Gregg Hilferding
Founder
Intro
Who is Gregg?
Gregg Hilferding is a tech leader and U.S. Army veteran with over 20 years of experience helping organizations grow and run more efficiently. His mission is simple: use technology to give people back more time. Gregg's all about finding practical, scalable solutions that work in the real world, whether it’s building tech that just clicks or reshaping teams to make sure they’re ready for what’s next.
As someone who’s spent years in software development, cloud computing, and system design, Gregg brings a broad skill set to the table. He's also passionate about AI, showing clients how to adopt and manage it responsibly. Known for breaking down complex ideas into plain language, Gregg is a go-to speaker on all things generative AI, agile workflows, and modern tech trends.
Outside the tech trenches, Gregg is all about developing people. He believes in creating work environments where everyone can thrive and is known for building high-performing, tight-knit teams that value both results and growth. Gregg’s leadership style? Clear, approachable, and focused on making an impact that sticks.
Expertise
What you can expect when Gregg joins your team.
01
Fractional CTO
If you’re looking for a CTO without the full-time commitment, Gregg’s fractional CTO services provide hands-on management of your cloud infrastructure, application architecture, and budget, ensuring your systems run smoothly and grow sustainably.
02
Agile Team Leadership
With Gregg’s experience in building high-performing teams, you’ll see agile methodologies actually work in your organization. He brings practical expertise in Scrum and Agile practices that help teams move faster, collaborate better, and deliver results.
03
Building to Scale
Gregg can design and implement a secure, scalable system that grows with you. Whether it’s a startup environment or enterprise-level expansion, expect an infrastructure that’s rock-solid, secure, and prepared for the future.
04
Generative AI & AI Adoption
If your organization is ready to step into AI, Gregg will guide you every step of the way. From training your team on AI best practices to implementing governance and compliance, he ensures AI adoption is safe, effective, and aligned with your goals.
Experience
A proven track record of leading teams, scaling operations, and delivering results.
2024 – Present
VP of Organizational Development
Sourcetoad · Tampa, FL
- Led strategic initiatives for scalable growth, along with new C-level roles (COO, CSO) to support expansion.
- Developed training programs for communication, evaluation, and leadership development, fostering professional growth.
- Consulted on scalable GenAI solutions, delivering training on legal compliance, prompt engineering, and AI governance.
- Product Leader for an internal tool integrating time tracking, project management, and task management systems.
2022 – 2024
VP of Delivery
Sourcetoad · Tampa, FL
- Led and developed a global network of 50 IT professionals, including engineers, project managers, and Scrum masters.
- Implemented a reorganization for future growth, enhancing business processes and operational efficiency metrics.
- Advanced UX capabilities across teams, elevating client satisfaction and product quality.
- Provided fractional CTO services, managing client infrastructure on Azure and AWS and overseeing budget and architecture.
2019 – 2022
Director of Engineering
Sourcetoad · Tampa, FL
- Led initiatives to enhance IT service delivery, including communication, capacity forecasting, and engineering practices.
- Doubled company headcount from 25 to 60 to support scaling objectives.
- Worked with PMO to streamline workflows, improving client satisfaction and reducing engineering meeting time by 75%.
- Designed secure, scalable AWS systems for clients, ensuring HIPAA and SOC2 compliance for sensitive data.
2014 – 2019
Owner
GreenBarLabs, LLC · Tampa, FL
- Completed over 40 web, mobile, and consulting projects on budget and on time, managing a small team.
- Specialized in UX design and consulting, focusing on customer-centric product development.
- Led DevOps work in AWS, overseeing EC2, RDS, S3, and more for secure, scalable web applications.
- Developed the PatchScan + BSA Licensing Authorization System, serving hundreds of thousands of users.
2003 – 2014
VP of Marketing
ClassB · Tampa, FL
- Drove 9x business growth, leading national advertising, SEO, social media, and event marketing campaigns.
- Developed a tech-enabled customer experience with an industry-first Ajax-powered online design tool.
- Managed art, customer service, and HR departments, championing team success.
- Secured BSA Quality Licensee Award yearly and spoke at multiple BSA Licensing Summits.
1999 – 2005
Specialist (88M)
U.S. Army Reserve · Lakeland, FL
- Deployed to Kuwait and Iraq in 2003 in support of Operation Enduring Freedom.
1997 – 2003
Full Stack Web Developer
Shirts & Caps, Inc. · Tampa, FL
- Developed and managed marketing websites and e-commerce platforms, driving customer success.
- Created an integrated survey tool, linking client feedback to specific products, enhancing service quality.
- Built a customer portal for order tracking and approvals, reducing support calls by 15%.
Skills
Technical Skills
- IT Management: Oversight of infrastructure, data, system architecture, and cybersecurity with a focus on agile practices.
- Software Development: Full-stack developer skilled in PHP, JavaScript, SQL, and frameworks like Laravel, VueJS, and React.
- System Design & Architecture: Expertise in scalable design, MVP development, and revenue-focused product delivery.
- Cloud Services: Proficient in AWS and Azure, with comprehensive cloud infrastructure knowledge.
- Data Management & Analytics: Database design and performance optimization, ensuring data integrity and usability.
- User Research & Data-Driven Design: UX insights through research and A/B testing, driving engagement through data-informed design.
Leadership
- Strategic Planning & Growth: Proven in organizational restructuring for growth, strategic foresight, and decision-making.
- Team Leadership & Development: Experienced mentor and coach, fostering high performance and continuous improvement.
- Project Management: Skilled in managing multiple projects, with a focus on on-time delivery and client satisfaction.
- Agile & Scrum: Certified ScrumMaster with extensive Agile experience, boosting team productivity and product outcomes.
- Budget Management: Aligned financial planning with organizational priorities, optimizing resource allocation.
Communication
- Effective Communication: Skilled in explaining technical concepts to diverse, non-technical audiences.
- Collaborative Relationships: Cultivates teamwork within and across departments, enhancing project success.
- Public Speaking & Presentation: Experienced in delivering impactful presentations at industry events and conferences.