One thing we’ve talked a lot on SaaStr recently is how especially important is it in the Age of AI for your VP of Sales to be a product expert.
But having watched a half dozen more sales execs wash out the past few months alone, I wanted to simplify it and be more direct:
The pattern is almost universal: mediocre sales execs (from AE to CRO) show up on Day 1 knowing almost nothing about the product they’re selling.
Let me be clear about what I mean by “knowing nothing.” I’m not talking about lacking deep technical expertise or being unable to explain every feature nuance. I’m talking about reps who:
- Haven’t signed up for a trial of the product they’re about to sell
- Haven’t spent even 5 minutes clicking through the core workflows
- Can’t articulate the basic value proposition in their own words
- Don’t understand what pain points the product actually solves
The Interview Red Flag
Jon Oberheide nailed it in response to my tweet: imagine a sales candidate who says “Um, I haven’t used it” when you ask what they think of your product during the interview.
Think about that for a second. This person wants to spend the next 3-5 years of their career at your company, earning a living by convincing other people to use your product, but they couldn’t be bothered to spend 5 minutes signing up for a trial and kicking the tires.
That’s not just lack of preparation. That’s a fundamental lack of curiosity and initiative that tells you everything you need to know.
The Counter-Pattern: Great Sales Leaders Know the Product Cold
Alessandro Chesser’s response highlights the flip side: “The best sales leaders I’ve worked with know more about the product they sell than nearly anyone at the company.”
This is absolutely true, and it’s not an accident. Great sales leaders understand that you cannot sell what you do not understand. They recognize that:
- Product knowledge builds authentic confidence. When you genuinely understand how your product works and why it matters, that conviction comes through in every customer conversation.
- Deep product knowledge enables consultative selling. You can’t be a trusted advisor if you’re fumbling through feature explanations or unclear on use cases.
- Understanding the product helps you sell to power. C-level buyers can smell BS from a mile away. If you don’t truly understand your product, you’ll never get past the mid-level blocker.
The Founder-Led Sales Advantage
DoTadda Drew makes an excellent point about why CEO-led sales is so powerful in the early days:
“That is the great thing about CEO led sales: they are closer to the code, closer to the use case (hopefully they are solving their own pain point), closer to the customer, and closer to the next step on the roadmap.”
Founders selling their own product have an unfair advantage precisely because they have this deep, visceral understanding. They built it. They know every decision, every tradeoff, every “why.”
The Dangerous Transition Point
This is exactly why I keep asking founders: “Why is it so dangerous when a founder steps out of sales once they hire a VP Sales?”
Because unless that VP Sales has spent serious time with the product, understands it deeply, and can transfer that knowledge and passion to their team, you’re going to see a drop-off in sales effectiveness.
I’ve seen this pattern play out dozens of times across portfolio companies and the broader SaaStr community:
- Founder is crushing it in sales
- Company hires a “professional” VP Sales
- VP Sales has amazing resume and experience
- VP Sales hires a team of reps with impressive backgrounds
- None of them spend real time with the product
- Sales velocity slows, win rates drop, deal cycles lengthen
- Everyone is confused about what happened
What changes? The product knowledge disappears.
Here’s the Hard Truth CEOs Ignore: This Isn’t “Fixable”
And this is the part that most founders and CEOs don’t want to hear, but it’s critical to understand:
If a sales leader or rep isn’t curious enough to know the product reasonably well before they start, they never will be.
This isn’t a training problem. This isn’t an onboarding problem. This isn’t something you can fix with better documentation, more product sessions, or a longer ramp period.
Curiosity is a character trait, not a skill you can teach.
When someone shows up without having explored your product, what they’re really telling you is: “I’m not intrinsically motivated to understand what I’m selling. I see this as just another sales job, not as a mission to help customers solve real problems.”
And here’s where it gets even worse: they will hire an entire team under them that doesn’t know the product either.
