How We Built our Exec Team in 4 Months

We were screwed.

At the mid-point 2019 my CFO and I looked at our plans for the next 24 months and realized we didn’t have a shot at hitting our goals without dramatically expanding our leadership team. While we had hit a home run with David, our VP of sales and Jamie, our VP of people, the bench depth we needed wasn’t even halfway there.

Our mandate was this: hire a CMO, CCO, VP of Product, VP of Engineering and several key director-level roles in 5 months or less.

They all had to be bona-fide A-players.

 They all had to be a strong culture fit.

And if I failed to get this done, our big plans for 2020 and 2021 would be pointless to go after. One of our board members even said “look, if you can just get half of these hires by the end of the year we’ll be OK.” Being “OK” generally doesn’t get the job done in a high growth startup.

We had to get them all.

4 ? months later, we had hired everyone.

And we did it without compromising on talent or culture. Here’s what I learned: 

1. Bark up the right tree to begin with

Searches go off the rails (particularly Seed and Series A) before they even start because boards or founders focus too closely on hiring for a specific title.

“We need a CMO”

“We need a CTO”

“We need a VP of Sales”

In many cases, it’s completely wrong. I made this mistake several times. Throw the title away.

Start by writing down exactly what this person needs to do in order make the company successful.

If you are a 30-person D2C company trying to scale customer acquisition from $1M/month to $10MM/month in 18 months then guess what? You aren’t looking for a CMO. You aren’t looking for a VP. You’re looking for a marketer who’s worked at a company with less than 50 employees who has scaled a D2C engine from $1m/month or less to $10M/month or more. 

Maybe that person is a CMO. Maybe they are a Sr Mgr. What matters is that they have done the one thing you need them to do, and have done so at a company roughly your size.

Title hunting leads to two problems. The best candidates self-select out before you have a chance to speak to them. And then the candidates you do talk too are often not very good. 

When Electric had a four person engineering team I mistakenly went looking for a CTO. A company with a four person engineering team will not need a CTO unless that person is a founder or a “CTO” in title only – which is a whole separate issue.

At an early stage, just hunt for a “head of” and then work the title out with the individual candidate based on the scope of their role. As the company gets larger and surface area is better defined, you can go looking for a VP knowing that anyone from director to SVP could wind up being a fit. 

2. Throw away the job description and focus on the 4-5 “non-negotiables”

When we were recruiting our CFO earlier this year my friend Jason Harinstein pushed me to come up with the 4-5 things that I absolutely needed an incoming CFO to do well in order to be successful here. 

When I wrote out the list, I realized just how useless formal job descriptions are (though you’ll need the useless JD as a formality, you functionally should not use it during the hiring process). This list becomes the filtering mechanism. 

Too often interviews focus on finding reasons not to hire the person rather than drilling down on whether or not the candidate is truly excellent at the few things you need them to be excellent at. Dial your list in and then screen candidates against it before moving them through the process in the first place. Here's what we put together for our CFO search:

By following this process we found that we disqualified a huge number of candidates who were a fit on paper, but hadn’t actually done enough of the things we needed; and we were able to learn this without going through a time-consuming interview process.

3. Stop caring so much about domain expertise

Steve Sloan from SendGrid gave me this advice when we were working on the VP of Product search. I had been getting conflicting advice on the importance of domain expertise, but he crystallized it::

“Really smart people can quickly develop domain expertise But learning how to properly prioritize, communicate and deliver takes years. Prioritize management over domain.”

Jason Harinstein echoed his point to me as well “I definitely wasn’t picked from central casting for the Flatiron CFO role” - in Jason’s case, he had been running M&A and strategy at Groupon prior to joining Flatiron.   

There are obviously cases where this might not work–like in highly-regulated or complex niche industries where domain is mission-critical to the role (perhaps a Chief Compliance Officer). But it’s worth seeing candidates from many different fields to gut-check any assumption on domain requirements. More often than not, strong leadership abilities will win out over subject matter expertise.  

