ABOUT CLEARLYTHEN
Empathetic Support and
Experience-Based Strategy.
Because rising to every occasion takes commitment.
WE SPECIALIZE IN
Advisory sessions, strategic planning, and engaging workshops.
(The kind that bring people together, introduce fresh perspectives, and result in strategies that last.)
1:1 Advisory Sessions
& Trusted Counsel
FOR LEADERS
Navigating complex issues with lots of ambiguity, high-stakes decisions, and potential paths forward—and no easy playbook to follow? You don't have to do it all alone.
Strategic Planning
& Management Consulting
FOR TEAMS & BOARDS
For organizations and leaders who are planning for, rolling out, and navigating change, and want support to make it impactful—and make sure it sticks.
Team or Board Training & Workshops
Virtual and in-person sessions are the quickest and most effective way to introduce new perspectives, bring everyone together, and move forward with meaning. We’re currently booking workshops, retreats, and team and Board governance training sessions.
Listen deeply. Answer honestly. Hold yourself accountable.
These values guide us in life, business, and leadership.
Presence
Listening deeply can be the difference between the status quo and a big breakthrough. We listen with intention and empathy, seeking to understand the unspoken, the hesitant, and the heartfelt.
Honesty
We offer unvarnished truths, even when it’s hard. Our role is to support, inspire, and sometimes challenge you to confront what needs to be faced in service of your growth and purpose.
Accountability
We have deep accountability to ourselves, one another, our organizations, our communities, and the world. That means we am accountable to you. It also means we will create accountability for you.
Social Justice
We’re feminists who understand intersectionality, yet we are always learning. Part of our work involves helping leaders identify where biases (internal or external) are coming into play.
Reconciliation
For us, Indigenous reconciliation in Canada is personal, and it means taking action in a good way. We’ve worked alongside, learned from, and grown because of our many relationships with First Nations colleagues.
Inclusivity
We are committed to being allies to the disabled, neurodiverse, racialized, and LGBTQ+ communities. Because of our own experiences and families, we believe autistic and trans rights are human rights, and everyone has the right to a safe, full, and healthy existence.
Meet Jonathan
Hi. If we haven’t met yet, I’m Jonathan Bennett.
Organizational leaders come to me for understanding, guidance, and an outside perspective. I started ClearlyThen with a simple mission: To help purpose-driven leaders go from being overwhelmed and stuck to thriving—quickly.
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Jonathan Bennett, C.Dir., FNI. Dir., provides sought-after strategic counsel to CEOs, executive teams, politicians, and boards of directors across Canada. With experience in urban, rural, remote, and First Nations communities, Jonathan’s expertise is in social purpose business strategy, governance, branding, change, and communications.
Prior, Jonathan Bennett founded Laridae, a leading management consulting and training firm in its space. As its first CEO, Jonathan grew Laridae from a start up to a leading firm in its space—Laridae is a proud B Corp. He sold the company in 2021.
Jonathan is a Special Graduate Faculty in Trent University’s M.A. Sustainability Studies Graduate Program. An experienced director, he currently serves on three privately held, corporate boards: Accerta (ON), OwlCrate (BC), and 11A Collaborative (NY), and is Co-Chair of a local non-profit, Peterborough Community Health Centre. He is a member of the Institute of Corporate Directors and is a Chartered Director (C.Dir.) and holds a First Nations Director designation (FNI.Dir.) from the First Nations University of Canada, where he also instructs. Previously, he has served terms on the Boards of CashCo Financial (AB), and as Chair of Ontario Telemedicine Network (OTN) and the Kawartha Haliburton CAS, and served two terms as a Board Director for the Writers' Trust of Canada.
A widely published and award-winning writer, Jonathan is the author of seven books. Born in Vancouver, grew up in Sydney, Australia, Jonathan lives with his family in Peterborough, Ontario, Canada.
Leadership is isolating.
I know because I’ve been there.
THE CLEARLYTHEN FOUNDER’S ORIGIN STORY
1995 - 2011
Executive Leadership
I started my career in book publishing, and at nights I wrote fiction. Published 7 books! Sat on my first Board. Started a family. During the days, I managed people, worked my way up, until I held an executive role at a large hospital—as the Chief Communications Officer, and Director of Planning. I managed people and budgets, was a part of a senior team that led a huge capital project (built a new hospital) and then an operational turnaround. Learned a ton. Was exhausted.
