GTM Engineer

This is Plane's first dedicated GTM hire, and you will build the function from the ground up. You own the outbound engine end to end, building systems and AI agents that turn an ICP definition into qualified meetings on the calendar. You work fluently with LLM providers like Anthropic and OpenAI, wire them into your outbound stack, and build custom systems whenever off-the-shelf tools fall short.

The craft here is cold outbound done well: strong data, real personalization, healthy email authority, and sequencing that earns replies. The audience is unforgiving. Plane sells to engineering, product, and IT teams, and to buyers with real compliance and self-hosting needs. These people delete generic outreach on sight. Your job is to make outbound specific enough, timed well enough, and relevant enough that a skeptical technical buyer replies.

Tools you should know This role moves fast and assumes fluency across the modern outbound stack from day one. You should be experienced and comfortable with:

• Data and enrichment: Clay or an equivalent orchestration platform
• Cold email and sequencing: multichannel cold email tools and LinkedIn outreach such as HeyReach
• Email authority and deliverability: domains, warmup, rotation, SPF, DKIM, DMARC, and sender reputation
• AI: LLM providers like Anthropic and OpenAI, and building agents or systems on top of them
• CRM: HubSpot

Role and responsibilities Outbound systems and list building

• Turn ICP definitions into targeted account and contact lists
• Source, scrape, and structure prospecting data from multiple providers
• Own the full path from raw list to live sequence, and keep it clean
• Segment by fit, signal, and deployment motion (Cloud, Self-hosted, Air-gapped)

Data and enrichment

• Build enrichment pipelines in Clay and similar tools that maximize coverage and minimize cost per record
• Use AI to research accounts and generate qualification and personalization inputs
• Integrate your data layer with the CRM and sequencing tools through native connectors and APIs
• Guard data quality: catch bad fits, dead emails, and duplicates before they reach a sequence

Cold email and sequencing

• Build multichannel cold email and LinkedIn sequences (email plus tools like HeyReach) that read as written by a human
• Engineer personalization at scale using enrichment and signal, not mail-merge tokens
• Run structured experiments on copy, cadence, channel mix, and offer
• Keep volume and relevance in balance so reply rates hold as you scale

Email authority and deliverability

• Own sender reputation across every domain and inbox you run
• Set up and maintain domains, warmup, rotation, SPF, DKIM, and DMARC
• Monitor bounces, spam placement, and blocklists, and fix problems before they compound
• Protect the primary domain by isolating cold sending infrastructure

AI, agents, and systems

• Use LLMs from Anthropic, OpenAI, and others to research accounts and personalize at scale
• Build agents and custom systems when off-the-shelf tools cannot do the job
• Hold a high relevance bar for a technical audience that punishes generic outreach
• Turn repetitive outbound work into systems that run without you

Signal-based prospecting

• Turn Plane's signals into trigger-based plays: GitHub activity, Docker pulls, self-host installs, community engagement, funding, hiring, and tech-stack changes
• Build sequences that fire when an account shows intent, not on a fixed calendar
• Prioritize accounts by likelihood to buy, not by list order

CRM sync and handoff

• Keep the CRM clean and in sync with your data and sequencing layers
• Route positive replies to Sales with full context and no delay
• Instrument attribution from sequence to reply to meeting to pipeline

Measurement

• Track reply rate, positive reply rate, meetings booked, pipeline created, and cost per meeting
• Report what works, for which segment, at what cost
• Kill what underperforms and scale what converts

You will be successful if you...

• Book qualified meetings and pipeline from outbound, repeatably.
• Keep email authority and reply rates healthy as volume grows.
• Make personalization that gets replies from technical buyers, not spam complaints.
• Build outbound systems and agents that scale without quality dropping.