Built by an AI operator,
not an AI vendor.

I spent the last 4 years as VP of AI at Ashley Furniture Industries — the world’s largest furniture manufacturer ($11B revenue, 1,125+ stores across 67 countries). I shipped 170+ AI initiatives across the business, including the agentic commerce integration with Perplexity and PayPal that launched in late 2025.

Before that, I ran AI/ML at Southern Glazer’s Wine & Spirits — a $25B beverage distributor with thousands of sales reps across all 50 states. I built their Next-Best-Action sales agent, which combined recommendation systems with LLM agentic workflows for field reps making thousands of customer visits per week.

Both roles taught me the same thing: multi-location operators face the same problems at every scale. The patterns at $25B look exactly like the patterns at $25M — just at different scale. And the AI tools built for enterprise IT teams don’t fit regional contractors with zero or one IT staff.

That’s why I started Crewdash. Regional electrification contractors — HVAC, electrical, solar, heat pump, EV charger installers doing $5–50M in revenue — deserve the same visibility that a $11B retailer has. Without the team or budget to match.

Crewdash is a software product, not a consulting engagement. It’s an AI ops co-pilot that sits above your existing field service software (ServiceTitan, Jobber, FieldEdge, HouseCall Pro, Workiz) and surfaces real-time intelligence your weekly ops meeting would otherwise catch days too late. Think Avoca AI for voice, then us for the intelligence layer above the whole stack.

The first 90 days include hands-on setup — me personally wiring up the integrations, tuning the agent on your specific data, calibrating the weekly Impact Reports to your operating cadence. After that it’s a product you run, with us in the background continuously upgrading what we’ve deployed as AI tooling improves.

No sales calls. No slide decks. The first thing we do is run an AI agent on your actual data and send you a 15-minute Loom video of what we find. If it’s useful, we keep going. If not, we’re really not surprised.

Background

• VP of AI — Ashley Furniture Industries ($11B)
• Director AI/ML — Southern Glazer’s Wine & Spirits ($25B)
• Master of Applied Statistics — UCLA
• Udacity Machine Learning Nanodegree

Currently building

• Crewdash — AI ops co-pilot for regional electrification contractors
• Co-Forge AI — with Duan Peng (Chief AI Officer at Ashley Furniture)

Where to find me

Email: josajima@cairnstone.io
LinkedIn: linkedin.com/in/jasonosajima
GitHub: github.com/jason-osajima