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Navigating the complex journey from startup to enterprise success requires more than just a great product—it demands strategic alignment with your customers' needs. 🎯
In our latest episode of The Hidden Chasm, Jenna Watson-Brawn breaks down why "Build it, and they will come" is one of the biggest myths in tech. 🚫
In our latest episode of The Hidden Chasm, Jenna Watson-Brawn breaks down why "Build it, and they will come" is one of the biggest myths in tech. 🚫
Creators & Guests
What is The Hidden Chasm?
An ongoing discussion of how tech debt and legacy solutions become barriers to growth and innovation for established SaaS companies.
You're listening to The Hidden Chasm, a discussion of how tech debt and legacy solutions become barriers to growth and innovation for established SaaS companies. The Hidden Chasm is sponsored by United Effects where our purpose is to help companies break free from legacy tech, improve retention, and empower M&A growth. Learn more at unitedeffects.com. Welcome to another episode of The Hidden Chasm, which you have to say with with that deep voice. You know, we've been exploring the chasm, from a lot of different angles.
Bo Motlagh:We spoke spoken to M&A advisors. We've spoken to product executives. We have some technology folks coming up soon as well. We've had the people angle, which has been really interesting. But I think one of the most important elements of any business is revenue.
Bo Motlagh:Otherwise, you don't really have a business. And to help explore this this particular angle is our friend and actually board advisor. Welcome Jenna. Jenna Watson-Brown. Jenna is a 15-year veteran of business development.
Bo Motlagh:I'm reading this. I always have to read. Jenna is a 15-year veteran of business development, sales, and growth coaching with proven successes leading enterprise sales as a senior executive. She now focuses her energy and experience on helping early stage companies find product-market fit, gain traction, and build revenue. She's currently the founder of Jenna Watson-Brown Consulting, affiliated with several accelerators and board advisor to several companies including United Effects.
Bo Motlagh:Welcome, Jenna.
Jenna Watson-Brown:Thank you very much. Excited to be here.
Bo Motlagh:Well, we're excited to have you. Obviously, Jenna, you've been working with us for a while now. And it's funny, you know, for our listeners, it's always funny when we have to do some digging on people we already know to figure out how these conversations are gonna go. As I dug into your past a little bit and saw your experiences in enterprise sales with Eventbase and then Motive and then moving into your coaching career now, just a really fascinating, journey. I'm sure a lot of people would, you know, would be interested hearing more about it.
Bo Motlagh:And I thought, you know, why don't you
Jenna Watson-Brown:just kick
Bo Motlagh:things off is tell us about yourself and how you found yourself on this call with us.
Jenna Watson-Brown:Yeah. And I I always say, like, I didn't take the easy path. And I I think once you get a taste of the startup world, it's really hard to let go. So I joined my first startup when I was 19, employee, I think, 9 or 10, 1st salesperson working alongside the CEO and was there for 10 years. And I joke that, yes, it was one company.
Jenna Watson-Brown:It had a couple different names over the years, but it was actually five different companies. Because in every different phase that we were at, whether it was bootstrapping, pivoting into enterprise, raising our first VC, raising subsequent VC, it was an entirely different company with entirely different challenges. And executives and board members and all of that evolved greatly. So that was where I really cut my teeth in sales, selling to the likes of SAP, Microsoft, Charles Schwab, really with not much experience and having to be self taught in a lot of ways. My background's actually in accounting, which I don't think you guys knew.
Bo Motlagh:I think you guys
Jenna Watson-Brown:Yeah. So I I I like numbers. So I've always liked numbers. I like algebra. I don't like bigger things than algebra, but I like, you sell this many of this and you get x.
Jenna Watson-Brown:That's my perfect kinda math. So that's where I started, and then over time, ended up taking over sales, leading sales, leading customer success. So understanding both pieces of that as well of not just getting that sale, but keeping that sale and growing that customer, which I think gives me a unique perspective on the importance of good fit customers, the importance of true product market fit. I've heard I can't don't know who to credit, but I believe product market fit actually comes in the renewal, not in the sale. Because a good salesperson can get just about anything sold, whether or not you need it or want it, and product market fit is actually the renewal.
Jenna Watson-Brown:Did you find enough value in that 1st or second or third year of the product to renew? So that's that's my background. That was the beginning of my enterprise and sales career. And then after that, moved on to, a couple other startups, Motive being one of them in a completely different space back to, you know, small scale, scrappy team, taking out the garbage, trying to, you know, do big deals with the likes of, you know, fortune 10 companies and and made some excellent progress there. But it it's, you know, I think building something from nothing and finding people with the problem that you can solve for them that they want solved is is, like, the thing I the thing I look for in all my work.
Jenna Watson-Brown:And so now I help start ups help and I'm starting to work more with little bit further old companies a little bit further along, like, you know, 5, 10,000,000 in revenue, but it's how do we build a sales motion, scalable or not, that is going to build the company in a way that is not cutting off your nose despite your face.
Bo Motlagh:Interesting. Well, first of all, backing up a little bit. So you you started you started at 19? Yeah. I was definitely not thinking about business or anything really at 19.
Jenna Watson-Brown:Yeah. I and it was it was a total fluke, like a kinda friend of a friend. Oh, do you wanna work here? And I had another job, and the husband of the owner of the company said, oh, I I really like you. Like, would you be open to trying sales?
Jenna Watson-Brown:I think you'd be really good
Bo Motlagh:at it.
Jenna Watson-Brown:And that's literally how it happened. And then, like, I worked alongside the CEO. I was like, k. Let's let's build this. I I would say I've always like, I I came out this way.
