Context Engineering Jobs in Toronto, ON (NOW HIRING)

• Team: 7 direct reports (4 software engineers, 2 quality engineers, and the Platform/DevOps team)
• Partnering closely: 2-person Product team and 4-person GTM team

We've been in the market for more than ten years, we're SOC-2 compliant with a single-tenant architecture, and we do all of it with a deliberately small team. That's the interesting part of this job.

We launched a full rewrite of our Conductor platform a few months ago and are midway through the effort to reach Conductor Modern. Over the next year (or so), this will give us the chance to migrate all our customers and partners to the new version and sunset our old code.

The role

You'll own engineering execution for Conductor : how the team is structured, how work gets from idea to production, and how quickly and reliably we ship. You'll drive the technical strategy and architecture direction, and you'll own the machine that turns that direction into shipped software.

This is a hands‑on leadership role, not a role that manages managers. With six engineers, you'll be in the code, in the reviews, and in the architecture discussions — while also being the person accountable for delivery, hiring, growth, and the team's day‑to‑day health. If you want a position where you can both set long‑term strategy and have immediate day‑to‑day impact, this is the seat.

As part of our modernization, you’ll be directly involved in any remaining architectural and technical decisions for Conductor Modern and be a key part of planning for the customer migration and the ultimate sunsetting of the existing codebase.

This is the third leg of the Sensei Labs stool, along with our established Product and GTM leaders. You’ll work closely with them to shape and implement Product’s vision and to enable our GTM team to sell and deliver value to our customers and partners.

What you’ll own

• Delivery. Planning, sequencing , and shipping against a roadmap you help build with Product. Predictable releases, visible progress, honest tradeoffs.
• The team. Coaching and growing six engineers, running performance and career conversations, hiring as we scale, and keeping the bar high without burning people out.
• Cloud platform and reliability. Architecture, scalability, cost, and operational excellence for a single‑tenant enterprise SaaS platform. Uptime, performance, and security posture are yours. You'll lead our Platform/DevOps team alongside product engineering, setting direction for infrastructure and application architecture, performance and scalability, cloud cost management, and the tooling that the rest of engineering builds on. Uptime, operational excellence, and security posture are yours.
• AI in the product. Partnering with Product on how Harmony AI evolves — agentic workflows, retrieval, evaluation, guardrails, and permission‑aware AI behavior in an enterprise context.
• AI in how we build. Making our SDLC substantially faster and more automated: AI‑assisted coding, code review, and test generation; CI/CD; automated quality gates. We want an engineering org where a small team ships like a large one, and you'll be the one who builds that.
• Engineering–Product partnership. Working shoulder to shoulder with Product on discovery, scope, and sequencing . You’ll be expected to have opinions about the product, not just the plumbing.
• Enterprise trust. Security, compliance, and the technical side of customer and prospect conversations when it matters.

What we're looking forCloud infrastructure and application architecture at depth.

You've architected, built, and operated production cloud SaaS at meaningful scale — not just supervised it. You’re fluent across both layers: the application architecture (service boundaries, data modeling, API design, and the patterns that keep a large codebase evolvable) and the infrastructure underneath it. Hands‑on depth in Azure and/or GCP is essential, along with container orchestration on Kubernetes, infrastructure as code, CI/CD pipelines, networking and identity, and the observability and cost discipline that keep a cloud platform healthy as it grows. You understand multi‑tenancy versus single‑tenancy tradeoffs, data isolation, performance under enterprise load, and what “SOC‑2 compliant” actually costs an engineering team.

Real product instinct.

You've worked in product‑led environments where engineering shapes what gets built. You can push back on a spec, spot the simpler solution, and reason about customer value — especially in complex B2B software where the user is an enterprise operator, not a consumer.

Team leadership with your hands still dirty.

You've led and grew engineering teams (roughly 5–20 people) as a player‑coach. You’ve hired well, given hard feedback, and relentlessly tuned the delivery process.

You've shipped AI or LLM‑backed features into production — and you've also rebuilt how a team works using AI‑assisted development and automated SDLC tooling. You can tell the difference between AI that creates leverage and AI that creates cleanup work.

Startup temperament.

You’re comfortable being both the strategist and the person who fixes the flaky test. You’d rather own an outcome than a headcount number.

Nice to have

• Enterprise PPM , EPMO , transformation, or professional services domain experience
• Experience with Microsoft 365 / SAP / Jira / Power BI integration ecosystems
• Background in selling or supporting technical evaluations with Fortune 500 or PE buyers
• Experience taking a mature product through an AI‑era re‑platforming or modernization

Your first year

• By 90 days — you know the codebase, the team, and the roadmap ; you've shipped something meaningful yourself; and you've given us a clear read on our biggest delivery and technical risks.
• By 6 months — the development lifecycle is measurably faster, with AI‑assisted workflows and automated quality gates that the team actually uses. Release cadence is predictable.
• By 12 months — engineering is a genuine competitive advantage: shipping AI capability into Conductor at a pace that surprises much larger competitors, with a team that’s grown in both size and capability.

Why this role

Small team, real enterprise customers, an established product, and an unusually good excuse to rebuild how software gets made. You won't be one VP among many, and you won't be managing a slide deck about AI transformation — you’ll be doing it, on a product whose entire premise is helping large organizations actually execute.