For Founders

How To Build Your First Executive Leadership Team

As a first-time founder, how do you go about building a great executive team? In this interview summary, Jared Fliesler shares tactics for effective executive recruitment drawn from his 15 years of former experience as COO at Scribd, VP at Square, director at Google, and GM at Slide.

 min read
June 24, 2022
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Note: If you’re an early-stage founder anywhere from pre-idea through pre-seed, consider applying to On Deck Founders.

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As a first-time founder, how do you go about building a great executive team? Jared Fliesler shares tactics for effective executive recruitment drawn from his 15 years of former experience as COO at Scribd, VP at Square, director at Google, and GM at Slide. This article is an abridged summary from his interview on Execs, our podcast where we interview executives from high-growth companies.

When it comes to leadership experience in scaling companies, Jared Fliesler has plenty to share. In a career path that’s passed through several high-growth companies, he’s had the chance to work with successful leaders such as Max Levchin, Keith Rabois, and Jack Dorsey. 

When asked about the secret to successful business scaling, Jared’s answer is clear: good recruitment, is the key to setting your company’s growth path.

The importance of recruiting ramps up as your company matures. When you’re looking to build out your first executive team, the stakes can feel huge. 

As a first-time founder, it’s normal to wonder:

  • How do I hire for a role I’ve never done before?
  • What’s more important, experience or potential?
  • What makes a good candidate fit for different executive roles?

In this summary of selected insights from Jared’s interview on our Execs podcast, we cover what you need to look for when hiring your first executive team, along with his thoughts on how to hire for specific executive leadership roles.

3 Things To Remember When Building An Executive Team

Regardless of whether you’re starting with operations, finance, marketing, or another role, there are some hiring considerations that apply across the board. Here’s Jared’s advice for starting the executive recruitment process well.

Orient around outcomes

Say you don’t have a finance background but you know you need to hire a VP of finance. Problem is, you don’t know exactly what their work will be because it’s not your area of expertise. 

The way to get ahead is to orient around outcomes: think not in terms of standard tasks but more in terms of what you need to do to get to the next stage.

Maybe the outcome is the next step or stage itself. Maybe it’s a place you want to get to as a company, or maybe it's a specific deliverable that you have or some other kind of accomplishment. 

Perhaps one of your outcomes is having an executive team with a certain set of archetypes.

You may need a functional specialist or domain expert; you may need them to be a visionary; you may need a cultural magnet that will instill your values in your company. You might need a great people manager and leader.

Orienting around outcomes focuses you on thinking big picture to resolve questions like:

  • What are we not yet great at?
  • Where do we want to get to?
  • Where do we need help with that?

This prevents you from getting stuck in the details and feeling like you have to completely understand a domain before judging a potential executive hire.

Check for culture fit

When hiring executives for any role, cultural fit is essential. Ask yourself: how is this person going to fit with the culture you already have? Then, how will they fit with the culture you want to have? And finally, where are the rubs?

Often there’ll be cultural things that you definitely don’t want in your organization. When you start seeing those in a conversation, you need to ask yourself how willing the person seems to be to change. If you find yourself digging your heels in opposition, that’s something you need to be careful about, especially at this level.

Balance experience with growth mindset

When you’re suddenly bringing a lot of people into your organization, the biggest tension is often between experience and raw ability. In other words, how much do you value experience, and how much room do you have for creativity and growth potential?

At higher levels, it’s natural to index around experience. The problems start when a candidate’s experience becomes a barrier to them adapting to your company.

Let’s say you’re talking with someone who’s worked for 10 or more years in their role. What’s their attitude towards that experience, and how will it fit with you? 

Ask yourself:

  • Do they think that just because they've done something for 10 years, they have it all figured out and you’re doing it all wrong? 
  • Do they have curiosity, even around something that they're an expert in? 
  • Can they take on things that might sit outside of what they've done in the past? 

Sometimes a candidate has so much experience that they think they have it all figured out.

Experience can indeed by irreplaceable, but that also needs to be balanced with a growth mindset, and demonstrating creativity when it comes to problem solving.

Check their motivation

When hiring, another thing that Jared always looks for across the board is motivators. He asks:

What are the things that get this person out of bed? Why are they having the conversation with me? Why is it that they're thinking about leaving their current role, and what inspires them?

Finally, does he believe that in this role and with him as their manager, he can continue to motivate them? Sometimes, Jared says, the answer is no. 

You might have someone interviewing for VP of finance but they seem to want to be your CFO. If you already have a CFO and they’re not leaving, you can’t give that role to that person. And even if you hire them as VP of finance, six or twelve months down the line someone else might offer a CFO role to them.

