Assembling an Executive Leadership Team is Daunting — Let Thumbtack’s CEO Help

Recruiting and hiring executives is difficult for any leader, but especially for first-time or early-stage founders who may not have enough knowledge to test candidates for skill in their area of expertise. Thumbtack CEO Marco Zappacosta has been there — and has a roadmap that'll help.

A DIFFERENT TACK FOR EXECUTIVE INTERVIEWS

CEO and Co-founder Marco Zappacosta launched Thumbtack after graduating college. One of his proudest accomplishments was not an innovation, but a realization — one that took nine years to fulfill to his satisfaction. "We've recruited heads of engineering, product, marketplace, finance, HR, operations, marketing and general counsel. For the first time in our history, we've filled all the seats... I've learned to leave reinvention to our product, not its guardians. I’ve realized how immensely valuable it is to have an experienced executive team."

For the first-time and early-stage founder out there, recruiting and hiring executives can be daunting. Zappacosta shares his four-step process for identifying and vetting his leadership team. From job descriptions to interview questions to references, Zappacosta shares his approach to executive searches to generate a stronger signal for better leaders.

1. Constrain your JD.

Zappacosta sees that a big mistake with executive searches is the extensive job descriptions. “Don’t describe the entire position in exquisite form, even though all those skills may be useful... You hire for lack of weakness rather than for an explicit strength.” At Thumbtack, hiring plans are focused around identifying and evaluating the three most essential skills to the role. This helps avoid hiring someone mediocre across the board rather than exceptional in the skills needed for the role.

2. Split your interview process to separate skill assessment from fit.

Zappacosta splits the initial interview with the candidate into two sessions. The first is to establish a rapport and gauge interest; the second focuses on unpacking experiences related to the position. This way, he can assess both interest and fit without conflating skills with personal compatibility.

• Interview Techniques
  • Name the job after this job: Evaluate the candidate’s ambition and alignment with business goals.
  • Find the invisible hand: Understand what drives the candidate.
  • Show me a worst: Determine how candidates address failure and vulnerability.

3. Backchannel to assess skill.

Once the second conversation concludes, Zappacosta initiates backchanneling to gather more information on the candidate's skills. Instead of asking for formal references, he prefers to reach out to contacts from different stages of the candidate’s career to get a holistic view of their strengths and weaknesses.

4. Present results of references and swap 360s.

At the end of the interview process, Zappacosta presents a summary of findings from his reference checks to the candidate. He discusses areas of excellence and improvement, offering an opportunity for the candidate to reflect and discuss their awareness of these points. He also shares his own 360-degree feedback to create a transparent and open dialogue.

BRINGING IT ALL TOGETHER

The confidence that allows founders and CEOs to launch and lead can backfire when it comes to evaluating other leaders. By constraining job descriptions, separating interviews into two parts, and rigorously backchanneling references, founders can better gauge the fit of prospective executive team members. Zappacosta emphasizes the importance of vulnerability and self-awareness, indicating that both parties want to ensure a successful match.