When $35M Deal Meets Startup Reality
Situation
Jitjatjo had just signed a $35M enterprise deal with Compass Group (world's largest foodservice contractor - 250K workers). One problem: we didn't have enterprise capabilities. No multi-tenancy. No compliance engine. No integrations. The company faced bankruptcy if we couldn't deliver. Previous enterprise transformations in this space took 18-24 months. We had 6.
Task
Transform a single-tenant marketplace built for 10K users into enterprise-grade SaaS supporting 250K workers while:
Building multi-tenant architecture from scratch
Creating compliance engine for 15+ pay rule types
Integrating with SAP, HRIS, and legacy systems
Managing hostile enterprise stakeholders who didn't trust startups
Keeping the plane flying while rebuilding the engine
Action
Built While Burning:
Architected complete platform overhaul during active operations - like performing heart surgery on a marathon runner
Created "Sync" API strategy preventing custom integration hell - 8 universal triggers instead of endless one-offs
Implemented 3-phase delivery (Alpha/Beta/GA) proving value while building
Defended startup capabilities to skeptical enterprise IT, Payroll, and Accounting teams
Technical Complexity Mastered:
Transformed single database to multi-tenant architecture with org-specific databases + shared core
Built compliance engine handling FLSA overtime across varying rates ($15→$20 = $23.90 OT rate)
Integrated AS2 protocol for SAP time/billing data (their 300-person payroll team's requirement)
Created payroll audit tools for compliance verification without disrupting operations
Stakeholder Aikido:
Converted hostile enterprise teams: "These guys actually know what they're doing"
Made their 20-year SAP experts partners, not enemies
Delivered working Alpha in 8 weeks to build trust
Let enterprise stakeholders "own" solutions while quietly building the future
Result
Saved the company:
Delivered on-time despite "make-or-break" pressure
Reduced enterprise onboarding: 6 months → 1 month
Expanded addressable market: <1M → <20M workers
Enabled 186% revenue growth and Series B funding
Cut Compass labor costs 17% through intelligent matching
But more importantly: Proved a startup could deliver enterprise-grade transformation faster than established players.
Key Insight
Everyone said startups can't do enterprise. They were wrong. You just have to ship incrementally while they're still debating architecture. Alpha proved we could deliver. Beta proved we understood compliance. GA proved we could scale. Each phase bought us credibility for the next.
The Pattern
This is what I do: Take "impossible" technical transformations with existential stakes and ship them through strategic phasing. At CCAoA, it was 4 years of stagnation. At Jitjatjo, it was bankruptcy if we failed. Different constraints, same approach: Ship early, prove value, build trust, then accelerate.
Technical Depth:
Multi-tenant architecture | AS2/SAP integration | Compliance engines | API strategy
Scale: 2→10 markets | 10K→250K workers | $35M enterprise deal
Stakes:
Company survival dependent on delivery
