These moments can feel isolating, but they’re more common than you might think.
I have coached over 150 talented founders, CTOs and senior engineering leaders facing challenges like these.
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As a first-time CTO at a growing tech-startup, Joel’s coaching has been instrumental in helping me step up to my new leadership role and to work through some of the most challenging aspects of scaling a company. After only a few months, I have seen really positive results. I couldn’t recommend his coaching any higher!
Here’s what that support looks like in practice:
My coaching programmes are flexible. We will explore what you are looking to achieve during an initial chemistry call and design a programme that will work best for you.
The length of the programme, frequency and length of sessions and the amount of support between sessions will all vary depending on the programme we agree on for you.
Explore coaching optionsCoaching sessions are via video call. This allows us to meet when and where works for you.
This can be anywhere in the world. I have coached engineering leaders based in Brazil, Canada, Colombia, the Czech Republic, France, Germany, India, Italy, Japan, Lebanon, the Netherlands, New Zealand, Portugal, Singapore, Spain, Thailand, the UAE, the UK and the USA.
I am based in the UK and, if the time difference between us is large, the times available for our sessions may be restricted. For example, if you live on the West Coast of the USA sessions are likely to have to be before 10am for you.
Joel played a crucial role as my coach during Florence’s rapid growth, both before and after our Series B raise. His coaching was instrumental to my personal development when I had to 4X the team and handle plenty of new challenges. He also helped me develop techniques for dealing with future challenges, which I’ve put to use successfully since our coaching finished.
I am Joel Chippindale. I have coached more than 150 engineering leaders, supporting them to build their confidence, accelerate their development, deliver on their goals, and navigate the complex challenges of leading in technology.
My coaching delivers lasting results: leaders who make better decisions, deliver more effectively, build stronger relationships with their stakeholders, and develop practical tools and skills they continue to use long after our work together ends.
I have a calm, thoughtful, and supportive style. I ask incisive questions that help you uncover your own insights and challenge beliefs that may be holding you back. Rather than simply giving advice, I create a safe space for honest reflection, while drawing on my own experience when practical guidance would help.
I have over 20 years of experience building, scaling, and leading software development teams, mainly in start-ups and scale-ups, including CTO and COO roles at FutureLearn and CTO roles at Econsultancy and Unmade. This means I understand the pressures you face—from scaling teams and navigating organisational change to building the cultures that enable both you and your company to thrive.
Joel doesn’t just give you answers—he helps you find them within yourself. His coaching approach unlocks the knowledge and skills you already possess, making solutions feel authentic and personally meaningful. The result? Better retention and real-world application because I felt the insights were truly mine.
I share these quotes from some of my coaching clients to offer you a tangible sense of the experience and benefits of being coached by me.
Joel’s expertise in implementing effective mechanisms for building and managing large engineering teams has been invaluable. His flexible approach to leadership and strategy has allowed us to tailor solutions that align with SMPnet’s unique needs. Whether it’s streamlining workflows, optimising team dynamics, or fostering a culture of continuous improvement, Joel’s guidance has been adaptive and responsive to the evolving challenges of scaling engineering teams.
I highly recommend Joel to any CTO seeking a coach with a nuanced understanding of organisational dynamics, coupled with the flexibility needed to navigate the complexities of growth.
I really valued Joel’s extensive experience as a CTO, which meant he could offer useful advice and support, as well as work through tricky problems with me. He helped me focus on strategic priorities even when there were urgent activities competing for my time.
Joel has an impressive ability to create a safe space and calmly discuss a range of topics and to provide useful input. His coaching would benefit anyone who is going through a difficult and stressful challenge in engineering leadership.
Joel coached me in a very important moment of my career, as I had just been promoted to CTO and also had additional new challeges including leading the product organization, going through an M&A and important cultural and strategy changes. At the beginning of our conversations I was feeling very overwhelmed and worried about doing a great job in my new role and ensuring my team and my company succeeded.
Having Joel as a coach was very valuable to me and had great impact on my team and company. As my confidence in my role grew, I’ve been able to better direct my team and we’ve been hitting our targets and constantly delivering value to the company. I recommend that any leader going through challenging and stressful times be coached by Joel.
Working with Joel has been transformative for my career as a senior technical leader. His unique blend of coaching and mentoring combined with deep expertise helped me navigate complex leadership challenges, guiding me to understand myself better than I could’ve ever imagined in the process.
Joel creates a space where you can think clearly, challenge your own assumptions and discover solutions you didn’t know you already had. I’m endlessly grateful for his guidance, it’s genuinely been life-changing for me.
Working with Joel during my transition into my first CTO role was transformative.
As an executive coach, he provided invaluable guidance that helped me navigate both the tactical and strategic challenges of C-level leadership. Joel was instrumental in helping me overcome imposter syndrome and build genuine confidence in my abilities. His coaching approach enabled me to develop new problem-solving strategies that delivered meaningful results for both my personal growth and my company’s success. After six months of working together, I’ve not only grown into my role but have developed a solid foundation for continued learning and development.
