Principle Engineer / VP of Engineering in Toronto

Location: Remote. Canada or US, Eastern-time overlap

Reports to: Founder (product direction) and General Manager (cadence and priorities)

Team: 4 engineers plus contractors today. You grow it to 7 or 8. Split: 50% in the code, 50% working on the system rather than in it.

About Us: Foreplay.co redefines the way marketers engage with ads—empowering them to save ads into a personalized swipe file, curate briefs, and spy on competitors’ entire ad libraries. Founded in 2021, Foreplay is a fast-growing, bootstrapped, and profitable SaaS company building the future of ad creative workflows. Based in Toronto, Canada, with a fully remote team across multiple countries, we’re a scrappy and fast-moving startup focused on helping marketers discover, analyze, organize, and leverage the best-performing ads. Today, more than 10,000 marketers, brands, and agencies use Foreplay to make their creative research and advertising workflows faster and more effective.

The Role: This is a player-coach role. Half your week is in the code. The other half is deciding what the code should be, who builds it, and how. You inherit a real distributed system: an event-driven pipeline that ingests about 2 million new unique ads a day from public ad libraries, enriches them on a self-hosted GPU fleet (transcription, creative classification, embeddings), and projects them into a 220-million-document semantic search index, a 50-billion-row ClickHouse warehouse, and a public API and MCP server that sell the corpus as data. Alongside it sits Lens, a performance-analytics product that pulls directly from Meta, TikTok, and LinkedIn ad accounts and compiles metric definitions into ClickHouse SQL at query time. It runs on about 80 bare-metal servers, across roughly 40 services and 70 repositories, in Node, Python, and Vue. Your job is not to rewrite it. Your job is to make it boring to operate, retire what should be retired, and ship on top of it faster than we ever have, using agents to do most of the typing. By the end of your first quarter, routine code at Foreplay should be written and routine bugs squashed without a human in the loop, and the humans should be spending their time on the problems that deserve them.

What You Will Own:

• The platform: Every service, every queue, every store, every server. You decide what gets consolidated, what gets retired, and what gets left alone. You own uptime, cost, and the fact that nobody at Foreplay should learn about an outage from a customer.
• The way we build: You define how work gets scoped, how agents are directed, how their output is reviewed, and how that scales across 70 repos and a growing team. Work is scoped as projects and jobs-to-be-done in Linear today; you will make it AI-first and AI-led.
• The team: Five engineers today, each of whom owns a piece of the system nobody else knows. You grow the team to 7 or 8, run their 1:1s, set their scorecards, and hold the standard.
• Shipping: You work with the founder and GM on what gets built, then you make sure it ships. You will personally ship things customers can see. Product opinion is expected.

Who we are looking for:

• At least 5 years shipping production code before coding agents existed.
• Fully bought in on agentic software development, with a specific and defensible opinion on how agent-driven work should be scoped, implemented, reviewed, and scaled.
• Still in the code and planning to stay there.
• Language-agnostic. Our stack is Node, Python, and Vue on Cloudflare, Kafka, ClickHouse, Postgres, MySQL, Firestore, and Elasticsearch.
• You have operated event-driven or streaming systems at real volume.
• You have product opinions and you argue for them.
• High agency. You default to shipping.

Bonus Points:

• You have led through the shift from manual to agent-driven development somewhere else.
• Background with Google Cloud, Firestore and Cloud Functions.
• MarTech or AdTech background, or you have been a heavy user of tools like ours.

Why people choose Foreplay:

• You’ll build at a scale most engineers only read about.
• You own the platform, the team, and the way software gets built here.
• You’ll define what an AI-first engineering team actually looks like.
• The business is already working. Bootstrapped, profitable, growing 75%+ a year for three years running.

Compensation: Competitive base plus an uncapped performance bonus tied directly to company growth.

How We’ll Measure Success:

• Within 30 days: You have shipped one thing customers can see or feel.
• Within 60 days: Routine code is being written and routine bugs squashed by agents without a human in the loop.
• Within 90 days: There is no single-owner system in the company.
• Within 6 months: The team is 7 or 8. At least one legacy generation of the platform has been retired.
• Within 12 months: Every machine reports its health to one view and alerts reach Slack on a threshold and on silence.

How We’ll Measure Failure:

• Within 30 days: You are still “getting context.”
• Within 60 days: Agents are your personal productivity tool, not the team’s process.
• Within 90 days: You have proposed a large migration or rewrite.
• Within 6 months: Headcount grew but leverage did not.
• Within 12 months: We still learn about outages from customers.