Dec 9, 2021 · 43m · saastr
Ask Me Anything About Customer Success with SaaStr CEO Jason Lemkin and ChurnZero CEO You Mon Tsang
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In this Ask Me Anything session, ChurnZero CEO You Mon Tsang and SaaStr founder Jason Lemkin explore how B2B SaaS companies can maximize Net Retention Rate, align sales and customer success teams, and build durable enterprise value through disciplined customer-centric operations.
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 79.6% of the talking time here. How this is scored →
Jason as informed peer 7.8 Guest teaching 0.4 Guest disagreement 0.8 Jason pushing back 2.9
speaking balance: gold is Jason, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 6:56 You Mon absolutist framing on NRR
You Mon asserts that NRR is a strict qualifying metric where nothing else matters if the number is bad, challenging typical holistic evaluation.
Hardest push from Jason ▶ 17:15 Jason rejects commission splittingJason flatly dismisses You Mon's proposed sales incentive tweak, asserting from direct experience that delaying commissions fails to change rep behavior.
Biggest teaching moment ▶ 23:15 You Mon prompts multi-variable sales alignment questionYou Mon reframes the discussion to address the systemic tension between aggressive sales incentives and downstream CS retention churn.
Jason holds their own ▶ 18:40 Jason details post-sales acceptance ruleJason demonstrates operational mastery by laying out the exact mechanism of requiring post-sales acceptance on non-standard deals to stop churn.
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 Evolution of Customer Success and Retention in SaaS | 8 | 0 | 1 | 2 | Jason delivers extensive historical context on the evolution of customer success, quoting specific enterprise SaaS benchmarks like Salesforce's 70% bookings from its install base. You Mon acts as an appreciative interviewer, framing questions around Jason's past quotes. | |
| NRR Benchmarks and Accelerating Time to Value | 8 | 1 | 2 | 4 | When You Mon posits that NRR is a strict qualifying metric where nothing else matters, Jason pushes back to add nuance, explaining top-quartile VC expectations versus founder operational realities. Jason also redirects the discussion toward time-to-value and rapid activation. | |
| Founder Mistakes and the Value of In-Person Engagement | 7 | 0 | 0 | 1 | In response to an audience mistake question, Jason reflects candidly on losing major logos by neglecting in-person visits. The tone is reflective and cooperative. | |
| Aligning Sales Incentives with Customer Success Sign-Off | 9 | 0 | 1 | 5 | Jason immediately rejects the idea of splitting or delaying sales commission payouts, presenting a concrete organizational mechanism where customer success must formally accept accounts before non-standard commissions are awarded. | |
| Core Valuation Metrics and Multi-Product Expansion | 8 | 1 | 1 | 4 | Jason outlines his three core metrics (growth, NRR, burn rate) and challenges You Mon by correcting margin vs. burn rate, while emphasizing that early multi-product expansion is critical for modern SaaS scale. | |
| Hiring Early CS Talent and Enterprise Customer Dedication | 8 | 0 | 0 | 3 | Jason differentiates SaaS hiring criteria, arguing CS allows for unconventional talent early on, and insists that first six-figure enterprise customers must have a dedicated representative assigned immediately. | |
| Migrating to SaaS Models and Instrumenting Product-Led Growth | 7 | 1 | 1 | 3 | Jason demystifies product-led growth by contrasting it with classic freemium models and emphasizing the non-negotiable role of granular instrumentation and data signals. | |
| Memorable Founder Interviews and Post-Pandemic Enterprise Cloud Adoption | 7 | 0 | 0 | 1 | Jason shares insights from top founder interviews and predicts the multi-year timeline for post-pandemic enterprise cloud transformation, closing on an upbeat collaborative note. |
Statements from this episode (20)
Lemkin: Adobe Sign is an approximately $300M ARR business
“And if you fast forward today, even though Adobe Sign has lost market share to DocuSign, a lot of it, which is, which hurts me as a founder, it's still almost a three hundred million dollar AR business, right?”
Lemkin: When unsure about sales strategy, invest in customer success
“If you don't exactly know what to do in sales, right? And sometimes we don't, right? If you're not sure, we're planning for next year, right? Hopefully we're all planning, 20, 22 planning it. And if you're not quite sure how to do that extra thing, how, where …”
Lemkin: 70% of Salesforce's new bookings come from existing base
“70%. 70%. That's the whole story. Think about that.”
