth? And that’s just human nature. So if you’re doing that research in advance of the discovery call and you have a pretty good idea of what their strategic goals and priorities are, you know, you start with some insight. Bring it back to them. You know, in our experience, we found through talking to to potential customers like yours that people are struggling with the following issue.

And we also find that with people struggling with that issue, they can solve it through whatever. Does that resonate with you? And just get them talking. If that resonates with them, you’re on the track to issue identification. And it gets them to open up because they feel they don’t feel alone. They don’t feel isolated. Yeah, someone else has that problem too. Well, that’s interesting. So do I. Oh, you do. Tell me more about that. And then all of a sudden you’re off and and on your way.

Those things called insight discovery openers is give them something that shows connection, understanding, empathy, and people do open up.

It’s really hard. I mean, like, I said early on, like, if you run really great discovery, you actually create urgency because great discovery points to a business outcome for solving the problem. If you understand the pain and it’s quantified in a way where you know if you could solve it, your prospect agrees there’s this economic benefit that they will realize, every unit of delay is equal to some value. So you could actually start to work with them to say, let’s agree we’ll we’ll get this done by the end of the quarter as an example.

If it doesn’t hit by the end of the quarter and extends a month, you know what a a month’s worth of lost revenue, lost time, lost economic value unit equates to, and you start framing it that way. That does create urgency, if only if you understand what that unit is worth to them. If you don’t, you’re basically playing their game. There’s no reason for them to try to jump over the procurement queue to get their deal done faster because you haven’t created the urgency and you haven’t aligned on it.

So to me, if you can create and understand that unit of benefit or economic measure, it creates a level of urgency already that wouldn’t otherwise be there.

It’s a lot harder when you’re selling vitamins. You could do it. And then it comes down to really understanding what their goals are and what achievement of whatever it is you’re giving them helps them achieve as opposed to pain reduction. But at the end the day, it is going be a lot harder. Then it comes down to budget. It comes down to process. It becomes down to really understanding how they move the deal forward and holding them accountable to a timeline that they set out early on.

You You don’t have the economics behind you, but you, have a timeline and a process and an agreed upon process. And that’s hard because that slips all the time.

Yeah, well, I’d start a discovery process, frankly, and try to understand what is it they’re selling and what is it they’re solving. Because here’s what I found with CFOs. CFOs. start oftentimes from a place of I’m not buying because I’m controlling the budget. The reality of CFOs are they are very rational actors. In fact, they’re some of the most rational actors within a business. They could be very objective and if you have something that adds demonstrable value, then they will buy it. So I think it’s a falsism to say my CFO gonna block.

What that says is you haven’t done a good enough job of showing the value and you haven’t made it a priority for the organization. It also says you haven’t brought the CFO along in the process, and that’s a huge exposure point. One of the things I always tell my team is keep your eye on the CFO. You have to get this to their desk in front of them and understand what they care about.

Well, you don’t say it like that because that’s to get you in trouble. I wouldn’t know. You They’re They’re front. Look, as part of our process for you to be successful, we found that we collectively need to engage the CFO because the CFO at the end of the day is the person that’s like, approved the process or not. Okay. Being very clear about your process front and giving them a roadmap to how the deal’s gonna progress is exactly how you bring the CFO. And then sometimes say, look, we’re not continue the lesson until the CFO engaged because we’ve seen all too often that these deals will fall apart if the CFO isn’t involved.

And I don’t to waste your time. I don’t wanna waste my time. It’s a very hard position to take. I always call it the power position. But if you know the CFO is gonna be there and you don’t take it, you’re just going down a long path to lead to a very unfortunate outcome. Pull it forward, be clear, be transparent. Bring the CFO in and you’ll have a lot more success. But if you if you know it’s out there and you avoid it, you’re really not serving yourself, your investors, your founder, your business.

You’re not doing them any good. Discounting.

Yeah. So let’s start with the utopian state, and then we’ll work down to the realistic state. Okay? The The utopian state is, well, I’ve done such a fantastic job doing discovery, uncovering pain, demoing perfectly against the pain point, quantifying value, putting out pricing that has a huge ROI, I don’t need to discount, and I’m gonna hold firm. Sure. That’s great. Let’s call that the utopian state. Let’s say you run a perfect process. Some percentage of deals, you just don’t have to. Right? The reality though is oftentimes even the company you’re working for has a tradition and habit of discounting at the end of quarter.

So you sort of set the market up for the discounting conversation. That’s a hard one to overcome because everybody’s waiting. You’re under pressure. You’d have to hit your number. Inevitably, you’re faced with, should I discount to close or not discount to close? That’s a very personal decision for the sales management team on whether to do it or not. I have discounted in the past. This is true. There will be something that is so important to the business that I need to do it, and that’s the reality of it.

