Gtm Engineer Outbound Automation

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 costTurn GitHub, Docker, and installation signals into timed playsSegment Cloud, self-hosted, and air-gapped deployment motionsMaintain domains, warmup, SPF, DKIM, DMARC, and blocklistsBuild research agents using LLM providers and custom toolingRequirements:
Proven cold outbound experience producing measurable pipelineExperience building enrichment workflows in Clay or equivalent platformsPractical ownership of deliverability infrastructure and sender reputationExperience shipping Anthropic or OpenAI models into systemsAbility to connect SQL, APIs, webhooks, CRM, and sequencing toolsApply outbound engineering, deliverability, and AI automation skills to Plane’s open-source work infrastructure from Canada.
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