Sheppard LLC helps technical founders, CTOs, and engineering leaders make better decisions at moments of real impact — scaling a team, shipping AI, or stepping into leadership for the first time. Engagements range from hands-on builds to ongoing advisory to a single focused session.
Fractional advisory for founders and CTOs scaling from a handful of engineers to a structured, layered organization — hiring sequencing, role definition, elevating first-line managers, and process that scales without slowing teams down.
A trusted outside perspective for first-time CTOs and senior engineers stepping into leadership. Session-based, working real decisions in real time, from someone who has led engineering and ML teams at scale.
A hiring process that actually predicts success: competency scorecards, a behavioral question bank, structured debrief protocols, and panel facilitation. Built for teams replacing ad-hoc interviews.
Clear-eyed counsel for organizations navigating AI adoption — model selection, build-vs-buy, data readiness, capability gaps, and a realistic read on what AI can and can't solve for your business.
Hands-on guidance for teams putting AI agents into production: architecture patterns, tool selection, evaluation frameworks, human-in-the-loop design, and the failure modes that bite at scale.
A structured four-day intensive for a product, strategy, or technical challenge that needs a real decision at the end — scoping, day-by-day facilitation, and a prototype tested with users.
A focused 60-minute session on a specific technical or leadership decision you want a senior outside perspective on. No retainer, no ongoing commitment.
Tell me what you're working through and I'll tell you whether — and how — I can help. Engagement pricing is scoped to the work.
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