Hiring The First VP of Sales

A make-or-break role for an early stage company

In a previous post, I wrote about what to look for when hiring senior executives. In short, look for people who get things done. I had lunch recently with an experienced technical founder and he admitted that hiring a head of sales still flummoxed him.

The right VP of Sales can help you get the traction you need to raise the next round of funding. The wrong hire might cost you six months of frustration. I’ve done enough hiring to see both extremes and everything in between. There’s more to it than the tropes of Glengarry Glen Ross.

The most important thing to consider is the stage of your company. Do you understand your ideal customer profile? Do you have product/market fit? Are sales repeatable?

The skills you need from a VP of Sales vary considerably whether you are pre or post-product/market fit. Don’t make the mistake of hiring the scaling VP when you’re still figuring things out. Otherwise you might find yourself with a large sales team, a well structured process, a perfect CRM implementation with no one hitting quota and not understanding why.

When you hire your first VP of Sales (or any senior executive) they should have major impact within the first 90 days. This could be helping the team to close a key customer, improving the sales process, developing new insights into customer needs, etc. They need to set the tone and cadence of the sales team while driving excellence. Closing deals is a key measure, but a leader also has to build alignment across departments so that the entire organization can succeed.

If you can, hire a VP of Sales who has experience with the market and customers you’re targeting. It’s not necessarily a deal-breaker, but if you’re selling to a very technical audience (developers, security, networking) it helps if you’re already familiar with the roles and personalities. Selling to developers is very different from selling to a line of business. Similarly, if your company has a concentrated vertical market focus, it can shorten the ramp time if you hire someone who already understands that market.

What’s Critical?

As you consider what to look for in candidates, think carefully about what needs to happen over the next six to twelve months. Try to determine what is critical and what is “nice to have.”

At the early stage, you are looking for a sales leader who can help you find product/market fit. Above all else, you need a partner who can be hands-on and collaborative. You want someone you can work with on deals. You can’t just delegate everything to your new sales leader and go back to coding.

That doesn’t mean you’re doing the Sales leader’s job, but founders should expect to be involved in early deals. Founders bring important context, credibility and contacts that go beyond what a new sales leader can provide. Founder-led sales aren’t scalable, but those early deals provide valuable feedback about what’s working and what customers are expecting.

Understanding the ideal customer profile, and the buying process is the most important job. Great sales and marketing starts from understanding the buyer’s journey and working backwards. Great VPs of sales do this naturally, and will seek to identify patterns that define an effective sales process.

You need to develop a hypothesis as to what is the ideal customer profile and then run experiments (e.g. sales pitches) to see whether this resonates with customers. If you can do these meetings face-to-face it will be that much easier to gauge the reaction. When do customers lean forward? When do they look at their phones? What questions do they ask? What do they need to integrate with? What concerns do they share?

Ideally you will have spent time listening to customers, understanding their environment, the problems they face and what they care about before you ever pitch them. If you haven’t done that, you might end up with happy ears when the customers politely tell you it sounds “interesting.” But don’t be surprised if they ghost you when you follow up. If there’s no pain, there’s no sale.

While your company no-doubt deserves a world class sales leader, someone who has scaled from $0 to $200m in ARR, understands product-led growth, can help you accelerate Enterprise sales, has managed channel partners, speaks four languages, can close deals across all timezones and programs in Python in their spare time, this is not a likely scenario.

First of all, most sales leaders who have successfully scaled a company do not want to go back to an early stage company that does not yet have proven product-market fit. And in the unlikely event that they decide to join an early stage company, it’s probably because they have an offer to be President or COO.

Hire the Up-and-Comer

Sometimes, the next best thing to the experienced VP of Sales is their understudy. Maybe they were a Director of Sales, or Regional VP reporting to the VP. Betting on an up-and-comer is a great way to bring in a leader who is ready for a bigger role and still has the hunger and drive to face big challenges.

You must be sure that this person has the experience and willingness to do the work required at your current stage. If they’ve grown comfortable with big-company budgets and large teams, ask them whether they are really prepared for the long hours and hard work required to find product/market fit.

There are lots of things a head of sales has to be able to do including hiring, setting quotas, building out the compensation plans, forecasting, and creating CRM reports. These tasks are all important, but they pale in comparison to what is most critical in an early stage company: identifying a repeatable sales process.

First VP of Sales at Zendesk

When I joined Zendesk, the vast majority of our revenue came from online sales. There was only one sales rep, Matt Van Loan. He was closing some deals, but he wasn’t getting much help from Marketing. He had a can-do attitude, knew the product inside and out and was willing to try new things. I hired the next handful of sales reps and soon everyone was making quota, shortening sales cycles and increasing the size of the deals. We had good product market fit, but the odd thing about having hundreds of online customers was how little we knew about them and why they bought from us.

Having exhausted my meager sales skills, I brought in Jim Cyb as the first VP of Sales. Jim and I had worked together at a short-lived startup and had stayed in touch. Late in our discussions, Jim asked me why I wasn’t hiring a more experienced, grey-haired VP of Sales who could run his or her existing playbook. The reason was simple: I wanted someone who could be a partner and together we would build the playbook for Zendesk.

When Jim joined, the first thing he did was take on the challenge of closing various misfit prospects that were outside our sweet spot. It wasn’t because he wanted to prove himself as a closer. He wanted the direct exposure to customers so he could hear for himself their concerns, their needs and help him better understand our target market.

It’s great to have a sales leader who is a good closer, but you’re not hiring them to be the hero who closes every deal. That’s an operating mode that doesn’t scale. A sales leader must have conscious competence. Meaning, they are good at the job and they know what makes them good, so that they can train others. Many sales reps are excellent, but if they operate through intuition, it is near impossible to replicate.

Jim created an environment for the sales team to share their findings on what worked, what didn’t so they could learn together. Then he worked directly with the marketing and product teams to create content, demos and marketing materials that could help us overcome objections.

Jim’s work at Zendesk helped drive a culture of customer focus. We created an environment where Sales and Marketing collaborated together rather than throwing rocks at each other. It was a performance-oriented culture, but bad behavior wasn’t tolerated. Hitting your numbers did not give anyone license to be a jerk.

Jim also brought an executive mindset to the job. That is, he thought about what was best for the company, not just his team. Inexperienced executives sometimes cling to the idea that they are there to present the needs of their department. With Sales, that can result in every issue being framed in terms of how it helps or hurts the sales team to hit their quotas. While that is often worth considering, it’s the wrong focus at the executive level.

As I hired other sales leaders over the years, I have looked for similar attributes. Do they have the willingness and curiosity to understand our customers and what makes them unique? Can they add value immediately to help up-level the sales team? Can they get on the same side of the table as Marketing, Product and Finance to solve problems? Can they create a high-performance, high-integrity culture?

I’ve been fortunate to hire leaders like Mark Burton, Chris Halligan, Marjorie Janiewicz, Colin Jones, Katie Kilroy, Jennifer Lawrence, Courtney Skarda, John Skubel, Jason Stutt, Lesley Young and others who continue to create outstanding sales teams and high-performance cultures.

Not every candidate will tick all the boxes, so be clear about what is nice to have and what is essential. But don’t compromise on integrity or collaboration skills. As with any important hire, do the reference checks yourself.

The picture above is Matt Van Loan, the first sales rep at Zendesk at our first sales kickoff meeting, held at a donut shop in Oakland before a customer call. Matt was a role model for many of the people we hired and had a stellar career at Zendesk and beyond.