Jenna Watson-Brown:So it sales was a natural tendency for me, and I'd always been entrepreneurial, like, even when I was 18 when social media first came out, even younger than that. And, like, businesses were trying to figure out how do you monetize. Like, I did my own little consulting on the side. It was helping companies set up Twitter accounts. And so I've always had that in me.
Jenna Watson-Brown:But, yeah, like, I I officially embarked on. And the first, I think, 5 years of my startup world was bootstrapped, until we were profitable, and we were selling to the likes of SAP, and really, really big companies with no marketing, no sales, no VC. So I know it's possible. I know it's possible, and I think that's where I can rub some people the wrong way because I I don't believe that you need all the flashy stuff to to get Yeah. Get off the ground.
Bo Motlagh:Well, I think that's been what something, you know, as Josh and I have worked with you that resonated with me is is is the let's just try this and make and see if that works. It's pragmatic and practical, which I love over, you know, theory and and process, which is fine because I'm a fan of process. But I think as opposed to something that's dogmatic and thinking through, you know, actual steps that work. As you've sort of moved through your career, so you started with startups, you then ended up in enterprise, and then you bet you're back to startups. Would would you say how did the the enterprise world influence how you coach start ups now?
Jenna Watson-Brown:Yeah. I I think with the enterprise world, what you learn is that you have to play by their rules. Like, you have to play by the end customer's rules. And when you're selling to Microsoft and you're selling 2, $3,000,000 of of business a year, doesn't really matter what you think or what you want or how you want the sales process to go. It just it doesn't matter in the same way that I think some startups think it does.
Jenna Watson-Brown:Like, oh, I'm gonna build this sales motion, and I'm just gonna do it. And that's the way it's gonna go. It's like, yeah, but this is how Microsoft buys. So I think it gave me a very deep and thorough understanding of, meeting customers where they are. And if you're selling to the enterprise and you're trying to do a lightweight PLG motion, but you're selling to a SVP at Microsoft, those two things don't work together.
Jenna Watson-Brown:I I don't believe in a sales motion for a sales motion. I believe in matching sales motions to the buyer. Sales motions to the buyer, the way they typically buy, their expectations. So I think it's given me a really big, a fee for the buyer and, and I think it's dispelled some of the myths of build it and they will come. Because I think a lot of startups, we had this conversation just earlier today, think that building the product is the hardest part of building a startup.
Jenna Watson-Brown:And I can, without a shadow of a doubt, say that that is not true.
Josh Smith:You mean you mentioned PLG, you know
Jenna Watson-Brown:Yes.
Josh Smith:Doing product led growth. Right? Yes.
Jenna Watson-Brown:Yes.
Josh Smith:And that that is a continuing trend even now. And I guess you would say that, that as much as folks certainly love to jump on the bandwagon and say it could be a panacea for for getting your startup off the ground, you would say, hold on. Wait one second. Let's take a look at exactly who those buyers are first and whether or not PLG is even a fit.
Jenna Watson-Brown:Yes. I think they say with PLG, and I I don't this is a stat that kind of people have different versions of. Like, if your product doesn't give them an moment within the first five minutes of using it, you shouldn't have to PLG. And if your product like, think of Calendly. Great example.
Jenna Watson-Brown:Put your credit card in, sign up, premium, whatever, you know, however you've come to Calendly, free trial. You try it. You send out your first meeting. You're like, oh my gosh. Someone booked a meeting.
Jenna Watson-Brown:I didn't have to go back and forth. That's incredible. There wasn't a stakeholder group to decide whether is the right fit. It didn't integrate with your architecture. It didn't integrate with it didn't need a security review, like but then when people say, oh, I'm gonna take this, like, highly specialized enterprise security product and put it with PLG.
Jenna Watson-Brown:It's like, well, that's not how the CISO buys. The CISO doesn't A: there's no AHA moment in 5 minutes. B: the price point is such that they're not entering in a credit card inform their credit card information. And, C: that's not how this purchase gets made. It's not an individual user using an individual tool.
Jenna Watson-Brown:So, of course, there's exceptions to everything, but I so often, I see founders say, oh, I like the sales process or I like this market. I'm gonna go after it. But completely ignoring who actually wants the product, who has the demand to solve the problem, and how do they typically buy, how do they typically interact with vendors, and the realities of the product you're selling.
Bo Motlagh:It's funny because we I mean, Josh and I had have gone back and forth on product led growth a lot as well. And you're right. It all it sounds so amazing.
Jenna Watson-Brown:Mhmm.
Bo Motlagh:It's like this yeah. Let's do that. And then you get into it and you're like, oh, that that didn't work. That seems like one common misconception. Are there other common misconceptions and challenges you see early stage companies face, pretty often?
Jenna Watson-Brown:One of the big misconceptions is around, like, I just need to show you the product. And if I show you the product, you'll be ready to like, that's all I need to do. And, like, I'm gonna do a demo and I'm just gonna show you the product and then that will happen. And it it depends on the vertical and the industry and the segment, all of those things of what you're selling into because there are some products that the sales cycle is one call, 2 calls, 3 days. But in most cases, the discovery demo portion is really about solving problems.
Jenna Watson-Brown:And you go back to the, you know, old adage of bad salespeople just showing you every feature when you care about one feature. And if you don't know what that one feature is because you didn't ask the right questions, well, you've just wasted 45 minutes for someone because, you know, they saw 90% of the things they didn't need to see, and then they, you know, somewhere in there, you kind of skimmed over the one thing they really care about. So I think that's one of them is that, oh, I'm just gonna show you the product, and that's it. And it's like, no. You actually need to understand this individual buyer, this individual organization, their specific needs.
