SaaStr CRO Confidential:Hiring a Great VP of Sales Today Sam Blond + Former Lattice CRO Dini Mehta

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Welcome to episode five of the CRO Confidential podcast series. I'm Sam Blonde, your host. We have an incredible guest today. I'm so happy to welcome to the pod Dini Mehta, who is most recently CRO at Lattice where she spent the last four plus years scaling the business from something like 30 employees in single digit millions of dollars of ARR all the way to several billion dollar valuation, hundreds of millions of dollars of ARR. And prior to that incredible experience as well that we'll talk about as part of the POD today. But Dini, welcome and so happy to have you.

Thank you, Sam. Super excited to be here, pumped to share. Cool.

Well, let's jump right in. We're going to spend the entire time today talking about sales leadership and specifically making the right sales leadership higher. And one thing that is counterintuitive in this environment of layoffs and slowed hiring is that I'm actually seeing more companies looking for a sales leader. And there can be a number of reasons for this. One is that 2020 and 2021, a lot of new companies were formed. Those companies are probably starting to find some product market fit looking for a sales leader. I'm hearing about companies where the first sales leader didn't totally work out and so they're looking for their next one. Folks like you and I have moved on from our companies. We need to be replaced as sales leaders. And so again, despite this environment of layoffs and slowed hiring, this sales leader hire is one that I'm actually hearing more and that's bit counterintuitive. The number one topic that founders discuss with me is how do I find the right sales leadership hire? The number one topic that folks that are in sales, whether it's SDRs A, is sales managers. When they meet with me. The number one topic that they bring up is how do I get in your shoes? How do I become a CRO? And so today you and I are going to go deep on both of these angles. Sort of like the founder perspective, what to look for in sales leader and also the sales rep perspective, how to become that person. Dina, you and I have sort of unique experience as CROs where we also do a lot of angel investing. I'm of course now full time investing at Founders Fund. I know you've worked with countless companies that have gone through this process of hiring a sales leader. Let's maybe start with what are some of the common pitfalls that you've seen founders make in terms of hiring a sales leader that have unfortunately set them back a bit.

Yeah, no, it's, it's, it's such a timely topic and you're so right. It feels like the activity on the leadership front around hiring sales leaders is actually heating up despite the, the macro environment today. I'd say there's a couple things that I see founders in companies consistently miss when they're looking to hire either their first sales leader or you know, a follow up sales leader. Because you know, folks like you and I have left one of the, one of the most common ones is just solely pattern matching logos on resumes. And I see this all the time where you know, the founders, they're, they, they want to hire that, that rock star VP of sales at this, you know, big company, abc. It's got this shiny logo and you aspire to become that company or you may be competing against that company as a startup, right? So you want to become that in 10, you think hiring from that hiring for that company makes what is, is sort of, you know, makes a lot of sense because you're like, they understand the market, they've done this before, they've been successful. Let me just hire them in my company, which is a completely different stage of build out and it'll just work out. And so I think overweighting logos on resumes and sort of purely going off of pattern matching versus being clear around your success criteria in months from now, 24 months from now, what does success look like if you found the right hire and then how do you design the right competencies and the right evaluation process around those must haves? Because if you're not intentional about it, it's easy for bias to seep in. It's easy to sort of go with a gut feel and just, you know, let me look at this sort of, you know, aspirational company and hire for it. And sometimes it may work out, you know, if you've got the right person that is that had been at those companies and are ready to take on the challenge of building out the org in your, in your company. So I think stage matters, but not solely going off of logos and resumes is one that, one that I see founders consistently make.

