Head of Marketing Full Time

Head of GTM (Marketing & Sales)

Date: April 2026

Location: Canada (Montreal preferred, North-East remote optional)

Commitment: Full-time

Contact: apply@jetty.io | Website: www.jetty.io

About Jetty

Jetty is infrastructure for long-running agentic AI workflows. We turn any AI coding agent into a managed, persistent workflow engine. Teams define missions in plain-English runbooks, and Jetty handles sandboxing, execution, artifact persistence, and evaluation. Think of us as AI hill climbing as a service.

We’re a venture-backed, early-stage team based out of the Mila Ventures space in Montreal — a vibrant hub for AI startups and research. Our leadership includes Rob Cipriani (former COO/CTO of Paper) and Tracy Milner (former CEO of BrainFx). Jonathan Lebensold, our founder and CEO, holds a PhD from McGill/Mila in privacy-preserving ML, was a researcher at Meta AI, and is the author of The React Native Cookbook (O’Reilly).

The Role

Our customers are technical builders: ML engineers, platform teams, and AI-native startups who evaluate tools by reading the docs and trying the API before they ever talk to sales. Growth at Jetty is product-led and your job is to make every step of that journey frictionless and fast.

You are Jetty’s first GTM hire and own the full revenue number. ARR/MRR and free-to-paid conversion are your metrics. You’ll build the funnel from scratch, beginning with developer awareness through to free-tier adoption, paid conversion, and enterprise expansion.

This is a hands-on, zero-to-one role with a strong DevRel core. You won’t be managing a team initially; you’ll be writing the docs, shipping sample runbooks, hanging out in Discord threads, onboarding the first paid customers, and building the PLG playbook that a team eventually scales. You should be as comfortable live-debugging an API integration on a call as you are writing a launch blog post.

We move fast. The right person for this role has a bias to action. You’d rather run a scrappy experiment today than plan a perfect campaign for next month. That doesn’t mean reckless — you reflect, you consult, you course-correct — but your default is to compress the cycle from signal to decision to action.

Responsibilities

• Revenue Ownership: Own ARR/MRR targets. Track, forecast, and report monthly. You are accountable for the number.
• Conversion Pipeline: Build and optimize the free-to-paid funnel. Instrument onboarding flows, run A/B experiments, analyze drop-off points, design upgrade prompts.
• Developer Relations & Community: Engage directly with ML engineers, platform teams, and AI-native builders. Build samples that get developers to value in minutes.
• Developer Marketing: Write blog posts, tutorials, case studies, and technical deep-dives that earn credibility with expert builders. Show, don’t tell.
• Activation & Onboarding: Own the self-serve onboarding experience. Instrument time-to-first-run, identify friction points, and eliminate them.
• Pricing Execution: Own tier packaging, pricing page, upgrade flows, and billing UX.
• Sales (emerging): As the business tier grows, handle outbound and inbound enterprise conversations. Build the sales motion that a future AE/sales team inherits.
• Partnerships: Work with Fractional President on LOI conversations and data aggregator partnerships from a GTM perspective.

You Bring

• 5+ years in developer relations, developer marketing, or product-led growth at a dev tools, API, or infrastructure company
• You’ve built a self-serve conversion funnel from scratch
• A DevRel mindset: you default to teaching, not selling. You’ve built trust in technical communities by shipping useful content, not campaigns
• Excellent writing skills — you produce developer docs, blog posts, and tutorials that technical builders actually want to read
• Data-driven: you instrument funnels, read dashboards, and make decisions based on activation metrics, not vibes
• Comfort with direct sales conversations
• Strong technical chops: you can read API docs, write code snippets, modify onboarding
• Nice to Have
• Experience with AI/ML developer tools, evaluation platforms, or MLOps
• Hands-on experience with LLM APIs, agent frameworks, or OpenAI-compatible tooling
• Track record growing a developer community or open-source project’s adoption
• Experience marketing to both developer and non-technical audiences
• Network in the AI/ML developer community

What we Offer

• We’re early — and that’s the opportunity.
• Hybrid work environment out of Mila Ventures (Montreal)
• Generous paid time off, including a full company shutdown over the holidays
• Flexible, adult work culture — we trust you to manage your time; we care about outcomes
• Competitive salary plus meaningful equity

And the part that matters most:

• You’ll own GTM from day one — not inherit it
• You’ll work directly with founders and leadership, with real influence on company direction
• You’ll help define how Jetty is brought to market
• You’ll join at the inflection point: post-seed, pre-scale, with early momentum and a lot of surface area to shape

This is a rare chance to be one of the first hires at a company with strong technical foundations and ambitious goals — building alongside a small team that cares deeply about what we’re creating.