Mar 17, 2018 · 36m · saastr
SaaStrPRO AMA with Jason Lemkin
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In this SaaStr Pro Ask Me Anything (AMA) session, investor and entrepreneur Jason Lemkin shares tactical advice on scaling B2B SaaS companies, addressing international expansion, sales and customer success compensation, marketing efficiency, and product trial strategies.
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 98.2% of the talking time here. How this is scored →
Jason as informed peer 8.0 Guest teaching 0.0 Guest disagreement 0.0 Jason pushing back 0.1
speaking balance: gold is Jason, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 34:00 Tyler's framing on client accountability
Tyler summarizes the free trial dilemma by positing it as an accountability mechanism, which is purely conversational rather than confrontational in this AMA format.
Hardest push from Jason ▶ 31:10 Jason rejects abandoning free trialsJason strongly pushes back against the premise submitted by an anonymous founder wanting to remove free trials, arguing that doing so permanently damages software quality.
Biggest teaching moment ▶ 0:04 Tyler sets the AMA structureTyler outlines the agenda and Reddit question workflow; in this AMA structure, no participant schools the host on domain knowledge.
Jason holds their own ▶ 8:00 Deep dive into TalkDesk and Automile scaling metricsJason demonstrates mastery of SaaS metrics by dissecting exact growth trajectories and operational differentiators of TalkDesk and Automile from pre-revenue to tens of millions in ARR.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Jason as informed peer | Guest teaching | Guest disagreement | Jason pushing back | Why |
|---|---|---|---|---|---|---|
| Blind Spots for European SaaS Expanding into the US | 8 | 0 | 0 | 0 | Jason delivers an extensive monologue drawing on his experience investing in over 20 European SaaS companies. He outlines specific pitfalls including establishing US headquarters in New York instead of the Bay Area, falling for big-brand resumes, and underpaying senior talent. | |
| Strategies to 10X Inbound Leads and Maximize Revenue Per Lead | 9 | 0 | 0 | 0 | Jason breaks down lead plateau dynamics and analyzes specific tactical playbooks from Greenhouse, Automile, and TalkDesk. He emphasizes increasing revenue per lead over pursuing unrealistic 10x inbound lead volume. | |
| Compensating Sales and Customer Success for Large Expansion Deals | 8 | 0 | 0 | 0 | Jason provides definitive compensation guidance for large land-and-expand enterprise deals, arguing founders must accept double-paying commissions to both sales reps and customer success managers to ensure execution. | |
| Value Capture and Pricing Models for Enterprise Cost Savings | 7 | 0 | 0 | 0 | Jason warns founders against trying to capture a percentage of cost savings unless savings can be proven instantly in-app, citing his historical enterprise sales experience with EchoSign at Comcast. | |
| Assessing CAC Spending and Blending Marketing Channels | 8 | 0 | 0 | 0 | Jason explains how to evaluate customer acquisition cost (CAC) by blending paid and organic channels, advising founders to double down on any channel that delivers at least a 1:1 payback ratio. | |
| Structuring Customer Success Teams for Multi-Million Dollar Accounts | 8 | 0 | 0 | 0 | Jason discusses organizational structure for multi-million dollar ACV enterprise accounts, advocating for specialized roles and sharing an anecdote about Salesforce's dedicated support phone at Groupon. | |
| Best Practices for Customer Success Variable Compensation and KPIs | 8 | 0 | 0 | 0 | Jason details best practices and pitfalls for CS variable compensation, cautioning that non-sales employees over-index heavily on bonus KPIs while citing Logikcull's success tying CS bonuses to NPS. | |
| Why SaaS Founders Should Retain Self-Service Free Trials | 8 | 0 | 0 | 1 | Jason forcefully argues against abandoning self-service free trials despite internal pressure from sales and product teams, sharing a personal frustration encountering forced SDR gating at an eight-figure SaaS company. |
Statements from this episode (17)
Lemkin: Expanding to NYC instead of SF is European SaaS's biggest mistake
“Unless your customers are in New York, unless you're doing financial services or some parts of ad tech or otherwise, going to New York is the worst idea.
you get none of the, almost none of the benefits of being in the Bay Area.
