The Missing Leadership Layer
The most common gap I see in technology organizations isn’t technical. It’s the leadership layer between executive vision and engineering execution.
Someone who can translate, challenge, and move things forward.
I’ve spent 20 years in that role — building ML teams, running design sprints with executive stakeholders, helping technical founders think through org design, and advising on hiring decisions where the cost of getting it wrong is high.
Through Sheppard LLC, I’m offering that same thinking as a fractional advisor and strategic partner.
A few of the things I work on:
- Roadmap and build-vs-buy decisions for AI and data initiatives
- Structured design sprints that get cross-functional teams aligned fast
- Technical leadership development — especially engineers stepping into their first CTO or VP role
- Org design and hiring process for data and engineering teams
If you’re a leader facing a high-stakes technology decision this year and want a thought partner who’s been in that room before, let’s find some time: calendly.com/joshua-sheppard — or email me at josh@sheppard.tech to discuss how I can help.