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Key Questions to Ask When Hiring a VP of Sales

The Betts Team
January 19, 2024

Hiring a VP of Sales is one of the most crucial recruiting decisions for an early stage tech startup, and these key questions will help you determine if a candidate is the unicorn fit you are looking for. Your interview should grant the insight you need to determine if a candidate aligns with your organization, your sales team and everything the role will take on, and making the right inquiries is the first step to ensuring you have found the right person for the job.

When to Hire and Interview a VP of Sales for a SaaS Startup

A VP of Sales is an important hire at every stage of the technology startup lifecycle, with a vital role to play from Seed to Series D. Their exact responsibilities may differ when it comes to leadership and hands-on duties according to the size of the company, but whether it is an early stage or later stage startup, the Vice President of Sales is always a team leader. They are the ones ensuring that teams of Account Executives (AEs) and Sales Development Representatives (SDRs) are performing at scale, keeping an eye on factors like performance, headcount and sales motion alignment.

All the above contributes to what your unicorn candidate for this job looks like – their leadership style, their go-to-market (GTM) strategy and techniques, and how well they understand your target market. The candidate’s background and experience should align with the purpose of the role. Additionally, their ability to delegate effectively and drive sales is crucial for achieving the growth necessary to scale up your business.

Questions About Past Roles & Responsibilities

These questions about the past roles and responsibilities of your Sales VP candidate should help you learn more about their career history, the experience they bring and what skills they picked up along the way that could make them a fit for this position. Think about the work and mentality this job will require, and look for signs of whether or not their background and approach lines up with those functions.  

  1. Experience with Sales Motion: Any candidate serious enough to make it to an interview should already have experience in sales and in a leadership position, but what you truly need to look for is for someone that understands your sales motion. Ask about their history with your industry, subsector, target audience, team structure – see how well they align with all the things that make your organization not a One-Size-Fits-All.
  2. Past Sales Teams: You can use this question to throw a bit of a curveball for the interview – ask the candidate about the past sales teams they have worked with, provide details on how those teams functioned and their thoughts on what could have been improved there. Their answers will not only give you more insight into their history, but also help contextualize answers to other key questions, especially when it comes to their experience in managing and building AE teams. 
  3. Strategy & Execution: Your Sales VP candidate should already be thinking of GTM strategies and tactics by the time they are being interviewed, leveraging the experience they have gained previously and applying it to your sales motion. Inquire about their approach to planning, communicating, and executing a go-to-market campaign. Ensure they can provide concrete examples from their past experiences to support their strategic thinking.”
  4. Software Experience: The tools of the trade are always evolving for sales, and anyone you recruit for an executive position needs to understand what their teams are using and how. Ask your candidate to run through the tools they have used before to see which of those – if any – align with your current stack, and delve into how they used them to gauge their proficiency.
  5. Collaborating Across Teams: A VP of Sales must be able to foster collaboration with other departments to strengthen your GTM strategy and help their team reach their goals. Ask how the candidate would engage and coordinate with everyone from Marketing to Product to ensure alignment.
  6. Tracking & Reporting: Modern tech sales are all about the numbers, and any new hire for executive leadership must be able to demonstrate data literacy and a mind for metrics. Ask your candidate how they have tracked performance previously and how they plan to turn data into reporting for the CEO.
  7. Leadership Style: A Vice President of Sales needs to be a leader by definition, but you must be sure that their leadership style aligns with your organizational culture and sales motion. Ask them how they have led teams in the past and how they would lead your AEs and SDRs, including how they would engage with situations that could create obstacles like a performance drop or internal conflict. 

Situational Questions for a VP of Sales

Situational questions are most effective for assessing a candidate’s problem-solving abilities, decision-making skills, overall knowledge, and critical thinking. These are often scenario-driven exercises where you present a hypothetical or ask them to recall a past event, and in either case allow for an open-ended response. Be sure to follow up on answers with additional inquiries to get to know the candidate better and how they approach challenges, work to achieve goals, and especially how they work with others.

  1. Professional Highs & Lows: The purpose of this question isn’t to get your candidate’s whole biography, but to explore how they tell their story and what it says about their motivations and drive. Ask them the things in their career that have stuck out, the wins they remember best, the losses and how they learned from them.
  2. Building a Sales Team: Invite the candidate to talk you through how they would go about scaling their team in different scenarios, from the ground up as well as on building on an established sales department. If they truly align with your sales motion, they will already know what your unicorn seller looks like and will outline what steps they would take to find and hire them, and most importantly also be able to validate why they need to be hired.
  3. Roadblocks: Think about the potential challenges that could impact your organization or market that you would want your VP of Sales to be able to take charge of overcoming, and lay them out in a corresponding scenario for your candidate. They should be able to leverage their experience in the field and in similar tech companies to explain how they would address the problem – bonus points if they seek to turn it into an opportunity for new wins.
  4. Market Awareness: Your candidate should be keeping an eye on trends in the market you’re selling into, and be able to provide data-driven or thought leadership insights on how to best take advantage or get ahead of potential developments. Ask them to provide their thoughts on the current state of your market and where they think it is going, based both on their own experience with your industry and sales motion as well as from any citable sources they can provide.
  5. Competitive Strategy: A perfect scenario for testing a Vice President of Sales applicant is having them conceptualize strategies to stand out against competition. Present your candidate with a choice of different brands within the market. Ask them to articulate how they would position the organization when engaging with prospects and addressing customers at risk of churn. Additionally, inquire about their strategy for guiding their team in executing this positioning strategy effectively.
  6. Team Culture: VP of Sales is such an important role for a tech startup because it is on the frontline of developing the culture of your sales team and aligning it with your sales motion. Directly ask your candidate how they plan to cultivate and contribute to your sales team’s culture – have them lay out the steps they will take explicitly, while drawing from their own experience with managing previous teams to validate their methods.
  7. Goal-setting: SaaS sales motions live or die by their contribution to revenue targets in a startup, so any executive leader you hire must be able to set realistic goals for AEs and Sales Managers to meet while giving them what they need to reach them. Evaluate your candidate against a variety of performance benchmarks and request a detailed explanation of how they would plan for, communicate, organize, and track these goals with their team.

Hiring a VP of Sales with a SaaS Recruiting Agency

Before you can interview your unicorn VP of Sales candidate, you need to find them, and navigating the current talent pool for a top seller and executive leader is its own challenge. A recruiting agency can help you track down your right fit candidate and consult you on how to make a competitive offer once you find them.

Betts is your best choice for sourcing GTM talent with a background in SaaS, being able to fill in the blanks for everything from the latest compensation data to key interview tips. Our hiring platform, Betts Connect, grants you access to one of the largest pre-vetted networks of sales, marketing and customer success professionals with experience in tech, and our Recruitment as a Service (RaaS) model enables you to take advantage of our solution combined with end-to-end recruiter support at a fraction of traditional agency costs. Get in touch with our team and discover how we can help you shorten your search for your unicorn sales leader.

Contact Betts here and get started on your hunt for your unicorn Sales VP candidate today.