Aug 25, 2022 · 55m · saastr
The Answers To Scaling, Hiring, And Everything Else: An AMA With Saastr Founder & Ceo Jason Lemkin
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this wide-ranging SaaStr AMA session, founder and CEO Jason Lemkin delivers practical, data-driven counsel on navigating venture downturns, scaling enterprise go-to-market motions, and executing disciplined hiring. He demystifies common startup clichés, emphasizing that long-term SaaS success depends on relentless customer focus, operational persistence, and systematic organizational scaling.
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 92.5% of the talking time here. How this is scored →
Jason as informed peer 8.2 Guest teaching 0.1 Guest disagreement 0.6 Jason pushing back 3.0
speaking balance: gold is Jason, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 46:43 Audience member pushes back on two-AE hiring rule
The audience member explicitly questions Jason's core recommendation, citing their own experience hiring a VP of sales with only one quota-hitting rep.
Hardest push from Jason ▶ 17:51 Jason rejects chasing macro megatrendsJason immediately rejects the premise of chasing futuristic megatrends, reframing the discussion toward practical margin improvements and enterprise targeting.
Biggest teaching moment ▶ 45:16 Jason acknowledges lack of marketplace domain expertiseJason candidly admits that he is not a marketplace expert and does not find the mechanics of two-sided network businesses compelling.
Jason holds their own ▶ 33:00 Jason dismantles the fantasy of stepping away from founder-led salesJason emphatically dismantles the myth that hiring a sales leader frees up founder time, explaining why founders must stay in the co-pilot seat to prevent sales collapse.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Jason as informed peer | Guest teaching | Guest disagreement | Jason pushing back | Why |
|---|---|---|---|---|---|---|
| Open AMA Kickoff and Learning from Public SaaS | 8 | 1 | 0 | 1 | Jason sets up the open AMA format, acknowledging that everyone is still learning while detailing granular operational metrics from recent public SaaS filings like ZoomInfo. | |
| The Valuation Freeze and Venture Capital Landscape | 9 | 0 | 1 | 4 | Jason pushes back on the panic surrounding a SaaS buying collapse, dissecting the exact mechanics of crossover funds, late-stage growth freezes, and VC portfolio triage. | |
| Advice to a Younger Self on Impatience and Compounding | 7 | 0 | 0 | 2 | Jason pivots the audience question on youthful advice into a strategic philosophy on patience, compounding returns, and long-horizon persistence like UiPath's decade-long journey. | |
| The Realities of SaaS Hiring and Talent Availability | 8 | 0 | 0 | 2 | Jason explains why tech layoffs rarely yield tier-one startup talent and rejects founder complaints about recruiting difficulty by citing historical talent scarcity. | |
| Deconstructing Vitamins Versus Painkillers in Enterprise SaaS | 8 | 0 | 1 | 4 | Jason deconstructs the cliché VC dichotomy of vitamins versus painkillers, demonstrating how foundational giants like Salesforce originated with simple, basic point features. | |
| Navigating Macro Trends, Upmarket Shifts, and Gross Margins | 9 | 0 | 1 | 5 | Jason dismisses speculative 'megatrend' hunting in favor of actionable tactics, advising startups to move upmarket to enterprise budgets and optimize gross margins. | |
| The Permanent Shift to Remote and Hybrid Work | 7 | 0 | 0 | 2 | Jason provides an on-the-ground analysis of commercial real estate dynamics in San Francisco versus Europe, explaining the permanent reality of distributed engineering teams. | |
| Competing and Differentiating in Crowded SaaS Sectors | 8 | 0 | 1 | 4 | Jason challenges the premise that crowded markets are disadvantageous, arguing crowded categories prove budget availability and reward focused 10x point features. | |
| Finding High-Impact Mentors and Avoiding Mediocrity | 8 | 0 | 0 | 2 | Jason warns against the negative ROI of mediocre executive coaches, outlining a structured framework for securing both near-term and long-term operating mentors. | |
| Strategies to Overcome Enterprise Budget Freezes | 9 | 0 | 1 | 5 | Jason provides concrete playbook tactics for multi-threading stalled enterprise deals before delivering an impassioned breakdown of why founders must remain active co-sellers. | |
| Aligning Marketing Expectations with Early Product Realities | 8 | 0 | 1 | 4 | Jason reframes an audience member's worry about marketing outpacing product fidelity into an asset, illustrating how forward-looking messaging reveals market demand. | |
| The SaaStr Europa Vision and Commitment to Diversity | 8 | 0 | 0 | 1 | Jason transparently reviews SaaStr Europa's financial metrics and speaker policies, urging the audience to actively drive diverse attendee representation. | |
| Applying SaaS Principles to B2B Marketplaces | 9 | 0 | 3 | 4 | An audience member questions Jason's requirement of having two quota-hitting reps before hiring a VP. Jason vigorously defends the rule to prevent the 'magician rep' fallacy. | |
| Hiring Early Account Executives and Final AMA Takeaways | 9 | 0 | 0 | 2 | Jason closes the session with foundational criteria for early AE hiring, mandating that founders must personally want to buy from their first reps before relinquishing control. |
Statements from this episode (27)
Lemkin: Founders must recruit superior talent and stay curious to remain CEO
“One, if you can recruit people better than you should still be the CEO, and two, I think you have to have a curious mind.”
Lemkin: ZoomInfo did not segment its sales team until $80M ARR
“Henry Sane, he segmented his sales team at eighty million in ARR”
Lemkin: ZoomInfo generates only 11% of its revenue internationally
“The fact that there's still only 11% international today, and why?”
