Head of Sales Hiring Guide
ZYTHR Resources •
September 19, 2025
TL;DR
This guide provides role overview, core skills, sourcing and screening strategies, interview questions, rejection criteria, evaluation rubric, selling points, red flags, and onboarding milestones for hiring a Head of Sales.
Role Overview
The Head of Sales owns revenue strategy and execution across the company. They define go-to-market priorities, build and lead the sales organization, set quotas and KPIs, design compensation, and partner with marketing, product, and customer success to drive predictable growth. This role is both strategic — setting the direction and metrics — and operational — hiring, coaching, and optimizing a team to hit targets.
What That Looks Like In Practice
Owning a $10M+ ARR plan, designing a territory and quota model, hiring and ramping AE and SDR teams, implementing forecasting and pipeline hygiene processes, negotiating major enterprise deals, and standing up enablement and compensation programs. At smaller companies the Head of Sales may be hands-on with key accounts; at larger orgs they build leaders to scale.
Core Skills
These are the non-negotiable, job-specific skills and experiences to include in JD and screen for. Aim for evidence rather than vague claims.
- Revenue strategy & GTM design Creates and executes multi-channel GTM plans, aligns messaging to buyer motion, and sets annual/quarterly revenue targets.
- Team building & people leadership Hires, coaches, structures teams (SDR/AE/AM), creates career paths, and improves rep performance and retention.
- Enterprise sales & negotiation Experienced in complex deal cycles, procurement, legal/contract negotiation, and closing multi-year agreements.
- Forecasting & pipeline management Implements reliable forecasting cadence, deal stages, win/loss analysis, and pipeline hygiene to predict outcomes.
- CRM and RevOps fluency Hands-on with Salesforce or equivalent, builds scalable processes, and partners with RevOps to automate reporting.
- Data-driven decision making Uses metrics and experiments to iterate on playbooks, compensation, and territory design.
- Cross-functional collaboration Works closely with marketing, product, and customer success to align product-market fit, lead generation, and post-sale adoption.
Look for measurable outcomes: ARR growth percentages, deal sizes, ramp time improvements, team size and retention.
Soft Skills
Soft skills determine how the candidate will lead, influence, and operate under pressure. These are critical for culture and long-term effectiveness.
- Coaching and mentorship Actively develops others, gives constructive feedback, and creates scalable training programs.
- Executive communication Conveys revenue story and needs clearly to the CEO and board; builds business cases for investments.
- Resilience and bias for action Makes timely decisions in ambiguous environments and recovers quickly after setbacks.
- Strategic thinking Balances short-term revenue delivery with long-term market positioning and scalable processes.
- Influence without authority Aligns cross-functional stakeholders and secures resources by persuading with data and clear plans.
Probe for specific examples that show behavior rather than abstract adjectives.
Job Description Do's and Don'ts
A strong JD attracts the right candidates quickly. Avoid vague or overly prescriptive language that either scares away senior talent or invites unqualified applicants.
| Do | Don't |
|---|---|
| State clear outcomes (e.g., grow ARR from $10M to $30M in 24 months). | Use vague phrases like "drive growth" without targets or context. |
| List required-scale experience (enterprise vs SMB) and team size managed. | Demand an exhaustive tech stack or 10 different industry specialties. |
| Mention compensation structure and equity range or band. | Hide compensation information or use 'competitive' without any reference. |
| Describe autonomy and decision rights for the role. | Imply micromanagement or ambiguous reporting lines. |
Keep the role focused on outcomes and required experience, and highlight culture and compensation range if possible.
Sourcing Strategy
Find senior, proven sales leaders through channels that surface measurable results and cultural fit.
- Executive search firms Engage firms with a track record in your vertical for confidential searches and to tap passive, high-caliber candidates.
- Senior LinkedIn outreach Target Heads/VPs of Sales in companies at your next stage (e.g., SaaS $10–100M ARR) and highlight growth opportunity and ownership.
- Employee referrals Activate internal network and alumni — referrals often yield better culture fit and faster close.
- Industry events and peer networks Conferences, roundtables, and LinkedIn groups often surface leaders open to new challenges.
- Targeted advertising and content Run executive-level content/ads (Webinars, Thought leadership) to attract strategic candidates.
- Internal promotion Consider promoting a proven senior AE/Director if they show leadership potential and runway to scale a team.
Prioritize referrals and targeted outreach; executive search can be used for critical hires or when confidentiality is required.
Screening Process
A structured interview process reduces bias and reveals the candidate's true ability to lead revenue growth.
- Initial recruiter screen (30 minutes) Confirm motivation, compensation expectations, notice period, high-level fit for stage/market, and basic track record.
- Hiring manager / CEO conversation (45–60 minutes) Discuss strategy, leadership style, past outcomes, and alignment on priorities. Assess cultural fit and vision for the role.
- Case study or take-home assignment Ask for a short GTM plan, territory/quota design, or forecast process tailored to your business. Evaluate reasoning, metrics, and practical steps.
- Panel interview with cross-functional leaders Include product, marketing, CS, and finance to assess collaboration, go-to-market alignment, and ability to influence.
- Reference checks (structured) Speak to former managers, direct reports, and peers about leadership, hiring, and delivered outcomes. Use a consistent set of questions.
- Final compensation and offer discussion Align on base, OTE, equity, performance milestones, and any transition/hiring support. Move quickly to close.
Keep the process efficient: 4–6 interviews over 1–3 weeks for top candidates. Provide clear evaluation criteria at each stage.