4. Handle the first call yourself

The search depends on the candidate’s first interaction with your company. You get one shot. After recruiters identify and screen a candidate, I do the first call myself for every executive hire.

This is time consuming and tedious. But there’s also nothing more important that you can be doing as a CEO than finding your next great executive.

By doing this two things happen:

- The candidate gets psyched out of the gate (see #5 for my POV on how to ‘pitch’), because they get clarity of vision and other essentials straight from you. If they don’t ‘get it’ after this first call they probably won’t ever get it. Only you can knock this out of the park.

- Allows you to develop conviction before anyone else on your team has to spend time with them. This also gives you exposure to the good and bad candidates which will help you make better judgement calls later in the process. 

5. Don’t “sell” on the first call, screening for non-negotiables and culture fit is the pitch

There is no greater sales pitch than an aligned set of values and vision. Temy (our Chief Customer Officer) and I were talking about this at lunch over the holidays. The first conversation we ever had we hardly touched on the business or role itself. We riffed on what we valued as leaders and managers, what we’ve learned, what we care about and the organizations we’re trying to build. By the end of the conversation, we both agreed that we’d love to find a way to work together.

The way you communicate your point of view on these topics will serve as a filtering mechanism for the folks who are likely to be the best fit to begin with.

Then, drill down on your non-negotiables. This should account for the bulk of the call (40 mins or so). If the candidate is a fit, the hour will be over before you realize it and it will be an invigorating conversation on both sides of the table. If it’s not a fit, it should be obvious to both of you. 

6. Don't be afraid to fire your recruiter

The only recruiters worth hiring are ones who:

- Have run a very similar search in your market in the last 3-6 months.

- Can be trusted to run a very proactive, professional and diligent process

A large part of the success of the search relies on your recruiter having a solid pipeline. And the only way they will have a real pipeline is if they have run a search like yours recently.

Even still, if you aren't getting at least 3-5 qualified conversations in the first 30 days of the search, then strongly consider firing them. With recruiters, if it doesn't start good it most likely won't get good. Eat the cost and move on. 

7. Run a proactive, highly-organized process from beginning to end

Our head of people Jamie has our exec interview cadence mapped out down to every individual touchpoint. Follow ups are prompt and friendly, instructions are clear and our culture shows through in everything. There are handwritten notes, there are clearly articulated next steps. There is no excuse for having a sloppy recruiting process.

8. Always have a final project and presentation

One of the best ways to tease out relevant competency and fit is to have final-stage candidates complete a project. The important thing is that this project should be an actual business problem you care about. And it should be something that the candidate will likely have to do in their first 30 days working for you. Then have the candidate come in and present the project to your team.

For example, when we hired David to run sales I gave him our 2019 projections and said “build a full plan down to the month on how you plan to deliver.” Sure enough, he came in with 14 slides outlining in detail how he would hit the plan. He also had additional slides about things he’d like to change, what he had concerns about and other things he would need to see in order to have confidence in the plan. It was a home run.

For the right candidates, this won’t feel like an interview it will feel like a regular meeting with your team. 

Despite having a very high bar prior to getting to this point, about 2/3 of our candidates get disqualified at this stage. 

9. Always get 2-3 backchannel references

My general rule of thumb is: if I can't independently verify that you're good at your job and not a jerk then you can't work here. It’s not more complicated than that. It’s shocking how many people (particularly sr executives) interview very well, talk the talk but either can’t deliver or are unpleasant to work with. Backchannel references will tease this out very quickly.

Given the sensitive nature of these discussions I would recommend that you work with your HR leader to nail down a process for getting these references that is highly-confidential and respects the delicate nature of an exec making a job change.

I’m sure not all of these principles will apply to everyone, but 90% of it should.

Great leadership will make running your company a lot more fun. Your customers will be happier. Your spouse will be happier. Investors will actually believe what you say.

The people are the company.