Use this curated, category‑based question bank to run a structured, signal‑dense interview for a Head of Sales. Each category includes specific prompts and what “good” looks like to help interviewers probe for depth, judgment, and execution skills.

Role Context & Strategy

• If you joined tomorrow, what would your first 90 days look like?
  Good answers: Clear discovery plan, stakeholder mapping, baseline of funnel metrics, quick wins, capacity model draft, and an explicit 30‑60‑90 roadmap tied to business outcomes.
• Describe the company’s likely ICP and segmentation based on our website.
  Good answers: Hypotheses with rationale (firmographic + pain), test plan, and a proposed territory or account prioritization approach.
• What are the top three revenue risks you’d assess first?
  Good answers: Pipeline health, win/loss drivers, forecast accuracy, hiring ramp/capacity, pricing/discounting leakage, CS handoff.
• How do you decide between PLG, sales‑led, or hybrid GTM?
  Good answers: Match motion to ACV, time‑to‑value, sales cycle complexity, and buyer behavior; crisp stage‑gating between SDR/AE/CSM/AM.
• Tell us about a time you pivoted GTM and what changed in metrics within 2 quarters.
  Good answers: Specific baseline vs. delta (e.g., SQL→Win%, cycle time), mechanisms (enablement, comp realign, messaging), and lessons.

Forecasting & Pipeline

• Walk through your forecasting methodology.
  Good answers: Bottom‑up + stage‑weighted + commit rigor; MEDDICC/exit criteria; risk and upside accounting; weekly cadence with deal sub‑reviews.
• How do you diagnose pipeline quality vs. quantity?
  Good answers: Coverage by segment, age by stage, slipped deals analysis, conversion heatmap, and source mix (inbound/outbound/partner).
• What’s your rule of thumb for coverage and how do you operationalize it?
  Good answers: Coverage factor by segment/ACV (e.g., 3–4x new logo), capacity‑aware targets, and weekly creation/aging dashboards.
• Tell me about a time you called a miss early. What did you do?
  Good answers: Early signal detection, reset with finance/CEO, re‑prioritize focus deals, and corrective actions on pipe gen.
• How do you prevent sandbagging and happy‑ear syndrome?
  Good answers: Evidence‑based stages, deal reviews with buyer verifiers, multi‑threading checks, and inspection of mutual close plans.

Methodology & Deal Execution

• Which deal methodology do you use and how do you make it stick?
  Good answers: MEDDICC/Challenger/Sandler with defined exit criteria embedded in CRM, coaching, and QBR artifacts.
• Show me a mutual close plan you’ve used.
  Good answers: Milestones, owners (buyer/seller), dates, risks, and an aligned go‑live/ROI checkpoint.
• How do you handle legal/procurement without blowing up timelines?
  Good answers: Early redline exposure, fallback terms, approval matrices, and pre‑negotiated guardrails with finance/Legal.
• What’s your discounting philosophy?
  Good answers: Value‑based pricing, approval thresholds, give/get, and guardrails to protect LTV and referenceability.
• Describe a complex, multi‑threaded enterprise win.
  Good answers: Org map, power sponsor strategy, executive alignment, competitive traps, and post‑sale success plan.

Leadership & Hiring

• How do you decide the next sales hire by segment?
  Good answers: Capacity model, ramp curves, productivity targets, and mix across SDR/AE/AM/CSM/SE.
• Walk me through your hiring rubric for AEs.
  Good answers: Competency matrix (discovery, narrative, negotiation, coachability), structured interviews, scorecards.
• Tell me about a mis‑hire and what you changed.
  Good answers: Root‑cause (process gap vs. bar), remediation steps, and updated rubric or enablement fix.
• How do you coach underperformers?
  Good answers: Joint diagnosis, 30‑day PIP with leading indicators, call review cadence, and clear success criteria.
• What culture do you build on the sales floor?
  Good answers: High‑bar, high‑care; clarity of expectations; celebrate craft; peer coaching; inclusive, ethical selling.

