Jul 10, 2024 · 33m · saastr
Fundraising from VCs and Hiring VPs in 2025: AMA with Jason Lemkin SaaStr CEO
0:00 / 0:00
▶ Watch on YouTube →
gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this SaaStr AMA session, CEO Jason Lemkin delivers actionable guidance for B2B SaaS founders on navigating modern venture fundraising, evaluating executive VP candidates, aligning go-to-market strategies, and optimizing post-sale customer onboarding.
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 91.1% of the talking time here. How this is scored →
Jason as informed peer 8.2 Guest teaching 0.2 Guest disagreement 0.4 Jason pushing back 1.8
speaking balance: gold is Jason, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 24:04 Agency founder challenges blanket dismissal
Phil interjects directly to counter Lemkin's prior assertion that agencies flush founder money away, defending honest operators against unrealistic competitor promises.
Hardest push from Jason ▶ 8:00 Lemkin rejects VC mid-market adviceLemkin forcefully dismisses the conventional VC recommendation to pivot down-market, telling founders not to listen to investors who do not build the software.
Biggest teaching moment ▶ 24:04 Operator perspective on agency market dynamicsPhil educates Lemkin on the reality of running a transparent agency competing against predatory firms promising AI magic and overnight product-market fit.
Jason holds their own ▶ 11:45 Lemkin exposes low-margin revenue restatementsLemkin demonstrates deep financial sophistication by explaining how zero-margin pass-through revenue artificially inflates ARR until board-level reconciliations enforce steep restatements.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Jason as informed peer | Guest teaching | Guest disagreement | Jason pushing back | Why |
|---|---|---|---|---|---|---|
| Fundraising Advice for Early-Stage High-Growth Startups | 8 | 0 | 0 | 2 | Lemkin delivers an extensive breakdown of executive hiring heuristics, illustrating his point with specific historical anecdotes from SAP, Gong, and early SaaS practices. The audience members ask straightforward questions without any confrontation. | |
| Balancing Product-Led Growth and Enterprise Sales Strategies | 9 | 0 | 1 | 4 | Lemkin provides detailed industry context from WebEx in 1998 to modern SaaS models, introducing his 40/40/20 customer segmentation exercise. He explicitly pushes back against the advice founders often receive from VCs to pivot down-market. | |
| Investor Multiples and Blended Gross Margin Transparency | 9 | 0 | 0 | 1 | Lemkin details public market SaaS multiples across cycles, citing Twilio, Shopify, Toast, and a personal portfolio example where blended non-software revenue had to be restated downward. The guest asks for guidance on gross margin optics in an open manner. | |
| Macro Predictions and Practical B2B AI Implementation | 7 | 0 | 0 | 1 | Lemkin openly acknowledges losing an $80k prediction bet on tech IPOs before giving practical guidance on tactical B2B AI workflow improvements versus consumer generative AI hype. | |
| Evaluating Marketing Agencies and Outbound Lead Generation Pitfalls | 8 | 0 | 0 | 2 | Lemkin bluntly argues that hiring agencies is usually flushing money down the toilet for early-stage startups, explaining why outbound BDR agencies fail due to lacking product domain depth. | |
| Venture Capital Deal Sourcing and Pipeline Mechanics | 9 | 0 | 0 | 1 | Lemkin demystifies venture deal flow dynamics, explaining how top funds like a16z mandate seeing every deal and how junior VCs source early-stage pipelines through upstream relationships. | |
| Agency Differentiation and Principal-Led Client Engagement | 8 | 2 | 3 | 4 | Phil pushes back on Lemkin's broad dismissal of agencies by sharing his experience running a seven-figure sales enablement agency and asking how to sell honestly. Lemkin counters with the principal-led operational model. | |
| Post-Sale Implementation Frameworks and Onboarding Velocity | 8 | 0 | 0 | 0 | Lemkin details onboarding cadence best practices, highlighting Veeva CEO Peter Gassner's 45/90/180-day executive customer touchpoint framework and tracking time-to-onboard velocity. | |
| Series A Fundraising Hygiene and Pitch Deck Discipline | 8 | 0 | 0 | 1 | Lemkin provides pragmatic fundraising hygiene advice for Series A rounds, referencing recent backlash he received on Hacker News to emphasize pitch deck freshness, pipeline size, and realistic capital asks. |
Statements from this episode (20)
Lemkin: Founders Hiring Unfamiliar Roles Should Have External Domain Experts Interview Candidates
“Two, if it's for a role you've never hired before, you don't know, find someone that's great at it, truly great and ask them to just interview your final candidate. Simple answers, but that sounds simple, but that always works.”
