Jun 24, 2022 · 35m · saastr
16 Ways to Level Up in 2022 with SaaStr Founder and CEO Jason Lemkin | SaaStr Software Community
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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 presentation, Jason Lemkin utilizes extensive survey data to deliver actionable strategies on optimizing sales capacity, evaluating executive hires, structuring compensation, and driving enterprise SaaS growth.
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 100% of the talking time here. How this is scored →
Jason as informed peer 1.2 Guest teaching 0.0 Guest disagreement 0.5 Jason pushing back 0.5
speaking balance: gold is Jason, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 27:53 Audience member flatly denies outbound viability
An audience member directly objects to Lemkin's assertion about sales outreach by calling out that it does not work in practice.
Hardest push from Jason ▶ 27:54 Lemkin refutes outbound skepticismLemkin directly counters the attendee's doubt, insisting that targeted outbound always functions when structured around lookalike customer profiles.
Biggest teaching moment ▶ 27:52 Audience interjection challenges outbound assumptionThe audience member provides the only contrarian friction in the session by questioning the universal reliability of outbound sales.
Jason holds their own ▶ 27:55 Lemkin lays out exact playbook for targeted outboundLemkin demonstrates domain authority by detailing how to leverage brand-name customer references to secure meetings across similar enterprise accounts.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Jason as informed peer | Guest teaching | Guest disagreement | Jason pushing back | Why |
|---|---|---|---|---|---|---|
| Maximizing Yield by Concentrating Leads in Top Reps | 0 | 0 | 0 | 0 | Solo keynote presentation segment by Jason Lemkin discussing survey data on rep performance. Because this is an uninterrupted monologue without guest participation, all interactive metrics are scored zero. | |
| Minimizing Sales Turnover and Designing Effective Comp Plans | 0 | 0 | 0 | 0 | Uninterrupted monologue examining sales team turnover and comp structure design. No guest interaction takes place. | |
| Upgrading Weak Sales Leadership Within One Sales Cycle | 0 | 0 | 0 | 0 | Solo monologue by Lemkin on evaluating VP performance within a single sales cycle. No guest dialogue occurs. | |
| Hiring Accretive Executive Leaders Without Strict Sequencing | 4 | 0 | 1 | 0 | Lemkin presents survey results regarding key executive hires; an audience member interjects briefly with a neutral reaction word without offering substantive opposition. | |
| Evaluating VP Candidates on Immediate Recruiting Ability | 0 | 0 | 0 | 0 | Lemkin delivers an uninterrupted monologue on vetting executive candidates on day-zero hiring capability and tracking logo retention. | |
| Strategic Pricing Increases Versus Squeezing Existing Customers | 3 | 0 | 1 | 0 | Lemkin analyzes pricing elasticity and warns against raising rates on the existing customer base, followed by a fleeting one-word audience interjection. | |
| Overcoming Market Excuses and Capitalizing on Growth Segments | 0 | 0 | 0 | 0 | Monologue breaking down budget survey data and explaining how to target growth sectors. No audience interaction occurs. | |
| Enforcing Product Mastery and Inspecting Sales Interactions | 0 | 0 | 0 | 0 | Solo lecture focusing on rep product knowledge, call review discipline, and founder oversight. No guest participation. | |
| Executing Targeted Outbound Sales and Optimizing SDR Ratios | 6 | 0 | 3 | 5 | An audience member chimes in with skepticism regarding outbound success ('It doesn't work'), prompting Lemkin to immediately push back with specific outbound methodologies and conversion benchmarks. | |
| Scaling Product Leadership with an Experienced VP of Product | 0 | 0 | 0 | 0 | Monologue analyzing product executive hires and why decreasing win rates can signal broader market capture. No dialogue occurs. | |
| Scaling Sales Capacity and Preserving Capital Efficiency | 0 | 0 | 0 | 0 | Lemkin finishes his presentation with a solo walkthrough of revenue modeling and sales capacity requirements. No dialogue. |
Statements from this episode (29)
Lemkin: A Single SaaStr Sales Rep Has Sold $23M in Sponsorships
“Even our little Saster team over here that, that sells sponsors, we have one person, and this is a great sales team, we have one that has sold twenty three million of sponsorships already, ok?”
Lemkin: Routing Leads to Top Reps Yields 20% More Closes
“You just close 20% more from the leads you already have if you concentrate them in your best reps.”
Lemkin: Cutting Bottom 10% of Sales Reps Boosts Revenue in One Cycle
“Literally move out your bottom 10%, and your revenue will literally go up in less than one sales cycle.”
Lemkin: Top US AEs should make $300k to $1M by segment
“In the U.S., your best AEs should be making 300,000 for SMB, half million for mid-market, and a million dollars for enterprise.”
Lemkin: Good sales reps should only leave for unattainable promotions
“The only reason an individual contributor sales rep should leave your company is for a promotion. They can't get at your company.”
Lemkin: First Great VP of Sales Boosts Revenue 20% to 100%
“How much of a revenue boost did you get from your first great VP of sales? 20% half got 20%, and about half got 40 to a hundred percent boost.”
