Head of Sales
Structured interview questions for Head of Sales, with what a strong answer surfaces for each one.
BehavioralScalable team leadership Describe the sales organization you most recently built or rebuilt. What did the structure look like before and after your takeover, and which three decisions had the biggest leverage?
What a strong answer surfacesThe ability to connect organizational decisions to impact (segmentation by account size, separating hunter/farmer, introducing an SDR function, re-cutting geography). Maturity: three clear decisions with reasoning, rather than a long list of cosmetic changes. Be cautious with candidates who only describe processes (CRM hygiene, new templates) and cannot name a real structural decision.
BehavioralSales hiring and enablement Tell me about a sales manager you hired and developed. What stages did the development have, and where did the person stand after 18 months?
What a strong answer surfacesA concrete example of hiring plus active development, not just hiring. A structured onboarding plan, regular 1:1s, documented expectations for 6 and 12 months, clear escalation or success moments. Weak signal: blanket statements such as she was great or I give my people room, with no traceable coaching footprint.
BehavioralForecast and pipeline discipline Describe a quarter in which your organization missed the revenue target significantly. What was the main cause, what did you communicate to the managing directors and the advisory board, and what did you change?
What a strong answer surfacesDiagnostic maturity at the org level (a pipeline-generation problem vs. a closing deficit vs. a hiring gap vs. a market shift), clean upward communication (numbers before explanation, clear next steps) and at least one lasting change as a result. Anyone who has never meaningfully missed the target has either run too-conservative targets or has not led at this level long enough.
SituationalStrategic GTM vision You take over our sales organization with 18 people and three sales managers. The last two quarters were 25 percent below plan. What do your first 90 days look like?
What a strong answer surfacesSequencing: diagnosis first (pipeline audit, 1:1s with each sales manager, listening to calls, reading the CRM for stage conversion and velocity), then hypotheses, then structural decisions. Anyone who starts week 1 with major reorganizations signals a lack of maturity. Bonus point for explicit expectation management toward the managing directors and the advisory board in the first 30 days.
SituationalExecutive alignment The managing directors announce that the sales budget for the coming year will be cut by 20 percent, while revenue is to grow by 15 percent. How do you structure this discussion and which decisions do you make?
What a strong answer surfacesThe ability to spell out trade-offs openly rather than either defending reactively or agreeing preemptively. A clear framework: which levers produce revenue per euro of cost most strongly (expansion before new business, higher lead quality before more volume, pipeline hygiene before hiring)? Which bets get parked? Anyone who keeps everything and cuts nothing has not understood the question.
SituationalSales hiring and enablement One of your sales managers, with five reports, has been underperforming for two quarters. She has strong personal quota attainment, but the team under her regularly misses its targets. How do you proceed?
What a strong answer surfacesDifferentiating between individual performance and leadership performance: recognizing the player-coach trap, addressing it clearly, working with a documented action plan and a deadline (typically 60-90 days). Clarity on two scenarios: the leadership upgrade succeeds, or a downgrade to a senior IC role or an amicable separation. Weak: just keep coaching with no deadline or no clarity on consequences.
CaseStrategic GTM vision We currently do 12 M€ ARR, with 80 percent from the German market. The managing directors want to reach 25 M€ ARR in 24 months and expand into at least two additional markets (plan: Austria and the Netherlands). Build the sales plan for this at a high level.
What a strong answer surfacesA structured plan with clear phases: a diagnosis phase in the home market (Is 25 M€ from Germany alone achievable? Pipeline math, capacity, win rate), then a market-entry decision per secondary market (local team vs. from Germany vs. reseller), a hiring sequence (which roles when), and risk assumptions. Anyone who simply scales proportionally (more reps equals more revenue) without market-entry logic is below the level.
CaseForecast and pipeline discipline Our win rate is 22 percent, the sales cycle is 110 days, average deal size 35 k€, pipeline coverage 3.5x. We are missing the quarterly target by 18 percent. What are your hypotheses, and which two measures would you implement in the next 30 days?
What a strong answer surfacesNumerical plausibility check: 3.5x pipeline coverage at a 22 percent win rate should arithmetically hit the target, so the gap is probably in closing weakness, in pipeline quality (inflated values) or in a velocity deterioration. A clean list of hypotheses with test logic, then two clearly prioritized measures, not ten. Anyone who does not compute out loud has not really steered a pipeline.
CaseStrategic GTM vision You are to decide whether we introduce an SDR function (inbound qualification plus light outbound) or invest the existing budget in two more Account Executives. What data do you need to decide, and how would you test it?
