Tech Lead at Fleet – Toronto

We're building vertical Fintech & AI for the $100B+ spent on ground transportation annually. We're starting with modernizing commuter benefits, plagued by costly, outdated solutions with low adoption that leave billions of dollars of tax and tons of emissions savings on the table. A congruence of new compliance regulation, return-to-office commutes, sustainability pressure, and government incentives has created the perfect market timing with compounding tailwinds for us. Fleet's vertical-SaaS and Fintech make it 10x easier for employers to comply with new mandates while boosting employee adoption by 3-4x compared to legacy solutions. We recently closed an oversubscribed Seed round led by one of the most respected climate tech venture firms alongside an extremely strong bench of co-investors and angels across Fintech, HR, Sustainability, and Transportation.

• Pivoted into Commuter Benefits in Jan 2023 due to new regulation
• Quick traction, early PMF w/ strong tailwinds: grew from 1 ? 10 customers w/ ~$250k arr in 8 mos
• Can learn from playbook used in adjacent benefits spaces like 401ks (Guideline, Human Interest), Family Leave (Sparrow), and Fintech charge cards (Brex, Ramp)
• Unique intersection of Climate Tech x Fintech x HR/Benefits x Transportation
• Early mover in a neglected, sleepy space with mostly large legacy competitors from 90s
• Catching a multi-decade wave transitioning to a compliance-driven market
• Unparalleled founder-market fit with 10+ years in transportation tech
• Founding team-level upside, growing team from 4 ? 12 this year
• Top-tier lead investor with decades of climate tech experience and among the most respected venture firms in climate investing
• Extremely strong bench of co-investors, angels, and advisors with leaders in each vertical incl. founders of unicorns and C-level execs across Fintech, HR, Sustainability, & Transportation

?? Superpower

• Experience scaling an engineering team from scratch

?? Bonus

• Startup experience (especially if CTO or founding engineer)
• Can recruit existing/prior colleagues
• Domain experience in – Fintech, Payments, Corporate Cards, HR / Benefits Tech
• Passion for Sustainability/Climate Tech, AI, Mobility/Transportation
• Located in Toronto, NYC, or SF

? Required

• 3+ years of experience in a team lead role
• track record of building and deploying successful web services at scale

IC/Dev Responsibilities

• Tech team lead contributor
• Build for scale
• Lead by example w/ best dev practices
• Incorporate AI-enabled dev tools into team workflows

Company Building

• Hiring engineers
• Iterating on Engineering team processes
• Full ownership of Engineering org
• (bonus) Short-term co-ownership of Product Roadmap
• (bonus) Involved in customer convos and discovery

Current Engineering Team

opportunity to evaluate existing team + hiring process to decide what to keep/replace

• 1 x Full-Stack Engineer (4 yrs experience)
• [currently hiring] 2 Sr. SWEs (6+ yrs experience)
• + 2 Waterloo Interns

Tech Stack

opportunity to evaluate existing codebase to decide what to keep/replace

• Python, Django for RESTful API
• Postgres, PostGIS
• React, Typescript for frontend
• React Native for mobile
• AWS; Redis; Docker