Nov 30, 2021 · 1h 3m · saastr
Scaling a Successful SaaS Sales Team w/ 20VC Founder Harry Stebbings and SaaStr Founder Jason Lemkin
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In an in-depth conversation, SaaStr founder Jason Lemkin and 20VC host Harry Stebbings analyze the tactical playbooks for scaling SaaS sales teams, hiring elite executive talent, navigating changing venture capital dynamics, and overcoming founder burnout.
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 85.8% of the talking time here. How this is scored →
Jason as informed peer 8.1 Guest teaching 2.2 Guest disagreement 2.2 Jason pushing back 3.3
speaking balance: gold is Jason, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 59:32 Harry Dismisses Founder-Led Funds
Harry aggressively rejects founders raising outside capital for side funds, asserting that time trade-offs make no financial sense compared to company equity value.
Hardest push from Jason ▶ 44:45 Jason Rejects Notion that Boards Are IneffectiveWhen Harry calls board meetings useless and ineffective, Jason directly challenges the premise by detailing lead investor fiduciary duties and executive accountability.
Biggest teaching moment ▶ 32:00 Harry on Astronomical Revenue MultiplesHarry introduces recent market deal data showing a fifty-thousand MRR startup raising at hundreds of millions in valuation, reshaping the valuation discussion.
Jason holds their own ▶ 14:30 Jason Breaks Down 10X Sales Rep DNAJason demonstrates deep operational mastery by articulating why top early reps must possess ACV familiarity, buyer trust, and the agility to adapt playbooks dynamically.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Jason as informed peer | Guest teaching | Guest disagreement | Jason pushing back | Why |
|---|---|---|---|---|---|---|
| Jason Lemkin's Path from Founder to Venture Capitalist | 7 | 2 | 1 | 1 | Jason recounts his transition from early SaaS exits to angel investing and partner at Storm Ventures. The exchange is warm and introductory with Harry teeing up Jason to reflect on Decacorn founder commitment. | |
| Venture Ownership Strategy and Rise of Operator Funds | 8 | 2 | 2 | 3 | Jason details why double-digit ownership matters and explains how operator-led funds are altering early-stage cap tables. Harry agrees with Jason's critique of traditional VC value-add alignment. | |
| Capital Influx and Navigating Startup Overfunding Risks | 8 | 3 | 3 | 6 | Harry raises the risk of overfunding early-stage startups, but Jason pushes back, arguing that great VPs know how to spend capital prudently while mediocre hires cause burn issues. | |
| Establishing Early Sales Foundations: Founders Versus Reps | 8 | 1 | 1 | 2 | Jason explains the playbook of founder-led sales versus hiring early reps, citing examples like Talkdesk and Algolia. Harry listens and seeks guidance on whether to hire a sales VP or individual reps first. | |
| Identifying and Hiring Early 10X Sales Talent | 9 | 1 | 1 | 2 | Jason provides an actionable hiring framework for early sales reps, highlighting ACV alignment and adaptability. Harry acts as an attentive interviewer validating Jason's insights. | |
| Setting Sales Quotas and Enterprise Sales Realities | 9 | 2 | 2 | 2 | Jason breaks down quota construction from early-stage compensation boosts to scaled enterprise multiples. He explains why enterprise founders inevitably remain acting heads of sales until reaching ten million in ARR. | |
| Addressing Founder Dependency and Combating Executive Burnout | 8 | 2 | 2 | 3 | Harry asks about founder burnout and dependency, prompting Jason to discuss finding key VPs who shoulder emotional weight. Jason clarifies that founders cannot expect every executive to act like an owner. | |
| Valuation Multiples, Secondary Exits, and Seed Disruption | 8 | 4 | 3 | 4 | Harry shares anecdotes on extreme revenue multiples and questions the existence of pre-seed rounds. Jason reframes the discussion around non-privileged founders and the disruption of traditional seed fund fund economics. | |
| Multi-Stage Seed Term Sheets and Lead Investor Dynamics | 8 | 3 | 3 | 4 | Jason analyzes how multi-stage funds writing seed checks change investor pressure and signaling risk. The two banter over light-touch investing versus lead investor obligations as fund sizes swell. | |
| The Value and Operational Rigor of Board Meetings | 9 | 2 | 3 | 6 | Harry calls board meetings largely useless, but Jason firmly disagrees, laying out the fiduciary requirements of lead investors and the accountability decks create for executive teams. | |
| Quick-Fire on Outbound Tactics, Remote Investing, and Funds | 8 | 3 | 4 | 5 | In a quick-fire round, Jason breaks down outbound sales shifts, remote dealmaking friction, and counterarguments to Harry's strong skepticism regarding founders launching their own venture funds. | |
| Backing A-Plus Founders: Owner.com and Final Reflections | 7 | 1 | 1 | 1 | Jason details his conviction backing Owner.com due to an exceptional CEO and CTO tandem. Harry wraps up the episode with mutual appreciation. |
Statements from this episode (29)
Lemkin: Five of my first six venture investments became unicorns
“Like, you know, the first four investments eventually became unicorns, five out of the first six.”