Jenna Watson-Brown:Again, that varies segment to segment because you may have a very homogeneous customer base, in which case there's more things you can you can rely upon between conversations. The other that I would say is that the founder can pass it off. I see it all the time. Oh, I'm gonna hire I'm gonna hire sales help. And I'm gonna hire sales help that is going to be a salesperson for me.
Jenna Watson-Brown:And I've never seen it succeed, both in startups I've worked with and in startups that I've, seen from afar. Hiring a salesperson too early usually does far more harm than good. And until you know what works, you cannot hire someone to do it for you. You if you have a founder, like a cofounder that is a sales expert, that's different. But if that person is not part of your founding team, I see it all the time, you hire an SDR or you hire an account executive, but you don't know what works.
Jenna Watson-Brown:So you're kind of trying to coach this person to figure out what could work in a sales motion, and I've just seen it fail 10 times out of 10 times. Like, I'm I'm yet to see that succeed before you probably, I would say, like, till you have, like, 10 happy customers, maybe 5 to 10 happy customers.
Bo Motlagh:Speaking of challenges, you know, for our listeners, as we've been digging into this hidden chasm concept, Jen has actually been a key component of that. She's been behind the scenes helping us med make heads or tails of what we've been learning and thinking through some of these concepts as well. So, so you're not new to this, Jenna. It would be interesting to maybe in your own words, if you if you could sort of maybe take a second and and a swing at what is the hidden chasm?
Jenna Watson-Brown:Yeah. And I'm gonna take a sales lens on it because I've I've been in these rooms, more times than I'd like to say. To me, the hidden chasm is the brick wall that an organization, usually an executive team, hits, once they've kind of not like, they're in the middle of the chasm. They hit this brick wall. And a lot of the times, the brick wall comes in the form of disappointing customers.
Jenna Watson-Brown:And that could be disappointing customers who asked for a feature, and another year has rolled around, and you made a commitment, and the feature is not yet built. And what you're hearing from the architecture or the technical team is, it's like, we we can't do this. It's gonna incur so much cost. Or it's the case that you have been building and building and building, and the things that the customers are experiencing are breaking. When it's been taken seriously and when I've really felt in the chasm as a part of an executive team is when you're disappointing customers.
Jenna Watson-Brown:And disappointing customers with your product, not with customer service or pricing, but the product either not doing something they need it to do, or not following through on commitments that you've made. Or in the case of, we have this innovative new idea, your top customer, it's a great idea, everyone agrees, you go back to the development team and they say, oh, yeah. That's gonna take 2 years. And I've been there. The tension between the growth and especially if you've taken on significant venture capital, the growth, the commitments to the board for growth, and the, technical realities of what you can do for your customers.
Jenna Watson-Brown:So I I think that's the first because never ever has that happened, and this has been a surprise to the technical team. Like, they've seen this coming for 16, 18, 20 months of we're gonna hit this wall. We're gonna hit this wall. We have to fix it. But usually, and I've been a a culprit, growth, growth, growth, growth.
Jenna Watson-Brown:I'm reporting into a board to hit my numbers for my team, and I am gonna just keep pushing. And in a lot of the cases, the CEO is also just gonna keep pushing the technical team to build and build and build. And then you end up with a house of cards that, that small breeze comes in, and you're you're left in a dark, hidden chasm.
Josh Smith:So much to say there. So I know, Bo, you have more to say. But when you get to that point where you suddenly realize, oh, too many broken promises here happening, or what are you saying it's gonna take 2 years, tech developers? Has there ever been a translation layer around you at that time? Because whenever I I mean, me, I'm not Yeah.
Josh Smith:I I'm technical, but I'm not that technical. I've been in many rooms where I've asked I've been with business folk asking why is it gonna take this long? And the answer I get, I cannot decipher. You know, I don't even know what they're saying.
Jenna Watson-Brown:But Yeah.
Josh Smith:Like, if you don't have that translation layer who's saying, hey. Okay. If we defer now because the incentive structure is towards growth and we're deferring the problem, I just want you all to know that when we hit it and we're gonna hit it and this is what it's gonna look like, you're gonna have the moment that, oh, okay. We realize how we got here. That does that happen, or is it more like, wait.
Josh Smith:Why is this happening? What's going on now? Like, does that make sense?
Jenna Watson-Brown:It does. I would say a good analogy is someone who, like, eats McDonald's for lunch 3 times a week, and it's like their doctor saying I had a I had a feeling Yeah. You just look like a McDonald's junkie. So it's like it's like your doctor saying to you, like, you're gonna get a have a heart attack. Like, you're going to have a heart attack.
Jenna Watson-Brown:If you eat McDonald's every 3 days a week, you're going to have a heart attack. I would say in some organizations and in times of others, there has been that translation layer. There's been that incredibly business centric VP of engineering or CTO, and they have been able to say, hey. This is gonna be the repercussion of the decisions that you're making. We're prioritizing x instead of y, and, you know, this is gonna come.
Jenna Watson-Brown:But just like we've seen with people, until you actually have the heart attack, it is very hard to change behavior based on like, we we devalue that future so much that that current, in the case of McDonald's, like, oh, I really want a big mac, overrides any value of the future. The other thing that I think comes into play, which is hard, and and I've seen this many times, is there's also a resentment that builds between the business side and the technical side of the organizations. So when you do hit that brick wall, I also think that is a hard part. Because you have the technical team be like, told you so. Like, what did you guys think was gonna happen?
