How to Hire a Great VP of Sales with SaaStr + Duo Security

On Disaster, since inception, I think we have over 3,000 pieces of content, but if you squint and you look closely, I think half are all about hiring a head of sales. This is the question everybody has. I think I, if you go to VP of sales on Google, you will see our content is like the whole first page and this may be the, like the only thing anybody ever cares about. So I thought the most fun thing would be to have a super, to kick off an informal session on how to hire a great VP of sales. Um, and, uh, Brendan, uh, I've known, he was my VP of sales, the first head of sales at LinkedIn. Head of sales at Talkdesk and a bunch of other amazing companies. Jennifer, who I've gotten to know today, will have an amazing story. She's already got 100 sales reps at Red Hot Duo Security distributed all across the country, right? Which I could barely deal with reps like in more than one office in Palo Alto. Like, I struggled. So I'm super excited to hear the playbook today.

Thank you, everybody. As Jason said, my name is Brendan Cassidy. I was his I was VP of Sales at EchoSign for almost 6 years, and that includes getting acquired by Adobe. Joining me is Jennifer Lawrence, who's the VP of Inside Sales for Duo Security. So between us, we have about 30 years of combined experience helping build startup sales teams or emerging growth technology companies. So we're excited to share a little bit of what we've learned. Some of which you'll agree with and some of which you won't. So we'll, we'll get started from here. So I think at a high level, when you look at founders and CEOs, there is a lot more optimism about being able to make this hire successfully than maybe exists in reality. So my role with Cassidy Ventures is I work with startups and venture-backed companies, CEOs, VPs of sales, CROs, and have certainly helped and assisted in a lot of companies in their VP of sales search. And the optimism that usually starts at the beginning of that search evolves over time to sort of a realistic worldview of how to get a VP of sales in or the right VP of sales in. So I sort of ballpark it at about 30, 30 VPs of sales or CROs have taken their SaaS companies to $50 million in ARR plus. That's an unofficial number, so you can agree or disagree with that. But that's not a lot of people. And when you talk about hiring your VP of Sales or your CRO for your startup, a list of 30 that have actually proven that they can do it and scale it from that sort of 1 to 30, 1 to 40, 1 to 50 range is a small list, and the odds are very, very low that you're going to be able to get one of those. Get one of those 30? Okay, so you didn't get one of those 30. So what do you do now? And I've been through this process with a lot of founders and CEOs, and I think what is critically important is that you are pursuing multiple fronts in parallel because this is an incredibly hard hire. It's the failure rate I would guess probably 8 in 10 startups probably fire or lose their first VP of Sales inside of a year. And I think at a high level, that's a year in the life of your startup you'll never get back. You're never gonna get it back. And you're always gonna be sort of paying down that debt of not getting it right or not figuring it out with your first VP of Sales. So just one of my learnings, and I think over time, is, is get a coach or three. And essentially what this is, is obviously you have your board and your investors, but this is sort of like your, your true board in a way, where you're going to get unfiltered feedback that is based off of experience and sort of in-the-trenches experience, which you're not always going to get from your investors. Not all investors have operational experience. Not all investors have experience running sales organizations or even managing sales or managing VPs that ran sales organizations. So, it's important to get honest, clear, concise feedback. And what I would do is just hire, you know, just bring on 2 or 3 people as advisors or consultants. Give them some sort of stake in the company, which is probably going to be equity. What most companies do is they hire these huge advisory boards. Sometimes 10, 15, 20 people, of which you're not gonna get a lot of distilled feedback. So, you know, and have these people be who you lean on for major decisions in your company, especially for hiring a VP of Sales or a CRO. It's critical. And I would even add that for CEOs to have CEO coaches, VP of Marketing to have VP of Marketing coaches, is a tremendous asset to have.