Lemkin: Never invest in founders without a 20-year commitment to scale
“When you don't see that, my rule is, and I've made this mistake since, don't invest. No matter how much you love the founder, you can love them as humans. They can be doing very well. But if you don't have this crazy 20 year commitment to building something hu…”
Lemkin: All core portfolio holdings maintain double-digit ownership
“All of my core positions are double digit ownership largest investor in most of them, and that one puts you in a good position if you get a unicorn.”
Lemkin: Investors should maximize share allocation in winning startups
“When you meet a winner, when you meet a winner, you buy all the shares. Now, if you can buy a quarter of the company, you buy a quarter of the company. If you can buy two percent of the company, you buy two percent of the company. But you either buy all of the…”
Lemkin: Reduced VC collaboration is strictly better for founders
“Without question. And without question, it's better for founders. Without question. Every element of venture that is, and I'm being binary when it's off course more subtle than this, but every much of the collaboration in venture did not benefit founders, righ…”
Lemkin: Over 100 operator-led VC funds exceed $50M in size
“The craziest thing to me in venture is there are over a hundred founder and operator led funds of over fifty million.”
Lemkin: Mediocre VPs of Sales spend 100% of large capital reserves
“What does a mediocre VP of sales do if there's sixty million in the bank? They spend it all. They spend, the mediocre ones, a hundred percent of them spend it all.”
Lemkin blames CEOs lowering VP hiring bars for wasted startup capital
“The great marketers don't spend money on, on programs that don't perform, right? So I think this is true, but I blame the CEOs for lowering the bar on hiring for VPs.”
Lemkin: Talkdesk CEO Tiago Paiva was sole salesperson through $2M ARR
“He was the only salesperson through the first two million of revenue.”
Lemkin: Hiring a VP of Sales before two working AEs fails 80%
“If you don't have those two AEs and you hire a VP of sales, 80% of the time it doesn't work because there's nothing for them to work with, right?”
Lemkin: Great VPs of Sales now wait for $10M ARR or unicorns
“The ones that used to join at one million, they're all waiting for a ten million ARR startup today or a unicorn, whichever comes earlier, all of them.”
Lemkin: Startups must only hire early sales reps experienced at their ACV
“The toolkit is roughly the same for every startup at a given ACV, at a given price point. So make sure they've sold in cloud, in SaaS at your price point, ok? Otherwise, don't fall in love with them.”
Lemkin: 90% of sales reps run one static playbook; 10X reps adapt
“What makes them 10 X, and it took me a long time to figure this out, is that they can change their playbook. 90% of sales reps, and this works out the bigger you get. They sell exactly the same way.”
Lemkin: SaaS sales quotas at scale range from 3x to 5x OTE
“At scale, we end up at these three X, four X, five X numbers, right? Which is quotas are an SMB, usually three X, your full, your fully burdened comp, your on target earnings, your OT, up to five X in the enterprise.”