Think about it. A VP Sales who doesn’t deeply understand the product will:
- Not screen for product curiosity in interviews (because they don’t value it)
- Not build product mastery into onboarding (because they didn’t do it themselves)
- Not hold their team accountable for product knowledge (because they can’t assess what they don’t possess)
- Hire reps who look like them: polished, experienced, great at “selling,” but fundamentally disconnected from what they’re actually selling
The result? An entire sales organization built on a foundation of product ignorance.
And They Will Lose to Competitors’ Sales Teams That Do Know the Product
This is where the rubber meets the road. In competitive deals, product knowledge becomes the differentiator.
When your rep is in a bake-off against a competitor whose sales team actually understands their product deeply, here’s what happens:
- Your rep gives generic pitches. The competitor’s rep speaks specifically to the customer’s exact use case because they understand the product well enough to adapt.
- Your rep stumbles on technical questions. The competitor’s rep confidently addresses them or knows exactly when to bring in an SE versus handling it themselves.
- Your rep sounds like they’re reading from a script. The competitor’s rep tells authentic stories about how other customers have succeeded because they truly understand the “why” behind the features.
- Your rep sells features. The competitor’s rep sells transformation because they understand the product deeply enough to connect it to business outcomes.
The customer feels the difference. They feel who actually believes in their product versus who is just trying to hit quota.
And you lose deals you should have won. Not because your product is worse. Not because your pricing is wrong. But because your sales team doesn’t know what they’re selling well enough to sell it effectively.
What To Do About It
If you’re hiring your first VP Sales or building out your sales team, here’s my advice after watching this play out hundreds of times:
1. Make product mastery non-negotiable from the interview stage. Before a new sales leader or rep gets an offer, they should have used your product. Not watched a demo. Not sat through product training. Actually used it themselves. If they haven’t taken the initiative to do this during the interview process, that tells you everything.
2. Make this a dealbreaker, not a nice-to-have. I know the pressure to fill a VP Sales role is intense. I know that candidate looks great on paper. But if they show up to the final interview not having explored your product, walk away. You’re about to make a very expensive mistake.
3. Test for product curiosity obsessively in interviews. Ask candidates:
- What do you think of our product?
- How does it compare to competitors you’ve seen?
- What would you change about it?
- Who do you think it’s best suited for?
If they can’t answer these questions with specificity, they haven’t done the work. And they never will.
4. Sales leaders must be product experts, period. Your VP Sales should know your product better than 90% of your company. If they don’t, you have the wrong VP Sales. Fire them before they hire a team in their image.
5. Build product knowledge into your hiring criteria for every sales role. Every AE, every SDR, every sales leader should be evaluated on product curiosity and product knowledge as heavily as they’re evaluated on quota attainment and sales skills.
6. Watch what they hire for. If your VP Sales starts hiring reps who also haven’t bothered to learn the product before joining, that’s your signal. They’re building a team that doesn’t value product knowledge because they don’t value it themselves.
The Bottom Line
You cannot sell what you do not understand. The lazy and the ones that crushed it in 2021 think otherwise. But you can’t. Not today.
You cannot create urgency around value you don’t personally believe in — or understand. And you cannot be a trusted advisor when you’re uncertain about what you’re advising on.
The mediocre sales reps show up on Day 1 treating the product as just another widget to sell. The great ones show up already having formed opinions, tested use cases, and developed genuine conviction about the value they’re bringing to market.
This trait isn’t teachable. It’s not fixable with better training or stronger onboarding.
A sales leader who doesn’t care enough to deeply understand your product before they join will never care. They’ll build a team that doesn’t care. And you’ll wake up 18 months later wondering why your sales motion feels broken, why you’re losing competitive deals, and why the magic from the founder-led sales days has disappeared.
The answer is simple: you hired people who don’t actually know what they’re selling. And now you have a culture where that’s acceptable.
Don’t make that mistake. Make product curiosity and product mastery the non-negotiable foundation of your sales hiring.
Because your competitors certainly will. And they’ll beat you because of it.
