Careers at Windkey

Vision

Talk to any developer in 2026, and they’ll tell you that programming with the latest coding agents feels like magic. That’s the exact word they use, again and again.

Windkey is bringing this magic to finance.

We’re building a flexible workspace for finance work, that can do “anything” a finance professional needs, efficiently and well, at the highest levels of quality and accuracy, and with zero compromise on safety, security and data governance.

We’re hiring founding and early team members to help bring this vision into reality. Join us!

Company

Windkey is an early-stage tech startup with in-person hubs in Toronto and New York. Our founders are Abraham Thomas, who previously co-founded Quandl (acquired by Nasdaq) and Jason Byck, who was Quandl’s CTO. Abraham and Jason have strong domain expertise (finance, data, distribution, tech) and rich industry networks.

We’ve raised USD 5M in pre-seed financing from Uncork Capital (investors in Groq, GPTZero, Tailscale, Gamma, Coder, Loft, Fitbit, Sendgrid, Eventbrite, Postmates, Poshmark, Docsend), Flex Capital (investors in Vercel, Mercury, Supabase, Replit, CodeRabbit, Perplexity, AngelList, Chime, Datavant, Airbyte), and Northside Ventures (investors in Datacurve, Boardy and more) with participation from other funds and angels.

Culture

Take ownership of meaningful problems with exceptional colleagues who are curious, collegial, and kind.

Every part of this sentence is essential:

• You’ll take ownership of product and business outcomes from end to end, using your judgement, expertise and taste.
• You’ll solve problems that are important for our customers, novel and interesting, technically challenging, and valuable to the business.
• You’ll work with, benefit from, and thrive alongside exceptional colleagues who attract other top performers like you.
• You’ll work in a high-performance but non-toxic environment, that marries extremely ambitious goals with secure high-trust execution.

Expectations

Windkey is not for everyone. We believe excellent people are happiest when working with other excellent people, and we’re building a company to enable this. We have high standards that we hold each other to, with grace but also with honesty.

We seek team members who operate with energy and at a consistently high velocity; who believe in excellence and care deeply about the craft of what they do; who embrace responsibility and ownership while delivering outstanding results; who are excited by what we’re building; and who are competitive and want to win.

We also seek team members who are curious and thoughtful; who are comfortable operating under ambiguity and imperfect information; who appreciate trade-offs, nuance, and distributional thinking; who are willing to admit error and course-correct; and who act like adults.

These are not easy. It’s best to specify the difficult parts up front, rather than waste your time and ours.

Role

We’re hiring for early-career roles in engineering and GTM.

Here’s what we’re looking for:

• Velocity, enthusiasm, and bias-to-action, combined with a high quality bar and meticulous attention to detail.
• Strong AI-native coding skills (for engineers) and fluent tool usage (for everyone), demonstrated in production.
• Experience building or distributing or both, within and outside the classroom. Show us what you’ve done!
• Excellent communication skills, both written and verbal.

If this interests you, please email us at careers@windkey.ai.