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

Based in Atlanta, GA — travel to client sites as needed

Senior-led

TEAM

No layers of junior staff — your expertise matters here

AREAS WE'RE HIRING

Where you might fit.

We don't post rigid job descriptions — we hire for capability and mindset. Here are the practice areas we're building.

TRANSFORMATION

Code modernization & legacy transformation

Deep hands-on experience with mainframe, AS/400, or other legacy platforms. You understand what these systems were designed to do — and how to faithfully reproduce that on a modern architecture.

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.

1

Curious problem-solvers

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

2

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.

3

Bridge builders

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

4

Outcome-focused

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

5

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.

6

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
Senior practitioners only — we don't layer junior staff over your work
We aim to respond to every application within 3 business days
Or reach us directly at careers@shepherdgroup.ai

WHY SHEPHERD GROUP

A firm where your expertise genuinely matters.

At Shepherd Group, we're not building a bench. We're building a team of experienced practitioners who can bridge the gap between business goals and technical execution — communicating confidently with developers and executives alike, and driving outcomes that stick.

We work on some of the most consequential technology challenges in enterprise IT: helping organizations escape decades-old systems using a deterministic AI platform that actually works. If that sounds like the kind of work you want to be doing, read on.