Women Entrepreneurs Reveal Their Most Pivotal Growth and Scaling Lessons
You’ve launched your business, and you’re already making magic. Fantastic! It’s time to punch up that success and take it to the next level. Whether it looks like growing your customer base, hiring a team, implementing new systems, or finding ways to be more efficient, scaling is the logical path to increasing revenue, chasing your dreams, and everything in between.
But just because it’s logical doesn’t mean it’s easy. In fact, scaling can prove a stumbling block for the savviest of entrepreneurs. To help ease the journey for you and your business, we’ve gathered thoughtful advice from 20 members of the Dreamers & Doers community. With their personal anecdotes and hard-earned lessons on your side, you’ll feel more empowered—and less prone to pesky mistakes—as you scale.
Crystal Foote
Founder of Digital Culture Group, LLC, crafting innovative, data-driven advertising solutions that deeply resonate with dynamic and evolving audiences.
One of the biggest challenges I faced while scaling was realizing that a delay in securing new partnership deals wasn’t a denial—it was an invitation to get creative. I learned to pivot, find new entry points, remain open to unexpected opportunities, and build value in unexpected ways until the yes came.
My advice for scaling: Stay rooted in your vision but flexible in your approach because growth rarely follows a straight path and rejection is often just redirection.
Bonnie Singleton
CEO & Data Storyteller of Pollinate Marketing, a data-driven marketing agency that transforms service businesses' growth potential into reality.
After doubling our revenue every year for five straight years, year six revealed a game-changing truth about scaling: the most powerful growth happens beneath the surface. While our top line stayed flat, we transformed our operational efficiency by streamlining our core offer, developing comprehensive team training systems, and creating repeatable processes that reduced delivery time by 25%. This "pause" in revenue growth became our most valuable scaling period, teaching us that sustainable growth isn't just about doing more—it's about building a foundation that can actually support more.
My advice for scaling: Before you chase more leads or new marketing channels, maximize what's already working.
Evelyn Sprigg
Co-Founder & CEO of JustUs Skincare, a climate-proof skincare that is made from earth's most resilient ingredients for earth's most resilient women.
When we were starting the company, we developed a very compelling and personalized experience for our customers. As we started to scale, one of our biggest challenges was figuring out how to handle the increase in volume while still offering an experience that felt high-touch for each customer. We had to identify which special touches made the biggest impact and which were possible to produce en masse. This took a lot of compromise.
My advice for scaling: Before you grow, spend time thinking about your values, your brand DNA, and your non-negotiables. You need to know where you can adapt and still keep the integrity.
Yewande Faloyin
CEO & Founder of OTITỌ Leadership & People Development, helping growth-stage companies build strategic leaders, high-performing teams, and a results-driven culture that delivers exceptional value to clients, investors, and the business.
One of the biggest challenges I faced was realizing that marketing alone wouldn’t drive growth. I needed a strong, systematic sales process, too. Once I embraced a data-driven, authentic approach to sales, everything changed, and the business started to grow consistently. If I had understood this earlier, I would have spent more time talking to prospective clients and less time tweaking marketing messages, which would have accelerated our growth.
My advice for scaling: Don’t get caught up perfecting your marketing if you don’t have a solid sales system in place. You can build a successful business with strong sales and no marketing, but the reverse isn’t true.
Sydney de Arenas
CEO of The Hive, a fully managed team ready to elevate your business and your life.
The biggest challenge was learning how to replace myself as we scaled because I was stretched too thin. I knew this was coming, but I didn’t have a clear roadmap for handling the small but crucial details that make delegation and growth truly effective. I spent months documenting everything I did, deciding who would take over each task, and assigning responsibilities. I brought team members into meetings, copied them on emails, and slowly shifted ownership.
My advice for scaling: Embrace a sink-or-swim approach. Not everything can be perfectly planned, but you can always adjust as needed.
Clara Ma
Founder & CEO of Ask a Chief of Staff, a premier executive search and career development platform dedicated to placing top-tier Chiefs of Staff and empowering professionals in strategic leadership roles.
One of the biggest surprises while scaling was how quickly organic word-of-mouth drove growth once we hit a tipping point. By deeply investing in our community—providing real value and fostering connections—we saw a ripple effect where members became ambassadors, helping us scale faster than any traditional marketing strategy could. It reminded me that scaling isn’t about doing everything yourself; it’s about building a movement that carries itself forward.
My advice for scaling: Don’t underestimate the power of community-driven growth. Instead of chasing quick wins, focus on creating meaningful relationships and delivering value, whether through mentorship, partnerships, or thoughtful engagement.
