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What To Look For In Your First Startup VP of Sales

You can hire a VP of Sales at various junctions in your company. For companies who are either pre-revenue or have a few million in ARR, you should be looking for a VP of Sales who is tasked with hiring a smaller team and building out a few reps.

There are a lot of nuances in a VP of Sales at a startup that are important to be on the lookout for during the interview process. The following are the top 5 attributes to look for when interviewing:

Strategic thinking and problem-solving skills

A VP of Sales should have the strategic capabilities to set the right vision for the company as well as the ability to create something out of nothing. There might not be a go-to-market strategy, a defined inbound/outbound process, or even a sales process for your company right now. The person you hire to be your VP of Sales needs to have the strategic capabilities to solve problems like these.

How to Screen: Have candidates present a 30-60-90 day plan to the executive team. You’re looking for their ability to identify the biggest challenges of the organization from a sales point of view and to come up with sensible solutions on how to attack those gaps. You’re also looking for basic organizational skills, presentation skills and the ability to communicate with the executive team.

Skills and network to recruit top talent

It’s crucial for your first hires to have strong experiences and relationships with your VP of Sales. One of the benefits of hiring a VP of Sales early on is getting access to their network and their experiences in recruiting some of your initial talent. If you can hire a VP of Sales who understands how to recruit and retain top talent, as well as someone who has a strong network of sales talent, you can accelerate your path towards the initial team.

How to Screen: Ask candidates how they would go about recruiting and building out their initial team. Ask them about their experiences retaining top talent and have them walk you through some specific examples where they had challenges with top or bottom performers and how they handled those situations. You’re looking for someone who can speak very intelligently about specific experiences they had with recruiting and retention.

Willing to do whatever it takes to make the company successful

In a startup environment, you need a VP of Sales who is willing to fight from the trenches and do the hard things – like closing deals, getting on calls, cold calling. A great startup VP of Sales is someone who’s willing to hustle, work long hours and handle responsibilities they’re not particularly excited about.

How to Screen: This is a very hard quality to screen for – you should try to get a sense of their mission and goals in an informal interview. Maybe some candidates come from a place where they crave to have more responsibility and impact and they’re willing to do the hard things. Maybe they’ve done this several times in their career and this is just what they want to do in their career.

You should also have an honest discussion with the candidate and set the right expectations – ask if they’re up for the challenge. Set conservative expectations around the amount of work necessary and the lack of resources available to help the candidate make an informed decision.

Hiring revenue generating talent? Download The Complete Guide to Interviewing Salespeople

Ability to collaborate and communicate with the executive team

Many VPs covet autonomy and don’t want a culture where the founders and executive team are too involved in the process. But a startup VP of Sales can’t simply be a corner piece. They need to understand they’re working together with product, engineering, and the founders on the same vision. Their ability to communicate and collaborate with others is extremely important.

How to Screen: Take one of the topics or solutions from the candidate’s 30-60-90 day plan and dive into it. Book a one-hour meeting with the candidate and have a working session where you collaborate, brainstorm and talk through the topics. You should ultimately have the mindset of coming up with a tactical roadmap on how you’re going to implement the plan. In this session, take note of how the candidate is conducting themselves. Are they collaborative and receptive to your ideas? Are they holding their opinion with conviction but open to being wrong and open to being a thought partner to you? You don’t want a VP of Sales that folds over and agrees with everything you say, but you also don’t want someone who has such strong convictions that they’re being illogical and not working collaboratively with you as a founder.

Ability to get you to your next milestone

A lot of founders evaluate a VP of Sales and make a hire thinking that they’ll be in that role for the next 5 – 10 years. However, it’s very hard to find a VP of Sales that’s appropriate for every stage of a company. Most likely, the VP of Sales you hire today is only going to be able to take you to your next major milestone before they either outgrow their skill sets or need to be supplemented with additional sales leadership hires. Make sure you have confidence that their experiences and their knowledge align with your 12 – 24-month goals. Find the candidate who’s going to be the perfect fit for the next 2 years, not the perfect VP of Sales candidate across the board.

How to Screen: Dissect their intuition, advice, and thoughts around how to take the business to the next revenue milestone in the next 1-2 years. If you find yourself believing and understanding the vision they have and the confidence they know how to get there, then you’re probably already a long way in with someone who could be a great candidate for that. If they don’t have many insights or can’t figure out how to get it done for the next 1 – 2 years, their level of experience is probably not deep or broad enough for you to have confidence in them as a candidate.

Ultimately, a VP of Sales hire can be a very expensive experiment, so you should try and delay hiring someone as much as possible. The longer you wait, the better sense you’ll have of what the candidate will look like and what your needs are for your startup. You’ll also have less risk of hiring the wrong person for the job too early. Take your time to get to know the candidates you interview and don’t rush the interview process – be slow throughout the process and find the right person for this role.

Jordan Wan

Founder & CEO of CloserIQ. Previously Sales Strategy & Management @ZocDoc, Head of Analytics @PayPerks and Trading Strategist @Bridgewater Associates. MIT Bachelor’s & Master’s in Computer Science. CFA Charterholder.