Stronger leaders. Healthier teams.
Better outcomes.

What We Do

  • Leader & Executive Coaching

    We’re trusted advisors, champions, and thinking partners in your development as a leader.

  • Team & Leadership Development

    Customized teaming engagements to meet your objectives. Let’s build trust, make faster decisions, lean into conflict, disarm drama, and more.

  • Organizational Development Consulting

    We’ll get to the bottom of the structural and/or behavioral issues holding you, your team, or your org back.

  • Offsite Design & Facilitation

    Whether at your offices or offsite, we’ll design and deliver interactive experiences that nail your objectives, AND are fun.

  • Facilitation Training

    Learn and practice the basics of facilitation to make your meetings and events more effective.

  • Speaking Engagements

    Bring us in to talk with your team, org, or conference on topics that matter for you.

Who We Are

Jill and Cara met in 2017 while working for Tableau.  One of their first big projects together was to translate a 6-month in-person leadership development cohort into an online program during the early days of COVID lockdown. They pooled their skills of learning design, business acumen, facilitation, and coaching to deliver the same quality of program in a virtual format. The program (for Sales Leaders at Salesforce) was a raging success and solidified their working friendship/relationship. Their next project was to build a facilitation course for Salesforce — which remains so popular to this day that it regularly has a waitlist for attendance.  

They make a great team because they each contribute something unique to the partnership. They have the tough conversations with each other. They use the skills they teach. And they have very different lived experiences and so bring different types of wisdom to their interactions. Oh, and they both love to laugh.

Cara Wilson, MA, ACC

I’ve been coaching leaders and teams from the front line to the C-suite for nearly 20 years.

  • One of my very favorite things about this work is to see a team or leader pick up a new skill or perspective as a result of working with me — and have them say things just feel easier now.  One client said: “Cara has a wonderful way of making hard work feel effortless.” 

    In my nearly 20 years of working with teams and leaders, I ran my own coaching and consulting business, I spent nearly a decade in healthcare coaching physician leaders and hospital administrators, and I spent seven years in tech coaching engineering and operations leaders at Tableau and Salesforce.  I have a special affinity for neurodivergent leaders, as I am one myself.

    My fascination with human behavior began as a young adult in the wilderness, taking unruly teenagers on month-long adventures as an Outward Bound instructor. I got curious about how the things I was learning about teams applied “in the real world” (and if we’re honest about it, I also got tired of being cold and broke). So I headed for a Master’s Degree in Applied Behavioral Science with a focus on Coaching and Consulting in Organizations. 

    When we work together, we will balance gravity and levity. We’ll talk about the hard things and we’ll laugh and celebrate your successes. I will be kind and direct — we won’t beat around the bush. I’ll toast to your strengths and I’ll call on you to step into your potential. I’ll encourage you to take different perspectives on your situation and to think about the systems that may be affecting it. It’s all about the “and.”

    I live on a blueberry farm in Poulsbo, Washington. When I’m not working, you can find me hiking in the woods, riding bikes and motorcycles, doing puzzles, or begrudgingly laboring around the homestead.

Jill Wicklund, ACC

Driven by my love for helping people make those most of their careers and workplaces, I’ve been leading and coaching individuals and teams for over 12 years.

  • I’m dedicated to supporting individuals in making bold choices that bring joy to their workdays, helping make complex challenges feel easier, and developing communication skills that foster healthy, meaningful relationships.

    As a Professional Coach holding an ICF certification and a half-dozen other stackable credentials, I’ve supported over 200 sales engineering leaders, portfolio managers, HR leaders and sales leaders, as well as individuals seeking career clarity. I’ve worked across multiple industries, including tech, healthcare, service and finance, and I bring a deep understanding of leadership development, career transitions, and creating productive work environments.

    When we work together, you’ll find an approach that balances honesty, warmth, and practicality. We’ll talk about what matters most to you, challenge assumptions that might be holding you back, and celebrate breakthroughs along the way. I’ll help you connect the dots between your personal values, career goals, and the systems influencing your choices.

    I live in Seattle, the rainy and beautiful city that I have called home since birth. I enjoy being in the forest, being humbled by my sons, and experimenting with creative pursuits. My personal journey balancing parenthood, career aspirations, and health challenges has shaped my commitment to helping others navigate their paths with clarity, courage, and intention.

What People Say

  • Cara has a million frameworks up her sleeve, makes complex topics approachable, creates space for people to be real and honest, asks the questions people might be afraid to ask, and most important, makes people laugh like hyenas.

    Grace Brelje, Salesforce

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We should talk.

How can we help? We’d love to know what you’re thinking.