Director of Product Design at baselane

Baselane is a rapidly growing banking and financial management platform for individual landlords and real estate investors. We are backed by leading FinTech investors, including Matrix Partners, Activant Capital, Collaborative Fund, Conversion Capital, Diagram Ventures, ThomVest, and many FinTech leaders from PayPal, eBay, Google, and more. We are building the future of financial services for the 12+ million individual landlords and real estate investors who own over 25 million homes in the United States. Our mission is to empower landlords with financial services, automated tools, and actionable insights to help them save time, increase their returns, and grow their investment portfolios. We are a seasoned team with deep experience in financial services and technology. We have previously worked at companies including The Boston Consulting Group, Morgan Stanley, Plaid, Harry's, Better, WealthSimple, RBC Ventures, Affirm, Relay, Instawork, and more. Learn more atbaselane.com. About the Role We are seeking a Director of Product Design to lead and grow our product design organization at a pivotal moment in Baselane's journey. This is an AI-first role. We believe AI is fundamentally reshaping how product design gets done, from research and ideation through to high-fidelity execution and dev handoff, and we are looking for a leader who is not just curious about that shift but actively defining it. You will set the AI-first vision for how our design team works, what tools we adopt, and how we ship faster and better than teams operating with traditional workflows. In this role, you will set the design vision, shape the team, and elevate the quality bar across every surface of our product. You will partner closely with our VP of Product, Engineering leadership, and the broader executive team to make design a defining strength of the company. This is a true player-coach role. Alongside leading the team, you will personally own the design work for one of our product pods end-to-end, from research and concepting through final execution. We believe the best design leaders set the bar through their own craft, not just by directing others — and staying close to the customer and the product surface is what makes org-wide standards real rather than aspirational. You will inherit a talented team of product designers, own the design system, and help drive cross-pod best practices. You will be responsible for translating company strategy into design priorities, defining what "great" looks like across the org, and building the structures, rituals, and processes that allow designers to do the best work of their careers. This is a hands-on leadership role. You will spend time in the work, in critique, and in 1:1s in equal measure. You will own headcount planning, recruiting, career paths, and the promotion framework, while also serving as the senior point of contact for design across marketing, sales, partnerships, and other cross-functional teams. This role is based in Toronto. We expect you to come into the office (downtown Toronto) at least twice a week for meetings and working sessions, with the flexibility to work remotely on other days. Responsibilities AI-First Design Leadership • Define Baselane's AI-first approach to product design, from research through dev handoff • Reshape workflows and tooling so AI is woven into the day-to-day, not bolted on • Set quality standards for when to lean on AI and when human judgment leads • Partner with Engineering on design-to-code workflows Strategy & Vision • Set and communicate the design vision and strategy • Translate company priorities into clear design roadmaps • Define what "great" looks like and uphold the quality bar • Own headcount planning and org design Player-Coach: Own a Pod • Personally own the design work for one product pod end-to-end — from research and concepting through final visual design and handoff • Set the bar through your own craft, not just by directing others • Stay close to the customer and the product surface to inform org-wide standards People Management • Lead, coach, and grow the product design team • Run 1:1s, feedback cycles, and team rituals that build a strong design culture • Own career paths, promotions, and end-to-end recruiting Processes & Ways of Working • Evolve design processes and partner cross-functionally with PM, Eng, Marketing, and GTM • Own the design system, Figma structure, and stakeholder feedback loops Must Have • 8+ years of product design experience, with 3+ years leading and scaling design teams at high-growth technology startups • Comfort and proven experience operating as a player-coach, leading a team while personally owning hands-on design work • Hands-on experience leading the adoption of AI tools and AI-first workflows, with a clear point of view on where the field is going • Strong people management skills, including hiring, coaching, performance management, and career development • Excellent design craft across UX, visual, and interaction design, with the ability to provide substantive feedback in critique • Experience defining and evolving design processes, design systems, and ways of working across multiple pods or teams • Excellent communication and collaboration skills, able to influence at the executive level • Fluency with Figma and the modern AI design tooling landscape Nice to Have • Experience designing for FinTech, banking, or financial services products • Experience working across both web and native mobile (iOS and Android) products • Experience partnering closely with founders or executive teams in a Series A to C environment What's in it for You • Be part of a high-impact, high-growth business • Be part of a dynamic, driven team with flat hierarchies and a get-it-done collaborative culture • The opportunity to define design as a core strength of a category-defining FinTech company • Training and development budget to ensure professional growth • Regular team events, game nights, and other social activities Practicals • Team: Product & Design • Reports to: VP of Product • Location: Toronto-based only, 2 days a week in the office. For this position, we will only look at applications from Toronto • Office: We have an office in downtown Toronto and expect you to be in the office at least twice a week • Start date: ASAP Benefits & Perks • Competitive compensation • Equity, ownership in what we are building! • High-quality Medical, Vision, and Dental Insurance • Life Insurance and Disability Coverage • Generous time off