Lemkin: Top Product, CS, and Sales VP Candidates Prioritize Customer Meetings First
“The best heads of product, the best heads of customer success and the best VP of sales will give you the same answer. I'm going to go meet customers. It's always the same.”
Lemkin: WebEx reached $1B ARR before Salesforce
“You know, WebEx was the first billion dollar ARR SaaS company that blew up even before Salesforce.”
Lemkin: Adding self-onboarding later is wildly difficult for SaaS startups
“First of all, if you don't start with a self onboarding, self-procuring service, it's wildly difficult to start later, which we talked about.”
Lemkin: HubSpot's CRM is a $700M business
“Sometimes HubSpot was right to do CRM when everyone said it was silly because your customers are in marketing. That's a seven hundred million dollar business today.”
Lemkin: Software companies need gross margins above 70% for public markets
“Today, the public markets absolutely care to an extent, right? And a software company really does need to have north of 70% margins.”
VCs ignore profitability but excuse margin flaws for hyper-growth startups
“And so they're not gonna give you credit because you're profitable. They're not gonna give you credit for lower growth because of macro issues. But what they will do is they get a little blind to hyper growth. Like they're so deaf because fewer companies are h…”
Lemkin bet $80,000 on weekly tech IPOs in H2 2024
“I did a couple of these like round tables with Harry Stebbins on 20 VC and I did 50,000 with him and then 10,000 with a couple other top, top investors that we would have an IPO a week in the second half of the second half of this year.”
Lemkin: Practical AI utility across SaaS will improve within a year
“Any area of SaaS where AI is even a smidge helpful today, and let's not be cynical. That's even a smidge helpful. I am just tactically bullish that in a year it will all be better. And we're all gonna benefit from these, as long as your CTO can take advantage …”
Lemkin: Hiring marketing agencies is mostly a waste of founder money
“Mostly hiring agencies is the fastest way to flush your money down the toilet as a founder.”
Outsourced SDR agencies fail because shared reps never learn the product
“Agencies for BDRs and SDRs never work with a few exceptions. The reason they never work is because with. 20 clients, you never learn the product.”
Lemkin: Allow your head of marketing only one trusted agency
“When you go to hire your first head of marketing, if they actually had a lead come in and actually can do gender and Duke and growth, they can't do everything themselves. And a lot of marketers will want to bring in a lot of agencies. Don't let them, you got t…”
Lemkin: VCs must either find overlooked deals or win competitive rounds
“For VC, you either got to find the ones that other people don't find, or you got to win. You got to win. Right. You got to be in all the deals and find a way to win, to beat the other people. Right. The later stage venture is all things, the more it's about wi…”
Lemkin: Venture capital is a sales and hustle business for almost everyone
“No, it's a frigging, it's a sales business and a hustle business for almost everybody. And the only folks that don't have to hustle like that, have massive inbound. And there's only a handful of folks where the founders pick them. It's only, it's very rare.”
Lemkin: Every agency deteriorates when principals stop doing the work
“And every agency deteriorates when the principals don't do the work, but also how do you scale if the principals don't want to do the work, right?”
Veeva Systems reached a $35B valuation raising just $3M in capital
“Peter Gassner, who is the founder of Viva, which is worth thirty-five billion. It only raised three million in primary capital.”
Lemkin: Most founders overestimate onboarding speed, risking instant churn
“Almost all founders find that fewer of their customers are onboarded as quickly as they think. Fewer, they're often shocked that they sign a customer and they just assume their team's gotten them up and going and they find out what, it's been 60 days, it's bee…”
Lemkin: Founders must avoid artificial urgency and pitch twice as many VCs
“Just assume you have to talk to more VCs than you used to. Don't play any games. Don't artificially constrain the process. Don't tell people they have 37 minutes. Be a little more chill and talk to twice as many people as you planned.”