For many women entrepreneurs overcoming adversity, the “scaling years” are shaped by the same forces that tried to slow them down: bias, funding roadblocks, personal setbacks, industry gatekeeping, and high-stakes pivots that had to work.
The women below share something bigger than impressive results. Their business scaling stories show how constraints can sharpen strategy—how pressure can force better systems, tighter positioning, and bolder leadership. You’ll see patterns that pop up again and again among resilient female founders: building credibility early, choosing a niche with urgency, turning lived experience into a competitive edge, and creating structures that support women in business growth long after the “motivational moment” fades.
Here are 10 leaders worth studying—starting with Cortavo’s CEO.
When a company grows fast, IT either becomes a growth engine—or a constant drag. Tiffany Bloomsky’s work at Cortavo centers on keeping that from happening. As Cortavo’s President & CEO, she sets strategic direction and works across departments to deliver “simple, reliable IT,” with experience spanning go-to-market strategy, branding, demand generation, and revenue operations.
The adversity: Managed service providers live in a high-pressure environment: nonstop support needs, security threats that don’t wait, and customers who can’t afford downtime. That pressure can fracture teams or create reactive “firefighting” cultures. Tiffany’s leadership has emphasized stability and people-first principles during difficult periods while still driving expansion.
How she scaled: Rather than treating IT as a back-office function, her approach ties operations, service delivery, and growth together—aligning sales, marketing, and the service experience so scale doesn’t break quality.
Takeaway for founders: When adversity shows up as chaos (tickets, outages, security scares, vendor mess), the fix isn’t “work harder.” It’s building repeatable systems and a culture that can handle load without losing trust.
If your growth depends on stable infrastructure, these Cortavo guides can help you think through industry-specific needs:
Heidi Hessler co-founded and leads Futurity IT, a company supporting disaster management teams with technology designed to be practical under pressure.
The adversity: Futurity faced a devastating internal shock when its founder, Robert Richards, died in a car accident—exactly the kind of moment that can stall a young company or derail a mission.
How she scaled: Heidi helped push Futurity from that crisis into broader deployment—expanding to work across dozens of states, supporting emergency preparedness, response, and recovery workflows.
Takeaway for founders: When the hardship is sudden and personal, the “scale plan” has to start with continuity: clarifying decision rights, protecting customer outcomes, and building confidence in the team’s ability to carry the mission forward.
Gabrielle Breton is a co-founder of House of Socials, a Montréal-based social media agency, with responsibilities spanning strategy, employees, client relationships, and project oversight.
The adversity: Agency growth is a constant race against moving targets—algorithm changes, new formats, budget swings, and crowded competition. That kind of instability is its own form of adversity: you can’t “set it and forget it.”
How she scaled: Gabrielle’s work reflects the agency reality of scaling by process: clear strategy frameworks, repeatable execution, and disciplined client communication—so delivery stays consistent even when platforms change.
Takeaway for founders: If your business depends on fast-changing channels, resilience comes from systems that outlast the channel—solid onboarding, clear deliverables, and reliable reporting that clients can trust.
Helen Georgio is known for building Buzz Talent and launching major fashion and events work tied to inclusion, diversity, and opportunity. Her talent-management agency has scaled significantly and expanded team capacity.
The adversity: Creative industries can be built on gatekeeping—who gets access, who gets visibility, and who gets considered “marketable.” Building a business that challenges those defaults means you’ll face skepticism, resistance, and a constant need to prove results.
How she scaled: Helen built growth around values as a strategy: representing talent from diverse backgrounds and building events that create opportunities while supporting charitable aims through This Is ICON.
Takeaway for founders: “Mission” scales when it’s operational, not just branding. If inclusion is real, it shows up in recruiting, partnerships, client selection, and how you measure success.
Dr. Joy Buolamwini founded the Algorithmic Justice League (AJL) after encountering discrimination in facial recognition systems—an experience that helped shape AJL’s mission to highlight and reduce AI harms and biases.
The adversity: Joy’s challenge wasn’t just technical—it was systemic. She had to persuade powerful institutions that biased systems were real, measurable, and harmful, then fight for change in a space that often moves slowly unless forced.
How she scaled: AJL combines research, storytelling, and advocacy to build public awareness and drive accountability—making the work accessible to communities most impacted while influencing policy and industry behavior.
Takeaway for founders: Adversity can become a platform when you translate personal experience into evidence, then build a clear mission people can rally behind.