Stephanie Skryzowski
Founder & CEO of 100 Degrees Consulting, providing CFO and bookkeeping services to nonprofits around the globe.
One of the most surprising wins I encountered while scaling was realizing that I had built a valuable, sellable asset through the systems, processes, and templates I created. Not only did treating my business like an asset ensure sustainability and free me from day-to-day operations, it allowed me to successfully sell a portion of my business when I was ready to pivot, proving the power of intentional infrastructure.
My advice for scaling: Focus on building strong systems, processes, and infrastructure from the start. Creating repeatable workflows, templates, and documented strategies not only makes scaling easier but also turns your business into a valuable asset.
Maria Coello
CEO of For Arts Sake Cosmetics, a mission-driven makeup brand that combines art, beauty, and philanthropy.
One of the toughest challenges we’ve faced in scaling is the mismatch between upfront costs and incoming revenue. For instance, expenses often have to be paid well before we get reimbursed, leaving us with tight cash flow at critical moments. If it’s not carefully managed, that gap can significantly slow growth.
My advice for scaling: Pay close attention to your cash conversion cycle. Ensure you have a healthy cash flow strategy in place so you’re not constantly waiting on revenue to cover expenses.
Grace Nguyen
Founder & CEO of LOUPN, an inclusive jewelry brand intended to encourage positivity, confidence, and love.
One of the biggest challenges while scaling was overcoming my own introvertedness and imposter syndrome. I shied away from being center stage most of my life. However, as I learned the importance of marrying my personal brand to my business’ brand, I pushed myself to be uncomfortable and challenged myself to practice speaking up.
My advice for scaling: Hiding from your weaknesses won't make them go away, so I'd advise any entrepreneur to face their weaknesses head-on and keep exploring them. The small improvements will compound to be massive achievements.
Kinsey Wolf
CEO of Polaris Growth Studio, a growth consultancy for future-focused technology companies, focusing on marketing and sales strategy and execution.
An important lesson I learned along the way is that, no matter what type of business you're building, customer retention drives growth. Growth simply doesn't happen unless they sign up and stick with you. Once I started building my growth strategy by thinking about what my customers love—then finding ways to amplify that message—big things started happening.
My advice for scaling: Momentum is magic! In the beginning, it takes a lot of effort to move forward just a little bit, but with consistency in your growth, you’ll start to see bigger rewards for the same effort.
Emylee Williams
Founder & Growth Strategist of Creative's Catalyst, helping women-led service businesses transform their messy spreadsheets into visual dashboards that show exactly where to focus their time and energy for maximum growth.
My biggest challenge wasn't a single moment; instead, it's been an ongoing dance with my own body and mind. As someone navigating chronic illness, PMDD, anxiety, and neurodivergence, I've had to completely rewrite the rules of what "successful entrepreneurship" looks like. It’s led me to build a business model that proves you don't need to sacrifice well-being for success and that honoring your limitations can lead to more innovative, efficient, and human-centered ways of working.
My advice for scaling: Stop looking for complicated solutions when your data already shows exactly which levers to pull for growth. I've helped over 30,000 service providers scale, and the pattern is clear: sustainable growth comes from understanding your numbers, doubling down on what's already working, and building systems that support your natural energy.
Lexi St. Laurent Hartmann
Founder of iHartContent, a bilingual, boutique agency helping female founders and thought leaders beat burnout with flexible, fractional marketing support.
Right as we were approaching our big stretch revenue milestone, I realized I had prioritized scaling over my original intention: to work only with brands that truly aligned with our values. It didn’t feel right. So, instead of pushing hard to reach the goal, I chose to slow down and take the time to recalibrate our values and client base. In the end, we still hit that milestone (and then some!), just a bit slower—and with our integrity and sanity intact.
My advice for scaling: Don’t be afraid to tap the brakes on your way to the top, especially if you find yourself out of alignment with what lights you up. Sometimes, the slow down is precisely what you need to catapult you forward.
Aditi Sinha
Founder & CEO of Point of View Label, a modern, functional workwear brand on a mission to end pocket inequality for women.
My most surprising success has been receiving orders from 11 countries and 27 U.S. states, including states not typically associated with high workwear demand! We realized that workwear and formal wear have many design codes in common, and women are choosing our products for formal occasions.
My advice for scaling: Find the people who really believe in you and your product—and seek their help when you need to. I have found that the way these people describe me and my products when I’m not in the room is way more powerful than any advertising.
