Welcome to One Pour Problems!
One Pour Problems

About One Pour Problems Podcast

Where Business Solutions Flow—One Sip at a Time

Welcome to One Pour Problems—a business podcast where real-world insights meet real drinks. Hosted by Charles IT, this show features candid conversations with local business leaders on the most pressing challenges facing modern companies.

Each episode begins with a guest sipping their favorite drink—be it bourbon, coffee, or craft soda—and sharing the story behind it. That simple pour sets the tone for thoughtful, relaxed discussions on topics like leadership, cybersecurity, compliance, company culture, and business growth.

Whether you're a CEO, entrepreneur, or simply passionate about building better businesses, One Pour Problems offers practical advice, inspiring stories, and strategies you can actually use.

About the Hosts

Foster Charles Profile Photo
Foster Charles

Founder & CEO of Charles IT

Foster Charles is the Founder and CEO of Charles IT, a cybersecurity and managed IT services firm serving organizations in highly regulated industries across the Northeast and Mid-Atlantic. Since founding the company in 2006, Foster has led Charles IT with a clear belief that exceptional service, passion, integrity, and continuous improvement are the foundation of strong technology partnerships and long‑term business success.

Under Foster’s leadership, Charles IT has grown from a small local provider into a trusted partner for healthcare, financial services, manufacturing, and other compliance‑driven organizations. He remains deeply involved in shaping the company’s strategic direction, ensuring that technology decisions support not just security and uptime, but also scalability, resilience, and real business outcomes.

A frequent speaker and panelist, Foster is known for his ability to break down complex topics like cybersecurity, compliance, and AI adoption into clear, practical guidance for business leaders. He has spoken at regional and industry events on topics including cybersecurity risk management, CMMC and regulatory readiness, and the evolving role of AI in the workplace, helping executives understand how to reduce risk without slowing innovation.

Foster is also a thought leader and published contributor, regularly sharing insights on cybersecurity best practices, compliance frameworks, and leadership through Charles IT’s blog and national media outlets. His perspective emphasizes proactive security, informed decision‑making, and building organizational cultures that treat cybersecurity as a business priority, not just an IT concern.

Beyond his work at Charles IT, Foster is active in the broader technology and business community and is a member of industry peer groups focused on leadership and growth. He lives in Connecticut with his family and remains passionate about building organizations where people can grow, teams can collaborate effectively, and technology enables, not complicates, progress.

Jessica Golle Profile Photo
Jessica Golle

Chief Revenue Officer at Charles IT

As Chief Revenue Officer at Charles IT, I lead the company’s go-to-market strategy across sales, marketing, and revenue operations—driving scalable growth, predictable recurring revenue, and customer-centric innovation. Charles IT is a leading managed IT and cybersecurity provider focused on helping organizations in highly regulated industries navigate complex compliance, security, and operational challenges.

With more than 25 years of experience in sales and go-to-market leadership—18 of those in the Managed Services and Managed Security space—I have built and scaled high-performing commercial organizations through periods of rapid growth and transformation. My expertise centers on creating disciplined, KPI-driven revenue engines that align teams, accelerate pipeline, and deliver measurable business outcomes.

Throughout my career, I’ve focused on serving compliance-driven industries such as financial services, healthcare, and other regulated sectors where security, risk management, and operational resilience are critical. I bring a deep understanding of how to translate complex regulatory requirements—ranging from SOC 2 and HIPAA to CMMC and NIST frameworks—into scalable, customer-focused solutions that drive both growth and trust.

Prior to joining Charles IT, I served as Chief Commercial Officer at Agio, where I oversaw Sales, Marketing, and Revenue Operations, consistently exceeding revenue targets while increasing pipeline velocity and strengthening strategic partnerships. My leadership contributed directly to the company’s successful private equity transaction at record-high revenue multiples—demonstrating my ability to not only accelerate growth but also maximize enterprise value.

I thrive in private equity-backed and high-growth environments where execution, accountability, and speed matter. My leadership style blends structure with practicality, grounded in enablement, transparency, and peer-driven accountability to unlock team performance.

Outside of work, I’m usually chasing Reposado (“Reppy”), my German Shepherd puppy, spending time at my Lavallette, NJ shore home, or embracing my roots as a Bronx-raised, proud aunt of eight—with a lifelong get-it-done mindset.

Trevor Davis Profile Photo
Trevor Davis

Account Executive at Charles IT

Trevor Davis is a Cybersecurity and CMMC Account Executive at Charles IT, where he helps organizations navigate cybersecurity, compliance, and technology challenges while aligning IT investments with broader business objectives. Trevor joined Charles IT through the acquisition of Merit Solutions, bringing with him a strong background in leadership, business development, and client relationship management.
Prior to entering the technology industry, Trevor spent nearly a decade leading teams and driving growth in retail management roles. That experience shaped his people-first approach to leadership and gave him firsthand insight into the operational challenges businesses face as they scale. Today, he leverages that perspective to help clients make informed decisions around cybersecurity, compliance, and risk management.
At Charles IT, Trevor works closely with organizations in regulated industries to strengthen their security posture, improve operational resilience, and prepare for evolving compliance requirements, including CMMC and other industry frameworks. Known for his consultative style and ability to simplify complex topics, he focuses on building trusted relationships and delivering practical solutions that create long-term value.
Passionate about professional growth and team development, Trevor believes that strong communication, accountability, and continuous learning are essential to success. He enjoys helping business leaders understand how technology can serve as a strategic advantage, empowering organizations to grow confidently while managing risk in an increasingly complex digital landscape.