Lemkin: Crossover funds and $1B+ late-stage tech rounds are completely frozen
“Crossover ventures it is, they're investing zero percent in the private market. All that money's gone at the top, okay? Then there's different types of growth, late growth and growth. Anything north of a billion is frozen.”
Lemkin: Seed-stage VC deal activity has dropped by half
“At the early seed stage, I would say folks are about half as active as they were 60 days ago.”
Lemkin: Target newer VC funds without troubled legacy portfolio baggage
“An insider tip, if you are fundraising, figure out, now's a good time from new funds and newer VCs that have less Baggage.”
Lemkin: UiPath took 10 years to reach $1M in revenue
“UiPath took 10 years to get to one million in revenue. 10 years to get one million.”
Lemkin: Single-digit tech layoffs do not solve SaaS hiring shortages
“The problem with small layoffs. Like if you lay off a small number of people, a lot of them are not the best people. So great. Like some company lays off four percent, like there are gems there and go find the gems and hire them. There really are gems in every…”
Lemkin: Hiring is better today because experienced SaaS talent actually exists
“Cry me a river that a hundred people want to hire your VP, but at least she exists. Like it's actually better today because the people exist, okay? It is better than it has ever been. And of course it's competitive because there's more startups than ever, but …”
Lemkin: Early Salesforce was a rudimentary SMB app with four tabs
“Salesforce was a very rudimentary SMB app for a brief period of time, but it was. It sold to very small companies. It didn't even have custom tabs. It just had four tabs out of the box, and even compared to, like, where Pipedrive was in 2013, it did less. It w…”
Lemkin: Startups succeed through 10x features, not immediate enterprise indispensability
“We all just really start with a 10 X feature. One little thing that matters to a buyer that someone else doesn't do or ignores or doesn't have time to do anymore. That's what matters, not, not immediately building, being irreplaceable your first year. It's not…”
Lemkin: Cloud startups should accelerate moving upmarket to enterprise
“So much of the money is going into bigger enterprises today in cloud that it's a good conservative bet to go to accelerate that six or nine months in your product roadmap. Go a little more enterprise now where there's less sensitivity, less volatility.”
Lemkin: Low-margin software and fintech businesses will remain out of favor
“It's gonna be a long time until folks are comfortable with lower quality revenue again, and what I mean is fintechs with 20% margins companies, you know, folks with huge, with, even, even folks like Twilio, one of the best companies in the history of, Cloud an…”
Lemkin: Brex and Ramp have 20-30% margins while Payhawk has 70%
“Brex is amazing in the US. Ramp is amazing, but those are like, 30%, 20% gross margin products. These guys, and probably others, are 70%.”
Lemkin: Classic SF SaaS Companies Will Never Get Workers Back into Offices
“We're never not going to be distributed, right? We have learned these skills the hard way, And we're all global, and it's never going back, and there may be segments that go back fully to the office, and certainly in places like London and Europe, it's more co…”
Lemkin: Crowded SaaS markets signal ample budget for single-feature products
“Crowded space means there's a lot of buyers and there's a lot of money. Crowded space means that, crowded space also means you don't have to do everything. You don't have to do every single function to still get a customer.”
Lemkin: Gong out-executed Chorus despite similar initial technology
“There was a couple years where they both were these point solutions for listening to your sales teams, and they were both great, but Gong out executed Chorus, even though, in his opinion, the tech was similar.”
Lemkin: Marketing rarely outweighs product before $10M to $30M in revenue
“There becomes these parody things where marketing is more important than product, but it, it's pretty uncommon, but before 10, 20, thirty million in revenue, and sometimes a lot later, so.”
Lemkin: Top potential mentors avoid mentoring while mediocre ones pursue it
“The best ones don't really want to be mentors anymore, and the mediocre ones want to be mentors, right?”
Lemkin: Top 20% of SaaS customers grow faster despite budget freezes
“A lot of SaaS companies are seeing 20% of their companies have freezes, but the top 20% are growing faster than ever. So instead of whining about the freezes, go hunt the 20% that aren't frozen.”
Lemkin: Hiring a sales head gives the founder zero time back
“When you hire a VP of sales or director or whatever, head of sales, this is how many minutes you get back in your day. Zero. Now. Now. What does happen is if they're any good, they re, they rework your calendar. Instead of the CEO being the opener, and the mid…”
Lemkin: Do not hire a VP of Sales before two reps hit quota
“Get two AEs that hit quota. One's not enough. If it's one, you don't know why. If it's one, the VP of sales doesn't know why. If it's two, the VP of sales is a hiring job mainly. If you have two hitting quota and the VP of sales is good, even if they're new, e…”
Lemkin: A startup's marketing website should be better than its product
“Your marketing site should be better than your product. It should be prettier. It should work well. It does, you don't have to write a lot of code on your marketing site, ok?”
Lemkin: EchoSign listed 20 fake integrations to gauge demand before building
“When we launched back in the, Adobe Sign, he put 20 integrations on our marketing site, of which we did none. Now other people do this. He's like, well, I'm not sure people want a Salesforce integration back then, but I'll make a page that says we have it, and…”
Lemkin: Go-to-market motions are dictated by ACV rather than product features
“If there is any genius in Sastra that's now 10 years old, it's abstracting product away from the fact that our go-to-market motions are pretty much the same at an ACV. Like, it sounds obviously, but 10 years ago, it's like, it was really disruptive that, hey, …”