It's really smart and similar to what comes to mind for me or at least my experience in the missteps that I've seen founders make here. To reinforce a bit, I would categorize the things that I've observed in really two categories. The first one being the bigger and that's around profile. And this is reinforcing a lot of what you just said, Dini, which is I have seen folks hire from companies that are too big. And I've seen a lot of mental gymnastics around this also where somebody tries to justify it with like, well, they joined Zendesk when Zendesk was 100 million in ARR, so it wasn't like that big. And you know, they hired them at less than a million dollars of ARR and it is still a radically different business at 100 million than yours today at 1. The other thing that I've heard again around this like mental gymnastics concept is yeah, but it was sort of like a startup within a big company, you know, like it wasn't an acquisition because those actually, those actually are okay. But it's like, you know, Salesforce started this new business unit and this person was sort of in charge of the business unit. So it was basically a startup. But they were at Salesforce like, no, just don't do it. And so on the profile side, number one, is going to hiring too big of a company. The second thing on the profile side is solving for domain experience. And you know, it's like again, I hear not, not excuses, but justification around this. It's like selling property tech or selling into real estate is different. Or selling into health care, it's just different. Selling into developers, it's different. And so, you know, for us we really need a who understands this space, understands the buyer comes with a Rolodex of companies that they're selling into. And like, that is the wrong thing to solve for. There are only so many really amazing sales leaders that exist to begin with. And if you limit your candidate population to a very small domain, like let's just say property tech or something like that, how many unbelievable property tech sales leaders are there? It's just like, so you ultimately end up sacrificing on higher quality for this concept of domain experience that's just so easy to pick up. And I know you've, you've been in a number of different spaces and clearly been unbelievably successful. And you know, I've done electronic signature, HR benefits, administration software and financial software with Brex. And so like good people pick this stuff up. And then the third thing on the profile side that I've seen folks mistake make a mistake on is this like perennial VP of sales where they have maybe some startup experience, but companies that like nobody's ever really heard of. And so like they've tried it a couple, two, three times. None of the companies have done super well. You really want somebody who has seen what great looks like at an early stage. And then the last thing that is different from the profile that I've seen folks make a mistake on is the timing. And it's generally, it can be hiring the sales leader too late, but it's generally hiring too early. Last week we had Matt Plank on and Matt Plank is the head of revenue at Rippling and he was actually the first sales hire that Parker made. And of course, like that is an exception to the rule that worked. And Parker and Matt knew each other incredibly well. So do not follow that unless you have a lot of confidence and have worked with the sales leader in the past. I'd say like the, the more common path here is hire a couple individual contributors, make them successful, then hire a sales leader to scale the team. So I have, I have seen folks make a mistake on the timing as well, passing it back to you just away from the common pitfalls. Just general guidance like what do you advise founders when they come to you on what to look for in a sales leader and how to approach making this higher?

Yeah, I mean, I think one of the things to start with, I think one of the things the mistakes are on the flip side is making sure that you're clear in terms of what does success look like, what does failure look like 12 months from now, 24 months from now? And I do that when I'm evaluating companies and working with founders. I want to ask them, like, what do you expect out of this role? What do you expect out of this person? Not just in terms of the revenue generation that you want this person to do, but also the company building aspect of it. Being a startup exec isn't just about being a sales leader. You have to be a general company leader. You have to think about the limited resources and bandwidth that you have in front of you. And it's important to make sure that there's strong alignment between the founder and the revenue leader because it's such a core partnership. And so I'll say, number one, start with the clear list of must haves that match back to your success criteria. 6 months, 12 months, 24 months, depending on the stage of the business earlier on. I mean, you'd say, you know, 60 days from now, what do you expect to see? 90 days, what do you. Because at that earlier stage, things move faster. Later stage, it's six months, 12 months. And so start with that success criteria. And I think one of the things that you said around the domain expertise is, is people get so locked in on, you know, I just want property tech or health tech. And you lose the opportunity around innovation because if you've done something a few times over, and it's true for me when I'm in a new industry, you partly because I just don't know and the ignorance forces me to think outside the box, get creative and rethink the playbook. And so I think the other addition to it is also starting broad in terms of experience and domain expertise, but getting narrow in terms of what you want from the role and the fit at your company. And of course it's going to depend based on the stage of the business, the maturity of the business. And there's two categories. One is the functional fit, like what are the must haves before you kick off this search? Deal sizes. I mean if you are an SMB business, hiring for someone that's done multimillion dollar deals at great startups, it's going to be a huge adjustment. Can it be done? Sure. But that's not the most natural path. And so deal sizes is a key lever Persona to some extent. Not that you know, you can pick up different industries and Personas, but having the awareness to learn a new industry and Persona and do have the ability to really understand what are the nuances in that specific market and industry and applying that to your go to market playbook, evaluating for that is important. And then the level, like are you open to a first time VP of sales, someone that's seen it, seen the journey from the early, early millions to hundreds of millions, but in the seat they were close to the seat, they were the second in command or third in command. And so is that level the one you want or is it, you know, and I would say early on that is a great profile to hire for versus someone that's been there, done that, where you're ready to really start scaling. And so one, the functional must haves are critical, the success criteria around it. And then the second piece, which is another trap that I see a lot of lot of founders and revenue leaders take on when they're picking their next adventure, is not spending enough time upfront in thinking about the right values fit. So you talk about the functional fit, like what the business needs and is this the right person? But there is an operating style, a leadership philosophy that a lot of revenue leaders and founders don't spend time thinking about because they're like, oh, we'll figure it out. And sometimes you do. But your company and your leadership team is unique. What you need, how you make decisions, the pace at which you like to execute, your level of urgency. I think how you hire people, how you performance manage folks. Those are things that a lot of people find out after the fact once you've hired and you're in the trenches and you can't solve for all of it. But I'm a huge fan of, you know, spending two to three dinners just learning about each other as people and how do we react to stress, how do we think about, how do we make, think about making high stress, high stakes decisions? So I think those are two, two categories. Functional fit, must haves and then think through your operating style and is that a match?

