Coaching
Executive & Career Coaching for the AI Age
The world of work is changing faster than most people can process and if you’re trying to figure out what it means for your career, your team, or the company you’re building, you don’t have to figure it out alone.
I work with executives, leaders, and ambitious professionals who are navigating their careers in the context of AI and everything it’s disrupting. Whether you’re wondering how to stay relevant, how to lead a team through uncertainty, how to make a bold career move, how to get your startup off the ground, or how to quit and retire early, I bring a rare combination of coaching and mentoring to every single session.
Here’s what makes this different: I’m not going to tell you what to do. I’m going to ask you the right questions until you know what to do and when I have advice from my years of experience, I will share it. We’ll end every session with practical, immediately doable next steps. Not theory. Not homework you’ll never get to. Real actions you can take this week and clarity that will bring you a bit of calm in the middle of the chaos.
What We Can Work On Together
Career Navigation in the Age of AI
Your role is changing. Your industry is changing. And the skills that got you here may not be the ones that get you where you want to go next. We’ll cut through the noise together and build a clear, confident path forward.
Executive & Leadership Coaching
Leading teams through uncertainty is one of the hardest things you can do. I’ll help you show up as the kind of leader your team needs right now and build the clarity and confidence to make hard decisions well.
Startup Advising
I’ve built and scaled products, led engineering and product teams, and navigated the messy, exhilarating work of building something from scratch. If you’re founding or growing a startup, I bring a hard-won, practical perspective to every conversation.
Career Transitions
Thinking about making a move to a new role, a new industry, or out on your own? I’ll help you get clear on what you actually want, identify what’s holding you back, and build a plan that’s honest, realistic, and genuinely exciting.
Financial Independence
Are you interested in the path to Financial Independence? The same path that allowed me to retire at 41? Would you like some help creating a plan and sticking to it? I’ll help you set-up a strategy from going over your finances with you to figuring out what to do when you have more freedom in your life.
How it Works
Every session is a blend of coaching and mentoring — I’ll ask the questions that help you find your own clarity, and I’ll share direct, experienced perspective when that’s what you need most. You’ll never leave a session without something concrete to act on.
I offer coaching in three package sizes so you can choose the level of support that’s right for where you are:
3-Session Package
A focused sprint. Great for a specific challenge, a decision you’re wrestling with, or a quick-start on a new direction.
6-Session Package
The most popular option. Enough depth to build real momentum, work through complexity, and start seeing meaningful change.
12-Session Package
A full engagement for leaders and founders who are ready to do deep work and make lasting shifts in how they lead, decide, and grow.
All sessions are conducted via video call and scheduled at a cadence that works for your life. Packages are priced to reflect the investment of working together seriously so reach out and we’ll find an arrangement that makes sense.
Let’s Start With a Free Convesation
Before we commit to anything, I want to make sure we’re a great fit for each other. The coaching relationship only works when there’s genuine trust and chemistry — and the only way to know that is to talk.
Book a free 30-minute session below. We’ll get to know each other, talk about what you’re working on, and figure out together whether this is the right next step.
A Little About Me
I retired at 41 after a career leading product and engineering teams at companies ranging from startups to Fortune 500s. I’ve navigated the chaos of hypergrowth, the hard work of building high-performing teams, and the deeply personal question of what to do when the career you built no longer fits the life you want. I write, I speak nationally on agile and product strategy, I direct the CS Marketplace and Capstone programs at UW-Madison, and I’ve coached and mentored people at every stage of their careers.
I bring the experience, the hard-won lessons, and the genuine curiosity about what makes people thrive to every coaching session.
Questions before booking? Email me at team@amberrfield.com. I’d love to hear what you’re working on.