How to scale your career alongside your startup: Mike Boufford’s lessons after 10 years at Greenhouse

For our first episode of 2023, our guest is Mike Boufford, CTO of Greenhouse, an applicant tracking system and recruiting platform. 

Mike has a unique career as an engineering leader. He wrote the first line of code at Greenhouse in May 2012, and he’s still there — over a decade later. This isn’t the typical path of non-co-founding engineers, who usually get layered or leave to start their own ventures.

In our conversation today, we focus on how founders build an environment that makes early employees want to stay, and importantly, how leaders can build the career skills and self-awareness they need to succeed at a startup long-term. Mike shares more on:

How his own motivation changed over time and how he managed his relationship with the company’s co-founders. 

The techniques he used to prepare himself for every next phase of growth and how his role would have to change in 18-24 months.

Why he read two books on every other executive’s area of the business when he joined the leadership team.

Mike also refers to his First Round Review article in the interview, which we definitely recommend reading: Why This Engineering Leader Thinks You Shouldn’t Aim for Zero Regrettable Attrition.

You can follow Mike on Twitter at @mboufford. You can email us questions directly at [email protected] or follow us on Twitter @firstround and @brettberson. 

For our first episode of 2023, our guest is Mike Boufford, CTO of Greenhouse, an applicant tracking system and recruiting platform. 

Mike has a unique career as an engineering leader. He wrote the first line of code at Greenhouse in May 2012, and he’s still there — over a decade later. This isn’t the typical path of non-co-founding engineers, who usually get layered or leave to start their own ventures.

In our conversation today, we focus on how founders build an environment that makes early employees want to stay, and importantly, how leaders can build the career skills and self-awareness they need to succeed at a startup long-term. Mike shares more on:

How his own motivation changed over time and how he managed his relationship with the company’s co-founders. 
The techniques he used to prepare himself for every next phase of growth and how his role would have to change in 18-24 months.
Why he read two books on every other executive’s area of the business when he joined the leadership team.

Mike also refers to his First Round Review article in the interview, which we definitely recommend reading: Why This Engineering Leader Thinks You Shouldn’t Aim for Zero Regrettable Attrition.

You can follow Mike on Twitter at @mboufford. You can email us questions directly at [email protected] or follow us on Twitter @firstround and @brettberson.