COMMAND DASHBOARD
Live signal — why now: Hiring a director to architect the revenue technology stack as the business scales beyond $100M ARR.
Executive pain hypothesis: Marketing, Sales, and Customer Success need a trusted, elegant data and automation layer that scales with the company.
Role mandate: Ashby is hiring for Director, GTM Engineering & Systems to own revenue systems, forecasting, and cross-functional operating cadence — the operational backbone connecting Sales, Marketing, and Customer Success.
Honest application risk: Likely requires significant technical GTM-stack depth. The executive brief should foreground architecture and implemented systems while acknowledging platform-specific learning.
Role details: Location: Remote, United States or Canada · Compensation: $240,000–$262,500 plus equity

Direct match to system architecture, automation, tooling, agent orchestration, revenue infrastructure, and translating operating requirements into executable workflows. Position Jay as an operating-systems architect who understands adoption, guardrails, business logic, and front-office automation—not just tool administration. The strategic gap is unambiguous: Ashby needs an operator who builds the revenue operating system from first principles — not one who merely maintains an inherited one.

Days 1–90Q1 — FOUNDATION
Days 91–180Q2 — BUILD
Days 181–270Q3 — SCALE
Days 271–365Q4 — OPTIMIZE
Conservative

Unified pipeline visibility and a reliable forecasting cadence established; manual reporting and triage materially reduced across Ashby's revenue team.

Target

Automated routing, qualification, and follow-up lift speed-to-lead and conversion; forecast accuracy and cross-functional operating cadence reach maturity.

Stretch

Repeatable revenue infrastructure scales Ashby's go-to-market output without proportional headcount, with real-time executive visibility across the funnel.

Strategic Summary

Core Opportunity

Ashby is hiring for Director, GTM Engineering & Systems at a decisive moment. Marketing, Sales, and Customer Success need a trusted, elegant data and automation layer that scales with the company. Without dedicated ownership of the revenue operating system, that pressure compounds as the company grows.

Execution Thesis

Direct match to system architecture, automation, tooling, agent orchestration, revenue infrastructure, and translating operating requirements into executable workflows. Position Jay as an operating-systems architect who understands adoption, guardrails, business logic, and front-office automation—not just tool administration. That is why this application is different — and why a conversation with Ashby is warranted now: Jay builds the operating system from first principles. Production systems, not theory.

Production systems, not theory. Revenue captured, not demos given.