I so much insight included in that answer and a number of different directions we could go. As I'm sitting here listening to you, I'm learning a lot. We're very complimentary to one another. I think you are much more process oriented than I am. And so your answer There is a lot around process which I think is so interesting and again, sort of complementary to where my mind goes. You talked about these success criteria that you want to define that are sort of like 6 months out, 12 months out and it's, I'm sure not one size fits all. But do some things come to mind in terms of what those success criteria might look like? Is it like revenue targets? Is it prioritizing the needs of the business at that time? Maybe just go one layer deeper in terms of how to define and structure these success criteria?

Yeah, I mean I think it again depends on the business and the business strategy. It's also a forcing function for founders, you know, that are typically running hard at and startups are whack a mole. You solve one challenge, there's another one popping up. And so it's, this is a forcing function to think about. Okay, over the next 24 months, what does excellence look like? In my go to market we have a new product launching and so I need someone to turn us from a single product company to a multiproduct platform. And so that is going to require someone to think outside the box, hire for new roles or we've got strong product market fit. Now it's all about scaling. We know, we know what we need to do. And so this person needs to recruit onboard and scale the whole operation where every cohort of hires that you're making is 20% incrementally better. The first 90 days is can you lay the foundation for the strong culture that can scale to hundreds of employees and hundreds of millions of dollars. And so I think that is those are the types of things that I want founders to give me specifics around because the revenue target is one piece of it. And in some ways that is the easier thing. It's the what, like what are we trying to do is yes, close revenue and scale fast, but the how we get to it is it product, is it team, is it geos? Like we need to go international, we need to segment and become regionally organized. We've got this wild west, wild wild west setup and now how do we get to a more sustainable scalable segmentation? So those are things they don't need to have the answers, but they need to know what are the biggest problems and what they hope to see from this revenue leader. Because I think it just, it helps with expectation setting, it helps with that early alignment and focus. I mean, you know, selfishness for me, it's helpful to see, okay, here's the things I need to get done in the next 90 to 90 days to 180 days. And so what can, what are the moves? How do I prioritize my time and my effort?