In that situation, you need to decide if that motivator is make or break for the person. You have to be honest with them and have that conversation before you both decide on your future.

What To Consider When Hiring For Specific Executive Roles

Once you’ve covered the basics, what are some specific considerations when you’re hiring for different roles for the first time? 

Jared outlined the main questions you need to ask yourself for each executive role.

Hiring a COO: Beware of “big company” thinking

Often, when people are hiring a COO or head of operations, they’re trying to hire an adult in the room. 

There are a few things you need to consider here.

How sensitive will this person be when making changes?

Some COOs will want to take their 100-page process and operations manual that they’ve created at their huge company as VP of operations and apply it to your company from day one.

Jared calls this “big company” thinking. To make sure you don’t get on the wrong side of it, check:

  • How does this person operate from their current place of experience? 
  • How much do they know about the situation your company is in?
  • Are they ready to build a bridge between those two points, or do they plan to come in guns blazing?

Basically, when someone comes into a COO role, they need to be thoughtful and aware about how they make changes. 

This doesn’t mean that your new COO won’t bring in new ideas, but first they need to be aware of why things are how they are. They also need to take into account where your company is and your stage of growth. 

These are sensitivities you need to feel out when you’re hiring.

How able and creative are they? How will they scale?

The other things you need to look for in an ops role candidate are:

  • Proven ability. Can this person really do this thing? Can they scale and evolve operations, teams, processes, and policies? How has their experience been with these things?
  • Creativity. Creativity counts in all roles, but it’s specifically important in ops. When this person goes into something that’s process-driven, do they have the ability to pause what they know and try something new? How creative can they get when it comes to applying what they know to your company in a way that fits your culture and stage of growth?
  • Personal scalability. It’s tempting to hire someone who’s exactly what you need right now. Instead, look for someone who’s worked on problems that are not just like what you’re facing today, but also what you can see yourself facing two or three years down the line.

Hiring a CRO: Clarify your needs and consider compensation issues

A CRO is generally one of the last hires when you’re building an executive team. At this point, you’ve already got a sales team and other directors in place. You probably already have a VP of revenue or sales.

The first question, then, is why you’re hiring a CRO in the first place. 

Why are you hiring for this role?

This comes back to outcomes. Why is your VP not enough, and what gaps are you trying to fill? There are very different roles for CROs, and you need to get clear on what you’re looking for.

  • Are you looking for a suped-up VP of sales who’s just going to take your successful sales process and do it even better?
  • Or are you looking for someone visionary who’ll imagine the future of revenue at your company? 

These are two different things, two different roles, and your hire will change accordingly.

How will you deal with compensation issues?

The second challenge with CRO hiring relates to compensation. 

Your CRO is probably going to be the highest-paid role in your company. What’s more, a CRO will often be used to getting cash bonuses in line with their performance every six or 12 months. They’re short-term motivated. This is different to a startup culture, where most team members are motivated more longer-term by the chance of equity.

So here, you both need to be prepared to flex a bit. 

You need to convince someone to bend to fit your means after leaving a large company, and as a startup, you need to accept that there will be a change in your compensation culture. 

And finally, you need to decide how far that culture change will go in your organization and how transparent you want to be about that. Also make sure you have a CRO who can maintain the boundaries of transparency, as they’ll have a lot of responsibility there.

Hiring for marketing: Look for brand vs performance fit

Marketing is one role that will change significantly according to your desired outcomes. As a result, the first step to a successful executive hire is deciding what kind of marketing you actually need.

What do they do best and what do you need?

When you’re building out a marketing team, know that there are two types of marketing:

  • Performance marketing is about driving and tracking specific short-term outcomes. This is like a Nike campaign that starts by asking what they can do to get X number of people to buy running shoes this quarter, and which current campaigns are effective and by how much.
  • Brand marketing is like creative development around who you are and how you communicate. This is like Nike running a “Just do it” campaign to give people good feelings about the brand.

The first thing to feel out is where your candidate’s specific abilities lie. How much experience do they have with each type of marketing, and how does that line up with your needs?

Is this someone who’s highly motivated by performance metrics when you’re not? Or conversely, is this someone who’ll be more creative, and leave you frustrated about where they’re spending money and time? 

Connected to this, how broad is their experience in different aspects of the role?

Even within types of marketing, the role can encompass comms, brand strategy, design, creative content development, and/or social media. It’s important to understand what your candidate has done so far and how much that lines up with what you need, both today and in the future.

