Jul 5, 2024 · 53m · saastr
Top 10 Go To Market Mistakes Founders Make Again … and Again with SaaStr’s 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 keynote presentation, SaaStr founder Jason Lemkin breaks down the critical go-to-market mistakes software founders repeatedly make across hiring, demand generation, product strategy, and customer retention. He provides practical, battle-tested frameworks to help SaaS leaders navigate shifting market conditions and maintain venture-scale 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 99.9% of the talking time here. How this is scored →
Jason as informed peer 0.0 Guest teaching 0.0 Guest disagreement 0.0 Jason pushing back 0.0
speaking balance: gold is Jason, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 15:55 Audience agreement response
In this solo presentation format, audience members only offer brief rhetorical agreement when prompted.
Hardest push from Jason ▶ 11:50 Pushback against candidates unwilling to travelLemkin recounts challenging a candidate and a mutual contact regarding a sales leader refusing to travel to Palo Alto.
Biggest teaching moment ▶ 37:15 VC profitability versus growth schoolingLemkin breaks down the mathematical realities of the venture model showing that profitability without growth fails to meet IPO thresholds.
Jason holds their own ▶ 52:30 Lemkin confronting vendor on product deficienciesLemkin shares how he bluntly told a vendor's customer success VP that their product failed to scale when they attempted an aggressive upsell.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Jason as informed peer | Guest teaching | Guest disagreement | Jason pushing back | Why |
|---|---|---|---|---|---|---|
| Mistake 1: Hiring a Sales Leader Who Doesn't Know the Product | 0 | 0 | 0 | 0 | Solo conference presentation by Jason Lemkin detailing why hiring sales leaders who do not know the product leads to failure. As a monologue segment, all interaction scores are 0. | |
| Mistake 2: Hiring a Sales Leader Unwilling to Carry a Bag | 0 | 0 | 0 | 0 | Lemkin gives a keynote talk on sales leaders refusing to carry a bag and suffering from burnout. With only brief background audience reaction, it functions as a monologue. | |
| Mistake 3: Hiring Product or Brand Marketers Instead of Demand Gen | 0 | 0 | 0 | 0 | Monologue presentation outlining why early-stage founders need demand generation over brand or product marketing. | |
| Mistake 4: Hiring 'Strategists' Over Pipeline Generators | 0 | 0 | 0 | 0 | Lemkin explains why founders must avoid hiring self-described strategists in marketing who do not have a hard commit pipeline metric. | |
| Mistake 5: Founders Prematurely Stepping Out of Sales | 0 | 0 | 0 | 0 | Lemkin addresses the common error of founders trying to step out of sales prematurely instead of acting as key deal middlers. | |
| Mistake 6: Slashing Marketing Budgets to Zero in Downturns | 0 | 0 | 0 | 0 | Keynote advice warning founders against cutting marketing budgets to zero during economic downturns. | |
| Mistake 7: Failing to Achieve AI Feature Parity | 0 | 0 | 0 | 0 | Lemkin delivers remarks on the necessity of maintaining AI feature parity against competitors in enterprise SaaS. | |
| Mistake 8: Misunderstanding Profitability vs. Venture Growth | 0 | 0 | 0 | 0 | Monologue on the realities of venture math, explaining that profitability without sufficient growth will not yield venture returns or IPOs. | |
| Mistake 9: Hiring Burned-Out, Bitter, or Fractional Operators | 0 | 0 | 0 | 0 | Lemkin warns founders against hiring cynical, fractional, or burned-out operators who are not fully committed. | |
| Mistake 10: Succumbing to the Big-Company 'Logo Hire' | 0 | 0 | 0 | 0 | Lemkin presents his test for avoiding logo hires from late-stage enterprise companies at early-stage startups. | |
| Mistake 11: Seeking Instant ROI and Misapplying PLG Motions | 0 | 0 | 0 | 0 | Monologue regarding the trap of expecting instant ROI from free marketing and attempting to superficially bolt PLG onto sales-led models. | |
| Mistake 12: Exploiting Existing Customers and Weaponizing Customer Success | 0 | 0 | 0 | 0 | Lemkin concludes his presentation on the danger of weaponizing customer success teams to aggressively squeeze existing customers for upsells. |
Statements from this episode (26)
Lemkin: Startups Fail When Sales VPs Refuse To Learn The Product
“The number one reason I see startups struggle at your stage. In today's world is they hire a VP of sales that either doesn't want to sell. Or doesn't ever want to learn the product.”
Lemkin: Require A Product Demo Before Hiring Any Sales Candidate
“I would never give anyone an offer letter before they give you a demo from CRO to junior SDR.”
Lemkin: Replace Sales VPs Immediately Once Fear Sets In About Sellability
“When fear sets in sales, it, it's almost unrecoverable. It's the one symptom where if you're ever deciding, should I give my VP of sales more time? We've talked about this for years since after. The numbers aren't improving, but things look okay, or this or th…”
Lemkin: Requiring Prospective Sales VPs To Close Deals Is 100% Mandatory
“I used to not be sure. Now I think it's a hundred percent required. They've got to sell themselves. And if you hear hesitation in their voice, they ain't gonna do it. If you hear a maybe, don't make the hire.”