Jenna Watson-Brown:And, again, then even if you have this incredibly business centric CTO, they're then dealing with a very unhappy team because this thing that they said was gonna happen happened. Nobody's winning. And now, you know, it it just changes the mood, I would say. And and I I do think that kind of thing matters because then you have 2 teams against each other instead of 1 team collectively working together. But I've I've had those excellent CTOs, and I we still ran fast toward that brick wall.
Jenna Watson-Brown:I think wherever possible, I've seen, you know, the the the really smart technical people picking off little pieces here and there to kind of prevent the brick wall from being quite as hard and quite as severe. But almost always, it takes that heart attack for people to actually clue in.
Bo Motlagh:It's it's interesting. So I think, maybe stepping back a little bit because I think hindsight is 2020. Right? And you can look back at this and analyze it. And you're describing something that are very similar to, what others on the on the show have described, in terms of that journey to the wall, basically, or 2,000 in this case.
Bo Motlagh:We could call it the hidden wall. But in that moment, I guess I'm curious about one of the things I think that would be helpful is to to to the listeners and in general is, you know, how in in emotional intelligence books, they they talked about actively being aware of of what's happening Yes. And and helping and maybe somebody who was in or is in the position you were in, helping them think through the immediate reaction. So in that moment, as you said, you weren't thinking about, oh, this is gonna be a problem. You were reacting in the moment to however the situation was unfolding.
Bo Motlagh:So thinking back to that, I'm curious, like, what was your first instinct? So when somebody said and you heard them say, we're going to have a problem and, you know, and obviously in hindsight, it was 1. But Yes. In that moment, knowing that you had your you had the the numbers that you were trying to hit that month, knowing and and maybe maybe there was some and there were other KPIs maybe that were happening. I don't know if there was any blame on sales as well.
Bo Motlagh:What was going through your mind in that moment as opposed to you sort of reflecting on it now?
Jenna Watson-Brown:Yeah. I think if I'm being completely honest, in that moment, when though because that this is not an isolated incident, but when that has happened to me and who else can I talk to?
Bo Motlagh:Okay.
Jenna Watson-Brown:And I think we get into that pattern of when we don't like the answer, this is me being completely honest. Yeah. We replace the technical people because we think this is a people problem. We don't think it's a technical prob like, we don't truly understand the magnitude. And so I think that that was always my first instinct of, well, like, who who else could give me a different answer in that that might which tells you exactly why we ended up in this position, the the problem kind of perpetuating.
Jenna Watson-Brown:Right? Because there's always someone within an organization that will give you the answer that they want. They will that you wanna hear. So, I think, like, in my most reactive state, that would have been what I would say. I think in, like, taking a deep breath and counting to 10, I would have seen well, I going back into that situation, I think the the key piece is that I wish I had done is expanding the time horizon.
Jenna Watson-Brown:And I think that's the culprit for a lot of these problems is when the time horizon is too short and when the KPIs are quarter to quarter, month to month, when the board is, you know, looking at metrics on a very short time horizon, you end up doing things that are really gonna hurt you down the road. And from a financial perspective, that does matter because your your lifetime value of a customer decreases dramatically. If you have a customer for 3 years instead of 7 years, that's pretty big deal. So I think I wish I had expanded the time horizon. And I think as a leadership team, that's a really good way to think about things.
Jenna Watson-Brown:And I think in startup world, that's hard because you're usually working on a short time horizon. But just zooming out a little bit, I would have been able to see, okay, this is worth fixing now because, yes, it will make the customer unhappy for, you know, this quarter, this year, maybe we'll even lose them. But that means I'm not gonna lose the other 10 customers that we're acquiring right now because we're gonna solve this problem today. And in a year, the problem will be solved. So I think that was a a big piece was just how small the time horizons and the result.
Bo Motlagh:And a lot of that comes back to just, you know, what is your 3 to 5 year strategy. Right?
Jenna Watson-Brown:And in a startup, I don't know and I I think it it happens at different phases, but when you've been bootstrapped and you've been, can we make payroll? Can we grow? Can we hire for 5 years? You raise VC. Like, there there does have to be a very intentional shift in the time horizons that you look at.
Jenna Watson-Brown:And I think that continues to happen as the organization grows from, you know, 10 to a 100,000,000, a 100 to 200,000,000, maybe the time horizon isn't the it's not the only thing, but I I know that we can get trapped in thinking what got me here is going to get me out of this. And that's I think that the big trap that I've seen sales teams fall into, I've seen executive leadership teams fall into is we just need to do more faster instead of saying we need to do this differently.
Josh Smith:One incentive that you mentioned, and I like the that you you looked at it from a top down is, like, what influences the incentive structures of the other departments is that short time horizon. Are there any other incentives that you see, in midsized enterprise organizations having to scale and grow rapidly? Are there any other incentives that you see that is influencing the outcome towards towards this brick wall, this cabin?
Jenna Watson-Brown:Hiring, I think, is an incentive. Growing teams, growing teams quickly. I've never met a manager that doesn't want a bigger team, or I've met very few managers that don't want a bigger team. And, you know, for every 8 people, you should have another manager. Like, it's and I think then you need to give everyone work, and then you need to give everyone revenue.
Jenna Watson-Brown:And I think that is besides just revenue targets, commission structures, compensation packages for executives, I think that is kind of an underlying piece is, like, people's individual career progression. And I wanna become a manager. You've had someone in the same role for 3 years. You want them to become a manager. You want their team to grow.