Janice Bryant Howroyd left North Carolina for Los Angeles with $1,500 and went on to build ActOne Group—starting the business in 1978 with a phone, a fax machine, and relationships she had built along the way.
The adversity: Limited capital, limited connections in a new city, and the added weight of building in environments that weren’t designed to support women—especially women of color—at scale.
How she scaled: She built credibility the hard way: client by client, delivering results, and turning service quality into durable trust. Over time, that compounding trust becomes a moat—one that’s hard for competitors to copy quickly.
Takeaway for founders: When funding isn’t available (or isn’t the right move), the “adversity advantage” is focus: sell what you can deliver exceptionally, then let referrals and reputation do what ads can’t.
Scaling looks glamorous from the outside: more customers, bigger launches, new hires, better margins. On the inside, growth often magnifies everything that’s already messy. For women entrepreneurs overcoming adversity, the challenges can come in layers—some are universal to scaling, and some are shaped by bias, unequal access, or extra scrutiny.
Here are the barriers that show up most often in real-world business scaling stories:
The women in this list didn’t avoid these barriers. They built companies anyway—by tightening focus, creating proof points, and building support systems that made growth sustainable.
Confidence isn’t a personality trait—at least not in business. It’s often the result of preparation, repetition, and results. In male-dominated spaces, credibility tends to be treated like a “tax” women founders have to pay upfront: more documentation, more validation, more demonstrations of expertise.
Many resilient female founders use similar strategies to close that gap quickly:
You’ll see these credibility moves throughout the list: from founders who turned rejection into better positioning, to leaders who created new standards in industries that initially resisted them.
Scaling rarely fails because the founder “isn’t smart enough.” It fails because the business becomes too dependent on the founder’s memory, availability, and personal output. Sustainable women in business growth comes from systems that turn effort into repeatable results.
Here are three system categories that consistently show up in strong business scaling stories:
Growth creates urgency, and urgency makes rushed hires tempting. The women who scale well treat hiring like infrastructure:
As volume increases, small inefficiencies become big problems. Strong operators build:
Repeatability is what makes scale possible:
For many founders, tech is part of this system layer too: secure devices, streamlined workflows, reliable support, and infrastructure that doesn’t collapse during busy periods. When operations are stable, leaders can spend more time on growth moves—partnerships, hiring, product, and strategy—instead of constant firefighting.
Cortavo delivers managed IT services that help growing businesses stay secure, productive, and supported without the headaches of juggling multiple vendors. Their team focuses on responsive help desk support, proactive monitoring, cybersecurity, and day-to-day technology management—so leadership teams can spend less time troubleshooting and more time building.
Whether you’re scaling a busy real estate office, a marketing agency with fast-moving workloads, or a law firm handling sensitive client data, Cortavo offers practical guidance and services built around real operational needs.
Ready to simplify your IT and protect your growth? Contact Cortavo to talk through your current setup, pain points, and what a better-managed IT plan could look like for your team.
Across every profile, the pattern is consistent: adversity didn’t disappear. These women built companies that could operate with adversity in the background—through systems, clarity, and choices that reduced fragility.
A practical lens for women entrepreneurs overcoming adversity is this: if growth is stressing your operations, the solution is rarely “more hustle.” It’s removing friction—tightening processes, shoring up security, improving communication, and building infrastructure that won’t buckle as demand rises.
And sometimes, the unglamorous work matters most: the tech stack that doesn’t crash, the support team that responds fast, the security posture that keeps a bad day from becoming a disaster. That’s where the right partners and the right IT foundation can protect women in business growth while you keep pushing forward—especially for founders scaling in regulated or high-velocity industries like real estate, marketing, and law.
The biggest barriers are cash flow and funding, finding real demand, and reaching customers consistently. As the business grows, operations can break without strong systems for hiring, delivery, and support.
Women founders often face tougher access to capital and influential networks, plus extra scrutiny when establishing credibility. Many also carry heavier outside responsibilities, which can limit time and risk flexibility during growth phases.
Women-led businesses create jobs, expand innovation, and bring new solutions to underserved markets. They also strengthen mentorship and representation, making it easier for future founders to enter and scale.
There’s no fixed difference in talent or ambition; the main difference is the conditions they often face. Women are more likely to encounter bias in fundraising and credibility, which can shape how they approach scaling and risk.