Lemkin: SaaS Startups Under $10M ARR Must Not Hire Product Marketers
“Don't hire someone that's a product marketer. You don't need at 2,000,005 million, even ten million air. You don't need 11 pages on your marketing site explaining How different segments of your market are critical.”
Lemkin: Startups Must Not Hire Brand Marketers Before Establishing A Brand
“You don't need a corporate marketer. You don't need a brand expert at your stage until you have a brand. When you, when everyone has heard of you can hire a corporate or brand marketer.”
Lemkin: Reject Marketing Candidates With 'Strategist' In Their LinkedIn Headline
“If you like a marketer. If they're smart, if they're intelligent, look at their LinkedIn and see what their first line is. If it says strategist, thank them, send them a blue pen with your logo on and do not hire them. Trust me, not 99% of the time.”
Lemkin: The Best Demand-Gen Marketers Display Quota Attainment On LinkedIn
“If you want a marketer to get you more leads, more opportunities, more pipeline, more customers, the best ones up until even 20, 30, forty million, all have one thing the same on their LinkedIn. Their first line is their commit.”
Lemkin: Sales Drop 90% Of The Time When Founders Stop Selling
“Not a hundred percent of the time, but at least 90% of the time sales falls.”
Lemkin: Top Sales VPs Turn Founders Into Dedicated Deal Middlers
“The great VPs of sales and CROs just change what the founders do and they turn you into dedicated middlers.”
Lemkin: Great Sales VPs Assign Their Startup CEO A Meeting Quota
“A great VP of sales will literally give the CEO a quota.”
Lemkin: MongoDB, Salesforce, And UiPath All Suffered Severe Growth Deceleration
“We talked about the shock to the system of Mongo going from 40 to 17%, Salesforce shrinking to single digit growth, UiPath cutting its guidance in half.”
Lemkin: Cutting Sales Harms Present Revenue While Cutting Marketing Harms Future
“When you cut salespeople, you cut your present, when you cut marketing, you cut your future and it's a tough call.”
Lemkin: Startups Lacking AI Parity Get Slaughtered In Enterprise Bake-Offs
“In today's world, if you go into a bake-off, a competitive bake-off, and your competitor is making real or fake promises with AI, and you cannot compete, you're going to get slaughtered, especially in the enterprise.”
Lemkin: Startups Decay Faster If Their CTO Cannot Integrate AI
“If your CTO by today, isn't sure how to, doesn't, isn't sure how to integrate AI into your product. Ask yourself if you need a new CTO. It doesn't mean get rid of them, but your competitiveness, I think is going to continue to decay and accelerate.”
Lemkin: Startup Growth Is Valued Up To 10x More Than Profitability
“For public companies, growth is still worth twice as much as profitability for startups. It's probably four to 10 times.”
Lemkin: The Current Tech IPO Bar Is $200M ARR Growing 40%
“To IPO today, you've got to be doing at least two hundred million growing at least 40%.”
Lemkin: Less Than 10% Of Top Seed Startups Maintain T2D2 Growth
“It's less than 10% of venture backed startups that hit this. Not 10% of all startups. Only 10% of folks that rate seed rounds from the top VCs even maintain this pace, right?”
Lemkin: Founders Should Never Hire Fractional Or Burned-Out Startup Executives
“You can't hire folks with three jobs or want to be fractional or want to run two businesses on the side or want to see how it goes or think they can be a fractional CRO for seven companies at the same time. It's too hard out there. You can't hire the broken, t…”
Lemkin: Zoom Stalled For Three Years After Hitting $4B In 2021
“Zoom in one year went from one to four billion in revenue from whatever mid-twenty-twenty-twenty-twenty-one went from one to four billion from twenty-twenty to twenty-twenty-one. Anyone know what Zoom's revenue is today? Four billion. So one year quadrupled an…”
Lemkin: Redact Prestigious Employer Logos From Resumes To Avoid Bad Hires
“If you fall in love with someone in any part because of that logo, literally, if you want, this is just for fun, print it out. If you can find a printer, take a black marker and black out the LinkedIn and for fun, hand around and say, would you still hire them…”
Lemkin: Adding PLG To A Sales-Led Startup Takes Years Of Commitment
“Magically bolting on a PLG motion to a sales led thing is not an instant solution to marketing. It's I see so many folks that they're struggling. What are you going to do? Our product's 60,000 dollars a year. Oh, we're going to go PLG. What does that mean? We'…”
Lemkin: Slack And HubSpot Recently Executed Their First Historical Price Increases
“Slack did its first price increase in history at eight months ago. I did a blog post. Every single leader in SAS that hadn't done a price increase did it. HubSpot did too.”
Lemkin: UiPath Grew 20% While Adding Zero Net New Enterprise Customers
“Last quarter UiPath. Its growth crashed, but it still grew 20 something percent, but it had no net new customers. It started the quarter with the same number of customers that even UiPath. How'd they do it? They drove their five, their customers up to five mil…”
Lemkin: Moving Customer Success Under Sales Weaponizes The Function
“I think the worst of all of this, what has made it the worst is when we've all decided that customer success should be part of sales. The worst of all of these trends, because what we've done is weaponized customer success. We've taken the one person in the co…”