Jenna Watson-Brown:So I think that especially in the startup world where people go into it to learn and grow quickly, I think that's an underlying current that pushes us faster towards the hidden chasm.
Bo Motlagh:That's really interesting. I mean yeah. So scaling up your your team too quickly. I'm curious, when you one of the things we we we sort of thought might be happening, and you'd be in a good position to tell us, is is there any blowback on the sales organization before or after these things begin to happen as well?
Jenna Watson-Brown:1000000%. Yeah. I mean, like, lively like, you you think you have a sales rep that's used to making 250 to $500,000 a year, and you're telling them, hey. I'm gonna say no to this $1,000,000 contract because we can't fulfill, you know, whatever product obligations or this customer's gonna churn. Like, you very meaningfully are impacting their quality of life.
Jenna Watson-Brown:And maybe it's not even that dramatic. Like, maybe they're not a sales rep making a $1,000,000. Maybe they're a sales rep making, you know, a $150,000 as the sole breadwinner for their family, and you're telling them, hey. We're gonna say no to this deal because our we can't fulfill on the the product promise that we made 6 months ago that we're gonna fulfill. Like, it there is a very, real impact on compensation that I think is also very different to the engineering organization because the developer gets paid the same kind of whether or not they do the thing or don't do the thing or do it well or don't do it well.
Jenna Watson-Brown:Yes. There's other pieces and things, but a sales rep, not to say it's better, but they have more to lose. So I think that's also why you get the sales teams are much louder and are willing to fight much harder. And I think that also perpetuates the cycle because you have a very loud sales team because their money is literally on the line. And you're overpowering an engineering team that, you know, is kinda saying, like, hey.
Jenna Watson-Brown:We're gonna break hit a brick wall. We're gonna hit a brick wall. Especially for a company that's not public. Like, liquidity, like, that stuff is still so far out, that unless you're immediately, you know, close to a raising a secondary round or people can get out or an IPO. But in most cases, what people take home today is the thing that matters to them, and you have a very, very loud sales organization.
Bo Motlagh:I mean, it it comes back to what you're saying. It's the it's a misalignment. Well, maybe that's a strong term, but it it's certainly, a competing Yes. Yeah. It's a competing, incentive structure, which, you know, maybe there's something there to look at because if I don't know.
Bo Motlagh:The developers and and the r and d organization should be incentivized the same way as sales, but, they're skin in the game.
Jenna Watson-Brown:They're in conflict.
Bo Motlagh:Yeah. Yeah. Exactly. And and there's a much higher risk reward scenario in terms of compensation for sales than there is, with r and d. It's really interesting.
Jenna Watson-Brown:And that's where, like, sales leadership and that longer time horizon, that 3 to 5 year or 1 to 3 year time horizon matters. Because if your sales leader understands that and can, you know, set the right expectations with the team and kind of keep them off that hamster wheel altogether, and work very closely with product and engineering to be in lockstep, the likelihood of that happening is is so much lower. But I would say in a lot of cases, you have these sales organizations that are very financially driven that can drive the company in a direction that doesn't serve it over the long term.
Bo Motlagh:Have you ever been involved with a company like this where you made strides out of the chasm, or or have you found it to be more of a, if you're in it, this is gonna be a long haul scenario?
Jenna Watson-Brown:I think I've I've definitely worked with companies making strides out. I think that that means that, you know, the problem with the chasm is you get out ish, but there's always like, the next chasm is kind of always coming. Right? So I think I've yes. I've seen partially the other side, but I won't say I've seen an organization, like, completely.
Bo Motlagh:Bridge the divide.
Jenna Watson-Brown:Yeah. Bridge the divide. Once you've replatformed, there's the next thing or there's m and a or, like, it's it's just a cycle.
Bo Motlagh:Going back to one of the points you were making was the, the distrust, mistrust that that can form between sales, product dev, and really I would imagine the executive, committee and the board. And I guess it's it's such a prevalent thing because, like you said, there's all of these misalignments. There's confusion about what the problem actually is. There's disbelief. How could we possibly be in this situation?
Bo Motlagh:Let me speak to your manager. And, and so what would you say? Because I think that's probably the biggest killer. Right? The moment that happens, the problem is 10 times harder than it was the day before, because now you've got to work together and now you're thinking through hindsight or maybe having seen it be addressed.
Bo Motlagh:What are some recommendations you might make, especially between sales and the engineering organization? Because I think that to me has always felt so out of sync in a lot of these companies. And I know that me and Josh, I would not speak for you, but I suspect you would agree. I've been in the role where it's like, I just want to talk to the salesperson, You know? Like, can we figure this out?
Bo Motlagh:And Yeah. That for some reason, it's always very difficult.
Jenna Watson-Brown:I think a key is actually start to the CEO. I think the CEO or the president of the company needs to reset the tone and reset some of the incentives and a lot and whether they're, you know, specific incentives like compensation or they're just expectation setting. Because what I've seen is the CEOs want it all. They want to fulfill the customer need in the short term, and they want to have the long term technical plan. And so I think what if the CEO can come into reality, address reality, and say, these are the short term pains we're all gonna feel to get us to this new, better, wonderful, brighter future, and lay that out.