You don't get the customers he…”
Lemkin: Fully burdened engineers in Paris cost half of SF rates
“It's crazy that Paris is half the price of San Francisco fully burdened for an engineer.
It's crazy that London is cheaper than San Francisco.”
Lemkin: Startups should not ask job candidates to take salary cuts
“What startups, my recommendation as a rule is don't ask people to take salary cuts.
I know you're the hottest startup that there's ever been that no one's ever heard of, but don't ask people to take salary cuts unless you have to.”
Lemkin: Greenhouse CEO hired 15 SDRs before doing real marketing
“So, so Daniel, the CEO, hired like, 15 SDRs before he did any real marketing.”
Lemkin: Automile had an 80+ NPS, the highest in his portfolio
“They had the highest NPS at any company I've been involved with, literally 80 plus in the last round”
Lemkin: Talkdesk grew from $1M to $15M revenue in 15 months
“I mean, talk desk went from one to fifteen million, I think in 15 months, which for the companies I'm involved with was a record.”
Lemkin: SaaS Startups Must Double Pay Sales and CS on Expansion Deals
“You have to pay twice. You have to pay sales for revenue that comes in after the contract is signed, and you have to pay customer success, however you're going to pay them, for the work they do. And when work overlaps over an extended period of time, you just …”
Lemkin: Pricing SaaS on enterprise cost savings fails 92% of the time
“I would caution you, I would say 92 times out of a hundred, that is a, that is The wrong business model.”
Lemkin: SaaS Startups Underspend If CAC Is Below 20–25% of TCV
“If you're not spending 20 to 25% of the TCV, of the total value of the whole customer's lifetime, in the early days, you're definitely under spending.”
Lemkin: Multi-million dollar SaaS accounts require dedicated project managers and specialists
“Big accounts today need someone that can whiteboard an account that can map business process change over multiple years. And in the early days, that's often the CEO or the founders, but that doesn't scale. So do I need a project manager? Yes. Do I need support…”
Lemkin: Groupon paid Salesforce eight figures annually
“Salesforce had just landed them as a huge customer. Back in the day, it was a marquee customer. I don't know how much they paid Salesforce, but I know it was eight figures a year.”
Lemkin: Customer success managers should have 10-15% variable compensation
“Having a modest amount of a customer success manager's money tied to either expansion in the account or NPS in their accounts and having it be around 10%, 15% of their total compensation is, is a good starter.”
Lemkin: Employees disproportionately fixate on variable bonus criteria
“My obvious learning is that people over index on variable comp. You pay someone a 100,000 dollars a year with a 2000 dollar bonus. You know what they do all day long? Whatever they get the 2000 dollar bonus for. That's all they do.”
Lemkin: Logikcull's NPS jumped to 50 after tying CSM goals to CSAT
“When he had his CSMs realigned around CSAT and NPS, his NPS went from negative to 50.”
Lemkin: Abandoning free trials leads to broken onboarding and mediocre software
“Once you give up free trials, you will never go back, and you will be able to have terrible onboarding, and you will be able to have all this friction behind the scenes, and you will be able to have many broken processes and things, and you will never build gr…”
Lemkin: Enterprise SaaS companies cannot retroactively build free trials
“Folks that I know that are enterprise that they get to a few million revenue. They try to build a free trial later. It's too late. Their DNA is too gone. They, everything's manual. Everything's manual data entry, manual this, manual that, and you'll never have…”
Lemkin: Upmarket buyers prefer manual sales and onboarding over free trials
“As you grow, most of your customers are not going to want to do a free trial. They want to be sold. They want to be onboarded. They want to be talked to the percent of your folks that will do a free trial will shrink radically over time, especially if you're g…”