Head of Sales Interview Questions
A Head of Sales drives revenue growth by building high-performing sales teams and designing scalable sales processes. The ideal candidate blends commercial instinct with coaching ability and data-driven pipeline management. These questions assess leadership capability, strategic thinking and ability to deliver consistent results.
Key skills to assess
Behavioural Questions
4These questions explore how the candidate has handled real situations in the past. Past behaviour is one of the strongest predictors of future performance.
Describe how you have built a sales team from scratch or significantly scaled an existing one.
Assesses team-building experience and hiring strategy
Tell me about a quarter where you missed target. What happened and what did you change?
Evaluates accountability, resilience and ability to course-correct
Tell me about a complex deal you personally closed that required navigating multiple stakeholders.
Assesses enterprise selling ability and stakeholder management
Tell me about a time you had to adapt your sales strategy due to a significant market change.
Evaluates strategic agility and market awareness
Situational Questions
4Present hypothetical scenarios to understand how the candidate would approach challenges they are likely to face in the role.
Your top performer is consistently hitting target but has a toxic effect on team culture. What do you do?
Reveals values-driven leadership and willingness to make difficult people decisions
The marketing team is generating leads but the sales team says they are poor quality. How do you resolve this?
Evaluates cross-functional collaboration and lead qualification alignment
A major client threatens to leave for a competitor offering a lower price. How do you handle it?
Tests negotiation skills and ability to sell on value rather than price
The board wants to enter a new market segment. How do you validate the opportunity and build a go-to-market plan?
Tests strategic planning and market entry methodology
Technical Questions
4Assess the candidate's domain expertise, tools proficiency and problem-solving ability with role-specific questions.
How do you approach sales forecasting and what methods do you use to improve accuracy?
Tests forecasting methodology and data-driven pipeline management
How do you design and implement a sales compensation plan that drives the right behaviours?
Assesses understanding of incentive design and unintended consequences
How do you identify and address bottlenecks in the sales pipeline?
Tests analytical approach to pipeline optimisation and conversion improvement
What CRM and sales enablement tools have you implemented, and how did you drive adoption?
Tests tool selection judgement and change management skills
Competency Questions
3Measure specific skills and competencies against the requirements of the role using structured, evidence-based questions.
Describe your approach to coaching underperforming sales representatives.
Tests coaching methodology and commitment to developing talent
How do you balance pursuing new business with growing existing accounts?
Evaluates strategic revenue diversification and resource allocation
How do you ensure consistent sales methodology and messaging across a growing team?
Assesses process discipline and scalable enablement thinking
Interview tips for this role
- Ask for specific revenue numbers and growth percentages. Strong sales leaders know their numbers cold.
- Include a role-play exercise where the candidate sells your product or handles an objection.
- Probe how they develop their team, not just how they personally close deals.
- Look for candidates who talk about process and repeatability, not just individual heroics.
Frequently asked questions
How do you evaluate a Head of Sales candidate track record?
Ask for specific revenue figures, team sizes, growth rates and quota attainment percentages across multiple roles. Verify claims through reference checks with former colleagues, direct reports and cross-functional partners. A strong track record includes consistent quota achievement, team growth and retention of top performers.
Should a Head of Sales carry a personal quota?
This depends on company stage. In early-stage companies, player-coach roles work well. In larger organisations the Head of Sales should focus on strategy, coaching and team performance rather than personal deals. If they carry a personal quota at scale, it typically signals the organisation has not invested enough in the team.
What is the most important quality in a Head of Sales?
The ability to build and develop a team. Individual selling brilliance does not transfer automatically to leadership. The best sales leaders hire well, coach consistently, build repeatable processes and create a culture of accountability and continuous improvement. Look for evidence of talent they have developed who went on to succeed.
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