How to Hire the Right Leadership Team for Your Startup

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Founder of Appboy and Investor
5 min read
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As the old adage goes: “You’re only as good as the people around you.” While it’s true in both life and business, it’s certainly magnified for entrepreneurs and startups, particularly early on in the process. With limited resources and endless competition, the line between success and failure is extremely small. That means it’s important to put the odds in your favor as early as possible, with an equal eye on both the short term and the long term.

Something I’ve learned firsthand, both as an investor in early-stage tech companies and as an entrepreneur, is just how important it is to give each C-level position (and really any hire for that matter) the appropriate amount of thought and research. While this may seem like a daunting task for those looking for fast growth, it’s well worth the effort and will afford long-term stability for your company.

To help you along the way, here are five tips that can optimize your C-level hiring process:

Related: What to Look For When Hiring Your First Employees

Hire people who are smarter than you.

As a CEO, you’re probably used to making the final decision. However, are you always the best person to make that decision? Great talent, who provide trustworthy perspectives and experience, always surrounds the best leaders. If you have implicit trust in your key hires, then you can count on them bringing new viewpoints and options to the table. The best teams are built around complementary parts so that any weaknesses are offset by another person’s strength.

Tip: Ask interviewees what they see as obstacles in a perceived problem area (real or theoretical). Their answers will tell you how they can spot things you may have missed.

Invest in experience, it pays dividends.

Hiring key personnel with a brilliant track record and/or immense experience may add to the payroll ledger, but you’ll quickly discover that this is offset by the value they bring. Beyond their direct skills and talents, the indirect benefit of adding talented and experienced people is they will speed your growth by shrinking the learning curve. The more expertise you bring in, the less ground-up time needed. Remember, time is money for any startup so any sort of acceleration benefits the bottom line. 

Tip: Make key hires in the most glaring holes in your company first to accelerate growth in those areas.

Related: How to Avoid Startups' Biggest HR Pitfalls

Bring on people that can attract talented individuals.

Strong executive hires bring many skills to the table but one of the most important traits is that intangible magnetism that draws talent to them. People within the company like them, want to be around them and learn from them. The level of this industry magnetism is a testimonial in itself about the executive’s abilities. If people are willing to follow this person around from company to company, then they are willing to put their trust, career and livelihood on the line. Added bonus and necessary component: People already within the company look up to them and want to learn from them. 

Tip: When interviewing references, try to gauge references on whether or not they would follow the leader from company to company.

Hire to define your company culture.

What do you want your company culture to be? From day-to-day interactions to short-term goals to long-term scalability dreams, your company culture is both defined by this and defines this. As CEO, you are the head of this beast. If you hire executives who aren’t on the same page as you and will make their own hires that go against the grain, it can spell disaster. On the other hand, when executives are a good fit, they will effectively act as a proxy for the CEO, increasing communication and efficiency. Clashing company cultures can unravel a company. 

Tip: Look past the titles and achievements on a resume, learn the how and why behind those achievements to gain some insight into the interviewee’s impact on company culture.

Remember that your team is your family.

Particularly for a startup, C-level hires are a CEO’s family. They are the confidants, lieutenants behind major decisions and co-pilots that steer the ship. You may actually spend more time with them than your actual working family, particularly near milestones. In times of distress, your “CXOs,” will help you make the critical decisions. Because of that, the executive team has to have more than just industry skill or experience. They need to complement each other and help the group become more than the sum of its parts.

Tip: Ask yourself if you would be comfortable traveling with this person or sharing a hotel with them if need be. Worst case scenario: Would you survive if you were stuck in the airport for a few hours with no one else but this person. If it’s a “yes”, chances are they would fit into the “family.”

Often times, as a resource constrained startup or early-stage business, the temptation may be to go with the easiest fit rather than the best fit when it comes filling out your C-level roster. But remember, your key executive hires bring much more to the table than their job description, and in many ways, those hiring decisions can make or break your startup. So be patient and go slow with your key hires to ensure they are the right fit.

Related: 3 Ways to Attract Top-Tier Talent in a Tech Hub

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