Jason M Lemkin
Jason Lemkin is the founder of SaaStr, the world’s largest community for software founders, and a veteran SaaS investor who has deployed over $200 million into B2B startups. After his last salesperson quit, Jason made a radical decision: replace his entire go-to-market team with AI agents. What started as an experiment has transformed into a new operating model, where 20 AI agents managed by just 1.2 humans now do the work previously handled by a team of 10 SDRs and AEs.
Communication Skills
Reduce friction between Product and Sales by allocating a fixed percentage of engineering capacity for sales-driven feature requests.
"Every quarter, give your head of sales a certain budget, whether it's story points or 10% of the pie chart... you've got to decide now each quarter. And if you want to change during the course of the..."
A successful sales meeting must always conclude with a clearly defined next action to maintain momentum.
"The best salespeople never leave a meeting without a next step. The next step does not have to be a check... but what's the next meeting? ... Whatever the next step is, 'What's the next step we can ge..."
Growth Skills
Forcing annual contracts on SMBs can kill conversion; it is often better to offer monthly terms that align with how customers want to buy.
"Going to annual contracts, on a spreadsheet, looks great... You know what's better? Letting customers pay what they want to pay. If it's you or me buying for ourselves, Lenny, we're still going to put..."
Hiring & Teams Skills
Use the 'first 14 days' question to identify leaders who are customer-obsessed rather than process-obsessed.
"What do you want to do your first 30 days? ... In B2B, if I don't hear from the VP of sales or the VP of product that I'm going to go meet customers, out, I'm out."
Require sales candidates to perform a live demo of your product to prove they have researched the value proposition and can handle the 'middle' of the sale.
"Give them time. And I don't like to judge too harshly, but whether it's the first interview or the second, they got to sell you this pen. But it's not 'Sell me this pen,' it's 'Sell me this app.'"
The ultimate test for an early sales hire is whether the founder would personally feel compelled to buy the product from them.
"Those first couple reps have to be people you would buy your own product from. That's it... when you go out as a first time founder and interview 30 reps... wait and interview 30 sales reps."
Hire sales reps who are moving from a more difficult or technical sales environment to your product, as they will find your motion easier to execute.
"One hint more than anything else, trust... got to hire someone whose last product was harder to sell. This is so important. This is a recipe for utter disaster. If you've, take someone in sales and th..."
Sales & GTM Skills
Hire two sales reps simultaneously to create a baseline for performance and ensure the sales process is repeatable rather than dependent on one individual.
"You need to hire one rep and you've got to hire two because otherwise, there's no A-B test. You have to A-B test humans. You've got to hire two as hard as it is, and there's just one cheat code to tho..."
Do not hire a VP of Sales until you have at least two individual contributors successfully hitting their quotas.
"You need two sales reps hitting quota closing deals before you're ready to hire a manager for them. Almost all VPs of sales, their job is to take you from rep three to 300."
Sales organizations scale effectively using a 'rule of eight' for management spans of control.
"In sales, I'm actually not sure what the tip of heuristic is in product... But the thing about sales is there's no efficiency... it's rules of eight. Eight SDRs, outbound reps need one manager, eight..."
The guest provides specific tactical advice on OTE ratios, base/bonus splits, and ramping strategies for early sales hires.
"It's usually 50/50, right? 50% base, 50% bonus for a sales rep."