Jenna Watson-Brown:I think that gives a more fertile ground for, you know, the head of the technical side, whether it's the CTO and the head of sales or revenue to collaborate, because that is the piece. Like, you have to be willing to make short term sacrifices, and both sides need to make short term sacrifices for the long term better future. So it's it's 1 +1 equals 3. In that, the engineering and the sales team both need to be grounded in the same version of reality, and they need to have confidence that they are both not gonna be asked to fulfill every short term commitment and every long term commitment that the CEO has or the board has set forth, because that is where you the gate is impossible to to do that without, you know, a massive injection of capital or resources or, you know, other external factors changing. So I think everyone needs to be on board.
Jenna Watson-Brown:We're gonna take our medicine now. This is what the medicine's gonna look like. It's not just the sales team taking their medicine. It's not just engineering taking their medicine. We are all gonna take our medicine.
Jenna Watson-Brown:This is what it looks like, and this is why. This is the 1, 2, 3 year plan. But when I've seen the onus fall entirely on one team to sacrifice in the short term, I think it does a lot of damage. When it comes to morale, it does a lot of damage.
Josh Smith:And as part of that that medicine taking, have you seen something I I don't know how to to describe as the per customer feature demands versus the more broad what is the benefit of implementing this, in the entire product in a way that benefits the business in the long term? That that tension where the short term thinking was paying off, you were converting leads faster, but you were incurring more debt because you were building so many one offs for specific customers.
Jenna Watson-Brown:Yeah. And that's that's I mean, that's the crux of it. Right? And I've been there with anybody. It's a habit to break.
Jenna Watson-Brown:And I think in my experience, like, whether you have a key of a group of customer advisers, you need to be transparent and get them on board with the plan. Because if they can also see thinking of your your biggest key customers, why you're gonna be saying no in the short term to some of the things that you used to not say no to, and what that long term payoff is for them. And if that long term payoff and that 1, 2, 3 year plan addresses their needs. I've seen that work, and I've personally had those conversations with executives and with board members of k. We're gonna say no now, and I'm sorry.
Jenna Watson-Brown:It's gonna be really uncomfortable. I know it's gonna put you in a hard spot, but this is why. And, I mean, obviously, working with the team to see if there's anything that you can do that kind of gives them a little bit of a cookie, like, you know, k. Whether that's pricing, whether that's something else that they want, but then enrolling them and and this is making sure that what you're building is going to address them in the long term. I would also say, in some cases, you may just have a bad fit customer, and you've been bringing them along and they've been costing way more than their work, it is never worth keeping a bad fit customer.
Jenna Watson-Brown:And so that would be, hey, customer. Like, this isn't this isn't working. Whether that's because of the customer's demand, whether that's because of the customer's use cases, maybe they're using the product in a very different way. But having that very open and transparent conversation and trying to, like, kill that dead weight, those are 2 things that I've seen help, to to then give you the breathing room that you need on the engineering side to not be constantly putting out fires and to instead be building.
Josh Smith:I don't even know if this exists, but to be able to have some sort of KPI or measurement of the deadweight per customer.
Bo Motlagh:I was gonna say, how often I don't know that that happens as often as it should is probably the right way to put that. But that's interesting. It's tricky because I think as you're working with these startups from on their journey from 0 to, like, let's say, 5,000,000, So much of that is opportunistic sales. Right? And and it's, you know yeah.
Bo Motlagh:You have a vision. That vision might need to change. And so you are you're doing the thing out of necessity that you hope you don't keep doing after some point. And there's this transition moment, which is probably very difficult to say. Well, when you get here, stop doing that.
Bo Motlagh:Where the things that got better have helped you be successful all of a sudden start to lead to some toxicity. It's gotta be fascinating from your perspective because in your work with these these early stage companies, and I would imagine you you probably see this mostly in that 5,000,000 category. Like, are you seeing things where you're just like, okay. This is good for an app, but, man, that's probably gonna be a problem later.
Jenna Watson-Brown:Absolutely. I mean, I think the biggest one is, relying on personal networks. I think that's the the biggest one. Like like, you hire a sales rep or you hire 2 sales reps, and they have really extensive personal networks, and they've built your first few $1,000,000 of sales through their personal networks. But, you know, there are some exceptions, but in most cases, you've actually not proven that you have a sales motion that works.
Jenna Watson-Brown:You've proven that if people get to know about your product, they wanna buy your product. So I think that's one for sure in that, like, I'd say, like, 2 to $5,000,000 range. Of course, you can look at the renewal numbers on that, and that will give you a better indication of, like, is there a true product market fit there? But I've seen that a lot of just relying on personal networks. And anytime you have a single point of of failure, especially when that person isn't a founder.
Jenna Watson-Brown:I would say it's different if it's a founder because that network couldn't go anywhere. That's a big one. I would say more often, though, I see people trying to scale sooner than they should.
Bo Motlagh:Mhmm.
Jenna Watson-Brown:That's actually the way bigger problem is people with 1 or 2 customers trying to then build this super scalable sales process or planning documents or opportunity criteria, or even at a few $1,000,000, they're like, oh, we need to hire this big sales team, and it's a crawl, walk, run. It is not a crawl, run. And it so I think that is more often people skipping steps of, okay, we did a whole bunch of things that aren't scalable. Now let's peel some of those off. Let's keep doing some of the ones that are most critical, but what do we think we could do that is scalable?
Jenna Watson-Brown:And then adjusting that instead of taking a band aid and ripping it all off at once because you can't troubleshoot and you can't tweak. And then you're just left with this, well, we had all these sales and now we have no sales, or we have less than we thought. What do we do? And it's like, well, you've changed 65 variables at one time. So I think that is more often the issue that I see.