I highly recommend Joel to any CTO / technology leader looking to accelerate their leadership journey.
The coaching programmes that I offer are personalised for you and the cost will vary depending on the programme we design for you. Coaching programmes start from £4,500 +VAT.
I also offer coaching scholarships to engineering leaders at startups or scaleups who identify as being from a group that is underrepresented in technology and cannot afford coaching yet.
Let’s have a call and we can explore your needs and how the coaching and mentoring that I offer can support you.
Let's talkOr you can email me at joel@monkeysthumb.co.uk.
Joel stands out not just as a coach but as a mentor, especially suited for senior technical leadership challenges. His advice is grounded in a deep understanding of tech, allowing him to toggle between coaching and advising as needed.
His calm and reassuring presence creates a safe space for open, honest dialogue, allowing vulnerability and growth. Each session felt like a reset, leaving me optimistic and more aligned with my professional goals.
If you’re at a crossroads in your tech career, do not hesitate to engage with Joel. His coaching goes beyond professional development; it is a world-class partnership that offers a transformative experience, equipping you to navigate both current and future challenges.
I coach engineering leaders who want to improve their performance at work.
The majority of my clients are the most senior technology person in their start-up or scale-up, perhaps the CTO, or Head of Engineering, or Director of Engineering.
I also coach leaders in larger companies and those in other senior engineering leadership positions, including Directors and VPs of Engineering.
In the words of Bill Gates, “Everyone needs a coach”.
You are likely to benefit from a coach if you want to improve your performance. If you want to serve your teams better. If you want to have more impact. If you want to accelerate your development. If you feel stuck.
I often say that if I could give my younger self one piece of professional advice then, it would be to, “Get a coach”.
I have written more about this in my blog post, “How does a CTO know when they need a coach?”.
My coaching programmes are flexible and we will build a programme that meets your needs.
In a typical programme we would start by exploring your goals for coaching and set an ambitious vision for where you want to be at the end of the programme.
We would then have regular coaching sessions and I will use coaching and mentoring to support you to:
I will recognise many of the challenges you face from my own experiences of being a CTO and so, where appropriate, will also be able to share these experiences with you.
I will also be available to offer support between sessions.
I can also support you to get feedback from those you work with.
The length of the programme, frequency and length of sessions and the amount of support between sessions will all vary depending on your needs.
Most of my clients have their coaching paid for by their employers.
Companies pay for coaching because of the high return on investment from the impact it has. It is a pragmatic way for companies to invest in the development of their best senior leaders by working through their challenges and transforming their learning directly into results for the organisation.
I can support you to think about the impact of your coaching programme in order to make the business case for your coaching. Let me know if you want to cover this in our chemistry call.
Mentoring is when you learn from the experiences of others. This can be very valuable and can accelerate your learning.
Coaching starts from the position that you are capable, resourceful and whole and that the answers to your challenges are already within you. A coach is a thinking partner who will support you in discovering these answers.
Coaching is often much more powerful than mentoring, in building your confidence and skills, and in arriving at solutions to your challenges that really work for you and your context.
I offer a combination of coaching and mentoring to ensure that you get the support that is most effective for you.
You are probably busy. You probably have a role where you are never “done”. In this environment it can be difficult to feel that you have the time to meet with a coach.
Coaching supports you to focus on what is most important. This helps you spend your time more wisely and have a greater impact in less time. Almost all of my clients feel like they have more time rather than less as a result of coaching.
If you feel that you are too busy for coaching, then this is a sign that you coaching would be particularly valuable for you.
Each coaching relationship is different, and as we work together we will learn what works best for you.
We will adjust our approach to coaching as we work together, identify and select the practices tht work best for you, and also explore the balance of challenge vs. support, of coaching vs. mentoring.
I also recommend the following to get the most from your coaching relationship
Be ambitious. You are more capable than you believe and with coaching support you can go further than you you give yourself credit for. If you don’t have clear goals when you start your coaching that is OK. Often the most important part of the work that we do together, is to identify where you want to go.
Be open. Coaching is a thinking partnership and the less you hold back, the more effectively we will be able to think together. I will keep everything you say confidential and hold you in unconditional high-regard in order to provide you with a safe space to explore your ideas and feelings.
Take action. Our sessions will provide you with space to understand yourself and your situation more clearly, challenge self-limiting beliefs and commit to actions to make change. However this will just be talk unless you also take action between our sessions.
Offer feedback. We will learn how to work together more rapidly if you offer direct feedback about your experience of being coached. This will support us to both adapt our approaches so that you can get the most from your coaching programme.
I can also recommend Evgeny Shadchnev’s article How to work with a coach that provides great advice for getting the most from your coaching relationship.
For any further questions, please send me a message.
If you’re ready to get started, then book a complimentary “chemistry” session. As part of this first meeting, there will be ample opportunity to ask any further questions you might have.