Top Interview Questions
Q: Tell me about the biggest revenue plan you built and the outcome.
A: Look for scope (ARR baseline and targets), levers pulled (pricing, motions, hiring), and measurable outcomes (growth %, time to goal). Strong answers include trade-offs and lessons learned.
Q: How do you structure forecasting and what signals do you trust most?
A: Good candidates describe cadence, data sources (CRM, conversion rates, sales activities), and leading indicators (pipeline coverage, win rates, deal velocity). They also explain how they address forecast misses.
Q: Describe your approach to hiring and ramping a new sales team.
A: Expect a repeatable process: role profiles, sourcing channels, interview rubrics, onboarding curriculum, early performance metrics, and remediation plans for underperformance.
Q: How have you collaborated with product and marketing to improve win rates?
A: Strong answers include cross-functional initiatives (outbound ICP alignment, feature prioritization based on deal feedback, joint ABM campaigns), with measurable impact.
Q: Give an example of a large lost deal. What did you learn and change?
A: Look for ownership, honest root cause analysis, and specific process or messaging changes implemented to prevent recurrence.
Top Rejection Reasons
Deciding on top rejection reasons in advance helps interviewers consistently filter candidates who can't deliver the role's outcomes. Use these as objective checkpoints.
- No demonstrable revenue growth track record Unable to show quantifiable results at the required scale (e.g., never led teams through similar ARR increases or market stages).
- Weak people leadership Poor examples of hiring, developing, or retaining talent; inability to provide references from direct reports or to discuss team-building.
- Lack of pipeline and forecasting discipline Vague or theoretical answers about forecasting and pipeline hygiene without concrete processes or CRM usage.
- Misaligned GTM or market fit experience Experience confined to a very different buyer profile or sales motion (e.g., only consumer or short-cycle SMB when you need enterprise).
- Cultural mismatch or poor stakeholder fit Indicative behavior that conflicts with company values or inability to collaborate cross-functionally.
Document examples from the interview to justify rejection and provide constructive feedback where appropriate.
Evaluation Rubric / Interview Scorecard Overview
Use a simple rubric to standardize feedback and speed decisions. Weight criteria according to your stage and priorities.
| Criteria | Rating Guidance | Weight |
|---|---|---|
| Revenue track record | Exceeded targets at scale; growth % and ARR context provided | 30% |
| Leadership & hiring | Built and retained teams; examples of coaching and org design | 25% |
| Forecasting & ops | Reliable forecasting process; CRM-driven discipline | 20% |
| Strategic GTM thinking | Clear multi-quarter plan with measurable levers | 15% |
| Cultural fit & communication | Clear alignment with company values and exec presence | 10% |
Collect scores and qualitative notes; require examples and metrics to justify high ratings.
Closing & Selling The Role
Senior candidates evaluate opportunity, team, runway, and comp. Sell the role by focusing on impact, autonomy, and upside.
- Lead with the vision and impact Describe the revenue opportunity, market timing, product differentiation, and the specific outcomes they can own in the first 12–24 months.
- Be transparent on comp and equity Share base, OTE, equity range, and performance milestones. Senior hires expect clarity and speed on compensation.
- Outline resources and autonomy Explain hiring budget, RevOps support, marketing alignment, and decision-making authority they'll have.
- Show career and legacy upside Communicate potential career paths, board visibility, and equity upside tied to company success.
- Address risks proactively Discuss known challenges (product gaps, competitive landscape) and the plan to mitigate them — honesty builds trust.
Tailor the pitch to the candidate's motivators: equity and upside for some, autonomy and resources for others.
Red Flags
Watch for behaviors or answers that signal future problems. These should trigger deeper probing or disqualification.
- Inflated or unverifiable metrics Vague numbers without context, or refusal to provide references who can confirm results.
- Blame-focused explanations Consistently blames product, marketing, or previous leadership without owning decisions or learnings.
- No repeatable hiring/playbook evidence Cannot explain how they hire, onboard, or scale teams beyond anecdotes.
- Reluctance to use CRM/ops Dismisses forecasting and data processes as administrative rather than critical to scaling.
- Overly prescriptive cultural demands Insists on rigid team structures or headcount before proving concept, indicating poor adaptability.
Onboarding Recommendations
A structured onboarding program shortens ramp time and sets the Head of Sales up for early wins. Tie onboarding goals to measurable outcomes.
- First 30 days: Listen and assess Meet key stakeholders, review pipeline and deals, audit CRM and forecasting process, and time with top accounts and top reps to understand current state.
- First 60 days: Build the plan Finalize hiring plan, territory/quota design, compensation adjustments, and a 6–12 month GTM roadmap with clear KPIs.
- First 90 days: Deliver early wins Execute priority hires, launch improved forecasting cadence, close targeted strategic deals, and show measurable pipeline improvements.
- Set OKRs and success metrics Agree with the CEO on measurable metrics (ARR, churn, ACV, pipeline coverage, ramp time) and reporting cadence.
- Prioritize leadership development Identify immediate coaching needs, create 1:1 and enablement cadences, and define performance improvement plans for underperformers.
- Operationalize RevOps partnership Establish dashboards, KPIs, and automation to reduce admin overhead and improve forecast accuracy.
Set 30/60/90 day milestones that include people, process, and revenue goals.
Hire a high‑impact Head of Sales
Use this guide to attract, assess, and onboard a Head of Sales who can scale revenue, build repeatable GTM motion, and lead a high-performing team. Follow the sourcing, screening, and onboarding recommendations to shorten time-to-fill and reduce ramp time.