CTO Coaching & Advisory
You shouldn't have to be making these decisions alone
I've been CTO at two early-stage startups and spent 15 years shipping products for companies like Clerk, GoDaddy, Cisco, and Soho House. I've been where you are - making architecture calls with incomplete information, hiring when you've never hired before, managing up to founders who don't speak your language.
I'm offering a monthly CTO coaching retainer so you have someone technical in your corner who's been in the seat and can tell you what's normal vs. what's a red flag.
For first-time CTOs
- You just became CTO and you're making decisions alone for the first time
- You're managing founders, navigating politics, and wondering if you're doing it right
- You need someone who's been there to gut-check your architecture and hiring decisions
- You want to know what's a normal growing pain vs. what's actually broken
For non-technical founders
- You have a small engineering team (or are about to hire one) and need technical guidance
- You need someone to bounce ideas off and gut-check what your team is telling you
- You want to evaluate architecture decisions but don't know what questions to ask
- You need help assessing whether your team is on track or spinning their wheels
$2,000/month retainer
Here's what you get:
- Weekly 30-minute call (or async when that works better)
- Unlimited async access via Slack or email for quick gut-checks
- Architecture and hiring reviews when you need a second opinion
- Someone who's been in your seat and can tell you what's actually urgent vs. what can wait
"Ben was an exceptional CTO and a true partner in the chaos of startup life. At WorkMade, we took on massive projects with ambitious timelines, and Ben had the rare ability to turn an idea from concept yesterday to a working build in production today. He knew exactly where to focus our energy for the biggest impact, operated with incredible agility, and made thoughtful trade-offs without ever compromising quality and security. Without needing to be asked. Beyond his technical skill, Ben was an incredible teammate and communicator. He knew how to adapt his style to whoever he was working with (whether it was breaking things down for a non-technical teammate or deep-diving with an engineer) so everyone felt aligned and heard. Working with Ben felt like having both a strategic visionary and a hands-on builder in one. Any founder/team would be lucky to have him in their corner."
"Ben was able to apply his front-end development and architecture experience from day one, helping us come up with and validate key architecture choices and avoid costly mistakes as we scale Kayako to be used by 10,000s organisations worldwide to support millions of end users. We found Ben's advice to be realistic and pragmatic, factoring in resource constraints, business needs of the day and balancing those with future scalability benefits. We are relieved to have had Ben part of our design process - his early contributions have saved a potentially limitless amount of developer time, pain and costs down the line."
Let's see if we're a fit
Book a kick-off call
Use the scheduler below to book a 20-minute call. We'll talk through what you're dealing with and see if this makes sense for both of us.
Book on CalendlyPrefer to Learn on Your Own?
Get the playbook instead
Not ready for 1-on-1 coaching? My First CTO playbook covers architecture decisions, hiring, managing founders, and everything else nobody explains about the CTO job.
The First CTO: The Job Nobody Explains
A playbook for the loneliest job in startups - everything I learned the hard way