Making your first sales hire is a big milestone. It means your business is growing, your product or service has traction—and you’re ready to start scaling. But for startups and small businesses in Bozeman, hiring a sales rep isn’t just about filling a seat—it’s about finding someone who can grow with your business and represent your brand authentically.
Here’s what you really need to know before bringing your first sales rep on board.
1. Don’t Hire Too Early—Or Too Late
The Trap:
Some founders try to offload sales too early, hoping someone else will “just handle it.” Others wait too long, stuck working in the business instead of on it.
The Sweet Spot:
Hire your first rep once you’ve:
- Proven your product or service solves a real problem
- Closed several deals yourself
- Built a basic, repeatable sales process (even if it’s not perfect)
This ensures your rep has something solid to work with—and you’re not asking them to build the plane while flying it.
2. Hire for Coachability and Curiosity, Not Just Experience
The Mistake:
It’s tempting to hire someone with a “killer sales resume.” But flashy results in a corporate setting don’t always translate to early-stage hustle—especially in a unique market like Bozeman.
What to Look For:
- Coachability: Can they take feedback and adapt quickly?
- Curiosity: Do they ask good questions and show genuine interest in your customers?
- Alignment: Do they understand (and care about) your mission?
Experience is great—but mindset wins.
3. Set Clear Expectations from Day One
The Risk:
Many founders assume their new rep will “just know what to do.” Without clear onboarding, goals, and processes, even a talented rep will struggle.
The Fix:
Document the basics:
- What your ideal customer looks like
- Your current pitch, messaging, and pricing
- Your sales tools (CRM, templates, scripts)
- Key metrics (calls per week, demos booked, close rate, etc.)
You don’t need a 50-page playbook—but you do need clarity.
4. Start With a Trial Period (and Mutual Accountability)
Why It Helps:
A 60- or 90-day trial gives both sides a chance to test fit. If it’s not working, it’s easier to part ways without bad blood.
Make it clear:
- What success looks like
- What support you’ll provide
- How often you’ll meet to review progress
Sales is a team effort, especially early on.
5. Keep Selling—Even After You Hire
The Biggest Mistake?
Founders who check out of sales the second they hire someone. No matter how good your new rep is, they can’t replace your vision, your relationships, or your voice in the market—yet.
Stay Involved:
Join calls, support key deals, and keep learning from customer feedback. This also helps your rep feel supported instead of thrown to the wolves.
Final Thoughts
Hiring your first sales rep is exciting—but it’s also a turning point. Get it right, and you’ll have someone who helps drive real revenue and growth. Get it wrong, and you risk lost time, money, and momentum.
Want help building your sales process before you hire?
We work with Bozeman-based businesses to build sales strategies and onboarding systems that set reps (and founders) up for success.
Crest Consulting 