Lemkin: Long sales cycles stop hurting SaaS startups at $20M-$30M ARR
“Long sales cycles don't matter at scale north of 20, thirty million in revenue. You're lining up so many deals at the same time that long sales cycles don't matter because if you have a hundred deals in flight, it actually starts to happen very predictably, ri…”
Lemkin: Enterprise SaaS founders remain effective VP of Sales until $10M ARR
“I've found that in true enterprise, like real enterprise, the founder is often the VP of sales until ten million.”
Lemkin: SaaS companies must reinvent product and strategy every five years
“SaaS is good in that you don't have to change the product like every week, okay? You're not, it's not Clubhouse or TikTok, you know, the competition level is, it's visceral, but it's slower, but you do need to reinvent yourself every four to five years, right,…”
Lemkin: Only hiring founder-like VPs can save founders from burnout
“What bails you out of tiredness again and again, if you get bailed out, if you do, Is that magical VP that you find that is more than a VP. That is almost like a founder. Almost like a founder, right? And that is the only thing that has saved me over time. And…”
Lemkin: 100x ARR valuations require at least 5x next-year revenue growth
“Basically a hundred X ARR startup has to at least quintuple next year with high quality revenue, at least quintuple, right?”
Stebbings: Pedigreed tech founders can raise $5M at $20M without pre-seed
“I don't think pre-seed actually exists anymore, bluntly, for the majority well, not for the majority, but for a lot of founders, whereby if you come out of a top Facebook, Twitter, Datadog, Slack, you name it, you can raise, you know, three to five on 20 like …”
Lemkin: Traditional $50M seed fund model no longer works for pedigreed deals
“Does the traditional 50, sixty million dollar seed fund work? I don't, I think it doesn't work unless you go with anything that has any proof, any social proof, anything privileged, it doesn't work, right?”
Lemkin: Multi-stage seed without Series A preemption is a severe negative signal
“It's a huge signaling problem. Of course, if Sequoia or Accelerant recent or Lightspeed has two years of data and they don't preempt the A, of course it's a problem. Of course it's a bad signal.”
Lemkin: Multi-billion-dollar VC funds do not care about losing $20M checks
“The funds are so big, and they're raising funds every 12 months, right? In my, we have different portfolios. In my portfolios, when the multi-billion dollar funds have come in and led the A or the C, they're barely invested. They're, and you know what? They do…”
Lemkin: An active VC can lead at most five investments simultaneously
“How many active investments can you be number one in? And it might be five. Like the traditional, the old school metric for board seats was, it was supposed to be 10, ok, but when you started to run the place, it would be 20. Ok, if you go back and talk, when …”
Lemkin: Startup board meetings primarily serve as forcing functions for VPs
“Until you're big, until you're at 40, fifty million, when board meetings really are about money around the table, right? Until that phase, board meetings are at least 50% for your management team to present. There is nothing, few things more valuable to a CEO …”
Lemkin: Slide decks force better board meeting rigor than Notion
“The work you force your management team to put into those slides for each board meeting forces organization, self-discipline, reporting, goal analytics that otherwise they just don't bother to do in Notion. They don't do it. They just write a stream of conscio…”
Lemkin: Great outbound sales works better than ever while mediocre outbound declines
“Great outbound works better than ever, but mediocre outbound is still works, but it's declining in its efficacy.”
Lemkin: Enterprise SaaS reps no longer do first meetings in person
“COVID changed it in that we are, like, I don't know what you see in your portfolio, but all of the enterprise SaaS companies I've invested in and work with, they're all going back to face-to-face meetings.
Nick met on Gainsight's talking about it, they're all …”
Lemkin: Fifty active startup founders will raise nine-figure VC funds
“There's too many founders that are going to raise nine-figure funds while they're running their own startups.
And it used to be a bad sign for the startup, right?
And it used to be like, how could you do anything other than run your own startup?
But it doesn't…”