Enablement & Tools

• What’s your enablement plan for a new product launch?
  Good answers: Narrative, objection bank, roleplays, assets by stage, certification plan, and measurement of behavior change.
• How do you use CRM to drive behavior (not just reporting)?
  Good answers: Required fields = exit criteria, dashboards by role, automation to remove toil, and WBR cadences.
• Favorite call review framework?
  Good answers: Specific checklist (agenda, discovery, value, next steps), 1–2 coached clips per rep weekly, score calibration.
• How do you partner with RevOps?
  Good answers: Shared metric definitions, lead routing SLAs, attribution policy, comp plan modeling, territory design.
• What leading indicators matter most?
  Good answers: Coverage creation, meetings with ICP, stage‑to‑stage conversion, multi‑threading depth, and cycle time.

Cross‑Functional Collaboration

• How do you feed market intel back to Product/Marketing?
  Good answers: Closed‑loop voice‑of‑customer, tagged notes, win/loss themes, and prioritized requests.
• Give an example of co‑selling with Partners.
  Good answers: Sourced vs. influenced pipeline, MDF usage, joint value prop, and governance for deal conflict.
• Describe the Sales→CS handoff that prevents churn.
  Good answers: Documented success plan, stakeholder map, value hypotheses, risks, and timeline for first value.
• What metrics would you align with Marketing?
  Good answers: MQL→SQL definitions, SAL SLAs, pipeline sourced %, cost per SQO, and content effectiveness.
• Tell me about a pricing/package change you led with Product.
  Good answers: Research basis, internal enablement, pilot, win rate/cycle impact, and churn/expansion effects.

International, Enterprise & Verticalization

• How do you open a new geo?
  Good answers: TAM, localization, compliance, channel strategy, initial playbook, and ramp expectations.
• Enterprise vs. MM: what changes?
  Good answers: Buying committee depth, security/legal diligence, POVs, exec alignment, and reference design partners.
• Vertical GTM example.
  Good answers: ICP within vertical, tailored messaging, proof assets, and alliances.
• Public sector or regulated sales experience?
  Good answers: RFP navigation, frameworks, procurement cycles, compliance requirements.
• Partner‑led growth you’ve executed.
  Good answers: Sourced/influenced split, enablement, deal registration, and shared forecast rhythm.

Compensation, Quota & Capacity

• How do you design AE comp plans?
  Good answers: 50/50 OTE, accelerators, caps avoidance, balanced new vs. expansion, clawbacks for non‑payment if needed.
• Walk me through your capacity model.
  Good answers: Ramp time, productivity curve, coverage factor, attainment distribution, and hiring lead time.
• What’s your POV on SDR comp and handoff?
  Good answers: Pay for qualified meetings/SQOs, accountability on show rates, tight definitions.
• How do you set quotas?
  Good answers: Top‑down meets bottom‑up, territory TAM, historic attainment, and product maturity.
• An example of right‑sizing the team during a downturn.
  Good answers: Data‑driven, humane approach, focus on core segments, protect pipeline and customers.

Ethics, DEI & Culture

• How do you drive an ethical selling culture?
  Good answers: Transparent forecasting, honest discovery, no pressure tactics, and clear escalation paths.
• What are your practices for building diverse teams?
  Good answers: Structured interviews, diverse panels, calibrated rubrics, sourcing beyond standard channels.
• Handling a top performer who is toxic?
  Good answers: Coach with clarity; zero‑tolerance for values breaches; protect team trust.
• Tell me about a time you made the team measurably better.
  Good answers: Specific mechanism (playbooks, coaching program, enablement sprint) with KPI improvements.
• How do you ensure accessibility and inclusion in your process?
  Good answers: Inclusive meeting norms, accessible assets, equitable territories and opportunities.

Case Study Prompts

• Present a 30‑60‑90 plan for our current stage. Provide 2–3 KPIs per phase and a risk register.
• Prospect an account live (5 minutes research, 2‑minute narrative, 3‑minute email/call outline).
• Run a 15‑minute deal inspection on a live or past opportunity: MEDDICC status, risks, next steps.
• Build a territories proposal for 6 AEs across NA/EU with rationale and capacity math.
• Draft a mutual close plan for a 100k ACV opportunity with procurement in play.

Tip: Adapt the depth to your ACV and motion. Use scorecards with evidence notes per category to reduce bias and improve hiring signal.