Together Software

Learn from the experts at your company.

Director of Design

$160K - $200K CAD / 0.20%
Toronto / Remote (US)
Job Type
6+ years
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About the role

About Together Software’s mission:

Hi, I’m Nathan, cofounder at Together Software. Learning at work is broken, especially at large or remote companies where employees don’t sit side by side anymore. Together matches employees with other colleagues they would have never otherwise met before, for learning, mentorship and networking. Think of it as peer-to-peer learning. Organizations like the United Nations, Airbnb, the NFL, Disney and 7-11 use us to run mentoring programs to up-skill their employees. 

Our mission is to help every employee find a peer, mentor or expert at their company to learn from.

We are growing quickly and have a rockstar team of 25. Our investors are the same ones that invested in Slack, Coinbase, and Instacart. We launched through Y Combinator in Summer 2019. To learn more about how and why we started Together Software, you can read here.

The Role

The Director of Design will initially be expected to do 50% individual contribution and 50% management of existing team members. As the team grows, you will be responsible for hiring. In the meantime, you will also be producing designs as a member of our product squads.

You will own:

  • Design system and standards

  • Process

  • User Research and Usability Testing

The way we work

  • Quickly
  • Effectively
  • Accountability and high degree of ownership: A startup culture
  • Attitude: Value to customers trumps everything else
  • Opinions: Have a lot of opinions on how to make things better, but comfortable with debate
  • Selflessness: Put the team’s interest in front of your own
  • Standards: We want to work with the best

Types of projects you could be doing

  • Acquisition: Helping us acquire more users and customers by creating growth features like free trials, invites, and more
  • Activation: Improving onboarding and how easy it is to find the perfect mentor (indexing profiles better) or start as an enterprise customer
  • Retention: Maximizing the amount a user learns from other colleagues, such as through meeting agendas, building a user’s expertise in a topic, etc. 

Design Skillset

  • Expert in UI/UX and Prototyping
  • User Research and Usability Testing
  • Design process
  • Design systems


  • 6+ years experience in Product/UI/UX design, management preferred but Staff and Principal roles work
  • Strong references
  • Ability to lead projects independently
  • Strong Figma skills including design system maintenance
  • Experience creating a collaborative design process that focuses on fast iterative design cycles
  • Ability to understand engineering / technical systems / engineering constraints to ensure successful execution
  • You have worked with a product manager and other engineers
  • Bonus: Experience in B2B SaaS

Interviewing at Together

  • Intro screen
  • Portfolio Review
  • Interview with panel (Head of product, director of design, Engineer)
  • Offer
  • Reference check


$160,000-200,000 CAD base + Additional Equity

Perks at Together

4 weeks vacation time

Comprehensive Health Benefits Package

Equity and annual stock bonus plan


Toronto or Vancouver

About Together Software

Who we are

Together creates software for enterprises to run internal employee mentoring programs. Our top use cases include launching an onboarding buddy program, first-time manager mentoring, or high potential talent and diversity programs. For example, the United Nations uses Together to connect employees globally (e.g. Colombia with Italy) over guided sessions to discuss future assignments, rotations, navigating the massive UN system, etc.

We are a Y Combinator Summer 2019 company with ~10 employees, and our customers include Disney, United Nations, Reddit and more.


To make employees and their companies more capable.

Together Software
Team Size:25
Location:Toronto, Canada
Nathan Goldstein
Nathan Goldstein
Matthew Reeves
Matthew Reeves