One of the biggest mistakes I see early-stage B2B startups make?
Hiring a sales rep—or worse, outsourcing sales to an agency—before they’re ready.
It’s an easy trap to fall into. Many founders see themselves as techies, not salespeople. They assume that once they have a great product, a sales rep should be able to take over and start closing deals.
But that’s not how it works.
If you’re an early-stage founder, here’s the hard truth:
The moment you start a company, you are in sales.
You’re not just building a product—you’re selling your vision to customers, investors, partners, and even potential hires.
And if you hire a sales rep (or agency) too early, you’re setting yourself up for failure. Here’s why.
Why Hiring Sales Too Early is a Costly Mistake
At an early stage, hiring a salesperson creates more problems than it solves. Here’s what typically happens:
1. You Don’t Have a Clear ICP (Ideal Customer Profile)
Your product might have a broad market, but in the early days, you don’t yet know exactly who your best customers are.
• Should your sales rep target mid-market companies or enterprise?
• Should they focus on founders, CMOs, or sales leaders?
• Should they reach out to tech startups, professional services, or manufacturing firms?
Without clarity on who they should be calling, your rep will waste time chasing the wrong leads—leading to frustration and failure.
2. Your Messaging Isn’t Proven Yet
Even if your product is great, you don’t yet know what messaging works.
• What pain points should your sales team focus on?
• What questions will get prospects engaged?
• What’s the best way to structure a demo?
If you can’t answer these questions yourself, how can you expect a sales rep to?
3. You Haven’t Handled Enough Objections Firsthand
Every sales call comes with objections:
❌ “We already have a tool for this.”
❌ “This isn’t a priority for us right now.”
❌ “How is this different from [Competitor]?”
As the founder, you are the best person to address these objections because you deeply understand the product, market, and vision.
A sales rep, on the other hand, will likely respond with “I’ll get back to you”—which often means a lost deal.
4. You Might Need to Pivot
What happens if, after a few months, you realize you need to pivot?
• Maybe your ideal customer isn’t who you thought.
• Maybe the messaging isn’t resonating.
• Maybe the feature you thought would sell isn’t the one customers care about.
If you’ve already spent money on a sales team or agency, all of that investment is wasted.
Instead of outsourcing sales too soon, founders should sell first.
What Founders Learn by Selling Themselves
By selling your product yourself, you gain critical insights that will shape your entire go-to-market strategy:
✅ What messaging actually resonates? – Which value props get people excited?
✅ What objections come up repeatedly? – How do you address them effectively?
✅ What are the best channels for finding prospects? – Cold email? LinkedIn? Referrals?
✅ Which personas convert the fastest? – Who are the decision-makers? Who influences them?
✅ What is the right sales motion? – Do customers prefer short demos or deep discovery calls?
This hands-on learning is invaluable. It’s what turns a product into a business.
Steve Blank once shared a story about a sales leader who lost a deal. Instead of reflecting on what went wrong, the rep simply moved on to the next one.
But Steve stopped him and said:
“No—let’s assess what happened.”
Why? Because every lost deal is an opportunity to learn.
• Did we lose because of pricing?
• Was the messaging off?
• Did we fail to handle a key objection?
• Was it the wrong ICP altogether?
Sales isn’t just about closing deals—it’s about understanding why deals are won or lost. This is why founders must sell their own product first. The insights you gain will make every future sales motion stronger.
If you hire a sales rep too soon, they won’t have this deep level of understanding. They’ll just move on to the next lead without extracting the lessons that could shape your entire business strategy.
Steve put it perfectly:
“A startup is a temporary organization in search of a repeatable sales model.”
Until you have that repeatable model, hiring sales is premature.
When Should You Hire a Sales Rep?
You should bring in a sales team or agency when:
✔️ You have a clearly defined customer, segment, and persona
✔️ You’ve tested and refined your messaging and sales process
✔️ You can predict how calls will go and what objections will arise
✔️ You’ve personally closed multiple deals with a repeatable approach
If you can check those boxes, you’re ready to scale.
Until then, founders should sell their own product.
Final Thoughts
Sales isn’t just about closing deals—it’s about learning what works.
As a founder, your early sales calls will teach you more than any market research ever could. They’ll refine your product, messaging, and growth strategy in ways that no hired sales rep can.
At Ziply, we’re in the trenches, closing our first 10 customers ourselves—and I’ll be sharing more insights along the way.
