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The Challenge

Built her entire career on the belief that hard work inside one law firm guaranteed security, until an unexpected layoff, after being told she did a great job, proved otherwise.

The Shift

Stopped tying her stability to a single organization and started treating herself as her own brand and biggest asset.

The Outcome

Now runs Outlook Advisory, serving multiple client organizations at once as a fractional COO, bringing 15-20 years of experience at a fraction of a full-time executive's cost.

Olivia Gamber

A Note From The Founder

Olivia Gamber, CEO

Melissa came to me as someone who had done everything right. She started with nothing handed to her, worked her way from staff roles at a law firm through management and into director positions, and eventually landed multiple COO seats. She was disciplined, technical, and quietly ambitious in a way that some people along the way actually tried to hold back.

What struck me first about Melissa was how much she had internalized the idea that security comes from performance inside one organization. She had been told more than once that she was too ambitious. She had watched failed entrepreneurship up close and it scared her. For seven or eight years she thought about starting her own business and talked herself out of it every time.

Then came the layoff. Not a performance issue, not a mistake on her part, just a business decision that had nothing to do with how good her work was. That single moment cracked open a belief she had carried her entire career: that if you do good work, you will be rewarded for it. Melissa had to decide what she actually trusted going forward, an organization's priorities or her own value.

What she built next is the reason I wanted to tell her story. She did not just find another COO job. She founded Outlook Advisory and became the asset she had always been, just no longer tied to a single employer's fortunes.

The Belief That Broke

Olivia Gamber

That's another thing you said that stood out to me. One organization doesn't define your stability. I think that's something a lot of people are having to come to that harsh reality. How is that mindset shift? When did that happen for you?

Melissa

So that all came together in my mind for me when I was in a layoff situation that I was not expecting, where I was told that I did a great job, and realized that okay, nothing is guaranteed.

Becoming Her Own Asset

“One organization doesn't define your stability as a professional. It's that you have built your own brand and you are your biggest asset.”

Melissa

You can put all your eggs in one basket with one organization and give it probably more of yourself than you should, or you can have your own business with multiple organizations making a broader impact with more than one company. And having the stability even if one client needs to go another direction, you have others on the bench with you on your team where you can really still have more stability.

I had frankly seen a lot of failed entrepreneurship. And it was a little scary to think of doing. But in really looking at it and evaluating it, it's not that scary when you really break it down and realize that unlike in another organization where you're dependent on their priorities and their budget and their profitability, when you work for yourself, you are dependent on yourself. And I believe in myself as an asset more than probably most other organizations.

Building The Fractional Practice

Olivia Gamber

When you reach the peak of your career and you're at the C-suite, it's like, where else do you go from there? I'd be curious to hear, tell me about this fractional executive model. How did you hear about it? How did you get into it?

Melissa

The fractional model is actually really great on both sides. For me, there's a good value, and I can continue growing, I can continue adding clients to the extent that I have the capacity to do so. So I'm not capped in that sense.

For instance, they might have a budget of 150k for a COO, but they can't find someone with enough experience and strategic mindset to really bring their organization to the level they want, where if they work with a fractional, you can get somebody who has 15, 20 years of experience, like I do...

“Don't hire a mediocre executive, rent a great one.”

Still Working On It

Melissa

You are the premium product. I think it's true that you have to recognize your own value and even sit down and write it down and quantify it. And even now I'm still doing that. Like I'm actually going to sit down sometime this week, hopefully, and be able to go back to strategy a little bit and go back to, okay, how are we describing our products and services.

Some people, when I place COOs at organizations, sometimes those interviews, they just talk about what they did. And some of them, they're very strategic and they really quantify the benefit that they're bringing to the table... not just having your laundry list of things that you've accomplished, but what those did and what the impact is.

“You have to recognize your own value and even sit down and write it down and quantify it.”

Ready to Stop Applying?

Melissa stopped waiting for one organization to guarantee her stability and built a practice around her own value. If you're ready to see yourself as the asset, let's talk.

Read the full transcript

Olivia: could you tell us a little bit about your journey and what that come up journey look like for you?

Melissa: deep down, I'm really more introverted and more of a technician. You know, I like to really get into the weeds on things.

Melissa: I had thought for probably seven or eight years about possibly starting my own business, but I think I was always a little scared to do it. Uh, and that's one thing that was a mindset shift for me was one organization doesn't define your stability as a professional. It's really that you have built your own brand and you are your biggest asset. And so I realized through my journey really with CE as well, that how having my own business

Olivia: How is that mindset shift? When when did that happen for you? Like when you really start to realize that?

Melissa: I had also had times where people had kind of tried to hold me back had told me I was too ambitious or things like that.

[Question shown on screen]: How is that mindset shift? When did that happen for you?

Melissa: I had frankly seen a lot of failed entrepreneurship. And it was a little scary to think of doing.

Melissa: I was in kind of a layoff situation that I was not expecting where I was told that I did a great job and realized that okay, nothing is guaranteed.

Olivia: tell us, like, how did you hear about it? How did you get into it? What did that look like?

Melissa: there's a good value, and I can continue growing, I can continue adding clients to the extent that I have the capacity to do so. So I'm not capped in that sense. And

Olivia: do. So I'm sure depending on the CEO you're speaking to, you may not even use the word. I'm a fractional executive. You're just speaking to where you add value, right?

Melissa: And sometimes I am simply a business advisor, whether that's taking those visionary ideas and putting them into a practical business plan that's actually based on numbers and reality and things that can be achieved. Um, so really be the implementer for that vision or helping them strategize on what their first priorities are. Uh,

Melissa: they might have a budget of 150k for a COO, but they

Melissa: 15, 20 years of experience, like I do. And

Olivia: what would you say to them right now? What advice would you give them? Because I know you're in the game still. You're always evolving and you're always building these connections.

Melissa: hiring for probably like six or seven different roles right now. So

Melissa: I believe in myself as an asset more than probably most other organizations.

[Question shown on screen]: What advice would you give them?

Melissa: you have to recognize your own value and even sit down and write it down and quantify it.

Melissa: you can put all your eggs in one basket with one organization and give it probably more of yourself than you should, or at least that was the case for me. Or you can have your own business with multiple organizations making a broader impact with more than one company.

Melissa: don't hire a mediocre executive, rent a great one.

Melissa: And some of them, they're very strategic and they really quantify the benefit that they're bringing to the table. And I think that's the key difference is being able to say what value you really add and thinking about that intentionally and not just having your laundry list of things that you've accomplished, but what those did and what the impact is.

Olivia: how did you, it sounds like early on you understood this and understood you needed to focus on that piece. Could you expand on that a little bit more?

Melissa: it's still something that I'm working on now, like working on exploring executive presence and what that looks like. And I've worked with CE to do that as well,

Melissa: even now I'm still doing that. Like I'm actually going to sit down sometime this week, hopefully, and be able to go back to strategy a little bit and go back to, okay,

Melissa: really just being out there and making connections and building real relationships with people, I was able to move into my first COO role.

Melissa: on the bench with you on your team where you can really still have more stability.

Olivia: not really being addressed, right? So I'm curious, like, are you seeing that too on your end as far as they don't have the budget for the talent they really need, but they need that perspective desperately?

Melissa: I'm actually reading a great book right now that one of my clients recommended to me that's called The Second in Command.