What a strong answer surfacesA clear decision framework: the current inbound-to-outbound ratio in the pipeline mix, the MQL-to-SQL conversion rate, AE utilization (do they spend more than 30 percent of their time on qualification?), median ACV. Pilot logic with 2-3 SDRs for one quarter before scaling. Anyone who argues for or against without data (SDRs always work / SDRs don't work in Germany) shows a lack of analytical discipline.
TechnicalForecast and pipeline discipline Which metrics do you review weekly with your leadership team (the sales managers), and which monthly or quarterly with the managing directors and the advisory board? Why this split?
What a strong answer surfacesWeekly: pipeline movement (new, won, lost, slipped), forecast update on the current quarter, individual 1:1 insights, hiring-pipeline status. Monthly or quarterly: ACV, win rate, CAC, velocity, magic number, the pipeline-generation source mix, cohort retention. Anyone who does everything weekly drowns the leadership team in reporting; anyone who steers only monthly loses the quarter.
TechnicalScalable team leadership How do you structure compensation-plan design for the salespeople and sales managers under you? How do you balance complexity, incentive effect and comprehensibility?
What a strong answer surfacesExperiential knowledge: simple plans beat complex ones. Typically salespeople at 60/40 or 70/30 OTE, linear commission over plan attainment with an accelerator above 100 percent, clear spiff mechanics used sparingly only. Sales managers usually at 80/20 with team revenue as the main component plus 20-30 percent strategic goals. Anyone who packs ten components into one plan has not seen in practice how a plan with eight variables paralyzes salespeople.
TechnicalScalable team leadership What requirements do you place on a sales stack (CRM, sales engagement, forecasting, enablement)? Which tools have you most recently introduced or removed, and why?
What a strong answer surfacesA pragmatic view: a minimal stack that carries the cadence. Salesforce or HubSpot as the single source of truth, Outreach or Salesloft for sales engagement with more than 10 reps, Gong or Clari for forecasting and call intelligence from a certain size. A concrete tool removal is a positive signal (it shows discipline against stack sprawl). Anyone who names 12 tools without explaining why they work together has not yet thought the stack through.
ValuesExecutive alignment Describe a set of managing directors or a CEO you worked closely with. What worked well in the collaboration, and what was challenging?
What a strong answer surfacesMature reflection on the sales-leadership-to-CEO axis. Naming strengths plus concrete friction points without blame. Anyone who only praises or only criticizes is not yet sufficiently calibrated at the executive level. Bonus: self-observation of where their own patterns contributed to the friction.
ValuesStrategic GTM vision What is your reading of sales work for the next 3 to 5 years? How, in your view, does the role of a sales leader in a mid-sized B2B company change?
What a strong answer surfacesA current view: buyers arrive better informed, expect price transparency and honest advice, are fatigued by automated outreach sequences. AI changes SDR work and research, but not closing. Data discipline and forecast quality become more important. Anyone still thinking in the language of closing and persuading is outdated. Anyone who bets everything on AI has not understood the profession.
ValuesExecutive alignment What was the hardest feedback you received in the last 12 months (from the managing directors, the team or the advisory board)? How did you react, and what changed as a result?
What a strong answer surfacesCoachability at the executive level: a concrete example, an honest emotional reaction (rather than practiced composure), a traceable behavioral change with an observable effect. Anyone who cannot name a piece of hard feedback either received none (which is rarely good) or filters it out. Both are warning signs.
Evaluation playbook
At the sales-leadership level, no single evaluation stage delivers a clear signal. Validation comes from accumulation across four stages, with particular weight on the case study and the backchannel references.
Stage 1: CV and first screen (45 min)
A first conversation to clarify three points: the size of the most recently owned organization (number of sales managers, number of reports, ARR size), the career trajectory (from IC to sales leadership in what sequence, with what gap story), and the motivation to change. Look for consistent tenure of at least 24 months in previous sales-leadership or sales-director roles. Be cautious with more than two moves at this level in the last 5 years without a plausible story.
Stage 2: Structured interview with the executive team (2 hrs)
Work through the 15 structured questions above, alternating behavioral, situational, case, technical and values. At least three interviewers: the CEO or a managing director, a peer C-level (CFO ideal for forecast discipline and compensation-plan depth), and an external sparring person (advisory board or an experienced VP Sales from the network). Independent scoring on the rubric before the debrief.
Stage 3: GTM-strategy case study (90 min presentation plus 30 min Q&A)
Give the person 5-7 days to prepare on a realistic brief: current ARR, team setup, three to five concrete challenges that actually occupy you. The person presents a 90-day and a 12-month plan to the managing directors and one of your sales managers. Assess: the quality of the clarifying questions beforehand, the structure of the plan, awareness of own assumptions, handling of push-back in the Q&A.