Like, there are times when you will be forced down a discounting path, and you have to make the tough calls. You may not like it, but at the end of the day, if you’re to do it, just do it with principle, do it with guideposts, do it so it doesn’t get out of control. Make sure the customer understands exactly why you’re doing it so it’s defensible and you try to ring ring it. Right? Like fence posts around it. Otherwise it does get out of control, and it’s a big problem.

Yeah. I mean, a discount is a concession. So you could start from a place of any discount you to contain Because you really shouldn’t discount your product if you’re solving customer issues and you’re pricing it appropriately. Right? You know, 10 to 15% discount or more is a problem. Like, I think 10% discount is really where you want be if at all. And from there, you’re looking at a slippery slope because ten, fifteen, all of a sudden becomes 30, becomes 50, and then you’re in a really bad spot.

So you may look at the root causes for why you’re discounting in the first place. It’s usually a process issue. It’s usually a product issue or a pricing issue.

Yeah. I mean, there’s a lot of ways to use data. My job as a sales leader is to make everybody wildly successful. Like, what I will tell my teams when they join me is like, my job is to get you set up for the next best job. So my job is to develop your talent and make you incredible at what you do. To be incredible at what you do, you have to understand the data of every single person in your organization. Because if you’re understanding what that process is and where the gaps are in their process, the data will tell you that.

It will tell you, for example, a sales rep is really struggling with discovery. They’re losing at a much higher rate in the discovery motion than another rep. Boom. I’m in there. I’m helping them. I’m diagnosing the issue. I’m getting them out of that hole onto success. The average time to close, win rate, loss rate, average transactions. Like, data is telling you a million stories about your team. Your job then is to figure out how do I coach and develop talents they could overcome those roadblocks to become wildly successful.

Data will also tell you your sales process as a whole. Is it working? Is it not working? Where do we slow down? Where can we speed up? What’s happening on pricing? Am I discounting? Am I not discounting? Am I upselling, cross selling, expanding? Data will tell you all of that. It’ll even tell you your sales motion. Where do I invest my time? For example, I’m a big believer in connecting dots on data to be able to prospect efficiently and effectively. An example, at Compass, a company I was at prior to coming to Grammarly, all real estate data is public.

So you could see every real estate agent when they did a transaction on the other side, who the other person was on the other side. I could understand the person on their side who is a prospect. I could see into their data and understand their volume. Was their business increasing. Was it decreasing? I could then ask my customer, did they enjoy working with this prospect, and were they willing to make an introduction to that prospect? I could do that all in the background with data. If the answer was yes, in Salesforce, those opportunities would be surfaced to my sales team.

So they would know exactly who to go after. So these are all different varying degrees of how to use data. But at the end of the day, data, if you’re a great CRO or a great revenue leader, use it. It’s your friend. It’ll guide your team, your process, and your individuals to success.

very often. No, it is not done well. If you just check my LinkedIn messages, it is done very, very, poorly. A A quick aside where it’s done really well, so this will give all prospectors out there hope. I actually came to Grammarly in in the most unusual ways. I got a cold email from the CEO of Grammarly, and the CEO of Grammarly reached out to me with a very precise message around his interest in talking to me because of a number of different reasons based on my background.

And it was a cold outreach. And I read the email, and I was like, wow. That’s a very interesting approach. I understand what they’re looking for. I believe there’s a good conversation to be had. I picked up the phone, and here I am as CRO Grammarly. But so I think that kind of prospecting is incredibly effective, but really understand your message, understand the person on the other end, do your homework at works. Where it doesn’t work is what’s happening today. Proliferation, AI, prospecting, proliferation of I know you you may have a problem with pipeline.

Do I? How do you know I have a problem with pipeline? I’m insulted now. Don’t don’t tell me I have a problem because I don’t. You know, it’s like all these things that go wrong today, people are just putting back at you.

I I loved it for so many reasons, not the least of which is the humility and the non alpha nature of that leader to be able to be like, hey, I’m looking for assistance here. I think you’re an interesting person to talk to. Well, let’s have that conversation. I just loved it.

Yeah, First of all, isn’t it crazy that it wasn’t tossed? Can you imagine a world where it wasn’t the thing? Always it’s so much easier to expand and retain a customer than go get net new. But everybody, all the glory is on net new, which is fine. But anyway

Yeah, I think that was a huge part of it. it. was also how investors thought about the value of the business and was their product market fit, and all of those things sort of led to this emphasis on net new. When you have this unbelievable opportunity with your installed base of customers who have already raised their hand. They said, I like the product. I want use the product. And if you’re not paying a lot of attention to how all the opportunities to continue to expand it, you’re missing the huge opportunity because it is all there in front of you.

