Hi, I’m Jessica MacLeod

Here’s what I’ve noticed:

The way we’re working isn’t working — and I’m here to change that.

Too often, I see teams filled with smart, mission-driven people struggling to collaborate effectively. Leaders carrying more than they should, burning out in the process. And systems — especially in the remote and hybrid world — that create more friction than focus.

We haven’t equipped teams with the skills to build trust, navigate conflict, or align on what really matters. We haven’t equipped leaders with the tools to stay effective and resilient in the face of complexity. And we haven’t designed ways of working that truly support meaningful, human-centered work.

I believe we can do better.

I work with teams, leaders, and organizations to clear the noise — building trust, simplifying systems, and helping people get back to work that actually works. Work that’s grounded in purpose, built on strong relationships, and focused on what really moves the mission forward.

A bit about me:

Before I started coaching and working with teams full-time, I spent over 15 years leading transformational work across government, tech start ups, and think tanks. I’ve always been drawn to roles where strategy and innovation meets empathy and social impact — helping people do better work together in complex systems.

I’ve led digital transformation initiatives, built customer success teams from the ground up, and advised cities, states, and startups on how to serve people more effectively.

Some of the chapters I’m most proud of:

  • I was VP of Customer Success at Promise, helping cities and public utilities launch equity-focused programs.

  • I led Customer Success at Authorium (formerly City Innovate), supporting innovation in public procurement.

  • I served as Director of Digital Services and Technology for the City of San Rafael, guiding their digital transformation work.

  • I co-founded U.S. Digital Response, matching tech experts with over 200 government agencies during the COVID-19 crisis and 2020 election.

  • I led Customer Success at Socrata, where I advised agencies like the State of California and City of San Francisco, and supported the company through its acquisition by Tyler Technologies.

These experiences shape how I think about leadership, systems, and change — and they remind me daily that clarity, trust, and focus are what actually move the needle.

I live in Northern California with my husband and daughter. You’ll usually find me hiking in the redwoods, cooking up something seasonal, painting, or at my local Zen Center. And in August of 2025, I’m publishing my first cookbook, Feasts on the Farm, with Chronicle Books!

You can keep up with my latest ideas and reflection on my Substack- Thought(ful) Leaders.

Client Results

  • “Working with Jess was incredibly valuable for us and our early-stage startup. She brought a thoughtful structure and exercises that gave us space to look at all aspects of our business in a one day intensive workshop. Jess is a talented coach and was particularly gifted at being a mirror that allowed us to see our business more clearly.”

    Dan Coe, CEO of Rally

  • “Can’t say enough good things about Jessica MacLeod! If you’re looking for coaching definitely take advantage of her offer. You won’t regret it.”

    Michael Wilkening, Former Secretary, California Health and Human Services

  • “I have been able to achieve more at work in a month because of Jessica’s guidance than I had in the six months prior to our coaching sessions. I have thoroughly enjoyed working with Jessica, and would wholeheartedly recommend her as a coach.”

    Vedika, A., Product Manager

  • “Jessica has a rare ability to think broadly about the critical long term challenges and opportunities facing her customers and company, while at the same time, be pragmatic about providing value in the here and now.”

    Oliver Wise, Chief Data Officer, US Department of Commerce

  • “If you're in her sector, you've heard buzzwords like "innovator" thrown around a lot. But Jessica is the real deal. She works with a mission and leads people to follow her.”

    Ian Kalin, Founder, TurbineOne

My Core Beliefs

  • Intention is everything

    Going to work for 8 or 10 hours per day isn’t a passive process. Whether we know it or not, we’re always becoming something and creating something. When we establish clear intentions, we not only think about the next win we want at work, but who we want to become and the impact we want to make in the process.

  • Bridging the inner and outer work

    Cultivating clear intentions and greater mindfulness is foundational to making meaningful improvements in your career or business. But it’s only when you take your clear intentions forward with confident and decisive action, that you see the results of your effort and the proof that you've made a positive change.

  • Accelerate your path to results

    As a life long learner, I will bring you the proven frameworks, tools, and strategies that have driven success in similar situations, so you can move forward with confidence. I'll help you adapt these models to fit your unique circumstances, so you’re empowered to take action and avoid getting stuck at the starting line.