Founding / Sr. Software Engineer
Cedar • Toronto, Ontario, CanadaAbout Cedar
Cedar is creating the most significant innovation in home affordability since the 30-year mortgage. By reimagining the land lease as a consumer-first model, Cedar makes homeownership more accessible and sustainable for a wider range of buyers. We are actually solving home affordability at scale – this is one of the most pressing problems in our country today and we are fixing it. Our structure meaningfully reduces both the upfront cost of purchasing a home and monthly costs. We expand the path to ownership for people who have been locked out of traditional markets and help existing homeowners access their equity at cost well below existing solutions. Cedar is already making a substantial impact for homeowners and we have material backing from top investors. Join our fast-growing and high-preforming team as we fundamentally change how people buy homes and create a new institutional asset class.
About the Role
As a Founding Senior Software Engineer at Cedar, you will be one of the earliest technical leaders in the company and a core partner in shaping both the product and the engineering organization. This role is expected to grow into a CTO-level position as the company scales. You will design and build core systems while helping define product direction, technical strategy, and execution standards. This is a high-trust, high-expectation role for an engineer who wants real ownership: shaping architecture, influencing product vision, shipping critical software, and building the team that follows.
You will operate end-to-end—from ambiguous problem definition through production deployment—balancing speed, correctness, and long-term durability, while working closely with product leadership to ensure what we build solves real customer problems.
What You’ll Do
Architect, build, test, and deploy core platform systems
Help define product direction by translating customer and business needs into technical solutions
Own critical initiatives from concept through production, spanning product, engineering, and operations
Establish engineering and product execution standards for quality, reliability, and velocity
Partner closely with product to shape roadmap, sequencing, and tradeoffs
Recruit, mentor, and help scale a high-performing engineering team
Make pragmatic decisions under real-world constraints while protecting long-term system health
What We Need
We are looking for a senior engineer with strong technical judgment who has operated close to the metal in fast-growing, high-accountability environments. You should be comfortable owning complex systems end-to-end, making architectural tradeoffs early, and operating in domains where correctness, security, and reliability matter.
This role requires someone who has seen systems scale—technically and organizationally—and understands how early decisions around data models, APIs, and workflows compound over time. You should bring a practical bias toward simplicity, a strong sense of responsibility for production systems, and the ability to collaborate tightly with product and business partners.
Experience building in fintech, prop-tech, mortgage, payments, or other regulated or financially sensitive environments is a meaningful advantage. Exposure to consumer-facing products—where usability, trust, and edge cases matter—is especially valuable.
Qualifications
7+ years of experience shipping and operating production software
Proven ability to design and own complex systems end-to-end
Experience in high-growth startups or similarly demanding environments
Strong systems thinking and sound engineering judgment
Prior experience mentoring engineers or contributing to hiring decisions
Why Choose Cedar? - This is a standard blurb on why someone should work with Cedar
Take real ownership early — the work is not theoretical
Grow through direct feedback, rigorous debate, and steep responsibility
Be pushed to develop judgment, not just skills
Build a track record that compounds — responsibility scales with performance
Cedar is built for people who want to operate at a very high level on work that matters. We run a true owner’s culture: high standards, direct feedback, fast iteration, and accountability to outcomes. You’ll have real responsibility early, you’ll be expected to think—not just execute—and you’ll be surrounded by teammates who push hard and care deeply about excellence.
This is not a company for people who need perfect clarity, gentle consensus, or predictable routines. The pace is fast, the problems are complex, and the bar is high. But the upside is rare: steep growth, meaningful autonomy, and the chance to do career-defining work with a team that treats the mission seriously and rewards success well.
If you want comfort, you won’t like it here. If you want to build, learn, and win—Cedar is the place.