And by the way, those reference customers make your net new acquisition a lot easier and, by the way, help you dramatically reduce discounting. Because when people hear the reference stories of all the benefit that they get from the solution, you essentially create the urgency around the solution, the need around the solution, the conviction it’s the business case you’ve laid out, and therefore, their motivation to hold you to a heavier discount, it ends up dissipating. And that that’s natural. That’s human. Right? You want the solution more, so you’ll do more to get it.

So So I’ve done it twice. I was at Eventbrite. Eventbrite. was a million product led growth company. I was brought to come in and build out enterprise motion on top of it. Grammarly the same. Everything about enterprise versus product led is different. Language is different. Messaging is different. Positioning is different. Customers are different. Product is different. Pricing is different. It really is a very different business. The differences have to be reconciled against the strengths of product led growth because they have to work together in there can’t be cannibalization.

There can’t be conflict. But founders need to understand it’s a very different business. It deserves different levels of staffing, different types of staffing, different capabilities from the marketing team, from the product team, from the security teams. And it it’s a very hard thing to do to build on top of the very successful motion because, again, the data will guide your enterprise motion because you have a lot of data coming out of product led growth. How you use that data to build a brand new enterprise motion is going be unique and different.

How you position and market is to be different than what you’ve done on the individual or consumer side. But it all, again, has to work together. And so it is a very complex but achievable thing. But it is hard. and founders, you know, it’s all different.

Yeah, There’s a point where you really understand your product led motion, where it is measured, it is calibrated, you know what dials to turn to be able to optimize spend against acquisition. You understand how to optimize retention and retention lifecycle motion is going to the point where you feel like you have some control. When you feel like you have some control, you’ll never feel great. When you feel like you have some, that’s the time. I wouldn’t encourage you to wait till it’s perfected, but I would encourage you to wait till you feel like you have control and visibility into the motion of the business, and then I start on the other side.

The testing happens organically. Like, the testing’s already there. It’s in the data. Because, like so for example, at Eventbrite, you started to see very large organizations adopting Eventbrite and deploying it in enterprise like ways. At Grammarly, you see the proliferation. I think at Compass, my alma mater, 30,000 employees, there were 3,000 people using Grammarly. It’s there. It’s in the enterprise. If If I were to look at almost any enterprise, Grammarly is there. And in a lot of product led motions, it already sits in the enterprise.

People are bringing their applications to work more and more The The signal’s already there. It’s already sort of being proven out that it can be used in that environment. Now should it always be used in that environment? No. Is it optimized for the environment? No. But there’s enough signal that you don’t really have to tip your toe in because your toe is already in the water. You just gotta see it and understand it for what it is.

Yeah, it’s a very hard one because cannibalization is the trickiest of all issues that you have to wrestle through. But remember, selling an enterprise license is very difficult and it’s very different. And the product led motion into an enterprise is very different than selling an enterprise agreement where the enterprise sanctions, supports and budgets for your solution. That deserves compensation. Separately, just getting an enterprise license in an agreement and then expanding it across the whole business is difficult as well, and that deserves compensation.

Their unique aspects of the same value chain start all the way through expanding to the whole enterprise, but each of those things are different in and of themselves, complex in and of themselves, and do require a degree of specialization that warrants that kind of compensation. Does that make sense?

Well, great discovery. Never changes. It’s always important. That would be number one. What sales tactics have died a death? Yeah. Cold call. Who Who picks up their phone? Like literally, who picks up their phone?

My piece of advice would be, and I do this for every role, I create a very detailed list of questions. It’s a question rubric for individuals, every line of leadership within the business, every function within the business. Same set of 20 questions. I go and I ask the same questions over and over again to every person in the business that I can. Because what happens is it speeds up your rate of learning. There’s pattern recognition that emerges. You understand strengths and weaknesses. And I think spending that time, it’s painful asking the same questions over and over again.

But if you just map it out, you’ll see the organization ways that it would take probably six to nine months to see, but you can do it within thirty days.

I’d like to see more women in sales leadership roles. If you really wanna find a great sales executive, hire a mom. Hire a mom because they know how to multitask, they know how to drive behavior, they listen, they have empathy, all of these things. I think it’s very hard for women, particularly younger mothers, to be successful in this field because there is a level of alpha. There’s a level of you gotta grind. You gotta put the work in. If you wanna find efficiency, find a mom.

They will be the most efficient people on the planet or dad. I don’t mean to be discriminatory with moms versus dads, but find a parent, particularly a parent of young children. More stuff will get done in an eight hour block than you could imagine. That’s what I’d like to see.

Yeah, I’m I’m always impressed by companies that make markets that that sort of take something and make it into something that they then own. I think you’d have to look at Gong. I’m just amazed at what Gong’s done. Now it’s very common in my profession. Everybody records calls. Everybody breaks down the calls. Every sales leader leverages the application. So kudos to them for not only creating the technology, then creating the market, the brand, all of it. I think they’ve done an exceptional job.

you. I have as well. And it’s a it’s an honor and a privilege to be So thank you, Harry.