Rockstar is recruiting for a mission-driven, venture-backed SaaS/AI company that is transforming the future of work. This client leverages cutting-edge artificial intelligence to connect people to meaningful careers and help industries access the talent they need to thrive. With a team of 30-50 professionals across the US and Canada, and main hubs in New York and Toronto, the company partners with workforce development agencies, government organizations, and employers to deliver personalized, AI-powered career guidance. The company is well-funded, having grown from 0 to 1 without external capital before raising a significant round led by JP Morgan. Rockstar is proud to support this client in their mission to unlock pathways between talent and opportunity and shape the future of work.

Join a mission-driven team that's using cutting-edge AI to solve one of the most urgent challenges of our time: connecting people to meaningful careers and industries to the talent they need to thrive.

A Lead Product Designer (with bias towards research and testing) is sought to join the team. Candidates who are passionate about design, enjoy having fun, and are results-oriented are encouraged to apply.

Important note: Data shows that men on average apply for a role if they meet 3/10 requirements while women often only do so if it’s 10/10. The company works hard to be clear and specific about what roles include and demand, and encourages applications from those who see a strong (but not necessarily perfect) fit between themselves and the opportunity.

The Role

As the sole product designer, this individual will play a foundational role in shaping the product experience from end to end. The Lead Product Designer will work closely with product managers, engineers, and users to design intuitive, impactful, and accessible experiences across platforms. From early research and user testing to detailed flows and high-fidelity prototypes, this role owns the full product discovery and design process and helps drive product decisions through insight and craft. A systems mindset is essential, as the design system will evolve as the company scales.

Your Skills and Experience

• Energized by the intensity and purpose of a high-growth startup and willing to roll up sleeves to help the team succeed.

• Excited by the opportunity to be the only dedicated product designer (for now!), and confident in managing the full stack of product design—from research to execution.

• Strong skills in product discovery and research, including:

• Running end-to-end user testing to inform product direction and iteration

• Synthesizing qualitative and quantitative insights into actionable product recommendations

• Conducting usability testing and communicating findings clearly to cross-functional teams

• Believes design is a tool to solve problems and drive impact, not just make things look pretty.

• Thrives in ideation sessions as well as in focused, heads-down execution of high-quality design outputs.

• Brings significant experience in product design and in building, managing, and evolving design systems.

• Detail-oriented and collaborative, supporting PMs and engineers by thinking through edge cases and user flows to ensure high-quality feature testing and implementation.

• Comfortable designing for multiple platforms, incorporating responsiveness, localization/internationalization, and accessibility (WCAG 2.0 AA) into work.

• Familiar with AI tools, early-stage prototyping, and video workflows to accelerate the design process.

• Adept with Figma, Loveable, Notion, and Miro.

• Bonus: Experience in B2B2C software, navigating complex user workflows, or designing for mobile (iOS/Android) platforms.

Location

This role will be based in Toronto, and candidates willing to relocate to Toronto on a reasonable timeline with a relocation package will be considered.

Hybrid Work Policy

The company places a high value on weekly face-to-face collaboration and team building. While daily office presence is not expected, the team comes in 1-2 times a week, usually on Wednesdays. The office is conveniently located at 325 Front St West (a short walk from Union Station).

Compensation

The base salary range for this role is $120,000 to $145,000 CAD, plus equity. This range reflects the varying levels of expertise and responsibilities that will be determined through the interview process, based on applied experience and other criteria established by the hiring committee.

Hiring Journey

The company believes in designing intentional and rigorous hiring journeys to help candidates determine if this is the best role and organization for them, based on unique skills, mindset, and experiences. The organization operates at high velocity with high intensity and wants candidates to have an accurate taste of what that feels like before joining.

Every hiring journey consists of thoughtfully crafted steps. For this role, that might look like:

1. Online Application

2. Initial Screen with Director of People & Culture

3. 1st Interview with Hiring Manager

4. Performance Challenge take-home assignment

5. Interview with team members from Product & Data

6. Final 1:1 Interview with CEO

Generally, this entire process takes around 4 weeks, although the timing can vary due to specific candidate circumstances.

Company Profile

To provide transparency, here is a basic picture of the company profile (size, stage, structure, etc.):

1. Problem Domain: Future of Work / Workforce Development - important that the problem domain interests candidates even if they haven’t worked in the space before.

2. Industry: SaaS / AI - technology and data are at the core of what is built.

3. Customers: Partners include workforce development agencies, government agencies, and employers/enterprises.

4. Structure: The organization is structured around the following key departments: Growth, Customer Success, Product, Engineering, Data, People & Culture, Finance & Operations.

5. Team: The team consists of 30-50 members across the US and Canada with main hubs in New York and Toronto.

6. Funding: The company was built from 0 to 1 with no external capital (a rare feat for tech startups) and has subsequently raised one round of funding led by JP Morgan, fueling significant growth.

Core Principles

• Be Curious

• Drive to Outcomes

• Raise the Bar

• Speed Matters

• Own It

• We Over Me

About the Company

The company is on a mission to unlock pathways between talent and opportunity using the power of AI. The focus is on personalized, AI-powered career guidance for job seekers, emphasizing skills over extensive resumes, and partnering with workforce development partners, governments, and employers to level access to opportunity.

This is a growing, venture-backed company focused on using technology to improve the lives and outcomes for people going through career transitions. The team is small and driven, united by a commitment to job seekers and workforce ecosystems. The company is not just building a business; it is shaping the future of work.

Accessibility & Equal Opportunity

The company will ensure that individuals with disabilities are provided reasonable accommodation to participate in the job application or interview process, perform essential job functions, and receive other benefits and privileges of employment. Please contact the company to request an accommodation.

The company is proud to be an equal opportunity workplace. Diversity is celebrated and there is a commitment to creating an inclusive environment for all employees. Discrimination on the basis of race, religion, color, gender identity, sexual orientation, age, disability, veteran status, or other applicable legally protected characteristics is not tolerated. People of different backgrounds, experiences, abilities, and perspectives are encouraged to apply.