Hiring Your First Salesperson - The Ultimate Guide for Founders.

Hiring your first salesperson is scary. Especially when you're selling into large companies, and the sales process is long, technical, and full of unknowns.

Yes, you led the first few sales of your product but you don't know how to run a deal clinic or a forecast call. You're expected to evaluate candidates for a role you’ve never done.

This guide will help you hire a salesperson who can actually bring in deals.

Hire a Builder

Most founders hyper focus on candidates who closed deals. But in early-stage startups, your first hire is an entrepreneur like you: They're building your sales motion by trying things, observing and course correcting. They need to be comfortable with:

• Reaching out to new companies cold

• Talking to multiple people inside large organizations — IT, finance, legal, end users

• Collaborating with Marketing, Product and Leadership to understand what's working and what's not.

• Learning fast and improving the sales process as they go

This is a role for someone who’s comfortable with chaos, thrives on figuring out things, and values the ability to impact the company over sales predictability and company perks.

💬 Interview Questions You Should Ask (and What to Look For)

1. “How do you find new customers to contact?”

✅ Good signs:

• Mentions using tools and methodologies such as LinkedIn, email campaigns, industry lists etc

• Has a clear, repeatable process

• 🚩 Red flag:

  • "I got my leads through Marketing" - May not know how to generate leads

  • “I don't do cold calls or emails.” " - Will refuse to do lead generation.

2. “How do you keep a potential sales opportunity moving forward?”

✅ Good signs:

• Talks about setting clear next steps, asking questions to qualify the deal.

• Works with multiple decision makers on the customer side

• Uses checklists or deal tracking templates to drive progress

• 🚩 Red flag:

  • "I build great relationships with my customers, they love me" - Confuses a customer's friendly attitude with being a trusted advisor who can influence a sale.

3. “Tell me about a deal you brought in — where you started from scratch.”

✅ Good signs:

• They explain how they identified the company and the right people

• Understood the customer challenges and how their product solves the challenge

• Worked through objections and closed it

• 🚩 Red flag:

  • "I reached out to my buddy who works there..." - not a repeatable strategy

  •  "We negotiated, We presented ..." Someone else led the deal and the candidate just tagged along.

4. “What would your first 30, 60, and 90 days here look like?”

✅ Good signs:

• Mentions learning the product

• Identifying best-fit companies to target

• Reaching out quickly to test what messaging works

• 🚩 Red flag:

  • “I'll send hundreds of emails to get meetings and figure it out as I go” - Might indicate an inability to learn the product and the customer needs, relying on volume rather than a thoughtful value proposition approach.

🚨 General Red Flags to Watch Out For

• Only worked at big companies and expects to receive all their sales leads and marketing messaging material from others.

• Doesn’t mention how they build a business case or deal with legal challenges.

• Avoids giving specific examples of a deal they led.

• The lone wolf - Provides no visibility into his sales activities (no reports, won't let others join his customer meetings), blames everyone else when a deal is lost.

• Asks questions that focus solely on the financials of the role (commission plan, company card, travel expenses )

✅ Green Flags to Look For

• Resilient when facing rejection.

• Understands how to work through customer objections rather than give up.

• Shows signs of discipline, curiosity, and self-management.

Final Word

Your first sales hire will impact your sales processes and direction. Hire someone who is self sufficient and comfortable with rapid changes and high levels of ambiguity.