A Startup Guide For Making Your First Executive Hire

By Kyle Wong. This article originally appeared on Forbes, October 17, 2013.

Starting a company is easy, building one is hard.

As a startup founder your job is to recruit a world-class team. The first step is to naturally surround yourself with a passionate founder team with complementary skill sets whom you trust and work well with. The next hires are smart individual contributors (often engineers or designers) who believe in your vision. After you’ve assembled a solid core team and found product-market fit, you are at the crucial stage at which you are ready to scale your business; one of the most important milestones is hiring your first executive.

Adding that veteran to your team can help accelerate your business by:

  • Establishing structure, clear roles, and paths to scale the team
  • Teaching best practices for new situations that come with scale
  • Aiding with recruiting and sales via their network
  • Creating a sense of legitimacy in the marketplace

With that said, it’s a complicated process that you want to take seriously and allocate sufficient time towards. Having recently gone through that process I wanted to share a few thoughts.

Don’t Hire Too Early

In Marc Andreesen’s essay on executive hiring, a startup should hire an executive ‘when it’s clear that it needs one’. For instance, when hiring needs to accelerate or when you need more process and structure and rigor to how you do things.

Simply put, if you haven’t found product-market fit, you’re better off keeping your burn rate low instead of hiring an expensive executive. While her experience and network can help accelerate your business, the business itself should be positioned in the right direction. After all, if you’re stepping on the gas while you’re stuck in the mud, you’re not going to go very far.

Know What You Don’t Know

Prior to bringing on an executive, it’s important to be self-aware and brutally honest about the existing skill set of the team. Understand whether those needs are industry skills, functional skills, or both.

Many startups begin with “founder-market fit” and a unique vantage point into the market that they are entering. For instance, at Pixlee, my cofounders and I have previously created companies together in our industry, and as young entrepreneurs, our peers are avid social media users. There are very few people in the world who have a better understanding of user-generated photos’ impact on brands better than we do. However with that said, none of us have ever scaled a business, managed a sales team, or negotiated complex deals with Fortune 500 companies. Understanding your weaknesses and inexperience is important, because it will give you greater clarity into the role you’re trying to fill.

Use Your Investors And Advisors

As one of my mentors once told me, “It’s very difficult to recruit for a position if you’ve never seen it done right.” In other words, it’s difficult to evaluate an executive for a position if you’ve never done the job before or if you’ve never worked with a similar position. I remember being so focused on a candidate’s impressive resume that I didn’t ask the hard questions to truly understand if they were effective at their job.

Luckily for an investor or advisor with the right operational experience, this is an area where they can add value. Those investors and advisors are also key to gaining quality leads. Based on my experience, I’ve found it really helpful to incorporate investors and advisors in the sourcing, evaluation, and closing of the right candidates.

Identify Your Must Haves And Deal Breakers

Given that every startup is different, it is difficult to generalize a perfect executive candidate. However, there are several considerations that are “must haves” and “deal breakers” for your first hire. In addition to having the right experience, she needs to be passionate about your space and what you’re building. You want the candidate who isn’t afraid to roll up her sleeves and be an individual contributor. Long debates about title, perks, severance, and vacation time are bad signals. Not to say that these topics aren’t factors, but they should be secondary to the opportunity to make a significant impact and the potential upside of joining an early-staged company.

Date Before You Get Married

After both parties have shown significant interest, the ideal scenario is to try out the arrangement for at least six weeks before either party commits long term. This trial is a two-way selling process. It’s an opportunity to see how the executive works and for her to get to know the team personally. During the trial period with our current CMO we did everything together from important client pitches to fun conversations over long outdoor runs. Without the trial period it is difficult to understand if someone is a good culture fit until you interact with her on a day-to-day basis and deal with adversity together.

Don’t Micromanage!

Congrats! You got them over the finish line! Now don’t mess it up by being a micro-manager. Your startup is your baby and it’s difficult to let go and delegate, but you have to trust your team members. In order to attract and retain great leaders and managers, give them the opportunity to execute.

Hiring your first executive is an important step in scaling your business. Don’t rush into it prematurely, and make sure you do it right because it’s an important building block in developing your business. It took us 4 grueling months to find our current CMO, and our business has grown exponentially ever since.