Jul 12, 2023 · 38m · saastr
The Cold, Hard Truths About SaaS In 2023: Part 1 AMA with SaaStr CEO and Founder 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 SaaStr AMA session, founder Jason Lemkin provides actionable guidance for SaaS leaders navigating macroeconomic shifts, covering capital-efficient growth, GTM org structure, hiring passionate 'pirates and romantics,' and resetting compensation expectations.
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 87.8% of the talking time here. How this is scored →
Jason as informed peer 8.7 Guest teaching 0.5 Guest disagreement 0.7 Jason pushing back 2.8
speaking balance: gold is Jason, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 36:10 Guest challenges Lemkin with regional salary data
The audience member pushes back on Lemkin's dismissal by citing concrete data that London customer success salaries have dropped 30%.
Hardest push from Jason ▶ 31:04 Lemkin immediately rejects the CS dumbing-down premiseLemkin flatly counters the guest's claim that companies are avoiding senior CS hires, stating he observes the exact opposite across early-stage startups.
Biggest teaching moment ▶ 36:10 Guest educates host on London market compensation compressionThe audience member introduces specific UK compensation deflation data that forces Lemkin to address market comp adjustments.
Jason holds their own ▶ 27:35 Lemkin details sales yield math and fully burdened cost multiplesLemkin commands the topic by laying out precise quota-to-OTE ratios and resource cost multipliers required for sales efficiency.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Jason as informed peer | Guest teaching | Guest disagreement | Jason pushing back | Why |
|---|---|---|---|---|---|---|
| Reporting Structure and Career Paths for SDRs | 9 | 0 | 0 | 1 | Lemkin delivers an extensive breakdown of SDR reporting structures and operational economics, distinguishing tactical from strategic approaches. He draws on real industry benchmarks, snowflake case studies, and standard comp packages (60/20 OTE) to explain SDR career retention. | |
| Founder Mental Health and Hiring Pirates and Romantics | 8 | 1 | 2 | 3 | Jimmy Smart asks about founder mental health and burnout mechanisms, but Lemkin initially goes on an extended critique of post-2020 tech workforce laziness. The guest gently interrupts to re-center the question on founders, prompting Lemkin's thesis on hiring 'pirates and romantics.' | |
| The 2023 Playbook for Bootstrapped SaaS Founders | 9 | 0 | 0 | 2 | Lemkin reframes the premise by asserting that the bootstrapped playbook never changed because lack of capital is constant. He shares detailed historical data and case studies (UiPath, Atlassian, and a 19-year portfolio company) on getting to $10M ARR. | |
| Identifying and Recruiting True Startup Romantics | 8 | 0 | 0 | 2 | A founder asks how to identify startup romantics without being fooled by candidates who mimic enthusiasm. Lemkin clarifies the core role of recruiting for early-stage founders and advises splitting the hiring funnel between top-of-funnel attraction and disciplined screening. | |
| Balancing Role Specialization with Sales Yield and Efficiency | 9 | 0 | 0 | 2 | Lemkin traces the historical evolution of SaaS specialization and the drop in sales yield post-2018. He gives concrete mathematical frameworks for required attainment and quota-to-OTE multiples (3x SMB to 5x enterprise plus burdened cost load). | |
| The Evolution of Customer Success and Compensation Realities | 9 | 2 | 2 | 7 | Lemkin directly rejects the guest's thesis that customer success is being 'dumbed down,' arguing founders want true VP-level owners but reject passive strategists. When the guest points out a 30% drop in London salaries, Lemkin contextualizes it within macroeconomic quota attainment realities. |
Statements from this episode (12)
Lemkin: Inbound-Only Sales Leaders Should Never Manage SDR Teams
“There are a lot of sales leaders who have only done inbound, ok? They have only responded to leads. They should not manage SDRs if humanly possible. They almost all fail.”
Lemkin: Standard US SDR Comp Package Is $80K OTE
“In the U.S., a classic comp package for an SDR, even today, might be a sixty-twenty package. An ADKOT, 60 base, 20, 20 variable for setting up appointments or revenue commits.”
Lemkin: SaaStr Had an SDR Generate $5M in One Year
“We had even one on our Sastra team that did five million in a year.”
Lemkin: A startup's first 50 employees must be 'pirates or romantics'
“Your first 50 employees, your first 50, have to be pirates or romantics. They have to be pirates or romantics. You know what I'm talking about. These are folks on your team that for reasons that almost don't make sense, live in, lead startups.”
Lemkin: Multiples will probably rise and venture capital will return
“Now's, now is your time, your window, and it won't last. We will get drunk again. Multiples will probably go up. Venture capital will come back. It always has.”
Lemkin: Big bootstrapped SaaS companies take 3 to 4 years longer
“On average, and I've written up the data, and I'll give you an example, it usually takes bootstrapped companies that go big, that have multi-billion dollar outcomes, another three to four years longer than venture-backed ones, and that sucks.”
Lemkin: UiPath took 10 years to reach $1M revenue before hypergrowth
“It took him 10 years to get to one million in revenue, and then he went from one to a hundred, I think, in three years, or two years.”
Lemkin: Full-stack AE model does not work for most SaaS companies
“He talked about how even Brex, which is, which was still relatively SMB for a long period, how the AE's had to do half of their own deals through outbound, and so he really described, in a way, a full stack AE, right, and people talk about that, and I think th…”
Lemkin: Rep quotas must hit 3.5x to 5.5x OTE to cover support costs
“And a simp, a simplistic way to boil it all down is, one, we have to revert back to sales closing three to five times what they take home. Three, at least three X for SMB, at least four X for mid-market, five X for enterprise. And you have to budget in there t…”
Lemkin: Most $1M–$10M startups want a VP of CS but can't find one
“I see the majority of startups I meet between 1,000,010 million want a true VP of CS and don't have one.
They want one.
They can't find the person.”