How do they use data in their decision making process?

A second consideration is how data-oriented your candidate is and how that fits with the rest of your team. 

Some candidates will have come from places that are less focused on data, but if you’re a data-driven organization, it’s important to have that same outlook across your executive board. How comfortable will your VP Marketing be with reporting in a way that fits your culture? Feeling this out will help you avoid clashes and misunderstandings between board members down the line.

Hiring for business development: Look for how they view success

Jared’s specific advice for hiring a BD executive covered scoping out communication skills and how the candidate views their role.

What does success mean for them and you?

With business development hiring, you need to understand how a candidate thinks about success. 

  • Is success for them all about getting a deal done, or is it more about building partnerships that lead to growth? How does this fit with your need? 
  • If they’re all about deal-making, are they comfortable getting deals to the finishing line and then killing them because they’re the wrong thing? 
  • How about going six months without getting a deal done because it’s not the right thing for the organization?

The key takeaway is that you need someone who will align with your own idea of success and be flexible enough for your environment.

How will their work support you, and vice versa?

Second, look at your candidate’s communication skills. Will this be someone who can communicate with the rest of the organization to make sure that you’re all supporting each other? Or is there a risk that they’ll be going out and doing deals for the sake of it, without checking first that this is something you need?

Hiring for finance: Check for fit, curiosity, and trustworthiness

Similar to marketing, finance roles can look very different depending on your skills gaps and desired outcomes. This is why you should start with the basics.

What do they do best and what do you need?

What do you need your CFO to do?

If you already have an amazing organization that’s closing the books really quickly and all your engines are moving, you're hiring a CFO for a value preservation role. You’ll want someone who’s more motivated to keep you compliant and help you execute on the things you need to do. 

On the other hand, maybe your finance team is broken, or you’ve been using an outside accounting firm to meet your needs. You might be struggling to close your books or answer questions from the board. 

In this case, you're probably looking for a CFO that can reset the team. You need someone who can uproot and rebuild, and who has a strong opinion about what needs to be done and how. 

In summary, you need to find out: is this someone who’s into value preservation and keeping things running, or can they punch through the ceiling and start doing things in a different and better way? And how consistent is that with what you need?

How much risk can they take? Can you trust them?

Other specific things to look for in finance hires are:

  • Appetite for risk. Often people in these roles will feel they’re there to tell you “no.” In a growing company, you need someone who can tell you “how.” For sure, if you’re doing something that’s going to get you arrested, you need to know, but you also want someone who can be curious about solutions, and not just defensive.
  • Ability to uphold trust and confidentiality. Any upper-level finance role is going to have access to a lot of very sensitive information. They know what people are paid and they know when bad things are happening at the company. How well can you communicate the level of transparency you need on these issues, and how well will this person maintain that?

Hiring for people roles: Prioritize curiosity and culture fit

Hiring a VP or chief of people officer is much like hiring for other executive roles: you need to think about the outcomes you’re expecting and what their motivators are. You should also look for scalability and alignment. 

Do they scale through people or technology?

How curious will this person be when faced with scaling needs?

People in this function are sitting around people, and that’s their skill set. Often, they’ll be more inclined to scale and solve problems by hiring people, just like a surgeon who recommends an operation because that’s what they do. Or they might tend to just hire the same way they always have, without thinking how appropriate that is for your organization. 

What you want to look for instead is curiosity. Maybe it makes more sense for them to think if there’s a technological solution that could address the same problem. Or maybe they need to think outside the box and switch their hiring strategy. 

How do your beliefs align?

Someone in a people role is often going to be your eyes and ears in your organization. You want to understand how they’re going to react to warning signs of problems. 

Say an employee has a complaint. Maybe they’d like to address it in an all-hands and you think that’s inappropriate. How will you deal with that? This comes down to feeling out your culture fit.

Look for what your candidate feels strongly about and what you feel strongly about, and think about how these things align. 

Good Executive Hiring Starts With The Right Questions

Our conversation with Jared shows that successful executive hiring comes down to answering these questions:

  • What are your needs? What outcomes are you looking for?
  • How does this person fit with your culture, and how could they adapt?
  • Where’s the right balance between this person’s relevant experience and their ability to try new things and think outside the box?
  • What motivates your candidate? Is it something you can offer and can continue to offer?
  • What are the specific challenges for each role, and how can you both address them?

With this knowledge in hand, you’ll be ready to start building your executive team with confidence, even for functions you’ve never led before.

Note: If you’re an experienced professional looking to gain clarity on your next move, check out Execs On Deck

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