CAREERS

Build the future of enterprise transformation.

We're building something new — a firm designed for the next generation of legacy modernization. If you thrive on solving hard problems and driving real results for clients, we want to hear from you.

STATUS

Now hiring

All practice areas open

LOCATION

Remote

We are a virtual practice - travel to client sites as needed

TEAM

Innovation Starts Here

Collaboration that energizes and unites

AREAS WE'RE HIRING

Where you might fit.

We don't post rigid job descriptions, we hire for capability, culture and an unwavering commitment to delivery excellence and client value.

TRANSFORMATION

Code modernization & legacy transformation

Hands-on experience with legacy platforms or prior experience working on code modernization initiatives. You understand the challenges in transforming to modern architectures and are committed to exceeding customer expectations.

QUALITY

AI-driven QA & test automation

Experience building rigorous validation frameworks for complex system migrations. You know how to prove functional equivalence and how to catch the edge cases others miss.

DATA

Data engineering & modeling

Legacy-to-target data mapping, transformation logic, and validation at scale. You treat data integrity as a first-class deliverable, not an afterthought at the end of the project.

ARCHITECTURE

Application architecture & system analysis

You can read a legacy system, understand its design rationale, its dependencies, its undocumented assumptions and design a modern target architecture that preserves intent while improving extensibility.

DELIVERY

Consulting & delivery leadership

Senior program managers and delivery leads who can hold a complex transformation together - managing risk, aligning stakeholders, and keeping clients confident from kickoff through go-live.

OPEN

Don't see your exact fit?

If you have deep enterprise technology experience and a track record of delivering in complex environments, we're interested regardless of how your background maps to the categories above.

WHAT WE LOOK FOR

The traits that define our team.

Curious problem-solvers

You thrive on figuring things out, especially in ambiguous environments where the answer isn't obvious and the documentation is thin.

Self-starters

You don't wait to be told what to do next. You identify the gap, form a point of view, and move, checking in where it matters.

Bridge builders

You communicate confidently across audiences, translating technical complexity for executives and business context for engineering teams.

Outcome-focused

You measure success by what you achieve for the client, not by the hours you log or the slides you deliver.

Collaborative

You make the people around you sharper. You share what you know, ask good questions, and build trust quickly with clients and colleagues alike.

Ready for the AI era

You're genuinely curious about how AI is reshaping enterprise technology and excited to be at the leading edge of that shift.

Interested? We'd love to hear from you.

We don't do lengthy application processes. Send us a note, tell us about yourself, and let's have a conversation to see if there's a fit.

All roles are remote, travel to client sites as needed
We are currently hiring experienced practitioners only

WHY SHEPHERD GROUP

A firm where your expertise genuinely matters.

At Shepherd Group, we are not building a bench. We are building a team of experienced practitioners who bridge the gap between business goals and technical execution, communicate confidently with both developers and executives, and drive outcomes that last.

We value your expertise and insights. Join us to work on innovative projects, collaborate with passionate colleagues, and continue your career growth.