What questions to ask a Head of Sales on a technical interview

Hiring a Head of Sales is crucial for driving your tech company's growth and meeting revenue targets. But finding someone who can balance technical understanding with strong sales acumen is challenging. Here’s a guide to questions that can help assess whether a candidate has the strategic, technical, and interpersonal skills needed to lead your sales team to success.

1. How do you approach building a sales strategy for a technical product?

This question evaluates the candidate’s ability to create a sales strategy tailored to your specific industry and product complexity.

Example: A SaaS company may need a different approach from a hardware manufacturer, so look for details on market analysis, customer pain points, and sales channels they would leverage.

Action step: Probe for specifics on how they prioritize features, conduct market research, and adapt strategies based on technical needs.

2. Can you describe your experience with complex sales cycles?

Complex sales cycles often involve multiple stakeholders, longer timelines, and deeper technical knowledge. This question assesses their experience managing these elements effectively.

Example: A cybersecurity product with high data security requirements might need an extensive sales cycle. Listen for their approach to stakeholder engagement, technical demonstrations, and closing.

Action step: Ask for specific examples where they shortened the cycle or managed complex deals with multiple touchpoints.

3. How do you ensure your sales team understands the technical aspects of our product?

This question checks for their ability to make sure the team is knowledgeable about the product and can convey its technical benefits effectively.

Example: A CRM provider may require the sales team to know integration possibilities. Look for whether they mention training, onboarding processes, and collaboration with the technical team.

Action step: Inquire about any tools or frameworks they use to bridge the gap between technical and non-technical team members.

4. How do you handle technical objections during a sales pitch?

Prospects often raise technical concerns; this question gauges their ability to navigate these objections with confidence.

Example: If a prospective client questions data storage or encryption, the candidate should show how they effectively clarify these points without derailing the sale.

Action step: Follow up with situational examples where they overcame technical pushback to successfully close a deal.

5. How do you collaborate with the product and engineering teams?

Effective sales leaders work closely with technical teams to ensure alignment on product updates and customer needs.

Example: A Head of Sales who has regular feedback sessions with the engineering team might be more effective at relaying client needs and adapting to technical changes.

Action step: Ask how they communicate customer feedback to the technical team and how they handle feature requests or technical questions from clients.

6. What metrics do you prioritize to evaluate your team’s performance?

This question gives insight into what metrics they find most valuable for driving technical sales.

Example: For a high-tech company, they might mention metrics like demo completion rates, time spent in the pipeline, or technical objections handled.

Action step: Ask how they adjust metrics for different sales goals and ensure team accountability.

7. Can you give an example of how you’ve supported a sales team member struggling with technical knowledge?

Supporting team members who need technical upskilling is essential for maintaining a strong, knowledgeable team.

Example: A Head of Sales might mention specific mentorship techniques, resources, or collaborative sessions with product experts that they’ve facilitated.

Action step: Probe for any training tools they use, such as CRM platforms, LMS, or peer-mentoring programs.

Conclusion: Choosing the right Head of Sales for a technical product requires more than assessing their sales skills; they must have a deep understanding of technical details, strong collaboration skills, and strategic insight. By asking these targeted questions, you can gauge whether a candidate is prepared to meet your company’s specific needs and drive sustainable growth.

Ready to refine your technical interview process? Reach out to us for additional resources on selecting the perfect Head of Sales for your tech company.