It's so smart. I'll try and compliment your answer. You talked a lot about process and I think the sort of like implementation or manifestation of some of your comments is around the structure of how you interview the things that you're solving for, what their, their 30, 60, 90 day plan or full year plan looks like, like where they are focused, focused, what you're optimizing for. I'll try and compliment your answer a little bit with the who, like the profile of the person and how to source these candidates. And if I were a startup founder today, anywhere from something like 1 million in ARR or even less than that to let's call it 30 or 40 million in ARR. The way that I would source candidates is I would take a spreadsheet and I would plug in the top 10 performing startup companies over the last, let's call it five to seven years. And on that spreadsheet are going to be companies like our former businesses Brex and Lattice. It's going to be businesses like some of the other podcast guests. There's going to be rippling, there's going to be gong, there's going to be divi, there's going to be other incredibly successful businesses like Flexport and Deal and more. And so you just take like 10 of these businesses. Within each of these businesses there are going to be three to five sales leaders that started as early sales reps and just crushed it and grew with the business. And this is similar to the type of experience that you had at Drawbridge that I had at Echo Sign and you know to take again some of these podcast guests. Zenefits alone produced as starting as AES, the head of revenue at Rippling, the head of revenue at Gong, the head of revenue at Modern Health, the former head of revenue at Trip Actions. Like all of these came out of Zenevits alone. And the same will be true for each of these, you know, several billion dollar valuation businesses that have experienced hyper growth. And so you know, you take 10 companies, you find out who the three to five folks that are in this category are that are now sort of like director, maybe VP of sales, but certainly not like the head of sales there. And you've just got 30 to 50 candidates. If none of those work out, do the next 10 best companies. But I think that is sort of profile that I would solve for and how I would source, you know, between the top 20 companies you just got 60 to 100 candidates right there. And again like reinforcing some of what you talked about the things I would solve for which is a little bit of the opposite of what I said last time around. Pitfalls or mistakes? Startup experience is a must have. You have to have somebody who has seen early stage, ballpark, deal size, something that you mentioned. Also you want somebody who has seen sort of a similar sales motion, whether it be transactional or enterprise depending on the segment that you're playing in. And then again just sort of like table stakes here is just crushed it in terms of performance and fast promotion path. If you see somebody who started early at an incredibly successful company and they've had five promotions, are now managing managers within this successful business that they started at at a very early stage. They've done well, they've been at the top of the leaderboard. I have seen, I'm not aware of a single miss. I've seen tons of misses on we hired from a big company. I haven't seen a single miss where we hired from the hottest tech startup of the sort of last generation. We hired somebody that grew their career there to come in and lead sales for us. And I think you're really, really mitigating risk at least with sort of like a candidate profile and sourcing standpoint. If you take that approach. We've spent a fair amount of time from the sort of founders perspective sourcing candidates, those sorts of things. One thing that I think would be really interesting is to talk about, I'm sure as a CRO you've had a number of folks that have met with you, SDRs, sales managers, AES saying what do I need to do to be in your shoes? How do I become the next CRO of the next lattice? And I think it would be helpful maybe just to start with talking through your personal experience. I referenced your time at Drawbridge, but I'd love to just understand your journey and your career, how you got to where you are, and then we'll evolve that into the advice that you provide to others.

Absolutely, yeah. Happy to walk through my story, which is somewhat unconventional in how I got here. I wasn't someone who knew early on that I wanted to be in sales or even tech. I'm originally from India and raised there. I moved to the US for college, so I'm an immigrant. My parents sent me here with the hopes that I'd become a doctor or an engineer, but unfortunately, neither was. Neither of those options were in the cards for me.

And so I imagine they're proud.

Yes. Now they are. Yes. Took them a while, but, you know, moved out west and I was lucky enough to fall into tac. And my first few jobs were generalist go to market roles. So I got to do a lot of roles except for sales. I did. I did account management, I did business development, I did customer success, I did operations. And so I tried my hand at a lot of different roles within go to market. But I shied away from taking on sales because I had this negative impression in my brain of what it meant to be in sales, which I know a lot of folks that. That, you know, a lot of successful sales folks that have eventually given it a chance, had this coming in where I thought it was about pressure tactics and forcing people to buy stuff they didn't want. But eventually notice that there's something really amazing about sales. It's objective, it's data driven. You can earn your autonomy, you can earn. There's a ton of monetary upside, and you can accelerate your career faster than any of the other roles because it's so objective and it's so data driven. You can't argue data. And so jumped into it. I got my first sales role at a company called Quantcast, where I was an ae. I did everything from prospecting. It was a full cycle, a role we didn't have. This was, I'm going to date myself, but there were no SDRs, BDRs. Then you did your own prospecting and you closed your own deals. And if you didn't prospect, you didn't close deals. It was all outbound. And I'm so glad I had that experience. And it was hard. The first eight Months and very quickly I realized that while the barrier to entry and sales is low, to be great you have to be really good. And so I worked at it for 12 months and consistently was at top of the leaderboard. And at that point I was like, this is the job for me for the rest of my life. And at some point it shifted for me where I realized I enjoyed helping others in my team close deals. Like I was finding higher gratification when someone else closed a deal that I helped versus when I closed my own deal. That's when I knew it was time for me to try management. And so got my first shot at frontline management at Quantcast. I did that for a bit and then I wanted to see if I could could build a go to market engine from scratch. Like if I had a blank slate, could I apply the learnings that I had I had gotten as part of this team at Quantcast. And so I went to Drawbridge where I had the privilege of scaling that go to market from the early days. I was there for five and a half years. We were past 100 million, so I've done the 0 to 100 plus a few times. And I did a lot of growing up as a leader, learned a ton about scaling myself, scaling the team, scaling the organization, and loved it it. And then at the end of that experience, I realized that I wanted to. I wanted to be at a company that valued people and culture and growth as much as I did. Like, I love winning, but I also care deeply about doing it in a sustainable fashion and building a culture where people can thrive. And so I wanted to help reimagine. Like can you reimagine the sales org where a younger me would have thrived, would have loved it. And so that's what took me to Lattice and I joined, you know, we were 800 customers single digit in revenue, 30 folks in 2018, and had an amazing four plus year ride where I got to see all the different phases, got to launch new offices, new products, new teams, and just was such a blast doing it.

