I turn founders into CEOs

Escape the operator trap.
Stay in your zone of genius.
The founder in you built this. The CEO in you scales it.

Let's chat See how I work

Choose Your Level of Support

$Operator-in-Residence service: fractional COO embedded in leadership team for scaling companies$

Operator-in-Residence

$500/month

Group coaching + peer advisory. Weekly hot seat format with 4 other founder-CEOs. Real problems diagnosed live.

Board of advisors, not support group
Working session, not networking
Real advice, not motivational fluff

Yeah, I want in

Strategic Coaching

$1,500/month

Your weekly CEO thinking partner. 1:1 strategic coaching, your agenda, complete confidentiality.

Thinking partner who's been there
Diagnostic coaching, not reflection
Build strategic thinking capacity

Let's chat

Leadership Team Coaching

$5,000/month

Whole-system diagnostic coaching. CEO support + team observation + leadership development.

See patterns you can't see from inside
Build team's diagnostic capacity
Coach the system, not just the CEO

I need this

Not Ready to Commit?
Try Office Hours First

Test the fit. Get real help. Decide what's next.

CEO Office Hours

Your low-risk entry point. Weekly open hours where you bring your most formidable challenge and watch me work in real-time.

Every Friday, 11:00 AM - 12:00 PM CT
Live diagnostic coaching on your actual problems
Group format - could be 1:1 or group depending on attendance
Experience my coaching style before committing to ongoing services

This is a trial tier, not a permanent option. After 4 sessions, you either upgrade to coaching or we part ways—no hard feelings.

$100

for 4 sessions

This is for you if:

✓ You're curious but cautious about cost
✓ You want to test fit before committing
✓ You aren't ready for weekly obligation
✓ You want real advice, not fluff

Peek behind the curtain

Experience my diagnostic thinking style firsthand. Watch how I work. See if we're a fit.

A coach who operated,
not a coach who read about operations.

I help founder-CEOs of 5-75 person companies build operational foundations and leadership capacity without burning out.

After 20+ years from scrappy bootstrapped startups to Fortune 50 giants, I diagnose what's actually broken—so you stop wasting money fixing the wrong things.

To the long version

Why Founders Work With Me

20+ Years In The Trenches

From scrappy bootstrapped startups to Fortune 50 giants. I've operated at every scale—not just studied it.

Diagnosis Before Solutions

Most problems aren't what they appear to be. I find root causes so you stop wasting money on fixes that don't stick.

AI-Enhanced Analysis

I process more context than humanly possible, finding patterns others miss while keeping the human judgment.

Visionary Operator

Not a coach who read about operations. I'm a visionary who deeply understands operations—I've been CEO, COO, and Chief of Staff.

What Founders Say

Every week, Tobey helps me cut through the chaos and focus on what actually matters. She sees consequences I miss and helps me make decisions that land well across the organization.

Zach

Founder & CEO, Mental Telehealth

Tobey helped me see how to make our abstract creative work measurable without losing what makes it special. She translated complex operations into plain English my team could actually use. For the first time, I had clarity on systems I'd been avoiding building.

Elliot

Founder & CEO, Full Service Video Game Audio Agency

As my company grew, managing everything from business development to HR became unsustainable. Motherlode helped establish the processes for efficient and sustainable business operations. THIS enabled me to focus on building great software products for our clients.

Keith

Founder & CEO, Boutique Software Development

Thank you for all the time and wisdom you've poured into this community. You have made us better in myriad ways – with better processes, improved communications, and a shared sense of mission. You have been a gift not only to our beautiful team as a whole, but to me personally.

Shoshanah

Lead Rabbi, Chicago Synagogue

Let's Chat

Book 30 Minutes

Ready to get started? Have questions? Let's talk about what's going on and see if I can help.

Send Me a Note

Not ready to talk yet? Drop me a message and I'll respond within 48 hours.