So what this doesn't mean is to hire this guy, right? It's the big company VP of sales. Can you see? Great. Everyone's like— I'm like, is anyone laughing? It's like that didn't go over well. So big company VP of sales. That's the guy or gal that walks in super polished from Salesforce. Any VPs from Salesforce here? I probably should have asked that first. So it's the guy or gal that walks in that's hitting numbers in the tens of millions on a quarterly basis for Salesforce. Super polished, shows up in a suit, even comes to the interview with his sales playbook. And you're reviewing the sales playbook and you're seeing things like how to get high and wide, how to shake the tree, and you're psyched. You're like, "This is gonna work. Like, this is gonna work for my company." But the issue is this. That person didn't build that playbook. They're executing on it. And when you're in startup mode, startup going to growth, and even growth mode going to scale, you wanna find someone who knows how to actually figure things out, not execute on a playbook that's been given to them. So I think that's really, really important. The other thing that I found with big company VPs of sales is they do a great job managing up, right? Like, great command and control of the metrics. They know how to have great relationships with their managers. Sometimes I've found it can be hard for them to roll up their sleeves and to get on calls with their reps and to move deals forward and to coach and to manage. And to provide an awesome customer experience and figuring out like, what are these customers' pains? How do we do great things with them? How do we map our selling process to their buying process? It's just something that they've never done. So don't hire this guy.

And I think I'll just weigh in a little bit there is the putting in the playbook is the pitch and the presentation and all the things that you have, the deck. Which when you talk about like big company VPs or traditionally, marketing did the deck. Marketing created the content. Marketing got the market feedback or research. And the reality is, is in a startup, sales is probably going to have to drive a lot of that. What is the sort of voice of the customer? And what is the pitch or the playbook? Nobody's going to figure that out for you. So what you end up touching as a VP of sales in a startup is everything. Sales, marketing, success, ops, and you have to be comfortable sort of moving between every discipline that is required in a startup. It's not just going to be about sales, and I think that's where a lot of times the struggle is for somebody that's just used to compartmentalized in sales. You're not going to have a sales ops person in the early stages, much less 10 sales ops people, so You're going to have to do a lot of that yourself. So— Sorry, I just had one request. Is it possible to mirror the screen? It's not possible. And just quick pause. We want to make this as interactive as possible. We'll have a Q&A piece on the end working with Slido over there. But as we move from slide to slide here, if you have questions— Feel free to ask it, and we'd love to address it as we move along. We won't always call on you after a slide's done, but feel free to raise your hand. Okay, step 2 is ask your coaches if you're a, you know, if you were a founder or CEO making this hire, who would be your top 3 choices? And again, this is how you're going to lean on this advisory group. Because great VPs of sales and CROs, they admire the work of their peers. Certainly Jennifer was somebody that I knew and respected even though she didn't even know me. When I wrote a blog about the top 5 VP of sales in tech that are women, she didn't even know, I didn't even know her. But I respected what she had done and what she had accomplished at Duo. Lean on them and get their recommendations because most VPs of Sales or CROs always, if they never found their own company, they always think they could found their own company. Probably never will, but they think they can. So they always have in the back of their mind like, hey, if I was gonna be a CEO or build my own company, who would be my top choices to be a VP of Sales? And then step 3, ask other founders and friends who their top 3 to 5 choices are gonna be. So obviously there's a lot of collaboration and camaraderie amongst the, certainly the early-stage founders in the Valley, certainly as San Francisco has become the sort of nexus point of startups, not just for people in the States, but people coming from overseas as they They talk, you know, they share stories. And what you should also do is share these, these sort of lists, because a lot of them have probably done this search fairly recently, and say, hey, who was your top 3 to 5 choices? And even if you don't think you can hire them, you should always, always try. You should always try and engage with the people that you think are the top candidates for your company or your search, because You never know. So, yep. So again, in parallel to all these other things, pick an executive search firm that specializes in sales leadership searches and is not going to be so big that they can't give you the attention you deserve. So there's some great smaller and boutique executive search firms. In the Valley, Cole Group, Matt Strand and Jamie, Jamie Talotta Green at Cole Group, great. You look at like Diversa Partners with Bill Beer and the team there is also fantastic. And then I know that Jenny has some recommendations as well.