Lemkin: Great VPs of Sales Show Impact in One Sales Cycle
“A great VP of sales should make an impact in one sales cycle or less.”
Lemkin: Having No VP of Sales Beats a Mediocre One
“You're almost better off without a week, with no VP than even a mediocre VP.”
Lemkin: More Time Never Turns a Mediocre VP into a Good One
“Just remember time never turns a mediocre VP into a good one. It just never does. And especially never listen to your VCs or investors that tell you this.”
Lemkin: Founders do not need to sequence executive VP hires perfectly
“You do not have to sequence it perfectly, and we've talked about this on Sastr. It's a classic post of what order to sequence it in, but the real key to understand, and this is not intuitive until you're later, is any great VP is accretive.”
Lemkin: Founders Should Spend 20% of Time Recruiting and Hire Opportunistically
“As founders, your job is spend at least 20, 20% of your time recruiting, half if you can, but meet all the great VPs, and if you think you need a VP of sales, but you find a great VP of demand gen, just hire her. If you think you need a great VP of product, bu…”
Lemkin: Half of any VP role is recruiting, especially in sales and engineering
“Any VP role is 50% recruiting, especially engineering and sales.”
Lemkin: Every successful VP of Sales brings hires with them on day zero
“I've never seen a single VP of sales succeed that didn't bring in one or two good people with them immediately when they joined. Never seen it. Not once.”
Lemkin: High NRR SaaS companies have lazy customer success teams
“High NRR companies are friggin' lazy, especially their customer success teams.”
Lemkin: Every churned customer in SaaS represents an organizational failure
“Every customer you lose in SaaS is sort of a failure. Someone failed. Sales oversold it. Your product let them down, or CS let them down. No one buys SAS products for fun. It's not fun to deploy, test, and roll out a SAS app in your company, and every single t…”
Lemkin: Raising SaaS prices 20% does not hurt high-value products
“It really doesn't matter if you're providing a lot of value if you increase your prices in even 20%.”
Lemkin: Raising prices on existing customers to hit quota only works once
“It's actually a completely weak sign when a VP of sales is missing a quarter, and he says, well, you know what, I'm not going to make it, but let's raise prices so that we can make my plan. It's a cookie. You raise prices on your base once. It works once. You …”
Lemkin: Only 13% of surveyed companies have VP Sales comp over 50% variable
“It was interesting to me that all out of over 2000 votes, only 13% said more than 50%, although all very few had almost no variable comp.”
Lemkin: 50-50-25 compensation structure remains effective for heads of sales
“I did an old Saster post that a lot of folks have used for a fifty-fifty-twenty-five plan. I think it works well today, if you can pull it off, which is half your head of sales comp is base, half is tied to hitting the plan for the year, and then 25% for blowi…”
Lemkin: Employees focus exclusively on the one or two KPIs tied to payout
“People really almost irrationally respond to incentives here, and they don't do anything else other than the number one or number two KPI they have that they're getting paid out on.”
Lemkin: The average SaaS product competes among 200 internal B2B apps
“The average SaaS company is one of 200 B to B apps deployed in their org.”
Lemkin: Product experts who close decently beat great closers without product mastery
“I'd rather have an expert in my product that's a decent closer than an amazing closer that doesn't understand the product. They won't close anything until your brand is just mega.”
Lemkin: 80% to 90% of SaaS companies now do outbound sales
“Everyone, I would say five years ago, maybe half of SaaS companies did outbound. I would say today it's like about 80 to 90%, as near as I can tell.”
Lemkin: Top SDRs generate 15-20 qualified meetings monthly and $2M pipeline
“We'd like 10 to 15 qualified meetings per SDR, and the best ones can do 15 to 20, and the best ones always generate about two million in pipe per year.”
Lemkin: Hiring Junior PMs from Big Tech Brands Is a Founder Mistake
“And 98% of you, 96% of you, I think, make the same mistake. You hire a junior person. Ok, I'm gonna go hire a product manager that worked on one pixel at Twilio, or worked on one little thing at some great company. They don't know how to ship products into pro…”
Lemkin: Hiring a VP of Product at $3M–$5M ARR Accelerates SaaS Growth
“If you hire a great VP of product at three, four, five million, and you have a sales driven motion, if you haven't done it, magic happens. A great VP of product immediately, her or his first two weeks will go meet with your top 20 customers, magically. They'll…”
Lemkin: An 80% Win Rate Means a Startup Lacks Marketing and Outbound
“It's a terrible sign if 80% of your deals close. It means you're doing no marketing. It means you're literally doing no marketing or outbound if 80% of your deals close.”
Lemkin: SaaS companies cannot cut their way to growth
“You can't freeze hiring and hit the plan. You can't cut your way to growth. It doesn't work. Whatever your issues are, cutting, sometimes you have to cut if you have two months of burn, but you can never cut your way to growth, and it especially doesn't work i…”
Lemkin: SaaS sales lacks scale efficiencies and grows linearly
“There's no freaking efficiencies in sales in SaaS. Like, you get engineering efficiencies. Everyone can use your same code base, but you barely get any efficiencies in sales once you hit a billion in ARR, and I don't think too many people here hit a billion in…”