Exec Recruiting

Bringing on VPs and Senior Directors to own critical functions of the company has as much impact and risk as bringing on a new co-founder. The following guide is being developed to share the structure of the process and to adjust and optimize.

Note: Senior Directors are included in the exec recruiting process because their growth path is into VP. The general expectation of all hires is to have the potential to grow into the next career stage.


At Mattermost we assess department head candidates in four areas:

  • Capability - Obviously a strong expert in their field
  • Culture - Able to cleary embody our leadership principles
  • Chemistry - Gel with CEO and leadership team
  • Workstyle - Works well online and offline, and in open source environments


Executive candidates should ideally come through the networks of the leadership teams, board or advisors, ideally from someone with hands-on working experience. Second best is from a strong executive recruiter with both a high quality network and candidates placed who are similar to the role we’re looking to fill.

Relationships with top exec recruiters are important and long term. They are experts in their fields and have seen more candidates than anyone.


We go really, really deep on exec recruiting. The interview process should take 20 hours or more for the the candidate to get to know our company and leadership team and for us to know the candidate. References and background checks weigh more heavily in department head recruiting than any other role.

The hiring process for a new exec should include:

  • Extended time with CEO - This could include 1-1s, phone calls, and multiple meals and extended discussions. Long phone calls on weekends are occassionally a way to find time to talk at length.
  • 1-1s with Leadership Team Member - Candidate should meet all the leadership team in 1-1s to mutually assess potential to work together.
  • (As appropriate) 1-1 Advisory Board meetings - Candidate may meet members of our advisory board with deep experience in candidate’s domain.
  • Memo - A written answer to a question from the CEO on a challenging issue under debate internally. The ideal candidate should be able to share a concise and persuasive written opinion that would influence the CEO, leadership team and board. The memo may be a topic of discussion in interviews.
  • Leadership Team Meeting - Candidate should participate in a leadership team meeting to simulate how the team might work day-to-day

General Attributes

Look for patterns for exec-level success:

  • “Wows” our team at how good they are in their domain
  • Communicates concisely, directly and respectfully
  • Naturally explains ambiguous, complex issues simply
  • Shockingly good at connecting high level strategy and vital, low level details
  • Rapidly develops empathy with others
  • Sees around corners
  • Develops a clear picture of their business and organization near term as well as at least 1-2 years in the future
  • Challenges directly while caring deeply
  • Strong written communication and attention to detail
  • Keenly self-aware and open about personal strengths and opportunities

Also check for anti-patterns:

  • Is not overly concerned with title
  • Avoids rat-holing in discussions
  • Doesn’t waste time
  • Doesn’t hide gap areas

Reference checks

  • Anything less than an outstanding recommendation from a reference should be a flag.
  • If you detect a “whiff of disfunction” there should be a flag.
  • To ensure the reference is complete, make sure to ask “is there any reason why you can’t fully comment on the performance of the candidate?”

Executive Onboarding

For new executives joining the team, there is a high ROI for providing time for the leader to learn about the company and build relationships ahead of taking action.

Day 1-7 - Learning

  • Exec drafts plan and works with CEO to edit it in the first week
  • Joins leadership team meetings
  • Extra CEO 1-1 time (first 8 weeks)
    • 25m Monday and Friday meetings with CEO to mindmeld (cancel at exec’s discretion)
    • Meetings cover company pitch, recruiting story, what’s sacred and other topics
    • Gives opportunity for exec to dig in and find the “why” behind decisions
  • Exec may start with no directs and inherit them later after a plan is developed for each role

Day 1-30 - Planning

  • Understand the company and the team
  • Go through onboarding materials
  • Go deeper into the product
  • Build relationships and understanding with leadership team and broader team

Day 31-60 - Starting to execute

  • Develop concrete plans

Day 61-90

  • Start to see evidence of execution


  • Outside of a few exceptions, if onboarding has been done properly and an executive isn’t working well with the rest of the team at 60 days, things are unlikely to significantly improve.