Yeah, we've worked with Aravina. They're actually based out of the UK but have a San Francisco office. They've helped me hire several of my directors and we've hired a couple of VP. As well. It's their boutique. They're awesome. They'll work with you on what are the leading indicators for success, what's the minimum criteria. They'll help you with references, back channels. They seem to have a pretty good handle on the market in terms of where the talent is. They found talent for me in Austin, in San Mateo, and also Ann Arbor, Michigan.

Step 5: Look for in-house solutions. So, As I've been in this business longer and longer, certainly there is a mindset for a startup or a founder or CEO to just make the hire. Like, hey, you may not have the perfect candidate. You may not have anyone that you would hire on your best day, but just make the hire. And hire fast, fire fast, et cetera, et cetera. But reality is that can actually cause a lot of harm and damage to the company, the least of which is you're going to potentially commit a year to somebody that shouldn't be your VP of Sales. But you can also take a Director of Sales or Head of Sales in the company that maybe is doing great work for you. Maybe you don't think they are the future of sales leadership in your company. Maybe you're not sure if they can become a VP of Sales yet. But the reality is, if you have something working, and the reality is, is if you're gonna hire a VP of Sales, something probably is working. You've found some formula, some product market fit, some growth to justify making that hire. Look long and hard at that internal candidate and say, is that a better person to lead us in the short term than make a hire out of expediency, make a hire that's a stretch fit for you. And I would pursue that track in parallel to everything else you do. And I think it's often bringing in a VP of Sales that's a non-fit topping your head of sales, maybe your founding head of sales or director of sales, often ends up having negative impact on the company. So, so step 6 is check the boxes. So, and this is all fairly standard stuff, but it's It's stuff that you have to do, which is, is this somebody that can support your current and next two stages of growth as a company? Are they comfortable running deals and hiring reps to support what you sell, whether that's sort of deal size, space, industry, vertical, et cetera? Do they have a list of people that they would hire when they come in as the VP of sales? I'm huge on this. Not everybody else is, but this is critical. Critical for me because one of my first sales jobs, I worked for a VP of Sales that had this phenomenal resume, and he was always asking me for referrals. And I said, why doesn't anybody want to come work for you? Right? Like, why does nobody that worked for you in the past want to work for you again? And so I think that's an indicator of what type of, you know, what type of leader that person is. Do people want to follow them? Do people want to work with them again? And then I would ask for the list. I don't think there's anything wrong with that as long as you're not, you know, randomly reaching out to those people. But audit that list of 5 and make sure they're fit for what you want to do. Step 7, if you get your A, you got to pay. It's not cheap, right? You talked about that list of 30 in the beginning. The odds are stacked. Long against you being able to hire any of them. But if you do get them, you're not going to be able to get them on the cheap because they have options. Not just options for other companies and VP of Sales and CRO roles, but they have options to consult that are lucrative. And they're not going to reach, right? They're not going to reach unless everything is just right for that opportunity. And that includes your company, you as a founder, are they a fit with you? Are you a fit with them, but also the comp and the equity and ownership. And I've seen a lot of times where a founder or CEO says, I don't want to pay that, right? And there are limits, right? I've seen some people get paid stuff that's just, you know, how could you ask for that, you know? And they said, well, they were willing to pay it, you know? So, but Jason knows what I'm talking about. So people that I have significantly more experience with where I'm embarrassed, like, wow, how could you possibly ask for that much money? But I think equity as well. And I think equity, if a VP of Sales candidate or a CRO is passionate about the equity stake, that they want or that they wanna get, I think that's a good sign 'cause that indicates their level of confidence that they can deliver for the company versus maybe a candidate that doesn't care about the equity and cares about the comp, especially when they want that comp to be heavily weighted towards the base. That can be a red flag.