Lemkin: Almost 100% of SaaS founders under-invest in customer success
“But if Salesforce at twenty billion in ARR and a three hundred billion market cap can get 70% of revenue from its base, that means who, any founder, CEO that is listening to this, It's under-investing in customer success. Almost by definition, almost a hundred…”
Lemkin: Series A/B SaaS startups must have top-quartile NRR to get funded
“So look, if you go meet with a VC and let's say your enterprise, ok, and your NRR is only a hundred percent in the enterprise, not good enough. It's got to be north of a 120 in the enterprise, right? Let's say your SMB and you're below 95%, not good enough for…”
Lemkin: HubSpot took a long time to reach 100% NRR
“HubSpot is an iconic company for larger SMBs, right? Iconic, right? But it took them quite a while to get to a hundred percent NRR, ok? It took them quite a while.”
Lemkin: Accelerating deployment speed is the best cheat to improve SaaS retention
“The other one that I think is almost a call that the people don't talk enough about is as activation rates and time to deployment. Right. And that is one of your best cheats here to improve things is to get your customers to deploy as instantly as possible.”
Lemkin never lost an EchoSign customer he visited in person
“We, I lost a lot of customers after I sold my company, but I never lost a customer I met.”
Lemkin: SaaS CEOs Should Do 10 Customer Zooms Weekly
“As a CEO, you've got to be doing 10 Zooms a week. And as a CS professional, you should be doing three to four day, right? If you can.”
Lemkin: Great sales leaders reject churn-and-burn deals as SaaS companies reach $20M–$30M ARR
“I don't think once you get to the next phase, whether it's twenty million or 30 or the next, that whatever your next phase is, I don't see the great VPs of sales wanting churn and burn deals.”
Lemkin: Requiring CS acceptance before paying commission is the best anti-churn hack
“Having customer, if you have enough trust with your head of customer success, have them have to accept the customer. This is the only hack I've seen. Not that the commission is delayed until deployment or renewal, but CS has to accept it.”
Lemkin: Any B2B business boils down to growth, NRR, and burn rate
“Obviously revenue growth, NRR and burn rate, any B to B company can be reduced to, you know, top line growth, NRR and burn. If I know the three of those, I know the physics of your business.”
Lemkin: Every billion-dollar ARR SaaS company relies on a multi-product suite
“If you look at every SaaS company at a billion in ARR today, two interesting things. One, they're growing fast at a billion. You know, we used to think that was almost impossible that you could grow 70% at a billion in ARR, but it's almost becoming commonplace…”
Lemkin: Never hire non-SaaS sales or marketing leaders when scaling
“For sales, marketing, product, and engineering, I would not take, I would not, if I'm scaling, hire someone that does not have a pure SaaS broker. There's too many folks that do. There's no point in hiring a salesperson that hasn't sold SaaS. I ain't gonna tak…”
Lemkin: Early SaaS startups can hire CS talent outside SaaS
“If you're below four or five million in revenue, so customer success is still hands-on. It's not all systems and process and tools, right? It's not all instrumentation. I can take more risk in CS. I can take someone that's smart. I could take someone that has …”
Lemkin: First enterprise customers must get a dedicated CS hire
“When you close your first enterprise customer, and maybe that's 50 K to start, maybe it's a hundred K later, it's a million or ten million or a hundred million if your Salesforce, that first 50 K to make, maybe it's 20 K if your product's 200 dollars a year an…”
Lemkin: SaaS customers demand quarterly innovation and will leave without it
“Really people want quarterly innovation in their vendor, and they're expecting it for that check. And you have, the idea that you have to re-earn your customer, right, which is part of retention, sometimes is a little alien to on-prem folks, the idea of re-ear…”
Lemkin: GitLab is not really a SaaS company
“GitLab just IPO to sixteen billion. It's not really a SaaS company.”
Lemkin: Product-led growth is useless without real-time data instrumentation
“You can't have product-led growth Isn't actionable unless you have instrumentation around it, right? What is actionable, right? What is the difference between product-led growth and classic freemium self-service viral word of mouth, which we've been doing for …”