Josh Smith:Yes. Like, you wanna stand behind the wave so you can see it and and adjust because if you say, okay. I'm gonna just stand in front of it and build this this huge, invest all of this money because I'm just looking at I'm connecting 2 dots and creating a straight line somewhere. Well, you can't see the wave anymore. And if something changes, well, you've you've just you've
Jenna Watson-Brown:Yeah.
Josh Smith:Expanded based on a perception of, like, a trajectory that is not always in a flat line up in up into the right. So
Bo Motlagh:You talked a little bit about, that that change starts with the CEO, and you gave some some examples of things that they should be doing to help when these things happen or when they find themselves in the chasm. Do you have any thoughts in terms of practical advice for a CRO, or or even a CTO or CPO who may find themselves in this situation?
Jenna Watson-Brown:I would, so I think there's 22 tendencies. There's one to stop the bleeding and then get to the root cause. And I think most people stop it stop the bleeding. And they say, okay. We stopped the bleeding.
Jenna Watson-Brown:I'm gonna kind of continue forth. I think stopping the bleeding and then getting to the root cause. I think looking at your people, like, a lot of the times, the people that got you into a situation aren't the people that will get you out of it. Like, it's it's a sad truth. There are some people that are really good at startups, and I would say myself included, like, I'm not a $2,000,000,000 salesperson.
Jenna Watson-Brown:Like, that that is not my wheelhouse. And there are people that are really good at getting you to a $100,000,000 or $50,000,000 that are not going to be able to get you where you need to go next. So I think that is that is hard. It doesn't mean that they are to be redundant, like, to be taken out, but how do you bolster them with people that have been on this path forward? So I think it's it's adding executives, adding advisors of people that have done this portion of the journey that you're about to do next, and also looking at vendors that have done this portion of the journey that you're doing next.
Jenna Watson-Brown:Because, again, you don't wanna be at 50,000,000 and look to a $1,000,000,000 CEO and say, okay. You're gonna be my mentor. How do I get to a 1,000,000,000? It's finding the right people that have done that 50 to $250,000,000 journey, because that's the journey you're on. Who can help with that?
Jenna Watson-Brown:Whether it's adding to your executive team, adding to your board, adding to your advisors, working with vendors that have done that portion of the journey. I think that's often overlooked because if everyone around you has only ever gotten to 50,000,000 Yeah. The chances that you're going like, who can help who can you learn from? Of course, adding your own flavor, adding your own spin. You You know, you're not looking for a playbook per se, but a guide or people that can help you avoid some of the common pitfalls.
Bo Motlagh:What about in in a scenario where maybe there maybe there is attention being finally given to the platform, the product. I'm sure from a sales perspective, if you're somebody who's tasked with bringing in revenue and all of a sudden you're being told that your product is going under, you know, major refactoring or things like that. That can feel scary. Right? Did you have any thoughts in terms of maintaining the sales momentum in an environment where everything is in flux like this?
Jenna Watson-Brown:So I would say 2 things. 1, find more like, you you always have a pocket of happy customers. And maybe the customers are using only 75% of the product, or they're really focused on a specific use case or feature, or they moved from a certain competitor and they moved to your product and they're just thrilled, and maybe they're 20% of your customers. Find more like them and incentivize the sales team to find more like them. So while your product is going under major overhaul, don't try and find more customers that are disgruntled or upset or wanting it to be different waiting for those new features.
Jenna Watson-Brown:Find more customers that are happy with it as it is today, and that the new features will help in the future. So kind of gearing the sales efforts, the marketing efforts, the events, the everything, all the activations you're doing to give them the best shot of success at customers that will be happy with the product while it goes through this transition. I think that's number 1. Number 2 is this is where the engineering team, technical team, product team needs to put on their sales hats. Yeah.
Jenna Watson-Brown:Sell this vision to the sales team. Like, it is your job to get the sales team on board with where you're going. And if it was a good plan and if it was well thought through, you've taken customer feedback, you've listened to customers. So there is something for them to get excited about, but it is your job to enroll the sales team, in what you're doing so that they can say, okay. Little uncomfortable right now, but in a year, I'm gonna be able to sell 2 x my average contract value because we're integrating a new product or because we're rolling out this new feature.
Jenna Watson-Brown:Help them understand how it's gonna help them make more money.
Bo Motlagh:That's so interesting because a big part of, you know, when I speak to technologists, architects, developers, a big conversation we eventually end up having is how to talk business effectively. Right? I think it's a really important piece of product development leadership to teach your technical resources how to speak to the business in and of itself in order to have that conversation. Exactly what you're saying. And know that, well, I think it would be really cool isn't a good reason.
Bo Motlagh:And, oh, you're going to lose a lot of money if you don't. Maybe it's a better one.
Jenna Watson-Brown:And we need to do it. That's a terrible reason as well. But if you can explain the potential revenue benefits, the potential new features and products, and this is gonna take your annual contract value from, you know, $75,000 to a $115,000 because we're adding these widgets. We heard from 80% of customers that they want it. That's a totally different conversation.
Josh Smith:Yeah. Yeah. That makes sense. The context that you like what you're doing now, sales, but here, let me tell you what the possibilities are where where you could be and what you could be achieving with with this this time, which may not be pleasant this time, but this time that we need to invest.
Jenna Watson-Brown:Yes. And then the other piece is, like, how is the executive team engaging with customers? Because that goes a long way. And when you're gonna be pissing off a customer, like, I'm thinking, let's say, you're doing a m and a. You're acquiring another key product in this space, and you're gonna integrate that product into your product.