[Speaker] So I put together, you know, if you've got this pool of candidates and you're going through the interview process, like what should matter to you? I think first and foremost is a track record of success. So past performance, past success, you know, you can predict future success by it. But like Brendan said, super important to make sure that stages are matched up and you understand, am I looking for a builder, a multiplier? Am I in startup mode, growth mode, scale mode? And to make sure you find someone that can do or that has done at least two of those modes before. I think almost more importantly is someone who's collaborative, and I believe they should be interviewing you for it as well. And if they're not, you should be worried. I interviewed Duo for it. It was one of the three reasons I left where I was at and came to Duo. It was super important to me to be part of something that was collaborative. I think a lot of companies say they are, but it's not until you're actually there that you can see if they told you the truth. So it's a little bit of a leap of faith, but there are ways for them to interview you for it and for you to interview them. One of the reasons I think it's so important is at some point you're gonna miss. You're gonna miss your quarter. And, you know, do you want sales and marketing pointing their fingers at each other? In past lives, I've been part of organizations where there's a miss, the CEO brings has leaders from marketing, has leaders from sales in a room, and marketing will stand up and do a PowerPoint and show the CEO all the reasons why sales sucks. And then sales gets up and shows the CEO all the reasons why the leads were shit for marketing. Let me tell you, people don't do their best work when that happens. And there's a lot of companies out there that are political. They finger point and it's just about them. So let me tell you a story. I'm at Duo, and our SDR org and our marketing org work together. One of their goals was, how do we get more out of MQLs? And MQLs are leads coming into the system, right? So leads are like dripping ice cream cones. You wanna get to them fast, and you wanna get to them well. So, they actually worked together to come up with a new way for us to get to customers and prospects right away. High-quality touch, high-quality reach-out. And from that partnership, we went from an average of 3.7 days from when a lead came in the door to setting up a meeting with a rep to 1.4 days. So those teams don't just come up with that out of nowhere. They come up with it because they're rowing in the same boat. Going after the same goal, right? It's, it's about partnership. When you're going from growth to scale mode, it's about small iterative changes. So you don't need 10 genius ideas to move the business forward every month because that's what you need in startup mode. Growth to scale mode is we're scaling out this SDR org. So the machine's already built, but it's not about being stagnant, right? It's about making small changes. And so this one small change allowed us to go from almost 4 days to 1.7 days of getting in front of a customer. Like, super proud of them. They're from completely different groups within the company, but a great example of how collaboration is supported at Duo and how much that matters. 3, culture of success. Culture of success is when lots of reps are hitting their number. I've got a number in my head. You know, we wanna have between 50 to 70% of reps hitting their number. Now you know there's orgs and boards and leadership teams that put together plans where only 20% of the reps hit their number. That is not fun to manage. And you can even have comp plans put together where the VP of the VP hits his number and none of his people hit theirs. Do you think people rally behind that guy? No. But that's a philosophy and that's how some people operate. So I think you wanna find someone who believes in a culture of success, has a benchmark in their head, like what does that actually mean for the reps? And that means that if the number was set too low in the beginning part of the year, that that VP's gonna raise it halfway through the year and they're gonna take care of their reps. And on the flip side, if it was set a little too high, that'll get adjusted as well and his or her reps will be taken care of too. And then fourth is servant leadership. So servant leadership I think is thrown around a lot. I think a lot of people have different definitions as to what it means. This is what it means to me. So as—

I thought it meant the opposite of what you think it is. Oh, okay. Or what you said it was.

He was like, what is servant leadership? I'm like, I don't know if this is a joke or not. And he really didn't know. So you're the first person I've met who didn't know, by the way.

Thank you.

