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Key Questions to Ask When Hiring a Director of Sales

The Betts Team
December 4, 2023

When hiring for an open Director of Sales job in SaaS, the questions you ask during the interview will help you determine if the candidate is the right fit for your team and for the position itself. Director-level executive hires are vital for helping you scale a sales team that is growing, both in headcount and in business scope. 

This blog will dive into what skills, experience and mindset you should be looking for when interviewing and what key questions will help you qualify your unicorn candidate.

Hiring a Director of Sales in SaaS

A Director of Sales at a SaaS company is a critical position to fill once your sales department has grown to more than a few teams or pods.The Sales Dir. typically reports to a VP of Sales or a Chief Revenue Officer in some organizations, while they in turn oversee the Sales Managers who themselves each manage multiple Account Executives (AEs), Sales Development Representatives (SDRs) and possibly Customer Success Managers (CSMs). A Sales Director will also often manage EAE (Enterprise Account Executive) teams in orgs that are selling to bigger accounts, including those that are scaling up their services to enterprise-level clients.

Experience is a big plus in choosing a candidate for Director of Sales, but an even important requirement is their level of personal skills. This position has two big functions – make sure deals are being closed and managing the sales team on the ground. Both of these roles are best served by a professional that can be personable with clients as well as your team members, that knows how to communicate and engage with stakeholders externally as well as internally. They will need to understand what your clients and your sales reps need to achieve the best outcome for your organization. 

Questions About Past Roles & Responsibilities

These questions will focus on learning more about the candidate’s background, experience and skill sets they have acquired throughout their career. A Director of Sales in SaaS needs to know only how to sell but also lead a team, with responsibilities that include setting quotas, overseeing product launches and driving go-to-market (GTM) strategies. The Sales Dir. will also often be in charge of building and scaling the sales team, from AEs and SDRs to Sales Managers who will lead their own teams or sales pods.

  1. Sales Motion Experience: Your sales motion is the approach and the overall methodology your org adopts in selling, from your target market to your specific operational tasks. A unicorn seller will align with your existing motion and contribute to its growth. Ask your candidate about their experience with similar sales motions, including any background in your specific part of the market, and how they have sold to your prospect personas before.
  2. Leadership Experience: A Director of Sales candidate should be able to demonstrate that they can lead multiple teams of sales reps. This will give you insight into their level of resilience, which also provides a glance into how they will react to change and burnout. Ask about their past leadership roles and go over the management responsibilities they held.
  3. Sales Team Scaling: Hiring a new sales executive signals the next leap forward, and your candidate should be able to help scale the department up. Ask them how they plan to position the sales team for growth, from increasing revenue to adding new headcount if needed.
  4. Client Portfolio & Network: Ask your candidate about the past clients they have worked with, how they engaged with points of contact and how they have maintained these relationships. This helps to gauge their ability to network and give them a chance to quantify their personal skills.
  5. Sales KPIs & Goals: Ask your potential Sales Director about how they go about setting goals and quotas for the team, as well as how they keep track of the team’s KPIs (key performance indicators) towards these targets. This will help you see how they handle planning as well as metric tracking.
  6. Stakeholder Engagement: For B2B sales, where and how an executive chooses to interact with key stakeholders can make a world of difference in closing deals. Ask how your candidate approaches engagement with prospects and clients, including what methodologies they have employed in the past.
  7. Collaboration: A big part of the Sales Director’s job will be coordinating internally with different teams. Ask your candidate for examples of how they have helped their sales teams collaborate with other departments to achieve success.

Situational Questions

Situational questions for interviewing a Director of Sales candidate will help you gain a better understanding of their decision-making, personality and approach to fulfilling their role and responsibilities. These should include hypothetical scenarios where they will have to showcase their ability to problem solve, as well as a deep-dive into past incidents that allow them to reflect on lessons learned.

  1. Most Challenging Experience: Ask the candidate to recall a time in their sales career where they faced a significant roadblock to their goals, how they got past it and what they were able to take away from the whole experience. Gauging how they respond to adversity will be a good indicator of whether they revert to solutions-based thinking and think quickly on their feet.
  2. Biggest Success: Ask your candidate about what they consider the biggest success in their career and why. This will give you more insight during the interview into their priorities and what drives them.
  3. Data Literacy: Lay out a scenario where the candidate would have to make a critical decision based on business intelligence metrics. This will help you test their confidence in their data literacy and determine how well they work with tools such as your CRM.
  4. Lost Deals & Negative Feedback: See how the candidate reacts to deals falling through or negative feedback from customers during sales negotiations. This will give you insight into their level of resilience, which also provides a hint into how they will react to change and burnout.
  5. Market Disruption: As the aftermath of the COVID-19 pandemic illustrated, it can be risky to assume that a market will always remain consistent. Create a scenario during the interview where changes in your industry bring new challenges to selling to your customer base and ask the candidate how they would pivot the sales team. You will also want to gauge how well they are keeping track of developments in your market and how that affects your sales motion.
  6. Coaching & Development: Ask your candidate how they would take charge of overseeing the professional development of your sales teams. As an executive leader, the Director of Sales should also be to see where junior AEs and SDRs need more coaching and be able to identify which learnings will help their team best.
  7. Team Performance: Ask how the candidate would respond if members of their team were underperforming, including what steps they would take to identify causes and rectify the issue. This will be a good indicator of their leadership style, emotional intelligence, and decision-making capabilities.

Hiring a Sales Director with Betts as Your Recruiting Agency

It will take time to source a Director of Sales candidate with SaaS experience that is the perfect fit for your team, but relying on Betts as your recruiting agency will help you take control of the costs of your executive talent acquisition. Leveraging our Recruitment as a Service (RaaS) model, you get the best of both worlds – search recruiting on-demand with our proprietary hiring platform, Betts Connect, and access to end-to-end support from a full-time Betts recruiter. 
Contact Betts here and see for yourself how RaaS will transform your hiring and help you land your unicorn Sales Director at a lower cost than traditional agency recruiting.