It's an incredible story. One shout out I think we both have some roots to Kansas City. It's where I grew up. I know you spent some time there or nearby, otherwise known as the Paris of the plains. And both, both sort of fortunately moved out west. You've now seen the journey from very early days of revenue to over 100 million twice. Very few people can say that they've done that. And as you were talking, what was going through my mind is There really aren't any shortcuts. You were at Quantcast for over two years. I don't know the exact timeline. You were at Drawbridge for five plus years. You were it in most recently Lattice for five plus years where you, you had your first CRO opportunity and it just, you can't really skip steps. It takes time to learn each of the different roles, starting with, you know, SDR. You started as AE, but you didn't have SDRs, and so you functionally were both. And so it's important as a future sales leader to really learn the SDR role, the account executive role, the sales manager role, the sales director director role, to sort of qualify and improve your probability of being successful. And so to that end, I love your personal story. Let's jump into what you tell folks when they come to you and say, dini, I want to be the next CRO of the next Lattice. What do I need to do to get there?

Yeah, I mean, that is the number one question I get any welcome onboarding conversation I'll have with new folks coming in, they're like, what do I do to be in your receipt? And in some ways, I'm not the best person to ask that question because I didn't know early on that I wanted to be in sales leadership or even a CRO, or even in tech. And so if, and, and so if you are someone that doesn't know what your path is going to look like, you're starting out in sales, you like the job, but you don't know where that's going to take you, that's okay, I was in your seat. And, and not knowing my path or what I wanted to do when I grew up forced me to develop a deep awareness around my skills and my interests. So as I took on new roles, I would view my journey in an 18 month increments. And I got to this because I had so much anxiety because I thought I was the only one who didn't know what I wanted to do. Well, everybody around me, all the other top performers knew they wanted to be, be, you know, they wanted to be CEO, they wanted to be CRO. And I was here. I was like, I don't know what I want to do next. And so just for my own mental sanity, I said, you know what? I'm going to look at 18 months perks, increments of saying how, how can I do more of the thing that gives me energy and continue to get really great at the thing I'm uniquely good at? And so how Do I work on my strengths and how do I work on things that give me more energy and I just take a more learning mindset to it versus, you know, here's the map that's going to get me to this end phase that really helped out. And I, even today I do that every 18 months. I look at the body of work that I've gotten the privilege to touch and I say, okay, what am I enjoying? What is sort of draining? And am I spending 70, 80% of my time on the thing that I love doing I'm good at and it gives me energy. And so to folks and of course, if you're someone who knows for sure that yeah, this is the path. And at some point I knew and at that point I'd say spend time with folks that are in that se to get exposure to what does the role of a CRO look like? And then spend time people in, you know, their path, getting to it because there's multiple paths to get to the same out to the same sort of end goal. And I've, I found it super valuable to talk to people that are one or two years a step ahead of me because I learned so much just from their learnings and the things, you know, the decisions that they made and the investment that they made in themselves. So I'd say say it's, you know, take an 18 months increments if you know, great, sort of identify the best in the space, learn from their experience so you can identify your own growth delta and then start to work on your work on those skill sets because you don't need to get the role to start developing the skills. Like you don't. You know, one of my early managers said that like, you don't need to, you don't need to be a manager to be a leader. And that is, that is something that, you know, I've, I kept close to my heart. And you know, when people ask me at lattice, 40% of my management team at Lattice was promoted from within. And the way I made promotion decisions were there was three things. One, consistency in performance. So I cared less about if you were the number one performer in a quarter, but I cared that you were hitting quota consistently quarter after quarter. Because consistency in performance is critical in management. It's a marathon and you have to sort of of pace yourself. So the consistency and performance was key. Two, were they perceived as a leader on the team? Because that is so key. If others, if a promotion feels like, of course we're going to promote this person. I've Done, you know, we've done the right decision. If it's, I don't see this like how is this person now my manager? That's a miss of, of perception and we made the wrong call. And then third, your ability to adapt because the role of a top performing ae me is fundamentally very different than one of a manager. Because as a manager you're a coach, you have less control but more accountability. And so how do you adapt to that reality? And do you have the, do you want it enough to. To want to do that? So I say those are some of the ways. That is some of the advice that I give folks that are starting early on and want to want to take the next step.