So this VP of sales, the leadership team is gonna demand, the org is gonna demand a lot from this VP of sales. Meetings to reports to meetings to more reporting. And all that's super important to the organization. But you really wanna find someone that at the end of the day knows that reporting up isn't gonna make the number. Get bigger. You wanna find someone who believes where, when he or she has to make a decision, my team or sending a report up, that they choose the team. They choose to invest in their team. Now, yes, you want them to be effective and efficient at reporting up and attending meetings, 'cause that's all super important. But what I found to be really successful is that person that actually just serves their team. Like, that's the number one priority. And then the last piece is keeping the bar high. It's easy to find B players and you're in a rush and you feel like this is better than no one. And let me tell you, like, that's not the way to go. I've made those mistakes and paid for them dearly. It's important to keep the bar high. And even if you get up until the very end where you have an A player and they've just done great and you're so excited, and you're at the offer stage and they start playing coy, just walk away. Like, it just isn't worth it. I've done that several times as well and it's either probably some of the best decisions I've made. So keeping the bar high when you hire this person and you want them to feel like that too because then they will teach and train all of their leaders to hire awesome people for you. And then obviously you go through all these interviews, the only one that really matters is the back channel. I don't know how many of you have gotten to OfferStage before and you've done references that they've given you. You're super excited and you call the back channel. They're like, "She's a liar." It's like, "Whoa, whoa, like I didn't pick up on that." We've hired some reps that we thought were rock stars until we got to the end. And the back channel's like, "Nope, big integrity issues." And they've saved my ass a few times. Back channels. Super, super important. Have a solid recruiting team that knows how to get them, knows how to get them in the right way without getting anyone in trouble. And do those calls yourself. And then lastly, advice for other women in tech who want to be leaders. So where are my girls at? Got, got a few here. All right. All right. So this is really for women, and it's also for people people who are early career who want to be leaders. So number 1, jump in before you believe you're ready. Number 2, I think this is super important. We all get really busy. We expect a lot from people, but remember to say thank you. It goes a long way. 3, this is something that I learned, probably, I probably, it was my biggest learning at Duo is to assume positive intent. 'Cause you're gonna get that email from the VP of marketing that signed you up for another conference the last week of the quarter, and you're like, "What a doofus. Why is he doing this?" And it's actually like, it's a really important thing that you can learn to pause, and before you have a negative reaction, you have to assume positive intent. Like we're all in this same boat rowing together. We're all trying to do big things for the organization and hit the same goals. So to pick up the phone and have a conversation, like assuming positive intent, I think takes you a really, really long way. And then I firmly believe the most important people in an organization are the doers. Like thank them and invest in them. They're the ones that matter. You treat them like anything else and you won't be successful. Care about the people around you. It's not just about hitting the number and you'll be surprised at what you get. Get back. And then almost last, and you can see that this is just about last, if you want to do big things at a company, you need to hit your number. And you notice that that wasn't first because I believe if you do these other things, the number takes care of itself. And then finally, I've got this big sign in my house actually that says, "Always hustle." And I teach my kids that and I teach my team that. I think hustling is super important. So I just wanted to end with some pieces of advice for people who, you know, want to do big things at their company or go big places.

Yeah. I'll want to add there is obviously the kind of bro culture of Silicon Valley has come into, you know, a lot of discussion of late. And certainly Jason M. Lemkin and myself have thought a lot about it. How do you change that? Like in your own world or your own experience. And I'm a big believer that you got to start early as a company, right? I think when you, you know, your first 10 sales hires are guys, it's going to be tough to diversify from there because there tends to be sort of a network effect of how you hire. And I think moving outside your comfort zone early on, and obviously you want to hire the best possible people for the job, but I think you have to force yourself to get out of your comfort zone and be more diverse in the people that you're talking to and interviewing and trying to have a diverse team because there's the benefits as a company over the long haul are probably too many to even, to even count. And the potential consequences of not doing it can be as dire as we've seen. In the last few days. So, yeah. So I think that's that. We were going to show a YouTube clip, but I don't think we can. So I think let's jump into some questions. Thank you, by the way. Sure.

