HIT · Health In Tech, Inc.

Dustin Plantholt’s departure from the newly minted role of Chief AI & Marketing Officer—explicitly tied to AI product strategy and marketing leadership—represents a material leadership shift during active development of 'AskTim', a core AI-powered benefits counselor platform. His immediate transition to a contracted capacity via his own entity, Plantholt Advisory Group LLC, signals continuity of technical oversight but also a structural reconfiguration of executive accountability and equity alignment. The $28,333.33 monthly fee and 500,000-share restricted stock award—vesting monthly over 12 months—tie compensation directly to sustained delivery against defined milestones for Midnight’s three-phase implementation: secure backend infrastructure, TypeScript-based Health Data SDK integration using zero-knowledge proofs (ZKP), and production readiness validation. Critically, the agreement mandates Plantholt’s personal performance as the designated Key Person, prohibits delegation without consent, and requires collaboration with Health In Tech employees—highlighting his irreplaceable operational role despite the title change. This arrangement mitigates near-term execution risk but introduces dependency on a single external contractor for mission-critical AI infrastructure delivery, with termination rights (10-day notice) offering limited recourse if performance falters. Investors should monitor milestone adherence, vesting triggers, and whether future leadership appointments address the permanent gap in AI and marketing executive ownership.