The tallest. Really, really insightful advice. Again, I think that there's so much process that is included in your guidance there and I'll try and complement some of that with what I say to folks. Most of the time these were folks with Brex, but I would say like generic advice would actually be even before like these folks had joined Brex because they were in this fortunate position. First is like solve for the quality of company and not o especially earlier in your career. And there are some signals that are helpful in determining the quality of the business. One of them would be like the quality of the investors. Are there tier one investors that have put money into this company and again that's sort of like positive signal that the business is going to be successful. The second one is around growth. Is the business business being successful? Are they what is their month over month growth and how does that compare to the peer set at that time? The third one is like the quality of the founder or founders and the team and meet with a bunch of companies, establish some sort of baseline for what you think quality looks like and join a company that is growing quickly as amazing investors. And you have a lot of confidence in the leadership team team because joining a business like that will afford you growth opportunities within the company and solving for sort of like thousands of dollars in terms of ote to potentially sacrifice the quality of the business is not the trade off that you want to make and now sort of like moving forward again. This was the most common common question and common conversation that I had with folks at Brex that met with me as like SDRs a sales manager. We preached at the sort of team level that you will be evaluated on three metrics. Those metrics are performance number one. We've talked about it on this podcast. Sales is very objective and so make sure that you are performing. I love Your performing consistently. Add on there, the latter two actually require no skill. So performance does require skills, effort and attitude. Don't. Anybody can be a hard worker and anybody can have a really positive attitude and rub off positively on their peers. And those latter two are even more critical in leadership positions because the people on your team are going to emulate your actions. And so if you aren't putting in the effort, why would people that are reporting you put into the effort? And the same thing is true with your attitude. If you have a negative attitude, that's going to rub off especially on your team as a manager. And so those three things are really table stakes in terms of qualifying to become a leader. Performance, effort, attitude. Two more things that I mention is sort of one on one with folks when they ask me how can I progress my career quickly. One is define your success by being the best. Define your success by being number one on the team and at Rex and you know, just sort of like philosophically the advice that I give to folks is you want 70% of the team, team over quota. And so if you're defining your success by being by being over quota, what you're effectively saying is I'm going to be in the top 70% and that's not that good. There's only one number one. And so if you define your success by being at the top of the leaderboard and you execute on that, the probability of you being promoted and sort of earning what you described, which was like when this person is promoted, does it make sense? If you promote the consistent top performer, that makes sense. And then the last thing that I'll mention is just never be satisfied with where you are and you can be sort of proud of your accomplishments that are, that are backward looking. But if you are promoted into that manager role that you've been working so hard to get to for the last 18 months, the last thing that you want to do is be satisfied with that promotion and feel like you've made it. That's really the start of what comes next. Be thinking about from here like what what am I working towards? And do everything you possibly can to get to that next level versus sort of being satisfied with the position that you have found yourself in. Dini, I'd love to continue. I feel like you and I could go for hours on this topic alone, let alone a other things that we could go into. But I think we're approaching the sort of like 35 to 40 minute mark. This has been such a blast and thank you so much for joining in your time, and I look forward to staying in touch and seeing you again soon.

Thank you, Sam. Super fun, Sam.