Sep 19, 2019 · 34m · saastr
How to Hire a Great VP of Sales with SaaStr + Duo Security
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
SaaStr and sales veterans Brendan Cassidy and Jennifer Lawrence present a practical playbook on how startups can successfully source, vet, and hire a high-impact VP of Sales. The session covers tactical recruiting methods, candidate stage-fit evaluation, compensation models, and strategies to avoid costly hiring mistakes.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Jason holds 2.7% of the talking time here. How this is scored →
Jason as informed peer 0.0 Guest teaching 0.0 Guest disagreement 1.0 Jason pushing back 0.0
speaking balance: gold is Jason, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 30:45 Firm rejection of VP of Sales as first hire
Jennifer immediately rejects the premise of the audience question, stating that founders must hire individual reps first rather than bringing in a VP of Sales prematurely.
Hardest push from Jason ▶ 0:21 Host framing on hiring difficultiesJason introduces the session by highlighting how founders consistently struggle with VP of Sales hiring before handing over the stage.
Biggest teaching moment ▶ 5:32 Deconstructing big-company sales leadersJennifer breaks down why hiring a polished VP from Salesforce often backfires, educating founders on the distinction between executing an established playbook and building one.
Jason holds their own ▶ 0:45 Host domain authority introductionJason references SaaStr's extensive catalog of over 3,000 articles on SaaS sales leadership to establish the foundational context of the presentation.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Jason as informed peer | Guest teaching | Guest disagreement | Jason pushing back | Why |
|---|---|---|---|---|---|---|
| The Reality and High Failure Rate of VP Sales Hiring | 0 | 0 | 1 | 0 | Brendan Cassidy delivers a monologue outlining the grim reality and 80% failure rate of early VP of Sales hires. Host Jason Lemkin is offstage, resulting in zero host participation. | |
| Step 1: Leveraging Strategic Coaches and Operational Advisors | 0 | 0 | 1 | 0 | Brendan and Jennifer detail the strategy of recruiting seasoned advisory coaches and warn against hiring big-company executives who only know how to run pre-existing playbooks. The host is not involved. | |
| Session Formatting and Audience Interaction Note | 0 | 0 | 0 | 0 | An audience member asks about mirroring the screen, after which Brendan explains how to leverage founder networks and peers for candidate recommendations. No host involvement. | |
| Step 4: Partnering with Specialized Boutique Search Firms | 0 | 0 | 1 | 0 | Jennifer and Brendan advocate for boutique executive search firms over generalist recruiters and suggest evaluating internal promotions over rushed external hires. | |
| Step 6: Vetting Stage Fit and Candidate Followership | 0 | 0 | 1 | 0 | Brendan highlights the necessity of vetting candidate followership and paying top-of-market compensation/equity for proven A-players. | |
| Essential Candidate Traits: Stage Fit, Collaboration, and Culture | 0 | 0 | 2 | 0 | Jennifer outlines key interview criteria including collaboration, quota distribution, and servant leadership, playfully teasing Brendan when he admits he didn't know the term. | |
| Conducting Rigorous Backchannel Reference Checks | 0 | 0 | 1 | 0 | Jennifer underscores the critical importance of backchannel reference checks and shares leadership advice for women in tech, with Brendan adding comments on proactive diversity hiring. | |
| Building and Managing Multi-Hub Inside Sales Teams | 0 | 0 | 1 | 0 | Jennifer explains Duo Security's strategy of establishing inside sales hubs in Ann Arbor, Austin, and San Mateo, contrasting Midwest and Austin culture against Silicon Valley egos. | |
| Q&A: Reps Versus VP of Sales as the First Sales Hire | 0 | 0 | 1 | 0 | In the Slido Q&A portion, Jennifer firmly rejects hiring a VP of Sales before hiring initial individual contributor reps, and Brendan discusses alignment between sales and customer success. | |
| Q&A: Playbook Necessity and Session Conclusion | 0 | 0 | 1 | 0 | Jennifer and Brendan dismiss the need for elaborate playbooks and heavy marketing collateral early on, emphasizing biased action and rep-driven learnings. |
Statements from this episode (20)
Cassidy: Only ~30 VPs of Sales have scaled SaaS to $50M ARR
“I sort of ballpark it at about 30, 30 VPs of sales or CROs have taken their SaaS companies to fifty 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, ah, yo…”
Cassidy: 80% of startups lose their first sales VP in year one
“I would guess probably eight in 10 startups probably fire or lose their first VP of sales inside of a year.”
Cassidy: Large advisory boards fail to provide founders with distilled feedback
“What most companies do is they hire these huge advisory boards. Sometimes 1015, 20 people, of which you're not gonna get a lot of distilled feedback.”
Lawrence: Startups must hire sales leaders who build playbooks, not just execute them
“When you're in startup mode, startup going to growth, and even growth mode going to scale, you want to find someone who knows how to actually figure things out. Not execute on a playbook that's been given to them.”
Cassidy: Top VPs of Sales Always Maintain a List of Peer Favorites
“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 reached, when I wrote a blog about the top five VP of sales and tech that are women, she …”
Cassidy advises startups to choose specialized boutique firms over large recruiters
“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 they deserve.”
Cassidy: VP of Sales candidate followership is a key indicator of leadership
“Do they have a list of people that they would hire when they came in as the, come in as the VP of sales? I'm huge on this, not everybody else is, but this is critical for me because one of my first sales jobs, I worked for a VP of sales that had this phenomena…”
Cassidy: Sales leaders prioritizing equity over base salary signal higher confidence
“Equity, if a VP of sales candidate or a CRO wants, is passionate about the equity stake that they want, or that they want to get, I think that's a good sign, because that indicates their level of confidence that they can deliver for the company, versus maybe a…”
Lawrence: Hire a VP of Sales with experience in at least two stages
“And to make sure you find someone that can do or that has done at least two of those modes before.”
Lawrence: Duo cut inbound lead response time from 3.7 to 1.4 days
“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.”
Lawrence: Sales organizations should target 50% to 70% quota attainment
“Culture of success is when lots of reps are hitting their number. I've got a number in my head, you know, we want to have between 50 to 70% of reps hitting their number.”
Lawrence: Walk away from top candidates who play coy at offer stage
“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.”
Lawrence: Backchannel references are the only executive interviews that truly matter
“And then obviously, you go through all these interviews, the only one that really matters is the back channel.”
Cassidy: Early all-male sales hiring creates network effects blocking later diversity
“I think when 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 …”
Lawrence: Promoted SDRs ramp 600% faster than external SMB sales hires
“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 th…”
Lawrence: Startups should hire sales reps before hiring a VP of Sales
“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 …”
Lawrence: Hire a VP of Sales at $8M to $10M ARR
“Like, I have an opinion. It should be between eight to 10 in ARR. If you want a really solid VP of sales, they're gonna want to come in. They don't want it to be too scrappy, and they don't want it to be too far ahead”
Cassidy: Shifting Customer Success to Account Management Increases Churn Risk
“A lot of companies are moving towards this account management model, which I believe is gonna be more, or, More risk for churn-centric environment”
Lawrence: Startups should hire sales reps before creating playbooks
“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? …”
Cassidy: Marketing should focus on demand gen over sales collateral
“As far as collateral and 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, et cetera, is what I want from my VP of marketing, and I'm happy t…”