Build outbound automation for Plane from Canada, using cold outreach, data enrichment, and AI systems to create qualified pipeline.

As Plane’s first dedicated GTM Engineer, you will build the function from the ground up. You will sell to engineering, product, and IT teams, including buyers requiring compliance and self-hosting. The work combines trigger-based prospecting, deliverability, and technical systems.

Key Responsibilities:

- Own outbound, qualified meetings, and pipeline at known cost
- Turn GitHub, Docker, and installation signals into timed plays
- Segment Cloud, self-hosted, and air-gapped deployment motions
- Maintain domains, warmup, SPF, DKIM, DMARC, and blocklists
- Build research agents using LLM providers and custom tooling

Requirements:

- Proven cold outbound experience producing measurable pipeline
- Experience building enrichment workflows in Clay or equivalent platforms
- Practical ownership of deliverability infrastructure and sender reputation
- Experience shipping Anthropic or OpenAI models into systems
- Ability to connect SQL, APIs, webhooks, CRM, and sequencing tools

Apply outbound engineering, deliverability, and AI automation skills to Plane’s open-source work infrastructure from Canada.

📌 GTM Engineer Outbound Automation (Calgary)
🏢 plane
📍 Calgary