Hiring your first sales rep is one of the riskiest and most misunderstood steps in building a startup. Most failures at this stage aren’t because of a bad hire — they’re because the company isn’t ready to hire in the first place.
And savvy reps? They can smell disfunction a mile away and will pass. That leaves you with less experienced reps who may fail — setting your go-to-market back months or more.
Here’s a checklist to help you stress-test your readiness and avoid wasting time, money, and market momentum.
1. Is your Go-To-Market (GTM) strategy aligned?
Hiring the wrong type of rep often stems from a misaligned GTM motion.
Founders often choose a sales model (PLG, enterprise, channel, etc.) based on preference, but it really depends on how the customer wants to buy.
If you sell a complex, high-ACV product but try to go PLG and hire a PLG rep, you’re setting everyone up to fail. Align your sales, product, marketing, and finance teams around the buying journey. No alignment? No rep yet.
💡 Use a GTM audit or alignment check to ensure everyone’s rowing in the same direction.
2. Is your culture truly ready for sales?
Sales teams bring a different energy and DNA compared to engineering-led teams. That’s a good thing — if your company is prepared for it.
Ask yourself:
- Is your company ready to value a revenue-generating org that runs differently?
- Are you OK with some messiness in how sales talks about the product?
- Will your team support someone who isn’t technical but is critical to growth?
- Is the company aligned that hiring sales is critical to growth and success, or some necessary evil?
If hiring a sales rep feels like a cultural threat, that’s a red flag. Don’t hire one until you’ve embraced the value of a true go-to-market team.
💡 Hold a listening session to figure out how the organization perceives sales and explore solutions for growth without a rep.
3. Can you clearly define your target customer?
Reps need direction. Anchor them on a Job-To-Be-Done (JTBD) — a straightforward customer workflow that contains a pain point your product solves. Let the rep build patterns around who’s doing that job, then refine your ideal customer profile. Think of a job-to-done as the universe of people doing the job your product solves for. The ICP is the subset of these people who are right for your product based on possible attributes like company size, maturity, integrations, or maybe industry vertical.
Bonus: If you can tell them the compelling event that makes customers consider a new solution, you’re ahead of most.
💡 Do a job to be done project to get everyoneon the same page. This will benefit not only sales but also product.
4. Is your sales process at the MVP stage?
You don’t need a repeatable sales machine — yet. But you do need:
- A few inbound leads to keep reps busy 50% of the time. They can hunt the other 50% although hunting is super inefficient
- A follow-up process for inbound leads
- Defined deal stages
- Pricing that a rep can use
- A way to demo or trial with a sales engineer
- Basic sales presentation
- List of objections and how to answer them
You should be able to walk a rep through a typical sales cycle, step-by-step, based on what you’ve done yourself.
💡 Start documenting your sales process
5. Can the rep run deals without the founder?
This is where things break.
If the founder, using the founder/CEO authority, is still making pricing calls, assigning engineers to demos, or doing all the selling, the sales process isn’t ready to scale. Hiring a rep won’t fix this. It’ll cause massive friction for the rep and make everyone question why a rep was needed. Carefully consider whether deals are getting done because of the CEO/founder’s authority or if the process will run without the CEO.
Delegating sales means reps can work a deal from lead to close without constantly waiting for the founder’s direction or decisions or direction to others.
6. Do you have a live pipeline and a few closed deals?
If you ask a rep to build a pipeline from scratch without proof that deals can close, it’s a massive red flag—for you and them.
Even a modest pipeline built through founder-led sales shows product viability and signals that a reps time will be well spent. If you don’t have a pipeline in a CRM of some magnitude to meet 50% of the reps quota in the first quarter of their hiring, you are not ready to hire a rep. Go back to founder led selling.
7. Do you have a system to keep sales enabled and informed?
Sales reps need constant input, especially in the early days.
That includes:
- Onboarding and ongoing training
- Shadowing and recorded call feedback
- Updates on new features and changing messaging
Startups shift fast, and reps can’t sell what they don’t understand. Someone—you or a product marketer—must own enablement from day one.
8. Are the basic sales sytems in place?
You don’t need an enterprise tech stack, but your rep will need:
- CRM (HubSpot, Salesforce)
- Knowledge base (Notion, Confluence)
- Call/video (Zoom, Chorus/Gong)
- Lead tools (ZoomInfo, LinkedIn Sales Nav)
- Pricing & quoting (Google Sheets, Hubspot quotes)
- Internal collaboraton (Teams, Slack etc.)
Please keep it simple. Don’t over-engineer your sales stack. Martech stacks are messy affairs. Out-of-the-box tools are more than enough. Don’t be the startup that assigns an engineer to build the martech stack and there is more custom code in salesforce than in the product (seen it).
Final Thoughts
Hiring your first rep is a high-stakes move — but if you can answer “yes” to all these questions, you’re not just ready to hire; you’re ready to attract great talent.
If not? That’s OK. You can bring a fractional GTM consultant to help you build the foundation and de-risk the hire. The consultant is not there to pontificate and advise, but the GTM consultant should play the role of CMO/CRO/product marketer and sales rep. If your consultant working with you can build the sales process and pipeline while doing some deals, you can easily transfer this to the first sales rep and reduce the hiring risk.
Photo by Clem Onojeghuo on Unsplash
