Are You Ready for Your First Sales Hire?
- You have a defined sales motion that you can teach to someone who knows nothing about your company.
- You have proven PMF and signed several paying customers in the last year.
- You have a documented sales playbook covering cold outreach, proposals, and contracts.
- You have a polished, repeatable sales demo.
- You have a clear TAM and lead list.
Creating a Job Spec and Posting
- Determine the Sales Cycle TypeThe right experience level depends entirely on your deal size and sales motion — hiring too senior or too junior for the role is one of the most common first-hire mistakes.
- Transactional/SMB: look for 1–2 years experience, high-volume comfort, and strong self-management
- Mid-market: look for 3–5 years experience with $10k+ ACV deals and a multi-stakeholder sales process
- Enterprise: look for 5–10 years experience with $100k+ ACV deals and a $1M+ quota track record
- Match the profile to where your current customers are — not where you hope to sell in 2 years
- Write a Clear Job DescriptionA clear, honest job description attracts candidates who know what they're signing up for and filters out those who don't.
- List all requirements explicitly — vague JDs attract a flood of mismatched applicants
- Draw inspiration from JDs at companies you admire for the right tone and structure
- Include growth trajectory and equity upside — startup comp is a package, not just base salary
- Look for candidates who are prepared, well-spoken, coachable, and competitive — flag these in the spec
Interview Process
- Structure the Interview PanelA structured panel with diverse interviewers and a consistent scorecard reduces hiring bias and improves decision quality.
- Include cross-functional interviewers from product and engineering — they'll work closely with this hire
- Assign each interviewer specific topics: company values, sales methodology, culture fit, or skillset
- Use a scorecard with defined criteria so all interviewers evaluate against the same standard
- Debrief as a group before making a decision — avoid letting any single interviewer veto unilaterally
- Give a Skills AssignmentA skills assignment separates those who talk about selling from those who can actually do it.
- Choose from a prospecting email, a product presentation, or a live sales call role-play
- Evaluate storytelling ability, communication clarity, attention to detail, and how well they personalized the work
- Give them enough context to do the assignment well — vague briefs test preparation tolerance, not sales skill
- Score the assignment against a defined rubric and share feedback regardless of the outcome
- Do Thorough Due DiligenceSales candidates are naturally skilled at presenting themselves favorably — go beyond the interview to verify what you've heard.
- Compare their LinkedIn profile to their resume for discrepancies in dates, titles, or companies
- Review their public social media presence for anything inconsistent with your culture
- Back-channel references from former managers before making an offer — not just the references they provide
- Ask references specifically about quota attainment, coachability, and how they handled losing a deal