How to scale your career alongside your startup: Mike Boufford’s lessons after 10 years at Greenhouse
Jan 12, 2023
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Mike Boufford, CTO of Greenhouse, shares insights on scaling a career at a startup. Topics include building a supportive environment, preparing for growth phases, reading books on various executive areas, and reducing attrition. He also discusses the importance of adapting, coaching team members, and evaluating hires based on versatility and adaptability.
Building a supportive environment and strong relationships with founders are crucial for long-term success at a startup.
Being proactive in anticipating and preparing for future responsibilities is essential for career growth.
Continuous learning and acquiring knowledge in different areas of the business are key to strategic thinking and positioning oneself for success.
Deep dives
Adapting and embracing change
Mike Buford, the CTO of Greenhouse, shares his perspective on the importance of being adaptable and open to change in order to have a successful and long tenure at a startup. He believes that aligning with the right founders and having the opportunity to learn and grow from experienced leaders played a crucial role in his career trajectory. Additionally, Mike emphasizes the importance of being proactive in adjusting oneself to the demands of a growing business and constantly looking ahead to anticipate and prepare for future responsibilities and challenges.
Creating a supportive and fulfilling environment
Mike Buford discusses the key factors that contributed to his long-term commitment to Greenhouse. He highlights the importance of creating a company culture that fosters growth, fairness, and respect. Mike shares his experience of being empowered to shape the engineering organization and make Greenhouse the workplace that he wanted to be a part of. The founders' trust, autonomy, and opportunities for personal and professional development were instrumental in his decision to remain at the company for over a decade.
Developing strategic skills through continuous learning
Mike Buford shares how he honed his strategic skills throughout his tenure at Greenhouse. He emphasizes the importance of continuous learning and proactively acquiring knowledge in different areas of the business. Mike embraced the challenge of preparing himself for every new phase of growth and transition, reading books on strategy and other executive roles, and seeking advice from experienced individuals. By engaging in strategic thinking, staying ahead of future requirements, and adapting his skills to match evolving responsibilities, Mike continually positioned himself for success in each stage of Greenhouse's growth.
Reflecting on Negative Labels and Behaviors
The speaker discusses the approach of observing negative labels and behaviors as separate entities. Instead of internalizing negative opinions about themselves, they view negative behaviors as observational data and use it as a starting point for self-reflection. By analyzing their actions, motivations, and beliefs, they are able to identify areas for improvement and devise a plan to change negative behaviors into positive ones.
Leveraging Feedback and Self-Reflection for Growth
The speaker emphasizes the importance of seeking feedback from peers and mentors to enhance personal growth. They mention participating in CTO pods and attending meetings where they request specific feedback on their thinking and problem-solving approaches. Through these conversations, they gather valuable insights that help them identify areas for improvement and develop strategies for professional development. They also discuss the impact of reading books on topics such as decision-making, communication, and negotiation, which provide context and enrich their understanding of various aspects of leadership and strategy.
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.
You can follow Mike on Twitter at @mboufford. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.
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