Where have all the executives gone? 9 lessons we learned from hiring our VPs

If you’ve been following my recent posts, you know that Knak has nearly doubled in size in the last few months. We’ve had a blast finding new team members to add to our collective skill set and offer new perspectives. However, there’s one area of our growth strategy that’s been a tough nut to crack: hiring execs.

Over the last few months, we’ve spent more time and energy than I ever expected looking for people to fill executive leadership roles. As odd as it might sound, it actually took longer to hire some of our vice presidents than it did to raise $25 million in venture capital financing.

So, in this post, I want to share some of the learnings we gathered in this process in the hopes that it might make things easier for others in the same boat.

How we got here

In a young start up, it’s typical for founders to do most things themselves. That works for a while, but there is only so much one person can do (especially as you start scaling), and there are only so many people one person can manage.

Our first challenge was to come to terms with the fact that we needed other executives so that we could free up the leadership team to operate more strategically. Here were some of the realisations that helped us get there.

First, the existing leadership team no longer had time to do everything. 

For starters, though we believe strongly in providing our employees with career development, coaching, and mentorship, we just weren’t able to do it properly. Our leadership team was just too busy with new projects and priorities. Consider my own role, for instance, I had always been personally involved in marketing and product development. But as CEO, I have a whole new range of tasks that take up my time. These include attending (and preparing for) board meetings; managing investor relations; and as well as a growing number of administrative tasks.

The same holds true for my entire leadership team. As such, we needed a new layer of employees that could help us — people with the bandwidth and the experience to manage, develop, and move our team forward.

We also realised we couldn’t focus.

As the original leadership team got stretched thinner and thinner, it became clear to us that we lacked not only time, but focus. We weren’t able to give the company’s various departments the full attention they each needed to flourish. Only someone who was entirely dedicated to the specific department — a vice president — could do that.

Finally, we acknowledged that to grow, we need people with experience.

Today, we’re strongly focused on growth, and that means boosting both our sales and our product offering. It’s often said in business that the quickest shortcut to growth is to bring in bright, experienced people to focus on key tasks. Guess what? It’s true. We need to get great people in place now so we can grow and scale the company.

Lesson #1: You can’t hire without clearly-defined job descriptions

It’s one thing to know you need to hire senior people, but quite another to know precisely what you expect them to do. You can’t just hire a vice president of sales, for example, and tell them to go figure out how to sell your product.

So, before we even started looking for people, we did the jobs ourselves so that we could develop a clear idea of what success looked like in that role — and documented it in job descriptions. This had the added benefit of helping us determine the skills and the personality needed for the role. Once we knew what we wanted our new executives to do, we started the candidate search.

Lesson #2: Patience is a virtue — and highly necessary

It took us close to four months to find a vice president for sales. Why? Because the conversations we had with candidates were a big part of defining the role. Because it’s hard to find the right fit of experience, personality, and availability. Because we’re operating in a fiercely competitive hiring environment. Because we were looking for the best of the best, and we didn’t want to settle.

Lesson #3: Hiring execs needs to be methodical

Up until this point, I had often hired based on gut feeling. But these executive posts were too important for me to rely on instinct alone.

We created scorecards for each post we wanted to fill. (Our VC investor, Insight Partners, worked with us to create them.) Now, during interviews, members of our leadership team have a list of very specific questions to ask. After the meeting, we compare notes, both in person and on dedicated Slack channels.

The scorecard process has been very helpful, even if the approach ended up being more rigid than we’d been used to.

Lesson #4: But you also have to trust your gut

We still ended up having to evaluate the personalities and values of the leading candidates — something that scorecards don’t measure. Could I imagine myself working with this person? Would I enjoy spending time with them? I still had to trust my gut to some extent. These questions came up when we offered a VP position to someone who just didn’t seem excited about the role. My instinct told me he was not a good fit; thankfully, he accepted another offer.

So listen for signals, and follow your instincts as well as your head.

Lesson #5: Never settle

It happens. You’ve sifted through dozens and dozens of applications, and you come across someone who seems like a reasonable fit. Maybe they’re not perfect, but who is?

It can be very tempting, when you’re tired of looking, to conclude that an OK person is probably good enough.

Resist that temptation!

When your goal is to build a leading product and company, “good enough” doesn’t cut it. You’re looking for someone who really wants to work with you, and where the enthusiasm goes both ways. If you harbour any doubts about the person, don’t hire them. What you should be feeling is, “I don’t want to lose this person!” If you’re not feeling a resounding yes, the answer is no.

Lesson #6: Alignment is key

We found it’s important for everyone involved in the selection of applicants to agree on who we want to hire. We all have to work with the new hires, so we all have to feel enthusiastic about having them on board. See the section above.

Lesson #7: There’s more than one way to do things

We tried four different approaches in our search for executive-level applicants. They could apply in response to a job posting; they could be referred to us by an existing employee; our HR people could try to recruit them; or they could be headhunted by an external contractor.

By far the most successful approach was when an existing employee brought us a candidate. Why? Because the applicant had heard about Knak from someone they trust, and was actively interested in working for us.

Other approaches worked well, but often in different contexts.

We had good success when people applied in response to a job posting. They would have done their research in advance, and if they applied it was because they were seriously interested in working for us.

External headhunters were also effective — probably because the people they approached knew and trusted them, and because (to some extent) they’re a disinterested third party with no particular stake in Knak.

Our own recruiters are amazing at what they do. But they faced a significant challenge when approaching people for executive-level positions. That’s because they were reaching out to people who were already employed, may not have known about Knak, and weren’t necessarily looking for a job. In other words, they had to work harder just to get people’s attention.

Because employee recommendations work so well, we decided we’d pay a referral bonus of $2,500 any time we hire someone that was recommended internally for an executive-level position. And to further help with the recruitment process, we redid our entire online Careers webpage before we started recruiting. We wanted it to truly showcase what it’s like to work for Knak. We also wanted it to reflect the reality that we now have to market Knak like anyone would market a product. Put yourself in a candidate’s shoes and make sure your website reflects their needs as well as yours.

Lesson #8: Our bootstrap mentality didn’t serve us anymore

After weeks of unsuccessful searching, we buckled down and hired an external recruiter to find us a VP of Sales.

Expensive? Yes. But it was worth it.

For me, the “Aha!” moment came when I realised that it wasn’t about finding the right person, it was about saving time and moving quickly to capture market share. And for us, that’s worth a lot.

This is all a logical extension of the realisation that we’ve moved beyond the bootstrapping phase of our corporate story.

Lesson #9: Moving fast is a must

Yes, I know I started off by saying that the recruitment process takes time. Nevertheless, we discovered early on that we had to make things move as fast as possible.

Why? Because the market is very competitive. We learned to compress the interview process. Insight Partners was incredibly helpful, vetting applicants, providing feedback, and helping us decide between a number of excellent candidates. Insight’s assistance gave us added confidence that we were making the right choices.

In the end, we were able to hire an incredibly talented group of execs onto the Knak team. They say good things take time and I think the people we have brought on are a testament to that. We hired a VP of sales, two VPs of marketing and a VP of product development in four months.

And, we are still looking for bright, passionate, people who are interested in our mission of empowering marketers to be creative. Interested in applying? See our new careers page for details.