Contractor workforce platform
The situation
Jitjatjo had signed a $35M deal with Compass Group — the world's largest foodservice contractor, 250K workers. The product was a single-tenant marketplace built for a fraction of that scale. No multi-tenancy. No compliance engine. No enterprise integrations. Transformations like this typically took 18–24 months. The timeline was 6 months.
I was brought in as Product/Solutions Architect — responsible for ensuring the product could scale to enterprise requirements while connecting to the way Compass actually operated.
What I found
The technical gap was clear. The trust gap was harder. Compass had a 300-person payroll team, 20-year SAP infrastructure, and no patience for a startup learning on their dime. Their IT, payroll, and accounting teams were openly skeptical.
The compliance complexity was real: FLSA overtime calculations across varying rates, AS2 protocol integration for SAP time and billing, pay rules spanning 15+ types across multiple jurisdictions. If you calculate overtime wrong on 250K workers, you get sued.
How I worked
Embedded with their enterprise teams. Didn't pitch startup capabilities — shipped a working Alpha in 8 weeks and let them react to something real.
Three-phase delivery: Alpha proved the team could deliver. Beta proved we understood compliance. GA proved we could scale. Each phase bought credibility for the next.
The turn came during SAP integration. Their payroll experts had spent 20 years with that system. Instead of treating their requirements as obstacles, I made them design partners. Built the compliance engine with them, not around them. Their audit tools, their verification flows, their sign-off.
"These guys actually know what they're doing." That's when a hostile stakeholder becomes a champion.
What it produced
Delivered on time under make-or-break pressure
Enterprise onboarding reduced from 6 months to 1 month
Addressable market expanded from under 1M to under 20M workers
17% reduction in Compass labor costs through intelligent matching
Series B funding enabled by proving enterprise capability
What I learned
Ship early, prove value, build trust, then accelerate. Enterprise stakeholders don't need a pitch. They need to see working software that respects their domain expertise. The same principle became the sequential iteration methodology at CCAoA — let the people who know the domain validate by interacting with the solution, not reviewing a deck.