Kelly Hubbell
Founder & CEO of Sage Haus, helping busy parents reclaim time by building their village.
One of my biggest surprises while scaling has been discovering the incredible pool of smart, talented professionals looking for part-time, meaningful work. Hiring part-time talent has not only allowed me to grow Sage Haus in a sustainable way, but it’s also reinforced that so many highly skilled people want flexible work—and when you match them with the right role, the impact is huge.
My advice for scaling: Think outside the box when it comes to hiring and delegating. You don’t need a full-time team to scale effectively. The sooner you embrace creative hiring and strategic outsourcing, the sooner you’ll free up time to actually grow your business.
Tamara Kostova
CEO of Velexa, offering a B2B2X investing technology platform which empowers any institution to capitalize on the demand for modern and ubiquitous investing solutions by the next generation of investors.
In the race for growth, we were chasing the biggest clients and coming up again and again against some incredible competition. I really believed that landing a major player or flagship client would define our success, but I Iearned that the real opportunity often lies in identifying a segment that is the perfect fit for our business—one where our unique value proposition solves a specific pain point. This has helped us become indispensable to our ideal customers, creating not just clients, but advocates.
My advice for scaling: Learn to identify and evaluate niche markets, craft a focused value proposition, and strategically position your business to serve an underserved demographic.
Lauren Fleming
CEO & Founder of Hem Support Wear, creating thoughtfully designed pelvic floor support garments that empower women at every stage of life to feel supported, confident, and in control of their wellness journey.
One of the biggest challenges I faced while growing my business was working with the wrong production partner early on. I trusted recommendations without fully understanding the technical expertise required, and the result was a costly mistake that set back my launch timeline significantly. I also learned that investing in true industry expertise earlier—even when it feels like a stretch—can prevent far greater costs down the line and set the foundation for sustainable growth.
My advice for scaling: Vetting partners thoroughly is one of the most important things you can do. It’s tempting to move fast in the scaling process and to trust recommendations, but taking the time to verify experience, request references, and understand the nuances of your industry can save you from expensive missteps.
Caitlin Daley
Founder & CEO of Face The Tiger, a bold, boutique consultancy, helping entrepreneurial women to live fully as their true selves—unapologetically and with unwavering courage.
As I was scaling my business, I often felt there weren’t many people I could genuinely connect with. I sometimes lost belief in myself and my abilities, even when circumstances were good. This made scaling feel lonely, slow, and uncomfortably quiet. Ultimately, I found myself a cheerleader on my way to success—someone who encouraged me in challenging times and celebrated my wins—which fueled my pursuits and kept me going on a positive, creative path.
My advice for scaling: Find yourself a co-visionary and meet with them weekly. This should be a person you admire and who has your best interests at heart and a strong belief in you, even when you do not.
Anouck Gotlib
CEO of Belgian Boys, creating whole ingredient breakfasts with a European twist so families can prep less, smile more, and indulge better!
Scaling brings a new challenge every day—from quality control hiccups and team growing pains to slow sales months, product discontinuations, and even a lawsuit or two! My biggest challenge wasn’t any one of those, though; it was summoning the emotional resilience to get through the tough times and maintain my optimism for the future. That perseverance—staying motivated and positive even on the hardest days—has been the true test while scaling our business.
My advice for scaling: Build a strong support system around you. Surround yourself with other founders at a similar stage; they understand what you’re going through, face similar challenges, can help problem solve, and will cheer you on. Seek out mentors who’ve walked this road before and who can offer perspective when things get tough.
Caryn Kent Dean
CEO of Once Upon an RFP, a strategic business proposal agency amplifying our clients' impact by helping them win corporate and government contracts.
Throughout six months of rapid business growth, a loved one of mine had multiple medical emergencies that required my support. Being a business owner is hard; being a caretaker is hard. Balancing those roles together was extremely challenging and overwhelming.
My advice for scaling: During challenging moments, give yourself grace and space to take a step back, take in the full scope of what’s happening, and develop a strategic approach to the problems at hand.
Catalina Parker
Co-Founder of Relatable Nonprofit, helping nonprofit professionals launch consulting careers.
One of the biggest lessons I have learned is that simplicity scales. Developing clarity in my messaging, systems, and sales processes made scaling much more effective.
My advice for scaling: Focus on one core offer and optimize it before adding more. Too many offers can dilute your impact and slow down your momentum.
All individuals featured in this article are members of Dreamers & Doers, an award-winning community that amplifies extraordinary women entrepreneurs, investors, and leaders by securing PR, forging authentic connections, and curating high-impact resources.
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