[FOREIGN LANGUAGE] Yeah, so most companies have one inside sales hub for a lot of reasons. Like, you want— they're generally early career. You want their managers with them. I actually have one out of Ann Arbor, one out of Austin, and one out of San Mateo. A total of about 80 people. You know, one of the things One of the risks with 3 inside sales hubs is people start doing their own thing, right? They have their own process, they have their different way to communicate, they're running their teams their own way. Um, but we thought it was really important to have something in Ann Arbor. So we have something at headquarters in the Midwest. We've been able to find just super smart college grads, bring them into the SDR program and quickly move them up to into the SMB org. In fact, when I look at my performers across SMB, the ones that came in through the SDR org, like hands down the most successful people, right? You already know that they're a culture fit. You're sure of the competence fit, and they ramp 600% more quickly than bringing someone from the outside. Now we have, you know, an office also in San Mateo, have an awesome solid team there. We decided to open an office in Austin because we couldn't find the talent fast enough in Ann Arbor. And Austin, what's cool about Austin is you've got all these other SaaS companies to pull from. So if you look at a track record of success, you can find reps that have a track record of success there. You don't have high ego issues where you may find elsewhere. Here.

Sort of like, like Silicon Valley. Okay.

And you don't have the loyalty issues you may find other places where it's just about job hopping and doing the next best thing. I love just kind of the like culture that we're building there, the types of people. In fact, that'll probably be our biggest inside sales hub going forward. So it's really fun to have 3 offices and it's a heck of a lot of work to make sure that the teams are in sync and doing the right thing. But so far I think we've made the right decision.

Great. Am I asking the questions? Okay. I guess I'll ask you this first question, which is, should a VP of sales be your first sales hire and why?

I mean, no, I would have reps first to show that your stuff works, that customers are interested, that prospects are interested. You're gonna find a couple amazing reps and you're a startup and you're gonna hire for aptitude at first. So I would start with reps and to make sure that you can figure some of this out. And as you get going, I'd hire a VP of sales. Like I have an opinion, it should be between 8 to 10 in ARR. If you want a really solid VP of sales, they're gonna wanna come in. They don't want it to be too scrappy and they don't want it to be too far ahead. And so I would definitely start with a few reps to get some of the kinks out and make sure that your product is awesome and people want to buy it.

How do you see sales and customer success working together and which comes first, assuming early sales are founder-led? Should I answer that one? I mean, obviously very closely. You're typically— a lot of people have a different definition of what is customer success. Customer success. Some people view it as an extension of sales, sort of an upsell type role, and other people view it as more support-heavy. Um, I'm a pretty firm believer that you want customer success focused on success and successful onboarding of the customer and sort of day-to-day management of the customer's experience. A lot of companies are moving towards this account management model, which I believe is going to be more, more risk for churn-centric environment. But your VP of Sales and your VP of Customer Success, when you have them in, should be tied pretty closely together. And certainly in my experience, they were— that's always been a great partner for me, and I think sort of vice versa. So just as you want your VP of Sales and VP of Marketing are going to work incredibly close together, you want your sales and success teams to be very tightly aligned.

Okay. How important is it to have a sales playbook created and marketing collateral available before bringing on your first sales hire? I mean, I don't think it's important. I'm a big fan of being a doer, like action. I'm not a big fan of like lots of meetings and plannings and PowerPoints and playbooks because by the time you put all that together, like your business has changed, right? So like bring in reps, have them learn to sell the hell out of what you have. And then document best practices.

Yeah, I mean, as far as collateral content, you know, from a marketing standpoint, that's where I'm least interested in marketing spending their time. So certainly focusing on sort of demand gen, MQLs, etc., is what I want from my VP of Marketing, and I'm happy to create the content and collateral collateral myself most times, and typically it's better than marketing, although, you know, it's just my opinion.

So I think that's all the time we have. Thanks, you guys.