Senior Engineering Manager - Fintech, Lodging

Hopper•Toronto, ON

1d•CA$325,000 - CA$430,000•Remote

About The Position

At HTS, we're rebuilding how travelers shop and book trips — and reshaping how hotel distributors, chains, and OTAs monetize flexibility. Hotels CFAR (Cancel For Any Reason) is one of HTS's fastest-growing fintech products: a cancellation service embedded directly into partner booking flows, letting travelers cancel for any reason and receive a refund, no questions asked. It's a B2B2C product — sold through partners, exercised by travelers, and powered by HTS. We're looking for an engineering leader who can do two things at once: run a high-performing product team building durable, scalable systems, and be a credible, partner-facing technical leader who can sit across the table from a partner's CTO, scope an integration, and ship it. This is an AI-era engineering leadership role, and the shape of the job reflects that: Small team, high leverage. You'll lead a tight team of ~3 engineers max. We're not scaling headcount linearly with scope — we're scaling output through AI tooling, sharper prioritization, and senior engineers operating with more autonomy. You ship, too. When you're not in partner-facing calls or unblocking the team, you're producing actual artifacts with AI — prototypes, integration scaffolding, technical specs, partner-facing API examples, internal tooling. The bar is "manager who codes with AI," not "manager who reviews PRs from a distance." Blended roles are the new normal. Engineers on this team have a real voice in product direction, and non-technical partners (PMs, Solutions, even Sales) contribute code in narrow ways with AI assistance. You'll lean into this — coach engineers on product thinking, set guardrails for non-engineer contributions, and treat the org chart as a guideline, not a wall.

Requirements

Experience leading engineering teams building B2B/B2B2C platforms with real, named external partners on the other side — not just internal stakeholders
A strong technical background across backend systems (APIs, orchestration, distributed systems), frontend SDKs / embedded UI, and cloud infrastructure
Direct experience as a partner/customer-facing technical leader — running solutioning calls, scoping integrations, owning SLAs, and unblocking deployments
Comfort with fintech, insurance-adjacent, or transactional products — money movement, refunds, pricing engines, contracts, audit trails
Experience with Scala or Java, REST APIs, OAuth2.0, and cloud infrastructure (GCP, AWS); frontend exposure (React, JS/TS) for SDK and merchandising work
A collaborative, product-minded approach — able to partner closely with Sales, Product, Risk, and Ops without losing engineering rigor
A bias for action and a passion for mentoring and growing senior engineering talent

Nice To Haves

Familiarity with the travel distribution landscapes a bonus — booking engines, agent portals, bedbanks, OTAs, PSS/inventory platforms (Sabre, Amadeus), or hotel CRS/chain systems — is a strong plus

Responsibilities

Lead the architecture, development, and rollout of the Hotels CFAR platform — including offer/pricing/order/exercise APIs, the merchandising and UI SDK layer, synthetic rate bundling, and the exercise/payout infrastructure
Own partner integrations end-to-end: scope technical solutions, lead solutioning calls, design integration patterns, and partner with sales and Solutions to move partners from Discovery → Solutioning → Development → Live
Drive the foundation work that lets us scale: partner management portal, configuration tooling, self-serve onboarding — the infrastructure that decouples partner growth from engineering headcount
Be the senior technical voice in partner conversations — translate between partner engineering teams, our APIs, and our product strategy; own SLAs, performance, and partner-specific requirements
Partner with Product, Risk/Pricing, Ops, and GTM to align engineering output to business outcomes: attach rate, contribution profit, partner launch velocity, and loss ratio
Foster technical excellence — architecture reviews, mentorship, raising the bar on the senior ICs and tech leads on the team

Benefits

Well-funded and proven startup with large ambitions, competitive salary and upsides of pre-IPO equity packages.
Hopper covers 100% of the premiums for group insurance plan.
Hopper offers life, short term and long term disability coverage.
HSA that covers eligible medical and dental expenses.
All employees and dependents have access to Dialogue’s telemedicine services, anytime, anywhere.
All employees have access to an RRSP plan with automatic pre-tax withdrawals per pay.
Very generous parental leave, much above industry standards!
Unlimited PTO.
Carrot Cash travel stipend.
Access to co-working space on demand through FlexDesk AND Work-from-home stipend.
Entrepreneurial culture where pushing limits and taking risks is everyday business.
Open communication with management and company leadership.
Small, dynamic teams = massive impact.