Executive coaching
A second set of hands for the hardest parts of the job
The job got bigger than it looked.
I coach founders and newer executives in tech who’ve got a specific problem and want someone who’s been there to help them sort it out. Many clients’ companies cover the cost, and everything we discuss stays between us.
- LengthThree months
- SessionsSix, every other week
- Each session50 minutes
- WhereOver video
- Between sessionsEmail anytime
- AvailabilityLimited
Who I work with
I’ve coached managers at every level and across functions. The people I enjoy most are founders and newer executives, whether they’re a few months or a few years into the job. Most are CTOs and VPs of engineering, but I’ve coached leaders in business development, human resources, and other functions too.
How I coach
Most coaches are trained to ask a lot of questions and hold back on answers. I’ll ask questions too, but mostly I’ll tell you what I’d do, why, and what happened the last time I tried it. Think of me as a peer who’s done the job.
And I’m in it right now. I’m a cofounder and CTO, hiring, shipping, and making the same kind of calls you are. So when you bring me something, there’s a decent chance I dealt with a version of it recently.
Between sessions you’ll have things to try, and you can email me whenever something comes up. We start each session reviewing what happened.
If you want a coach who asks questions until you find your own answer, I’m probably not the right coach for you.
What we work on
A few of the problems clients have brought me.
Building a team from scratch
A cofounder and CTO was building his first team. We shaped his early team culture, put in a hiring and onboarding process light enough for a small company, and worked out what to do about an early hire who wasn’t growing with the org. He hired and onboarded every role in his plan.
A CEO who went around him
Another cofounder and CTO had a CEO who kept pulling engineers into experiments and side projects. We worked on how he could manage up. He helped his CEO see what the detours were costing the team, got them aligned on what they both wanted, and gave the CEO a separate outlet for the discovery work he loved to lead.
Leaders who were hard to lead
A cofounder and CTO had some very challenging engineering leaders reporting to him. We worked on giving them feedback they could act on and lining up their interests with the company’s. He reset those relationships, and his reports became far more effective on the team.
Plans that kept slipping
A VP of Engineering couldn’t get his team to hit the commitments in his plans. I shared a model I use for leading organizational and cultural change, and he used it to pitch his team on where things stood, where they needed to be, and a concrete plan to get there. Six months later the team was consistently hitting its deadlines and moving with real urgency.
Too many fires
A new VP of Engineering was buried under an expanding list of obligations. I taught her one of my core principles, deciding which fires to let burn. From there we worked on prioritization and delegating well. She finally caught her breath, got her schedule back in balance, and got much better at managing what her stakeholders expected.
People or technology
An engineering leader was torn between managing people and going deeper as a technical leader. We worked through where he had the most leverage and how to build his role around it. He was promoted to the company’s first ever principal engineer.
How it works
A free 30 minute call
Tell me what you’re working on, I’ll share how I’d approach it, and by the end we’ll both know if it’s a fit.
Three months together
If we are, we work together for three months. That’s six 50 minute sessions, every other week, over video.
Keep going if it’s working
If it’s working, you can extend another three months. Many clients renew.
I only take on a few clients at a time because I’m running a company too, so spots are limited. Fees fit most professional development budgets, and I’ll walk you through them on our first call.
I work for you, not your company. Even when your company pays, I don’t report back, and everything we discuss stays between us.
What clients say
“It’s great to have specific examples of how he has dealt with similar situations previously and help me think through to second order solutions. I highly recommend a coach to anyone who is thrust into a more senior leadership position than they are used to and I can personally recommend Sean.”
Unmesh KurupHead of AI and ML at Intuition Machines“110% recommend his coaching to anyone looking for tools and accountability with a side of genuine humanity. Every session has been the highlight of my week, and some of the best guidance I’ve received in my professional life.”
Sarah WellmanSenior Director, Partnership Development at Equal Opportunity Schools“Over our sessions he helped me work through some genuinely difficult people management challenges, think through my career trajectory, and develop better frameworks for stakeholder communication. I left every session with something actionable.”
Keith BourgoinVP of Engineering at Crayon“I worked with Sean to strengthen my skills as an engineering leader, and his advice was practical, specific, and timely. He helped me become better for the people I serve.”
Vinoj ZachariaDirector of Software Engineering at FloQast“Working with Sean for the past few months was one of the best decisions I’ve made in my career to date. Each session was a true highlight of my week, densely packed with insight, actionable recommendations and compassion.”
Stephen YoungPrincipal Engineer at Customer.ioNeed someone inside your company for a while instead? I also work as a fractional CTO, run assessments and strategic projects, and advise founders and boards. How that works →
Questions people ask
What’s your coaching style?
Practical and direct, with a lot of real examples. I’ll share what I’ve seen work, what I’ve seen fail, and what I’d do in your spot.
Are you certified?
No, and that’s on purpose. What I bring is twenty years of doing the job. I’ve been a CTO four times, built leadership programs for more than 1,000 people, and mentored founders at Techstars, MassChallenge, and Founder Institute.
What happens in a session?
You bring whatever’s weighing on you that week, usually a specific problem. We dig into it, and you leave with something to try before we talk again.
How much does it cost?
Fees fit most professional development budgets. I’ll walk you through them on our first call.
Can my company pay for this?
Yes, and that’s often how it’s done. I can invoice your company directly.
Does my company hear what we talk about?
No. I work for you, not your company. Even when your company pays, I don’t report back, and everything we discuss stays between us.
Can I reach you between sessions?
Yes. Email me whenever something comes up. I’m always happy to field a question.
Do you only work with engineers?
No. I’ve coached managers across functions. I most enjoy founders and newer executives, and most of them happen to be in tech.
Where are you?
Boston, but all coaching happens over video, so it doesn’t matter where you are.
If any of this sounds like where you are, grab 30 minutes
Worst case, you leave with a few ideas to try.