Sheppard.
Services

Pragmatic technology leadership, in whatever shape the work needs.

Sheppard LLC works with technical founders, CEOs, CTOs, and engineering leaders on the decisions that carry real weight: scaling a team, shipping AI, stepping into leadership for the first time.

Ongoing engagements

Advisory

A standing relationship on a regular rhythm, say a weekly conversation or a half-day each month. We work through strategy, key decisions, and direction. I stay available between sessions for the questions that come up along the way.

One flat monthly fee

Fractional

A hands-on, embedded engagement. I work directly with you and your team on a regular cadence and go deeper on execution: analysis, planning, reviews, and the artifacts the work calls for.

One flat monthly fee
Intensives

Full-Day Working Session

A single focused day on one problem. A good fit for a decision that needs concentrated attention, or a kickoff that sets direction quickly.

Priced per session, on its own or alongside a retainer

Design Sprint

A structured five-day process to solve a big problem or test a new idea before committing real resources, following the Design Sprint method developed at Google Ventures (Knapp, Zeratsky & Kowitz).

Priced per sprint
Where I help

Subject areas I advise on, across any of the engagement shapes above.

AI strategy
Model selection, build-vs-buy, data readiness, and a realistic read on what AI can and can't do for your business.
Engineering org growth
Scaling from a handful of engineers to a layered organization: hiring sequence, role definition, and process that holds up.
Technical leadership
An experienced outside sounding board for CEOs, CTOs, and engineering leaders on the calls that don't have a clear answer, from running an established org to stepping into the role for the first time.
Hiring systems
Interview processes that actually predict success: scorecards, structured debriefs, and calibrated panels.
Included in every engagement

Ongoing engagements run at a sustainable pace, up to about an hour of preparation and three hours together on any given day. Work that needs more concentrated time is scoped as a Full-Day Working Session or a Design Sprint.

Have a decision worth a second opinion?

Tell me what you're working through and I'll tell you whether, and how, I can help. Pricing is a flat monthly fee, scoped to the work.

Start a conversation