The Opportunity

Toronto, ON
Can work Remote
Full-time - Permanent

Marcus Daniels, Lauren Robinson and I (Ben Yoskovitz) founded Highline Beta with the mission of building better ventures. Our thesis is this: by unlocking the assets within large companies, we can help them grow beyond their core through internal and external innovation. 

We're blending an innovation consulting business with a venture studio and venture capital business, giving us the ability to build new businesses in a number of ways. We're building a team of exceptional people that are excited by the prospect of working at a company that's doing something different and delivering incredible value. 

We love building businesses. We love the mission of finding meaningful problems to solve, and then solving them with the right solutions. We love helping others achieve their goals, whether it's an innovation leader inside a large company or a founder that's scaling her startup. Everything is a puzzle that needs to be figured out, and we spend our time at Highline Beta putting the puzzles together.

Our Venture Studio is focused on building new startups - quickly validating new opportunities and launching them alongside top-notch, fundable founders. These startups have access to our corporate partners as well as our venture capital fund. Together, we co-create new startups that have unfair advantages in the market. For example, we recently co-created Relay in collaboration with American Family Insurance to transform how reinsurance deals are made.

As the Head of Design, you will report to the Founding Partner & CPO, Ben Yoskovitz, and be responsible for helping founders of seed-stage startups build and grow their business. You will join as an experienced designer with a proven ability to grow early-stage B2C and B2B startups from first users through to project-market fit. You will join the Venture Studio team and work alongside senior leaders from product managers like Chris Chae, engineers like Gary Fung, and collaborate with Senior leadership like Founding Partner & CEO, Marcus Daniels. If you are passionate about building businesses that solve meaningful problems and drive real impact, balancing both user needs and business outcomes, this role is for you. 

What you'll do


  • Generate, validate and evaluate startup opportunities
  • Support founders in building, launching and growing their startups from idea to seed stage 
  • Design and execute experiments to validate key assumptions around desirability, viability, and feasibility of business ideas
  • Conduct customer and market research, product discovery, prototyping, demand testing, and business model development
  • Use design thinking and hypothesis-driven frameworks to make insight-driven design decisions
  • Form an opinion on a potential founder's mission and idea, capabilities, and business model 
  • Advise and provide guidance to founders on design vision and strategy
  • Product design, brand development, and creation of MVP through public launch and seed investment
  • Support recruitment of talented and conducting due diligence on entrepreneurs looking for their next adventure
  • Write Studio investment memos and present opportunities to Partners

What you'll need


  • 8+ years of broad experience in product design, including user research, service design, interaction design, and visual design.
  • You have deep experience with launching new products and/or businesses from scratch and have practical knowledge of startup innovation frameworks (e.g. Lean, JTBD, DVF, etc.)
  • You have worked in a hypothesis-driven product development environment and are comfortable working alongside product managers and engineers in an iterative, agile manner.
  • You are adept at using "no code" website building tools such as Webflow, Wix, Squarespace and Shopify.
  • You have a design portfolio that includes a variety of mobile and web applications in both B2C and B2B contexts.
  • You have a growth mindset with the drive and discipline to master your craft every day.

A little bit about us

Highline Beta

At Highline Beta, we celebrate our inclusive work environment and welcome members of all backgrounds and perspectives to apply. We are committed to providing reasonable accommodations and will work with you to meet your needs. If you are a person with a disability and require assistance during the application process, please don't hesitate to reach out! 

Are you interested?

Work With Us

Interview Process

  1. Role Alignment with Ben Yoskovitz, CPO + Founding Partner
  2. Remote interview with a member of the Venture Studio team
  3. Panel interview with cross-functional HLB team members, including case study virtual white-boarding session
  4. Remote final interview with Marcus Daniels, CEO + Founding Partner, and Ben Yoskovitz, CPO + Founding Partner
  5. Conduct references & security checks
  6. Offer

Following the advice of Canadian health authorities, to mitigate the risk of potential spread of COVID-19 and support social distancing, all recruiting activities including interviews and new hire onboarding will be conducted virtually.

Working with Us

  • Competitive salary and employer-paid health benefits, including paid parental leave and access to Inkblot Therapy
  • Stock Options
  • Bonus based on performance of role and company
  • 4 weeks of vacation per year plus additional flex days if needed
  • A diverse team who is committed to inclusion

Salary: $150,000 base salary + potential startup equity incentives + potential variable cash bonus

Highline Beta is an accelerator builder, a venture studio, and a corporate innovation firm. We identify and build new venture & growth opportunities.

  • We are advisors and builders.
  • We are passionate about innovation and growing businesses. 
  • We are genuinely curious.
Apply Now