Jenna Watson-Brown:But it means it's gonna be clunky for a little bit, and, you know, they're gonna be upset. Well, call from your CEO or a call from someone explaining the vision, explaining the the value, and explaining what they're gonna get out of it at the end goes a really long way.
Bo Motlagh:So that's an important piece because it's a question for me, actually. So I'll ask you is is, I've seen this happen, which is the company is in the midst of, you know, they know what what they've been doing isn't working all of a sudden. And so a reaction to that is is what, you know, I guess you could call like visionary syndrome. Somebody sits down and comes up with this brand new concept of how everything is gonna be different and looks completely different. They might even invest in, you know, somebody to come in and drop what this whole new vision of is gonna look like.
Bo Motlagh:And most of the time I mean, it's great. It's an amazing idea and maybe and and and in many ways, it may address the the business and market issues, although it certainly wouldn't immediately address the technical issues that have led them there. But it is also somewhat divorced from the reality of their current scenario and it's like, while you're trading the hardships of of your existing reality with the hardships of a reality that doesn't even exist yet. And then they go out and start trying to sell that, which from a startup perspective is is like, well, that that makes sense. You're you're selling something before you build it so that you can get paid to build it.
Bo Motlagh:From an enterprise perspective, I don't know if you're it feels very risky, but maybe maybe that I don't know. I'm curious what your thoughts are.
Jenna Watson-Brown:Yeah. Risky is a really, really good term to use. I think there's a balance. There is getting a little ahead of your skis, selling something that's coming. But the enterprise needs to be excited about what they have today.
Jenna Watson-Brown:So it will not exempt you from users reporting bugs on your platform. That doesn't help necessarily. It can buy you more credibility and more time, but it is absolutely a balance. And I think too often people unveil this entire new version of their product all at once. And I I for the enterprise specifically, like, I was speaking with a customer the other day, and they have a a SaaS tool, and they changed the color of something.
Jenna Watson-Brown:Mhmm. And someone complained. They changed the color from blue to white. And someone complained because they were used to it being blue, and it is now white. It is still incredibly legible.
Jenna Watson-Brown:It was like a decoration. It was not actually a key piece of the UI. So I think these visionary moments, people think, oh, I'm gonna unveil this entirely new thing, and, you know, we can think of some SaaS tools that the 3 of us use where they unveiled a new menu and all at once. And while it's maybe better for us in the long term, like, that was a hard adjustment to make. So, of course, there'll be some things that you need to do all at once, but I would say too often, it's like, oh, 3 point o.
Jenna Watson-Brown:We're gonna take everything and blow it up and make it different and better, is often not the solution, and the solution is more iterative.
Josh Smith:The delta between what is now and all the muscle memory that people have to know what is now, all the comfort they have, even if it's terrible, they've gotten it to work. They figured it out. And the dealt between that and the new thing, that's change that needs to be designed, and it's often not applied. The new thing's designed, but the the path and the journey to handhold someone to the new thing, that's often missed.
Jenna Watson-Brown:Yeah. And the same with entering a new market. Like, we're gonna go up market. We're gonna go down market. Okay?
Jenna Watson-Brown:Great. And you have a sales team that is an expert in one market, and now you think you're gonna apply it to a new market. Or we're gonna integrate we're a SaaS tool that is a $150,000 a year or bought a competitor that's $5,000 a year. And now we're gonna try and integrate it all together. I think the vision is important and the vision is there, but the connection, like, strategy in action, I think is the critical, critical piece that often gets missed, and then you end up with a bungled, half baked, not on time, frustrated situation.
Jenna Watson-Brown:And that's where you get these customers that are sitting on legacy tech for years years years because they won't move to the latest version, because it doesn't meet their needs.
Bo Motlagh:It's another version of the, build it and they will come fallacy you were talking about. It it's just a much more expensive version.
Jenna Watson-Brown:Absolutely.
Bo Motlagh:I think we covered a ton of ground. This was really cool. Jenna, thank you so much for making this time. You know, wanna open up the mic to you here. Spotlight is on you.
Bo Motlagh:Anything you want to plug or talk about? Go ahead. Let everybody know.
Jenna Watson-Brown:I would say feel free to reach out if anyone listening to this wants to talk more about start up sales. But my if I could put it on a billboard, and I'm gonna put it on this billboard now, please, please, please don't hire sales too early. You need to be able to repeatably sell yourself as a founder. If you cannot repeatedly sell this yourself, you will never have luck with a salesperson. You need to learn to get good at sales.
Jenna Watson-Brown:So I think for founders, that's what I'm gonna leave we with. And then for any execs that are listening to this that are, focused on kind of that 50 to 250,000,000, I'm in this stack. Like, find people like Bo, like Josh. Find people that have done this part of the journey before, because you will be far better off. And I think thinking what got you here will get you out of it is a hard path.
Bo Motlagh:We really appreciate that plug. How would people reach out to you?
Jenna Watson-Brown:Great. Jenna Watson-Brown on LinkedIn, or jenna@jennawb.com as my email. So feel free to reach out there, but LinkedIn is also great.
Bo Motlagh:Awesome. Well, this has been another episode of The Hidden Chasm. Thank you, and stay tuned for more. You've been listening to The Hidden Chasm brought to you by United Effects. If anything in our conversation resonated with you today, please reach out.
Bo Motlagh:We'd love to hear from you. Email us at podcast@unitedeffects.com, or simply visit us at unitedeffects.com or thehiddenchasm.com. Thanks for listening.