ABOUT US
Practitioners who have been on both sides of the problem.
We were founded by enterprise technology veterans who spent their careers building and deploying mission-critical applications for some of the world's largest and most innovative technology companies.
OUR STORY
Built by practitioners, for practitioners.
Shepherd Group exists to solve one of enterprise IT's most consequential challenges: helping organizations escape the cost, risk and constraints of legacy platforms through a pioneering, AI-powered modernization approach that consistently delivers results where others have failed.
We didn't enter this field from the outside. We built applications on the very platforms that enterprises now struggle to modify, maintain, and escape. That insider knowledge is not incidental; it lays a strong foundation for transforming legacy applications, not just translating old syntax.
We came together because we witnessed firsthand how modernization projects fail, wasting millions of dollars and years of effort due to inadequate tooling, flawed methodologies, and a fundamental misunderstanding of what legacy systems were actually designed to do.
So we built a better approach: one anchored in deterministic AI, deep domain expertise, and genuine accountability for outcomes, not just activity.
UP TO 30%
Reduction in IT operating costs within 2 years of successful migration
100%
Of code transformed — not ~80% like generative AI tools deliver
30 YRS
Average founding team experience in enterprise technology
WHAT WE STAND FOR
Our principles.
Every engagement we take reflects a set of commitments we don't compromise on.
Outcomes over activity
We measure success by what you achieve, not by hours billed or slides delivered.
Transparency by default
Full traceability, clear audit trails, no black-box translation. You see exactly what we did and why.
Risk reduction first
We design every engagement to reduce your exposure — in budget, timeline, and operational continuity.
OUR TEAM
The people behind the approach.
A tight team of senior practitioners — no layers of junior staff, no handoffs to generalists.
Scott Lyon
Scott has spent his career applying technology to deliver high-impact business results for clients across a variety of disciplines and industries. Prior to founding the Shepherd Group, Scott was a Managing Director in Accenture’s EPM practice where he focused on Finance transformation and AI adoption. Before Accenture, Scott spent years as a Go-to-Market leader for multiple hypergrowth software companies where he developed outstanding teams, accelerated revenue and built trusted relationships with clients. Scott is a regular presenter at industry and client events including the National Retail Federation (NRF), Gartner’s CFO Forum, The Product Management and Sales Management Associations.
When not working, you can find Scott outside swimming, biking or running, at an early morning F3 bootcamp, or enjoying pickleball or golf with family and friends.
Alison Chappell
Alison brings nearly two decades of executive-level experience leading complex, mission-critical technology programs across financial services, ERP, and government, and a track record that speaks for itself. As Senior Director of Clearing Technology at Intercontinental Exchange, she led global software initiatives with cross-functional teams of 200+, launched new clearing houses, modernized legacy systems, and built the enterprise clearing data repository from scratch. She's known for bringing order to complexity, rallying diverse teams around shared goals, and making technical strategy legible to the people who need to act on it.
When she's not delivering enterprise transformation, Alison is soaking up the almost-perfect Georgia weather - playing tennis, reading by the pool, watching her son play baseball and her daughter cheer, and grinding through CrossFit WODs.
"Trust is earned in drops and lost in buckets."
— Kevin Plank