Aaron Waters
CEO & Founder, Pumpkin Business Services
"From my many years helping companies navigate cyber security compliance regulated by the federal government, I saw an opportunity to build systems that give professional firms real confidence in their compliance — and a clear path into the AI revolution."
A lifetime of technology — focused on what matters most.
Pumpkin was born from decades of hands-on experience across computer repair, enterprise IT, military service, and managed technology — all converging on a single mission: making compliance understandable and achievable for professional and financial firms.
The first business
Aaron's technology journey began right out of high school when he launched his first computer repair company. Solving real problems for real people — that hands-on mindset became the foundation of everything that followed.
IT consulting & deeper expertise
Building on his repair roots, Aaron moved into IT consulting, working with businesses on infrastructure, networking, and technology strategy. Each engagement deepened his understanding of what companies truly need from their technology partners.
Three years serving the country
Aaron spent three years in the military, an experience that sharpened his discipline, precision under pressure, and commitment to doing things the right way — qualities that now define how Pumpkin operates every single day.
Growing a local technology leader
After the military, Aaron joined a new managed IT service provider in Monterey, California. He helped grow that company into a strong local technology leader in the Monterey area — building a reputation for reliability, expertise, and genuine client partnership.
Pumpkin is born
After selling his stake in the Monterey MSP, Aaron turned his focus to a problem he had seen repeatedly: professional and financial firms struggling with the difficult and often misunderstood world of legal and cyber security compliance. Pumpkin was founded to develop the systems, support, and applications that give these firms real confidence in their compliance — and help them embrace the new age of AI to stay competitive and thrive.
Every professional firm deserves
confidence in their compliance
and a clear path into AI.
We exist to tackle the difficult and many times misunderstood subject of legal and cyber security compliance — developing the systems and support that give professional and financial firms the confidence to operate securely, stay compliant, and compete in the new age of artificial intelligence.
Compliant
Built from the ground up for IRS Publication 4557, SOC 2, GLBA, and the specific regulatory realities of professional and financial firms.
Confident
We develop systems and support applications so your firm is never guessing about its compliance posture — you know exactly where you stand.
AI-Ready
We help firms break into the new age of AI, stay competitive, and thrive in the artificial intelligence revolution without the guesswork.
How we actually work.
Culture isn't a slide deck at Pumpkin. It's the decisions we make when no one is watching — and the standards we refuse to compromise on, even when it's inconvenient.
Client-First Always
Every decision, every build, every call — we ask ourselves if it genuinely serves our clients. Not just today, but five years from now.
Integrity Over Everything
We handle sensitive financial data every day. We hold ourselves to standards that go beyond compliance — we hold ourselves to trust.
Bias Toward Action
We don't wait for perfect. We ship, we learn, we iterate. Speed combined with care is the formula for real impact.
Radical Transparency
We say what we mean, share what we know, and own our mistakes. Our clients deserve honesty, not spin.
Relentless Curiosity
The technology landscape never stops moving. Neither do we. We're always studying, experimenting, and pushing further.
Community & Access
Great technology shouldn't be reserved for Fortune 500 firms. We're on a mission to make enterprise-grade tools accessible to every practice.
We hire for character. We train for skill.
Every person at Pumpkin has been selected not just for their technical ability, but for their genuine care for clients and their commitment to doing the right thing — even when it's harder. We believe the best technology teams are also the most human ones.
The future of professional services runs on intelligence.
We believe the next decade will see the most dramatic transformation in how professional services firms operate in over a century. AI will handle the repetitive. Automation will reclaim billable hours. And firms that embrace this shift early will leave their competitors behind permanently.
Pumpkin is building the platform that makes that transformation real — not theoretical. Not a whitepaper. Not a demo. A system that works on Monday morning during the most critical deadlines, when your staff is overwhelmed and your clients need answers now.
Our roadmap for the next three years is the most ambitious we've ever attempted. And we're doing it with the same discipline and care that got us here.
AI Receptionist
Every firm should have a 24/7 intelligent front desk — without the headcount.
Predictive Compliance
Know your exposure before the regulators do. Real-time risk scoring for every client file.
Unified Intelligence
One platform connecting VoIP, security, and AI — seamlessly orchestrated.
AI-Driven Growth
Helping professional firms break into the new age of AI, stay competitive, and thrive in the artificial intelligence revolution.