A woman with blonde hair smiling in front of beige curtains.
About

I am not a specialist.
I am a translator.

Hello. I'm Chris.

I think in wholes, notice incoherence before I can name it, and connect what others keep separate: teams, organizations, systems, ideas. That's not something I developed. It's how I'm built, and it shapes everything I do.

My work spans finance, systems, facilitation, and writing — not because I couldn't pick a lane, but because the lane was never the point. The through-line is coherence: finding where something broke and helping restore it. Whether that's a chart of accounts that doesn't reflect reality, a partnership that needs alignment before legal drafting begins, or a piece of writing that's circling something it hasn't quite named yet.

I write at Almost Structured on Substack — autotheory, lived insight, gestalt processing out loud. The writing wanders wherever it needs to: phenomenology, coherence, work, home, parenting, the occasional systems critique. I write first for my own processing. I'm glad when it helps someone else find their footing too.

I also make visual art and music. I co-host a podcast with my husband. The credential is real, and so is the rest of me.

I work well with people who show up with care and can receive honesty in return. If that's you, I'm glad you're here.

If you've ever needed the whole picture and been handed a piece of it — you already know what I mean.
“Chris has a way of listening and making you feel heard while still having constructive conversations.”

— Devon Hermes, formerly of The Gallina Companies

Now

Owner, Christyn Stephens CPA. Fractional finance consultant for solopreneurs and small to mid-sized organizations. Writer at Almost Structured. Author of Bewitched Moon: Emergence. Co-host of Candorland with Jason Stephens.

2022–2025

Chief Financial Officer, YesLMS. Owned FP&A, financial evaluation of strategic initiatives, cross-functional partnership, and financial infrastructure for a SaaS learning platform.

2015–Present

Fractional finance and accounting consulting across SaaS, professional services, food service, small manufacturing, and mission-driven organizations.

2011–2015

Senior Accountant, University of Wisconsin–Madison, Division of Housing. Budgeting, forecasting, and reporting for residence halls and dining operations totaling $50M+ in annual revenue.

2008–2011

General Accounting Manager, The Gallina Companies. Multi-entity accounting, audits, tax filings, and compliance for real estate development and property management.

2003–2007

Purchasing Supervisor / Corporate Tax & Real Estate Analyst, Maurices, Inc. Financial and real estate analysis for new store development, procurement controls, and tax compliance.

1996–2011

Development Controller, The Great Lakes Companies / Shakopee Crossings. Progressed through five roles over fifteen years at a property management and development firm with a commercial and residential portfolio. Advanced from project accounting and financial reporting to managing a team of three. Performed cost segregation studies previously outsourced to an external CPA firm. Served as sole accountant for a 200-acre mixed-use development. Continued as a part-time remote consultant after 2003.

Credentials

Certified Public Accountant, Wisconsin — License #19344-1 · Verify →
B.S. Accounting, Upper Iowa University