I help tech founders & CTOs get moving.
Coaching first time/early stage CTOs and tech founders to cut through the noise, focus on what matters and test ideas within hours not months.
- Need help working with product, your board and your CEO?
- Unsure about right technical architecture for your stage?
- Need technical guidance on your AI/LLM app?
- Want to set the right culture and avoid the wrong one?
- Want to hire and vet the right people and build a world class team?
- Worried you are not going fast enough?
- Unsure if you will progress enough to raise your next funding round?
- Want to know exactly how to find problem/solution and product/market fit?
- What to add just enough process to avoid chaos, but not enough to slow you down?
- Feel like you never have enough time to do all of this?
“A great mentor for me… Chris is very experienced both in the technical side of setting up a well functioning tech team, but also in the business side, possessing a keen eye for strategy and a good sense for what will and will not work in any given environment. If you’re a startup looking for someone to help build a great team, or you need someone experienced to help develop a sound tech strategy, I would thoroughly recommend Chris.”
“Chris has clearly learned a *lot* about the world of being a delivery-focused CTO, he has a very clear understanding of the need for pragmatic planning, knowledge sharing, team up-skilling and the paying down of technical debt… I hope to continue to learn from Chris’ experience.”
“Chris is fantastic at building self-sufficient teams and giving them what they need to deliver impactful product changes and experiments. He provides a lot of freedom while setting clear goals, which creates highly productive teams in early-stage startups. At the same time, he’s an empathetic leader who always keeps a pulse on team morale. This is an extremely punchy combo when it comes to pre-product-market-fit companies, where hyper focus, productivity and seeding the right company culture are key.”
I have led 5 startups over 20 years:
- I cofounded 4, and was an early CTO at one
- 3 were bootstrapped, 1 backed by super angel + 1 by VC
- 3 were B2C, 2 were B2B
- 1 was an agency, 4 were product companies
- I scaled teams to 5, 12, 25 & 50
I have been through a wide variety of startup experiences multiple times. I can help you hire great technical teams, set culture, find product market fit and build just enough tech. I’ve also got several years of experience working on AI products so can help you build robust LLM application that scales well and that your customers love. Read more about me here.
Why Founders and CTOs Need a Coach
Coaching helps founders and CTOs grow and achieve their goals. A startup has high stakes and huge potential value so getting support makes a real difference to your success. I have benefited from a number of excellent coaches and mentors over the years, and my startup experience has been vastly better and less stressful thanks to them.
Every technical leader faces common challenges:
- Making tricky architectural decisions under uncertainty
- Hiring and managing high-performing engineering teams
- Scaling up to manage high level tech strategy
- Scaling down to manage team performance and troubleshoot code
- Constantly learning new technology and figuring out how to apply it to your business
Having someone in your corner who’s been through these challenges before, as I have at multiple startups, is the difference between struggling alone and confidently moving forward.
Coaching vs Mentoring
I am part coach, part mentor.
Coaching is a conversation to move you from where you are now, to where you would like to be. You get independent assistance to help you move forward without any judgement or anyone telling you what to do. You find your own answers and are then supported while you make changes.
Mentoring is benefiting from past experience, knowledge and mistakes to help you make better decisions. You can be coached by a non-expert, but a mentor can provide lots of extra value as they have been in your position before.
A founder or CTO benefits from a coach but working with someone who has been through the same challenges before is much more valuable. I have walked this journey through several startups over 20 years and can help you avoid plenty of mistakes and find a way through the maze of uncertainty.
My Recent Articles
How To Avoid Bad Startup Culture
If you are not paying attention to your startup culture, I have news for you: you are already building a culture into your company. Chances are that is not the culture you want.
Every company has a culture. It is a summation of all the habits and practices that make up the work. It is every choice, good or bad, made by every person involved. Every action sets a precedent, a “how we do things here.”
This is how we are wired. We are naturally social beings and are strongly predisposed to fit in to the group we find ourselves in, and to emulate their behaviour. This reinforces culture further, and compounds when more people are involved.
A culture grows like plants in a garden. You cannot stop the life from growing, but you can decide how and where it grows. Left unattended, weeds will grow alongside the flowers. The key is recognising this and putting in the work to shape it.
Here is a quick primer on how to do the minimum to avoid bad culture, and how to get good culture going with a little attention every so often.
Read moreHow to Build a Robust LLM Application
Last month at Cherrypick we launched a brand new meal generator that uses LLMs to create personalized meal plans.
It has been a great success and we are pleased with the results. Customers are changing their plans 30% less and using their plans in their baskets 14% more.
However, getting to this point was not straightforward, and we learned many things that can go wrong when building these types of systems.
Here is what we learned about building an LLM-based product that actually works, and ends up in production rather than languishing in an investor deck as a cool tech demo.
Read moreWhy Hybrid Work Works
As someone who lives an hour and a half from my London office, I love working from home. I can help my teenagers out of the door in the morning, and I am present when the family comes home. I can have coffee with my wife Ellie before we start work. I prepare dinner during my lunch break, and receive deliveries. I can contribute more effort during my day to Cherrypick, free from distractions, interruptions and the long commute. I would struggle to work effectively five days a week in London.
I also love working from the office. It is an opportunity to spend real time with the people I work with. Communication is easier and I spend less time on screens. I can train less experienced colleagues much more efficiently than video chat. I can ask for and give advice and help in person, cutting down long feedback cycles. I would struggle to work effectively five days a week from home.
Much of the debate around hybrid working appears to be a zero sum argument about why working from home is “better” or “worse”, and why working in the office is “more” or “less” productive.
One is not better than the other; they are just different. I think we need both for a balanced life.
Here are some pointers for how to have a productive conversation about hybrid in your team.
Read moreSee the Archive for more articles.