When Success Needed a New Definition for Markita Billups

Markita Billups wanted to redefine her relationship with work.

She'd been working since she was 13, so that relationship was deeply familiar—steady, dependable, and all-consuming. But after years of building her career, she realized it was time to imagine something different.

When she stepped away from an executive leadership role at a startup, Markita found herself in unfamiliar territory: the space between what had been and what would come next. For the first time in years, she wasn't rushing toward another job. Instead, she paused. As the mother of two young daughters, that pause brought new clarity about what she'd been missing and what she no longer wanted to sacrifice by default.

Starting Blackbird Strategic Solutions wasn't part of the original plan. But Markita felt drawn to create something that united her clinical training, executive operations expertise, strategic advisory experience, and gift for helping leaders navigate complexity. Today, she partners with healthcare and healthtech organizations to accelerate growth through operational clarity, financial rigor, and strategic decision-making.

Read on to learn what continues to inspire Markita's work—and how she's building a business that's as intentional as the life behind it.

What are some of the most meaningful impacts your work has had so far?

Helping leaders move from complexity to clarity. Throughout my career, I have often been brought into moments where the stakes are high, the path is unclear, and leaders are carrying more than they can realistically hold alone. Through Blackbird, I serve as a strategic advisor and thought partner to healthcare and healthtech leaders navigating growth, change, and organizational complexity. 

I am proud of the measurable outcomes to which my work has contributed: stronger productivity, improved margins, clearer workflows, and more aligned leadership teams. But the impact I value most is the moment when a leader can finally see the next right move and make decisions with more confidence, rigor, and alignment.

In what ways have your upbringing or past experiences contributed to how you operate as an entrepreneur?

My upbringing and past experiences taught me that you do not need permission to pivot. I have been working since I was 13 and have been on my own since I was 16, so responsibility became familiar to me early. That shaped my resilience, but it also taught me that being capable does not mean every season of life requires the same kind of sacrifice. As a Black woman leader, I have been aware of and have personally experienced challenges across my career trajectory, but I have tried to use those experiences as momentum and as a reminder of my own agency. 

One of the most important lessons I’ve learned is that passion for a mission has to be paired with discernment. I can be deeply invested in meaningful work while still being honest about where my leadership, judgment, and impact are best placed. That discernment helped me move from clinician to executive leader—and eventually to founder.

Have you discovered any underappreciated leadership traits or misconceptions around leadership?

One of the most underappreciated leadership traits is translation. In complex organizations—especially in healthcare—leaders have to translate between strategy and operations, clinical priorities and business realities, financial constraints and human impact. Many organizational challenges are not caused by a lack of intelligence or effort; they happen because people are operating with different language, context, incentives, and definitions of success. Clarity is another underappreciated trait because it creates the conditions for better decisions. 

A misconception I have had to personally unlearn is that leadership means carrying everything. Sustainable leadership is not about becoming indispensable to every decision, but about creating the conditions where the right people can make the right decisions with the right information.

Has your definition of success evolved throughout your journey as a leader?

For much of my life and career, success was tied to capacity: how much I could carry, solve, achieve, and deliver under pressure. That version of success was understandable because work had always been a place where I knew how to succeed. But as my life changed—especially as a mother and as a leader—I began to question whether success could still be defined only by achievement and sacrifice. 

Today, success is much more connected to alignment. It is about doing meaningful work, building a strong business, serving clients deeply, and still having presence, choice, flexibility, and peace. I still care about excellence and outcomes, but I no longer want success to require self-abandonment.

What’s the biggest misconception others have around entrepreneurship?

That it simply equates to freedom. There is freedom, but it comes with a level of responsibility and self-confrontation that people do not always see. When you are building your own business, you have to define the value, communicate it, price it, sell it, deliver it, and stand behind it. For years, I assumed entrepreneurship required a level of certainty I did not yet have, even though I knew how to lead teams, scale operations, advise executives, and navigate complexity. Eventually, I had to stop waiting for the full map and start moving with the evidence, instincts, and experience I already had. 

Entrepreneurship is freedom, but it is also a mirror; it shows you where you are ready to lead, where you are still waiting to be chosen, and where you are being invited to choose yourself.

What would you tell your younger self if you were to start your entrepreneurial journey all over again?

Do it scared. Every time. Bet on yourself. 

For a long time, I believed that if I followed the straight and narrow path, it would eventually lead me where I wanted to go. In many ways, that path did serve me, but I eventually realized that the same goal can be reached in many different ways and there is not one right path or one acceptable way to build a meaningful career or life. 

Other things I would tell my younger self: Be more playful with the unknown. Treat some risks as experiments, not permanent verdicts. Don’t be afraid to ask for help; the right people are not burdened by your ask, and many of them are waiting and willing to help.

What’s next for you and your company?

The next chapter for Blackbird Strategic Solutions is about deepening our role as a trusted strategic partner for healthcare and healthtech leaders navigating growth, complexity, and change. I am building Blackbird to meet leaders at different moments in their growth. Sometimes they need a thought partner to help them think through a high-stakes decision, sometimes they need strategic guidance over time, sometimes they need embedded operational leadership, and sometimes they need support expanding their own leadership capacity. That’s the throughline across my work in Strategic Advisory, Fractional COO support, and Executive and Leadership Coaching. 

I am also especially excited to support more clinicians who are moving into or advancing within non-clinical roles, who want to strengthen the business, leadership, and operational skills required to grow. 

On the organizational side, I would love to partner with more healthcare founders building intentional models of care, including independent specialty practices, direct-care models, and healthcare businesses that sit at the intersection of clinical excellence, access, patient experience, and sustainable growth. 

What’s next is more than just growing a company. It’s building a body of work around clarity, care, financial rigor, strategic decision-making, and sustainable growth.