2011- 2021
Entrepreneurship
I struck out on my own, founding a management consulting firm, Laridae. The company grew. We became a B Corp and served hundreds of organizations across Canada. Strategic planning, branding, management and leadership training, governance. I sat on more Boards. Became a Chartered Director. So, 10 years in, and things were great. Except I’d become… unfulfilled. I was ready for a change. So, sold the company to an amazing colleague in a management buyout, sold the building, and I struck out on my next adventure.
2021 - Now
Advisory and Strategy
I launched ClearlyThen—an advisory and strategy practice. Now in the “portfolio phase” of my career, I sit on corporate boards, guest on podcasts, work one-on-one with leaders across North America—and with a network of other consultants—I lead teams and boards in strategy, workshops and training. Since going all in on this, I’ve honed my approach, blurring the lines between advisor, mentor, coach, and strategist and finding my lane. But in 2025, I reached my personal capacity—which meant making a cautiously optimistic phone call to Rachel Carrigan: The one person I knew would be perfectly suited to help.
Meet Rachel
Hi, I’m Rachel, a consultant, planner, strategic communicator, and systems thinker who helps businesses and social purpose organizations bring their vision to life.
After working at various non-profits, I spent nearly a decade as a management consultant, guiding more than 70 organizations across Canada. Here, I learned to blend deep listening, strategic insight, and clear communication in ways that inspire meaningful and lasting change. Now, I bring to consulting and advising what I’ve always brought to leadership: empathy, purpose, and a commitment to building sustainable organizations.
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Rachel Carrigan is a consultant, strategic communicator, and systems thinker who helps executives and founders bring their visions to life. At ClearlyThen, she leads organizations through strategy development, coaches leaders, engages stakeholders, and facilitates teams, groups and Boards.
Prior, Rachel was the Director of Consulting Services at Laridae, a leading management consulting and training firm. Over nearly a decade, Rachel drove growth across the division, managed the staff team, and delivered solutions for social impact leaders and organizations through strategic and operational planning, communications strategy and collateral, re-branding, stakeholder engagement, and governance projects.
Rachel has held leadership, fundraising, and communications roles in local and international organizations in the education, health care, social services and human rights sectors. An experienced director, Rachel served a term on the Board of the YWCA Peterborough Haliburton, most recently as the Vice-President, and on the Executive Team for the Peterborough Area Fundraisers Network.
Rachel is based in Peterborough, Ontario, with her husband, two kids and corgi.
Meet Catherine
As a Remote Executive Assistant, Catherine provides high-level support to executives and business leaders. Currently working alongside Jonathan and Rachel, Catherine helps streamline scheduling, manage priorities, and enhance workflow efficiency, enabling him to focus on key business objectives. She takes a proactive approach, anticipating needs and handling tasks with precision and professionalism. With a passion for problem-solving and organization, Catherine brings clarity and structure to the lives of busy professionals.
Trusted by organizations like:
Together, we’ll come up with elegant solutions to the problems that come across your desk—or keep you up at night.
From HR to crisis comms to safe space to just rant, I’m here. To give you what you need, at any given moment.
✔ HR Issues
✔ GR and PR
✔ Board and stakeholder relations
✔ Organizational structure
✔ Professional growth
✔ Succession planning
✔ Personal brand development
✔ Mentoring & leadership development
✔ Board Governance 101 training
✔ Strategic planning
✔ KPIs & performance management
✔ Custom workshops, and more…
“Jonathan's leadership support has been invaluable to me. As I became a new business owner, his sound, trustworthy advice and encouraging messaging throughout my journey served as cornerstones to my company's growth. I'm so grateful to have had Jonathan in my corner; his expertise spans across multiple areas and he's great at understanding people. I highly recommend Jonathan as an advisor and mentor: he is wise, intuitive, and always helpful.”
— Misha Munim, Lawyer | Equity, Diversity, Inclusion Consultant
ARE WE VALUES-ALIGNED?
Let’s work together.
If you’re here, you’re ready.
BUT WHAT’S IT REALLY LIKE?
Hear Us In Action
By listening in on actual conversations with real (and fully consenting) leaders, you’ll experience the essence of the advisory, mentorship and strategy work we do—and gain practical insights you can apply to your leadership journey. Listen on Apple, Spotify, YouTube, anywhere!