Stage 4: Backchannel references (3-4 structured conversations)
At this level, by far the most important signal. Call 3-4 references: a former CEO or managing director (supervisor), a former sales manager or senior AE (direct report), and a peer C-level (CFO ideal). Prefer backchannel over the person's official reference list. The same 5 questions to all: What is the biggest strength? In which setup would you not hire this person again today? How are they under pressure? An example of a difficult decision under your observation? Would you yourself work for or with them again?
How to recognize a great hire
| Trait | Below bar | On bar | Above bar |
|---|---|---|---|
| Scalable team leadership | Leads a single team directly, has not yet led sales managers below them. Thinks in IC output, not team-of-teams output. Compensation and stack decisions are inherited, not designed. | Has led 2-3 sales managers with a total of 10-20 reports. Maintains a recognizable leadership cadence (weekly 1:1s with sales managers, a monthly org review). Has owned a compensation plan and a tool stack in live operation. | Has built an organization of 25+ across several sales managers and led it through a scaling phase (10 M€ to 25 M€+ ARR). Compensation-plan and stack decisions are documented bets with an observable effect. Develops sales managers themselves rather than only hiring them. |
| Strategic GTM vision | Reacts to set targets with no own thesis on the market or segment choice. SDR introduction, market entry or the segmentation question are answered by gut feel, not data. | Formulates a coherent view of ICP, pipeline mix and market-entry sequencing. Can defend or reject an SDR-pilot decision in a data-driven way. | Has owned at least one successful market entry (geography or segment). Makes GTM bets in 90-day steps with clear success indicators. Recognizes when the current model hits its limit before the numbers show it. |
| Forecast and pipeline discipline | Forecast swings by plus-minus 25 percent versus the landing. Pipeline math is not computed out loud. CRM hygiene is left to the sales-manager level, with no own audit cadence. | Forecast accuracy at plus-minus 10 percent over the quarter. Knows the status of the top-10 deals by heart and can explain the math of the quarterly landing in two minutes. | Clearly separates no-decision from delay, parks stagnant deals with discipline. Forecast accuracy at plus-minus 5 percent. Has established an own audit routine (spot checks on individual deals, a monthly deal review with the sales managers) that runs on without their presence. |
| Sales hiring and enablement | Hiring by gut feel, no documented scorecard or interview process. Onboarding is a mix of peer mentoring and learning by doing. Ramp time is not measured. | A structured hiring process with a scorecard and a multi-stage interview. An onboarding plan with clear milestones for 30, 60 and 90 days. The ramp-time median is known and stable. | Has run, over at least two years, a hiring funnel that predicts actual performance. An internal enablement program with documented playbooks (discovery, demo, negotiation). At least one internally developed sales manager in the track record. |
| Executive alignment | Communication to the managing directors is reactive and mostly defensive. Difficult messages (a forecast miss, a hiring need, a budget request) are delayed or wrapped up. | Established monthly or quarterly routines with the managing directors and the advisory board. Delivers numbers before explanation, with a clear thesis and next steps. Carries bad news early. | Used by the managing directors as a sparring partner for whole-company questions, not just sales questions. Own blind spots are nameable, feedback loops with the CEO are established and productive. |
30 / 60 / 90 day success plan
By day 30
- 1:1 with each sales manager (three meetings in the first two weeks), listening to at least three calls per sales manager and one call from each of their reports
- A full pipeline audit at the organization level: stage conversion, velocity, win rate, pipeline coverage per sales manager, the top-20 deals of the quarter with an own risk rating
- A structured conversation with the managing directors, the advisory board and peer C-level (CFO, CMO, CTO) on the current view of sales, identified friction points and explicit expectations for the first 90 days
- A diagnosis memo with 3 hypotheses on the main cause of under- or over-performance, explicitly without solution proposals at this phase
By day 60
- An operational steering cadence established: a weekly 45-minute pipeline review with the leadership team, a monthly 90-minute org review with the managing directors, a 1:1 cadence with each sales manager firmly anchored
- A documented action plan for each sales manager who is above or below plan, with clarity on consequences after a further 90 days
- A first robust forecast delivery to the managing directors with clear plausibility logic and risk assumptions
- A strategic recommendation on at most two structural decisions (e.g. SDR introduction, a segmentation pilot, a hiring sequence) for discussion with the managing directors
By day 90
- A sales plan for the next 12 months approved: hiring sequence, ICP refinement, pipeline-generation mix, compensation-plan adjustments if needed
- At least one major structural decision implemented or started as a pilot (a reorganization, a new segment, a function introduction)
- A hiring pipeline for the next two open sales-manager or senior-AE roles actively built
- A first observable improvement on a core metric that can be causally attributed to your own measures (not a market effect, but a leadership effect)