We’re Hiring: Head of Engineering

Location: Waterloo, ON    |   Toronto, ON   | San Francisco, CA | Sault Ste. Marie, ON

Job Code: 004-222-1501


Applications are reviewed on a rolling basis. For earliest consideration apply before July 26th at 11:59pm Pacific time.


To Apply

Please email careers@skritswap.com your:

  1. Resume
  2. Cover letter
  3. Contact information for 3 references
  4. Linked In profile + any relevant links

with the subject line: “[YOUR LAST NAME] Head of Eng 004-222-1501”

Looking to break new ground in a bleeding-edge development environment at one of the Top 20 Most Innovative Companies in Canada? We’ve got a unique opportunity for you with plenty of interesting problems to solve and opportunities to grow! Imagine “Google Translate” but, instead of different languages, skritswap works with different reading levels. At skritswap we make information accessible to everyone, regardless of their backgrounds and circumstances. bringing the next level of information accessibility to the world: changing the complexity of information.

Skritswap is a dynamic Canadian AI start-up that is changing the way people communicate. 

We’re looking for a Head of Engineering to lead, grow, and shape the Engineering team at Skritswap. This is a unique opportunity to join a high growth start-up as an early team member. Interested? Keep reading!

The Opportunity

The Head of Engineering is responsible for overseeing the development and maintenance of skritswap products. This role will be responsible for managing the Development and Product Management teams.  As a hands-on Head of Engineering at Skritswap you will be a vital ingredient to the success of a growing company helping the world communicate more effectively with anyone about anything. This is a chance to lead a team and company that are changing the way people communicate.


Duties and Responsibilities

  • Lead the development team and execution of Skritswap products
  • Contribute to formulating the strategic direction and goals of the organization
  • Inspire creativity and innovation through leadership; collaboration and continuous learning
  • Collaborate with computational linguists, Developers and other team members to design and develop software in a series of steps involving documentation, data structures and processes to meet designated needs
  • Oversee development and enhancement of technology stack, lifecycle development, testing and deployment procedures
  • Decide the methodology for approaching datasets and data representation
  • Collaborate with others to architect appropriate solutions of scale for future growth and expansion

Within 1 month, you will:

  • Be fully supported through completing our company-wide onboarding program. You’ll learn about skritswap’s history, business details, and future direction.
  • Work closely with the CEO to develop a custom 100-day success plan 
  • You will learn about skritswap’s history, business details, and future direction while participating in the company-wide onboarding program
  • Work closely with our lead engineer, Chris, to learn our tech stack in depth
  • You will dig into some code about 50% of the time
  • Working with tools like Harvest and Trello to collaborate with the team

Within 3 months, you will:

  • By now you will find yourself getting involved in our management meetings
  • Have made a visible impact on Skritswap’s technology that all users experience
  • Develop internal documentation for your features and systems so other engineers and stakeholders are brought along with your decisions
  • Contribute to weekly tech debt work
  • Contribute on improving the engineering teams process and approach
  • Run daily scrum meetings

Within 6 months, you will:

  • Take on Product Management entirely
  • Coding 30% of the time
  • Build, launch, and support the implementation of new features 
  • Own our DevOps process
  • Join in on external facing meetings with the CEO
  • Lead the growth of the engineering team through recruitment, interviewing and attending industry events and meetups


We’d love to hear from you if you have:

  • Have past experience building and leading productive engineering teams in a high growth start-up environment 
  • Exhibit a high degree of accountability and embrace autonomy
  • Have experience building a robust and scalable service-backed product and infrastructure
  • Enthusiastic about working broadly or going deep depending on the context of the challenge at hand
  • Care deeply about building resilient infrastructure favoring simplicity over complexity
  • Have a point of view but are low ego

We really love folks who:

  • Have proven experience in programming techniques and processes, infrastructure, databases, and application development
  • Have previous experience building products with Python
  • Have exposure to programming with Django experience
  • Have familiarity with the NLP/AI industry

Does this sound like you? Awesome! Send us your application and we will get back to you within 24 hours. Doesn’t sound like you? That’s okay! Apply anyway, we are growing and would love to hear from talented folks. 

The Interview Process

We look forward to learning more about you! Our process includes a phone interview, two in-person interviews, and a take-home challenge designed to assess your skill set and not totally interrupt your schedule.

The Environment

This role mainly works out of a dynamic office setting and requires travel 30% of the time. We are committed to providing reasonable accommodations and will work with you to meet your needs. We believe the best workplaces are flexible. We offer a supportive and flexible environment for our team to ensure they can do their best work when and where it works best for them. This role works out of our beautiful offices, with an opportunity to work remotely up to 3 days a week.

Skritswap is an equal opportunity employer. We embrace diversity and equal opportunity in a serious way. We are committed to building a team that represents a variety of backgrounds, perspectives, and skills. The more inclusive we are, the better our work will be. If there is anything we can do to create a more comfortable interview experience for you, please let us know.

To Apply

Please email careers@skritswap.com your:

  1. Resume
  2. Cover letter
  3. Contact information for 3 references
  4. Linked In profile + any relevant links

with the subject line: “[YOUR LAST NAME] Head of Eng 004-222-1501”