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 clearly embody our leadership principles

  • Chemistry: Gel with CEO and leadership team

  • Work style: 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 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:

CEO Informational (25m)

First meeting with CEO to learn about the company and understand potential to work together. A letter from the CEO will be sent in advance to share about the opportunity.

CEO Chapters Interview (85m)

This interview may happen after the informational or after talking with other members of our leadership team, depending on the role. One of our leadership principles is self-awareness and in this interview we ask candidates to reflect on their career in terms of "Chapters". We discuss five questions for each chapter going back in time:

  • What were you hired to do?

  • Who did you work for?

  • What were the low points/most difficult challenges for you?

  • What would your manager rate you on a scale from 1 to 10?

  • Why would they give you that rating?

The questions are a framework for understanding how a candidate approaches opportunities for personal growth.

1-1s with Leadership Team (55m with different leaders)

Candidate meets leadership team in 1-1s to mutually assess potential to work together. May also include key staff and potential new reports. Most meetings are remote, though if a candidate is in the Bay Area in-person meetings are an option. 1-1s include:

Extended time with CEO (varies)

This could include 1-1s, phone calls, Zoom meetings, Mattermost discussions, coffees, walks, or meals depending on the circumstances. After the Chapters meeting you are welcome to sign-up for the Mattermost server and message the CEO at @ian.tien.

"Ask Me Anything" with CEO (85m+)

An opportunity for the candidate to ask the CEO anything. This may happen over a dinner. This is an opportunity for the candidate to drill down into the CEO and the business, discuss any issues or concerns, and have the candidate self-assess whether they feel they would have a 90% or better probability of success in the role and in the culture.

Memo and Leadership Team Discussion

A concise 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 goal is not to be correct, but to share your thinking and participate in a "healthy conflict" among executives, who may approach your topics from different points of view. Ideal memo can be read in about 5-10 minutes. In some roles we may ask for a slide deck in addition to the memo.

(As appropriate) 1-1 Advisory Board meetings

Candidate may meet with 1-2 board members and 0-2 members of our advisory board with deep experience in candidate's domain.

  • Tomasz Tunguz (Board Member), Managing Director at Redpoint

  • Andrew Miklas (Board Member), co-founder of PagerDuty, partner at S28 Capital

  • Adam Gross (Advisory Board), former Heroku CEO, DropBox SVP Marketing

  • Zach Urlocker (Advisory Board), former Zendesk COO, Duo Security COO, MySQL SVP Marketing

  • Alan Black (Advisory Board), former Zendesk CFO

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, especially if the candidate was previously topped

  • Avoids rat-holing in discussions

  • Doesn't waste time

  • Doesn't hide gap areas

  • Doesn't hide unfavorable information, especially if we are likely to find it during reference checks

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 on-boarding 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.


While we try to be as open as we can in our processes, there remains some information that if shared early could bias our decision making. For that reason, we store confidential process information about exec recruiting in a permissions restricted G Doc.