Tips for Hiring Executive-Level Leadership for Your Startup

Young companies have a unique set of requirements for their leaders. What skillsets and qualities should you look for when hiring executives for a startup?

Creating a solid leadership team is crucial for your startup to keep growing. But unlike large enterprises or legacy companies, startups have unique needs, and thus executives need to have a specific mix of skills and qualifications.

Before you get started in your search, create a set of goals and a plan of action to help you reach them. For example, consider the new hire’s responsibilities and what personality traits will help them succeed in the position.

We will be walking through these tips to get you started:

• Know when it is the right time to hire an executive

• Focus on hiring cultural fits, not just qualifications

• Remember – executives have a big impact on brand reputation

• Work with an executive search firm like Drive Talent

Know when it is the right time

You may be putting off the inevitable, continuing to take on all aspects of running your business yourself. Founders can be especially slow to delegate tasks since they are used to doing it all. But part of a successful executive hiring strategy is knowing when to take the leap and bring in new leaders.

One rule to live by, the 50 Percent Rule, states that it is time to get help when you are only accomplishing half of all the tasks that a business function requires. If this is the case, executive-level help will keep you moving forward.

Focus on hiring cultural fits

Of course, education, professional background, and qualifications are all important considerations when hiring executives. But, it is crucial that the person you hire fits in culturally with your team and can align with your company’s core values. In many cases, these considerations may be more important than hiring based on past experience alone. 

When interviewing, consider committing a portion of your questioning to personality and work culture. Ask them about their vision for a successful workplace and where they would feel most comfortable. What kind of environment would allow them to succeed?

Go over your startup’s values and vision, and ask them if they share those values. How have they shown a commitment to those values in previous positions? What has always driven them in their career path?

Remember that you are interviewing each other, and they will be assessing if your company fits into their ideal career trajectory. The relationship should work well for both parties.

Remember the reputational impact of executives

Hiring an executive for your startup should go beyond the normal vetting process. This person will be representing your brand, and their actions (past and present) matter. Because their own professional reputation may be scrutinized by your audiences, here are some tips to ensure you are being extra careful:

• Reach out to your networks to find candidates that someone you know can vouch for.

• Ask for references and actually use them. Inquire about weaknesses as well as strengths.

• Conduct a more vigorous background check, including financial, professional, criminal, and even academic records.

• Hold multiple interviews in the process to get to know the candidate in various settings. This also may include allowing other team members to be involved in interviewing and screening.

There may not be a perfect executive, just as there is no perfect person, but it is still important to fully vet everyone being considered for the position.

Hire an executive search firm

Even with the best of intentions, you may just not have the time to put enough energy into the hiring process to ensure all these considerations are followed. Fortunately, executive search firms can do a lot of the heavy lifting for you. They know how and where to find the right candidates who will align with your goals and vision. An executive search firm will have many resources, so your candidate pool is wider, which is especially important when you are hiring an executive.

The team at Drive Talent is ready to help you with your search. We specialize in finding executive-level talent with a focus on sales, marketing, and the cannabis industry. We know how important it is to find the people who align with your startup’s goals and culture, and we help you find long-term hires.

Drive Talent is a woman-owned firm based in Chicago. Contact our team to learn more about our approach and how we assist clients like you in finding the right executives.