With almost two decades of practical expertise in high-growth, fast-paced environments, Keegan Chapman, Chief Marketing Officer of Filevine is known for creating cohesive teams, breaking into new markets, and bringing plans to fruition.
She thrives in the unknowns of building something new and excels at new market expansion and strategy, assembling a sales force, creating sales process and organization structure, and developing sales talent no matter the tenure.
Keegan’s strategic thinking and comprehensive grasp of the client journey help her connect the dots across departments to truly make an impact in Filevine’s ongoing expansion in the legal technology sector.
From Sales to Strategy: The Journey to CMO
Keegan initially entered the sales world because that’s was where opportunity existed for recent marketing graduates. She felt lucky to start at Groupon during its pre-IPO phase, using a unique mix of sales and marketing to help small businesses attract customers through thoughtful promotional campaigns.
From there, Keegan became a GM at an early-stage sales bootcamp startup called Victory Lap, where she managed multiple channels and learned how the entire go-to-market funnel works together. Later, she joined Equilibria, where she gained deep experience in influencer marketing, social, and wholesale. Throughout this journey, Keegan noticed how rare it was to find sales leaders fluent in marketing fundamentals or vice versa. That insight inspired her to start her own go-to-market strategy consulting practice.
“Filevine was one of my clients. I started by supporting their CRO and CEO, then joined the team full time, helping organize the BDR, marketing, and partnership functions to deliver consistent pipeline. Over time, I built out the top-of-funnel organization and eventually stepped into the CMO role. Now I get to do what I love, which is build great teams that drive meaningful business growth,” Keegan explains.
Keegan recalls that when she entered the marketing and business development field, she didn’t set out to work in business development – it just happened naturally. Over time, she realized how powerful it was to understand the full picture. “If I had known as a sales rep what I know now about marketing, I would’ve been even more effective. That’s something I now pass on to my BDRs: leverage intent signals, understand the full customer journey, and you’ll become a stronger rep,” she reflects.
Earning a Seat at the Table Through Grit and Empathy
One of the challenges Keegan faced as a woman in business, was being overlooked and underestimated. Throughout her career, she had people express surprise at her competence or assume she would be more sensitive than she is, and recalls how early in her career, she overheard a manager say they didn’t think she would last two weeks.
“That lit a fire in me. I’ve always been a hard worker and fast learner, but that moment gave me a chip on my shoulder and pushed me to prove myself. As a leader, it’s made me more empathetic. I remember how it felt to be doubted. I focus on creating environments where people feel supported, encouraged to take risks, yet also held accountable,” she shares. “Some days I feel like just another professional in the room, and other days I feel underestimated. My focus is always on staying grounded in who I am, delivering meaningful work, and building something I’m proud of.”
Keegan notes that it was strong communication, commitment to outcomes, and relationship-building that helped bridge those gaps and ensure she was seen as someone who deserves a seat at the table.
Driving Growth with Heart, Innovation, and a Clear Vision
In terms of leadership strategies, Keegan has learned both from formal leadership programs and being thrown into the deep end. Her approach is a mix of structure and humanity. “I seek to understand first, especially when something isn’t working, and I prioritize managing the individual, not just the outcome. I encourage experimentation, reward growth, and try to ensure that everyone on my team feels they’re better for having been part of it,” she says.
As Filevine’s first-ever CMO, Keegan believes she brings a unique perspective to the CMO role, especially given her sales-driven background in a sales-driven company. She cares deeply about the customer experience from first impression all the way through onboarding. This informs how the firm crafts messaging, creates “aha” moments, and builds consistency across the funnel. “As our company grows, we’re evolving how we show up by highlighting our strengths in AI, data, and innovation. We are an innovative, customer-first organization, and a true thought leader in legal tech,” she adds.
Keegan notes that innovation is at the core of everything Filevine does. The team is constantly building new AI tools, launching new channels, refining their messaging, and following deals from start to finish to understand buyer behavior. She pushes her team to evolve beyond what’s worked in the past and lean into what’s next, a mindset that has helped them grow quickly and sustainably.
“Filevine is in a unique position to reshape legal tech. We’ve built AI that’s context-aware, ethical, and embedded in a powerful end-to-end platform. What’s next is being louder about that message to market and helping legal teams transform how they work and serve clients,” Keegan explains.
AI-Driven, Customer-Centric, and Future-Focused
Keegan observes that AI is changing everything about marketing by affecting how people search, process information, make decisions, and seek advice. Its influence is evident in both how we sell and how we buy. She highlights the importance of constantly learning, adapting, and innovating to stay relevant, and warns that the marketers who stop learning will fall behind.
In terms of technology influencing business development and marketing in the legal tech sector, Keegan notes that lawyers often become business owners by necessity, not by design. “That’s where technology steps in. We’re building end-to-end solutions that aren’t just templates. They’re personalized, AI-powered platforms that make data accessible and teams more efficient. This allows firms to serve their clients better with fewer tools and less complexity,” she explains.
Filevine ensures that its marketing strategy aligns with customer needs and business objectives by staying close to its customers through constant feedback: calls, events, surveys. They also have in-house legal experts who help them stay ahead of the curve, such as their Chief Legal Futurist’s team whose entire job is to help them build for the market years from now, not just today.
Keegan believes that a brand isn’t just a logo, and what makes a brand truly successful and memorable in today’s competitive market is in how it speaks to its customers, the experiences it creates, and the problems it solves. “To me, a great brand feels like a partner, not just a vendor. That’s how we approach our relationships with customers,” she affirms.
Staying True, Leading Boldly, and Lifting Others Along the Way
Keegan recalls that while she never had one formal mentor, many people helped shape her growth along the way, whether through a challenge, a piece of advice, or simply setting an example. “Mentorship is everywhere if you stay open to learning,” she insists. She notes that the biggest challenge for women in leadership roles today is that unconscious bias still exists.
However, she also believes that one of the biggest challenges that women face is overthinking. “There’s so much noise around what we should or shouldn’t do or how we should or shouldn’t act. I’ve learned that staying true to myself and pursuing projects I’m genuinely excited about leads to the most impactful work,” she says boldly.
To aspiring women leaders looking to make an impact and break barriers in leadership, Keegan offers the following words of wisdom: Don’t try to do everything. Find a real problem worth solving, something that makes a meaningful business impact, and focus on solving it well. That’s how you build a reputation for getting things done. Trust your gut. Women often have exceptional emotional intelligence. When you stay grounded and take care of yourself, your ability to lead with both heart and mind becomes a superpower.
Keegan also reflects that if she could share one piece of advice to her younger self, it would be these two things: First, don’t climb the corporate ladder just because you think you should. Pick roles you’ll be proud to tell stories about. Second, don’t burn yourself out. If you don’t take care of yourself outside of work, your role becomes your only identity. Set the right boundaries and build the habits to keep your cup full so you can also be strong in your work.
Conclusion
In her dynamic career journey, Keegan Chapman’s desire is to be remembered as a coach first, and to leave a legacy of coaching and lifelong learning. She leads with the belief that business outcomes matter, but the real impact is helping people grow into better, stronger professionals, because then the outcomes are infinite.
Keegan doesn’t measure her success by awards or titles; instead, she looks at how much the people she’s led have grown. She believes that the best way to know if she did a good job is if her former teammates leave with more skills, more confidence, and better tools for what’s next. According to her, that kind of development has a cascading effect, influencing others and creating a wider effect on the tech ecosystem.
