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The Challenge

Reached the final round of the hiring process eight times, only to have CEOs walk away at the last hour.

The Shift

Stopped chasing another COO title and made the decision to bet on herself as a fractional COO instead.

The Outcome

Runs a fractional COO practice on scope-based retainers, with contracts locked down to roughly 23 pages of negotiated terms.

Olivia Gamber

A Note From The Founder

Olivia Gamber, CEO

When I met Emily, I could see it immediately: the drive, the range, the operator instincts built across 15 industries and 34 years of work. What I could also see was how far she had been ground down. She had just come out of a SaaS COO role she believed in, an ending she describes as traumatic, on top of years of grinding CEO-COO relationships before it. By the time she came to me, there was almost no Emily left.

Most of my work with her that first month was never going to be strategy. It couldn't be. She needed to be brought back to herself before she could be repositioned for anything. So we started there, with the healing, before we ever touched a resume or a pitch.

What happened next is the part I love telling. Emily went back into a W2 COO search, landed a role, and then watched that company shift under her. For two days she freaked out. Then something clicked. She stopped trying to force her way back into a model that had already cost her so much, and she asked a different question: why not bet on herself instead. That question became a fractional COO practice built on her own worth, her own pricing, and contracts she controls down to the line.

GROUND DOWN TO NOTHING

Olivia Gamber

Let's start at the beginning. When we met, you were in transition and you were really focused on getting that next COO role. What brought you here to Career Evolved?

Emily

It was even longer, really. The last 10 years of my life... how incredibly grinding it can be. The CEO-COO relationship is an incredibly rewarding, but also an incredibly challenging one. And I had unfortunately gone through quite a few CEOs that I'd been really ground down. And then the one prior to me coming to Olivia was a SaaS startup that I really believed in. And the ending of that was really traumatic.

So by the time I came to Olivia, I was like a fraction of myself. There was like almost no Emily left. I didn't recognize myself, my anxiety, my self-worth, my entire core, my being was just so raw. And that was really brought to our knees. And that was me, but it was more like I was brought to my stomach and was like crawling and clawing my way. Because I was so, so low.

“By the time I came to Olivia, I was like a fraction of myself. There was like almost no Emily left.”

THE LIGHT BULB MOMENT

Emily

The COO position that I went into after career evolved, the company had a major shift. And at first when it happened, I was like completely freaked out... And then I realized, I was like, why am I trying to force something that is no longer serving me? Why am I going to even consider trying to find another COO job?

Having gotten to the finish line... it ended up being eight times with different organizations for at the last hour, the CEO to turn around and say, I'm just not ready. And I thought, I can't go through this anymore. And it was like within those couple of days, there was this light bulb moment. And I was like, why don't I go fractional? I would no longer be basing my security on somebody else.

“Why wouldn't I bet on myself as opposed to putting my future in someone else's hands?”

REBUILDING AS A PREMIUM PRODUCT

Olivia Gamber

So it's like a shift because now you're like a premium product. You're not a person producing outcomes always available. It's a big shift in how you're delivering and perceiving your value.

Emily

I don't work by the hour. I have retainers based on the complexity and scope of the engagement. I've always been very, very good at negotiating. One of the things when I came to Career Evolved, Olivia was like, okay, you are so run down. I want you to read this book... I always had a ton of confidence, but not a lot of self-worth. And this book and Olivia, the combination of healing and what that gave me was incredible.

For me, it's not exactly about realizing my worth, it's just maybe re-realizing my worth and reconnecting with that person.

“It's not exactly about realizing my worth, it's just maybe re-realizing my worth and reconnecting with that person.”

NEVER GOING BACK

Emily

Well, first of all, being a fractional is in no way degrading. It's really upping your game... it is actually leveling yourself up in every possible way because now you function as a CEO, but get to do the COO role that most of us really love.

For me, you'll never get me to go back to W2.

Emily

It hit so hard. And I knew with absolute certainty, it was what I was meant to do. And it just served me in my life in so many different ways that it was just such alignment that even through the hard times while I'm building this business, there's a quietness inside of me now that I could have never had before.

“For me, you'll never get me to go back to W2.”

Ready to Stop Applying?

Emily stopped chasing another COO title and built a practice on her own terms. If you're ready to do the same, let's talk about what that looks like for you.

Read the full transcript

Olivia: when we met, you were in transition and you were really focused on getting that next COO role. And, you know, what brought you here to Career Evolved? And,

Emily: So by the time I came to Olivia, I was like a fraction of myself. Okay. There was like, there was like almost no Emily left. It was, um, um, I didn't recognize myself, my anxiety, my self-worth, my entire core, my being was just so raw.

Emily: And that was, you know, really brought to our knees. Um, and that, that was sort of me, but it was more like I was brought to my stomach and was like crawling and clawing

Olivia: what so many are afraid to say out loud when they're going through this. Cause you know, nobody expects these transitions to be as hard as they are.

Emily: it is really hard at 49 years old to be like, Oh my God, in some ways I feel like I'm so starting over. And that's terrifying, you know, from a financial standpoint and

Olivia: what made you even want to consider that leap?

Emily: having gotten to the finish line five, well, it ended up being eight times with different, different organizations for at the last hour, the CEO or the CEO, excuse me, to turn around and say, I'm just not ready.

Emily: the company had a major shift. And at first when it happened, I was like completely freaked out. Um, I was like, dear God, I'm just starting to find ground again. And this is happening. And I went through a day or two of complete freak out. And then I realized, I was like, why am I, why am I trying to force something that is no longer serving me? Why am I going

Emily: of like within those couple of days, there was like this light bulb moment. And I was like, why don't I go fractional? Um, I would no longer be basing my security on somebody else.

Emily: why wouldn't I bet on myself as opposed to putting my future in someone else's hands?

Emily: it's given me, it's given me that freedom. It's given me stability, um, with everything that I've gone through.

Emily: going fractional since then has just been totally liberating because it's giving me all of those things. It's giving me that freedom. It's giving me that ability to have balance. It's giving me that ability to put

Olivia: what made you see that shift from fractional feeling like it was degrading your value to now you're seeing it as the best model for you?

Emily: And I knew with absolute certainty, it was what I was meant to do.

Emily: I have worked in 15 different industries.

Emily: this year would be 34 years that I've been working.

Emily: I needed the healing. I needed that process. Um, which incidentally brought me totally back and then more some, because then I could embrace all the things that I had built and learned along the way. And

Olivia: how did that shift with all of this?

Emily: And this book, Worthy, it, and I've actually sensed that one of my current female CEOs that I'm working with, because she's having a lot of imposter syndrome. I recommend it to her and she absolutely loves it. But even if men or women, there's always this sense of, like, I always had a ton of confidence, but not a lot of self-worth. And this book and Olivia, the combination of healing and what that gave me was incredible.

Olivia: what was the biggest shift that got you to get that big leap? Because you're obviously able to command more for your value and your time.

Emily: for me, it's not exactly about realizing my worth is just maybe re-realizing my worth, um, and reconnecting with that person.

Olivia: what would you say to them, you know, right now?

Emily: I'll tell you guys, I love AI. I have been one of those people that was an early adopter. But I know it for what it is. It's not going to solve every problem. It's not going to

Olivia: how savvy you are at AI. So I'm glad to hear that you say that because it'd be easy to go high volume, high automation, right?

Emily: you would have had to build your own personal avatar, train it on all your years of experience. 99% of the people out there don't have the time, the knowledge, the skill set to put