WORK WITH ME

Become Someone You Can Count On

I also work one-on-one with a small number of women. Two ways to start.

Connie Woolsey in a black blazer, arms crossed, smiling warmly at the camera

Where to start

One Thing, or a Pattern?

One thing you can name: start with Set the Standard. No application needed.

A pattern that keeps showing up: apply for private coaching.

Not sure yet? Take the $27 Ownership Audit. Take the Audit

Connie Woolsey leaning toward the camera in a black tank top and glasses, with a warm, quietly confident smile

SET THE STANDARD

Get Clear on What Matters

Get clear on what matters and leave with your own Standards Document. A 90-minute one-on-one session.

$497 · one 90 minute session

No application needed. Pay for your session, then pick a time on my calendar that works for you.

Book Set the Standard

Do the work, hold your standard, and come back ready. Complete Set the Standard and sign your Coaching Agreement within 30 days of your session, and your $497 comes off your 3- or 6-month program.

PRIVATE COACHING

Private Coaching with Connie

For leaders ready to do the deeper work over time.
Sessions every two weeks, with support in between.

You don't have to know how long you need. You apply, we have a free 30-minute Explore Working Together call, and we talk through what's really going on. Then I'll recommend three or six months based on the work.

3 months. We set your standards, find the patterns that break them, and move what you've been avoiding. The goal is evidence that you can live by your own standards.
6 months. We have time for real life to test those standards. We hold them, rebuild them and raise them. The goal is a track record, so you know how to come back to yourself.

Private coaching starts at $2,500. Payment plans available. Complete Set the Standard and sign your Coaching Agreement within 30 days of your session, and your $497 comes off your 3- or 6-month program.

Apply for coaching

If you have any questions, email [email protected].

Connie Woolsey seated on a stool in a leather jacket.

“Connie is the coach who actually hears you, and then helps you name what's been holding you back. Her approach is challenging in the best way: she pushes you past where you've been comfortable, and she does it with both honesty and warmth. She showed me how to take ownership of my own life, and she'll do the same for you.”

Headshot of JD DunwoodieJD Dunwoodie, Marketing Leader

“Connie is the reason I bet on cannabis, and a huge part of why that bet paid off. She showed me that leadership isn't about keeping everyone comfortable: make the hard call, have the damn conversation, do the work and never be so impressed with yesterday's win that you stop chasing the next one. Authenticity, transparency and unapologetic honesty were the Connie playbook, and I rolled with it. Made it my own and somehow went from Store Manager to Regional Director in three years. It's a wild ride that has Connie's influence all over it.”

Lourie Moyer, Regional Director

Do what you said you'd do, especially on the days you don't feel like it.

How it works

What Happens Next

01You apply and book your call. Tell me a little about where you are, then pick a time for your free 30-minute Explore Working Together call right after you apply. Times start two business days out so I can read your application first.
02I read your application before we talk.
03We talk. It's a free 30-minute call.
04You decide. I'll send you what I heard, what I recommend, and the investment the same day. Take the time you need, and if you want to talk it through, we'll set up a follow-up call that week.

I read every application before we talk. If it doesn't look like a fit, I'll let you know before our call.

A little about me

Author, speaker, and founder of CBW Collective.

Read my story

In their words

What leaders say

“Connie Woolsey has an exceptional gift for connecting with people and bringing out the very best in leaders at every level. She teaches others to make thoughtful decisions and take ownership of their results, creating the conditions for talent to grow and thrive. Connie understands that success takes courage and often means tackling truly difficult challenges. Her genuine, uplifting encouragement helps people learn that with hard work and perseverance, they can overcome whatever comes their way.”

Jim Petersman, District Manager

“I partnered closely with Connie for over three years as her HR business partner. She is a leader who balances empathy and operational excellence, making tough decisions while remaining relatable and inspiring. I witnessed her growth in accountability and ownership, making her not just a respected operator but a mentor who commanded trust and attention from hundreds. When Connie spoke, the team listened, and followed. She is truly one of the most talented leaders I've worked alongside in my career.”

Headshot of Alicia CatataoAlicia Catatao, Vice President of HR

“Connie is an effective operator and builder of teams. She built Sunnyside's Florida retail from the ground up into a market leader, then successfully translated those learnings across states, no small feat in a complex, fast-moving environment. What sets her apart is how she does it: with a genuine, people-first approach that develops strong teams and prepares leaders for what’s next. Connie doesn’t just drive results, she builds organizations that can sustain and scale them. Any business navigating transformation would benefit from her leadership.”

Cory Rothschild, President of Retail, Cresco Labs
Connie Woolsey standing in a black tank top, tattooed arm showing, with a relaxed smile

Good questions

What people usually ask me first

What's included in coaching?

It starts with a 90-minute Set the Standard session. Then sessions every two weeks, weekday text support, and a Weekly Ownership Check-In to help you keep your word to yourself.

What happens at the end?

You're either done for now, or we decide together to keep going.

Who is it for?

My work focuses on women leaders who keep their word to everyone but themselves. If that sounds like you, whoever you are, you're welcome to apply. Private coaching is for a pattern that keeps showing up, not one thing you can name. It fits if you're ready to look at your own part in it and do the work over three or six months. If you can name the one thing, start with Set the Standard.

Is this therapy?

No. This is practical, forward-looking work.

Does my $497 count toward coaching?

Complete Set the Standard and sign your Coaching Agreement within 30 days of your session, and your $497 comes off your 3- or 6-month program.

Refunds?

Set the Standard: If I have to cancel, I'll reschedule at a time that's convenient for you. If I can't hold your session within 60 days of the original date, you'll get a full refund.

Ready When You Are

Apply for coaching

Forge Your Freedom.

CBW Collective

Become someone you can count on.

The CBW Collective LLC, PO Box 17, Clarksville, FL 32430
[email protected]

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