Hi. I'm Bobby.

I've been leading teams and building things my whole career. Over the past 20 years, I've worn a lot of hats: stage producer, program manager, founding engineer, chief of staff, engineering executive, and technical advisor.

I learned to build things with people as a producer and president of the Yale Dramatic Association. I never enjoyed the spotlight but loved the process of bringing together all the unseen components that made a show possible.

It turns out that producing theater and shipping software are very similar. I worked at Microsoft for 7 years as a technical program manager. In addition to all the "hard skills", I learned to operate effectively in complex organizations, manage teams, and influence people and projects without leaning on direct authority.

I joined Textio as the first employee and grew alongside the company, leading the engineering team at multiple stages from pre-prototype through Series B. I built foundational parts of our stack and led a cross-functional team of engineers, data scientists, ML/NLP practitioners, and TPMs as VP of Engineering. Along the way, I wore a lot of different hats and learned about leading in a startup at multiple different scales.

Now, I focus on helping startup leaders feel less alone and more supported in their jobs as a coach and advisor.

I am a coach and advisor

Throughout my career, I occasionally had the good fortune to stumble upon a mentor or coach who accelerated my development and helped me navigate the nuances of leadership.

But more often than not, I didn’t have that person and it was a pretty lonely job: guiding my team, ensuring we hit our goals, investing in my own growth, keeping my own head above water - all while looking around and realizing I’m the only person at this company, doing this job.

I don’t want you to feel that way. I don't want you to feel alone in this journey. Because you don't have to be.

What I offer is a blend of coaching and advising. I’ll be in your corner, working closely to help you navigate the ups and downs of your job. I want to learn about you, your team, your company, and your technology - and then use that knowledge to help you make better decisions, grow as a leader, and become more resilient.

I’m equally comfortable brainstorming architectural trade offs you’re weighing as I am debugging a tricky interpersonal interaction. No matter what we’re working on, I will approach it with empathy, curiosity, and support.

Some profiles of folks I love to help:

Are you an engineering leader who is trying to stay ahead of your growing team and company? Does every day feel like you’re fixing the bike while riding it? Does your role and what is needed seem to change every few months? I’ve been there. I can help you.

Are you an early team member who is making the transition from “making” to “leading”? Is this your first time jumping into a management role? Do you feel like an island between the founders and the rest of team? I know what it feels like to take on all the risk and responsibility as an early employee and I’ve navigated many role shifts. I can help you.

Are you a Founder/CEO who is struggling to work effectively with your technical co-founder or Head of Engineering? Do you want to demystify the world of engineering and build your confidence working with and leading one of the largest parts of your company? I can help you.

If any of the above sound like you and you’re looking for extra support to thrive, I’d love to connect!

Get in touch

You can use this form to send me an email and I'll get back to you.