The key responsibilities of a VP Sales are:

• Hiring a team of high-performing individual contributors and managers
• Driving the conversion of leads to paying customers
• Building a sales methodology, reporting and forecasting system, and team compensation plan that supports that conversion
• Relaying customer feedback to broader team and acting as the voice of the customer on pricing/packaging plans.
• Leading and motivating their team to accomplish objectives on time
• Collaborating with management team to achieve company objectives

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Hiring and Management
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How do they create a strong pipeline of candidates and maximize close rates? Do they have people that would follow them to a new company?

• Ownership of as much of the hiring pipeline as is realistic (esp. closing)
• Dedicates substantial time to hiring, and can articulate the specific techniques for closing (e.g. team lunches, building empathy, connection with candidate, etc.).

What do they look for in the salespeople they hire?

• Intellectual horsepower, competitiveness, coachability, desire to learn, teamwork, grit. Can be a variety of answers but should know exactly what they look for.
• How do they evaluate candidates on those dimensions?

How have they structured their teams, and how many people were in those orgs?

• Should have rock solid answers on this subject, as this should be a big priority.
• Should walk through how and why they structured the GTM motions into their teams. Where did inside sales, field sales, channel sales, etc. sit?

Can they manage across geographies? Have you done so in the past?

• If this is or will be applicable for your role, ask for examples of managing remote teams or individuals. Candid description of challenges and what they learned.
• How do they ensure remote teams have ability and support to be successful?

How do they approach turning around underperformers?

• Clear communication, established timeline, and concrete milestones in an improvement plan. Holding the person accountable for meeting those milestones and making the hard call in the case the employee doesn’t succeed.

How do they motivate a team, retain top performers, and foster a strong sales culture?

• Starts with an appropriate and thoughtful incentivization and comp plan.
• Looking for empathy and the deliberate creation of an environment where the team feels supported, invested in, and safe to learn from their failures.

How big of a team do they need? How would it be organized and what support resources would their team need?

• Even if they don’t have the right answer yet, they should be able to explain their rationale and what they’d need to know to make the decision.
• If their first plan of action would be to triple the team size, they may be stronger on people management and big picture strategy decisions than the tactics and process of sales. Make sure you align here.
• Would they want to hire sales engineers or other sales support roles? Have the experienced efficient sales & sales support orgs beyond your scale?

Have they successfully mentored people? Can they share stories?

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Sales
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What were they hired to do in their roles and did they succeed?

• This is an important distinction - did they successfully deliver on the specifics of what they were hired for, or did they ride the wave of a successful company?
• Were they hired on as a Director of the West and then promoted to VP Sales 6 months before they left? Understand the arc of their career and tenure.

What were their success metrics in their last few roles? How did you do against them?

• Does this reflect what they said they were hired to do? Does this reflect what you want them to do?

What were their teams metrics, and what were they focusing on daily, weekly, monthly?

• Why did they choose those metrics, and what were they trying to accomplish by assigning those metrics over others?
• How did that guide their decision-making?

What was the state of the sales org and process at their last company when they joined? How did they prioritize assessing their challenges?

• Should be able to give a holistic view of what was working and what wasn’t, and why their changes made valuable improvements.
• Bad answers will blame product or marketing or CEO/Board decisions for their challenges, good answers will focus on what they did to improve sales, regardless of what problems they were faced with.
• Did they inherit their team? Hire it themselves? Restructure it or fire people?

How much of their time was spent in front of customers in their last few roles?

• They should understand how their time breakdown reflected the needs of the business at that time. Their experience should also reflect the needs of your business - don’t hire someone who spends 80% of their time in the field to operationalize your sales process, or vice versa.

What did ACV and sales cycle length look like at their last few companies? What changes have they made to raise ACVs and shorten the sales cycle?

• Should have experience dealing with sales cycles similar to yours. Are they primarily skilled at operating in high velocity, low touch environments, or are they strongest on complex, 6-7 figure deals with long sales cycles?
• Do they have experience with bottoms-up sales, top-down sales, or both?
• How complex were the sales, did they deal with multiple decision makers?
• Were the changes they made effective?

How have they prioritized customer segments or verticals and why?

• Should be able to speak to the reasoning behind focusing on a segment or vertical, and the metrics that support that. CAC, LTV, deal size and product considerations should ideally play into their answer.

What industry or buyers have they sold to?

• With the biggest distinction being IT buyers vs. line-of-business buyers, ideally they’ve had success selling to the same decision makers as you need. If they haven’t, can you get comfortable with their ability to learn the nuances?
• If your product has a technical buyer, do they have strong enough technical acumen to work with your target audience and articulate your product’s value?

What’s an example of a time they lost a deal to a competitor?

• Do they blame it on external factors or do they learn from it and want to improve things so it doesn’t happen again? Are they competitive? Do they go into the specific way they positioned themselves against their competitor?

Where has their responsibility started and ended in the customer lifecycle?

• Has to match what you need. Breadth across multiple functions is the defining distinction between a VP Sales and a CRO.
• At what point did marketing hand off a lead to them? Did they handle the SDR team? Have they ever managed other pieces of marketing?
• Who owned the number for account growth and renewal? How did they work with the customer success team?

What tools are in their tech stack, and why did they choose them?

• Do they have a thought-out view on why they choose to use specific products, or is it habit-driven, or did they inherit them? How did their team help with the decision making? Would they do it the same way again?

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Management Team Success
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What are the keys to success in working with the management team at this company?

• Building relationships with each of the key executives, especially the ones that they’re working with frequently (Product, Marketing, Customer Success)
• Communicating clear expectations and forecasting for what the sales team can and cannot deliver
• Standing firm on things that don’t make sense for their team but working to collaborate whenever possible
• Establishing an efficient customer feedback process that the Product and Marketing teams can utilize.

What has your relationship with Marketing leadership looked like in your last few roles?

• Likely the most important relationship, and can sometimes be contentious. Why did they work well or not work well with their Marketing peer?

What do they need from their CEO to be effective in their role?

• Does this align with what you’re going to be able to deliver on and what your management style looks like?