Vice President of Software Engineering

Ultrassure is building AI-powered contract intelligence for the insurance and reinsurance industry. Our platform, UltraContract, is trusted by insurers, MGAs, brokers, and reinsurers processing $3B+ in premium across North America, the Caribbean, and the United Kingdom. We’ve raised a pre-seed round and are on track to close our seed this summer. We’re a small, focused team that ships daily and moves fast.

The Role

We’re looking for a VP Engineering to lead product engineering at Ultrassure. You’ll own delivery, technical direction, and team growth while staying close to the code and the product. This is a hands‑on leadership role in a ship‑daily environment where engineering is a core advantage.

You’ll work directly with the CEO and product leadership to turn customer needs into a reliable, scalable platform, and you’ll build the systems and culture that let a small team move fast without breaking things.

What You’ll Do

• Own end‑to‑end execution across the UltraContract product: frontend, backend, infrastructure, and AI integrations
• Set technical strategy and architecture for scalability, reliability, and speed of iteration
• Establish a high‑velocity engineering operating rhythm (tight loops, fast releases, excellent quality)
• Build and coach a strong engineering team: hiring, onboarding, career development, performance management
• Create and maintain engineering standards: code quality, observability, security, and incident response
• Partner with stakeholders across the business to prioritize the roadmap and deliver customer value
• Drive pragmatic DevOps and platform improvements to support ingest pipelines, deployments, and uptime
• Use AI developer tooling effectively and set best practices for shipping with it day to day

Our Stack

Frontend

• Next.js, TypeScript
• Vue, JavaScript (Note: replace with Django, Python if preferred)

AI & Infrastructure

• AWS and Azure for ingest orchestration

Development Tools

• Claude Code and Codex, we ship with AI tooling daily

What We’re Looking For

• 7+ years building production software, including leadership experience (team lead, manager, director, or VP)
• Strong full‑stack and systems instincts: you can guide architecture decisions and unblock the team quickly
• Demonstrated ability to run high‑ownership teams that ship frequently and reliably
• Experience with TypeScript/React/Next.js and Python/Django (or very close equivalents)
• Comfort with cloud infrastructure and DevOps practices across AWS, Azure, or GCP
• Experience integrating AI/ML APIs and tooling into real product workflows
• Excellent judgment on tradeoffs: speed vs. robustness, build vs. buy, iteration vs. refactor
• Based in Toronto and able to work from our Bay & King office 3 days per week

What We Offer

• Competitive salary and meaningful equity in an early‑stage company
• Gym and squash memberships included
• Hybrid work with a central downtown office at Bay & King
• High autonomy, high impact, your work ships and matters