The Harder-to-Sell Heuristic
Only hire reps whose last product was harder to sell than yours — never easier.
- Difficulty
- Easy
- Time to result
- ~weeks to results
- Steps
- 4
- Confidence
- 92%
Sales performance is close to binary across environments: the same person can be a star selling one product and utterly fail selling another. Lemkin's single strongest predictor is directional difficulty — if the rep's last product was even a smidge harder to sell than yours, arriving at your company feels like weights coming off their feet. If it was easier, they simply lack the skills your product demands, and they melt. He offers three concrete difficulty axes to compare on.
Origin
Jason Lemkin, from hiring at EchoSign — most vividly Sam Blond, who came from Intacct (cloud financials, at a time when nobody trusted their financial statements to the cloud) and instantly became number one — and from watching the inverse failure repeat across his portfolio.
Core principles
- 01Sales skill is not portable in the abstract; it is portable only downhill in difficulty.
- 02Difficulty has axes you can compare: technical depth, competitiveness of the category, and business-process complexity.
- 03Coming from number four in a crowded, undifferentiated category is a great sign — they had to sell with no natural advantage.
- 04In hiring we always give and never get what we want; the difficulty check is the one concession you must not make.
How to run it
- 1
Score the candidate's last product on technical depth
Was their prior sale more technical than yours? Someone who sold a complicated API to VPs of Engineering can usually go sell a business-process app. The reverse — a business-process seller moving into B2D — mostly fails.
Pro tip Developers do not suffer fools; a rep who survived selling to engineers has a durable edge.
Watch out This is the axis Lemkin is most emphatic about: 'the technical one, man, trust me.'
- 2
Score competitiveness of the prior category
A more competitive prior market is a positive. The ideal profile: they were the number four player in a space where no buyer could tell the products apart — and they still did well.
Pro tip If you are number two, a successful number-four seller will find your job easy, even though you feel crushed by number one.
- 3
Score business-process complexity
Compare integration count, workflow depth and how much organisational change the buyer must absorb. Reps who sold a simple business process routinely melt when the sale requires deep integrations and process change.
Pro tip Ask them to walk you through the most complex deal they closed, integration by integration.
Watch out A rep who can only say 'we're the Gong for X' collapses the moment the prospect asks how the Zendesk and Salesforce flows actually work.
- 4
Reject on an easier prior product, no matter how much you like them
If the last product was easier to sell, pass — however great the resume, the references, or the rapport. Use the sell-me-this-app demo to control for it, but do not talk yourself out of the signal.
Pro tip Ask the reverse question of a star performer: 'why are you crushing it when everyone else is struggling?' A blunt 'this is much easier than my last job' confirms the model.
Watch out This is where founders 'give' in the hiring process and regret it.
In the wild
EchoSign's first SDR, Sam Blond, came from Intacct — cloud financials in an era when buyers said their financial statements were crown jewels that could never go to the cloud. Selling EchoSign was hard, but it was not that hard by comparison. Asked why he was crushing it while everyone else struggled, he said simply: 'this is much easier than Intacct.'
→ He went SDR → SMB AE → mid-market AE → director of sales → head of sales, later becoming CRO at Brex and a partner at Founders Fund.
A portfolio company doing $20M+ had reduced its genuinely complex product to the pitch 'we're the Gong for X' — great for getting VC meetings, absent from its own homepage. The senior sales exec they hired could say nothing else. When a prospect asked how the deep integration with their business-process flow and Zendesk worked, and how data moved to Salesforce, the exec repeated the tagline.
→ The $600,000 deal was lost — an illustration of a rep melting on business-process complexity beyond what they had sold before.
Common mistakes
Hiring the star from an easier, better-known product
The rep who crushed quota at a category leader with brand, partners and integrations has none of the skills to sell a feature-poor challenger with a subtle 10x feature. Their track record was environment, not skill.
Assuming B2B reps can sell to developers
B2D is the same beast with a different buyer. Lemkin sees B2B reps melt in B2D repeatedly, because developers will not tolerate a rep who cannot answer technical questions.
Treating a mis-hire as a moral failure
Someone can be excellent in one sales environment and completely fail in another — it is more binary than any other function. Find it before you hire; root it out fast if you missed it; and know they may go on to be wildly successful elsewhere.
Is it for you?
Best for
Founders and sales leaders evaluating rep or VP candidates, especially when the resume is impressive but the product context differs
Not ideal for
Hiring for a dominant, well-known category leader where brand does most of the selling and 10 scripted questions plus a sales engineer suffice
From the transcript
“you gotta hire someone whose last product was harder to sell”
“if you take someone in sales and their last product was easier to sell they will have none of the skills to sell your product”
“what really works Lenny is if you hire someone from the number four in a space”
“he came to me and I said Sam why are you why are you crushing it when everyone else here is struggling he's like this…”
From the episode
Building a world-class sales org
Jason Lemkin (SaaStr)