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Are you looking to join a rapidly-growing, profitable company and help them continue to scale? Have you successfully led a product that supports a high-volume user base? If so, this may be the right opportunity for you.

Who is Smile?

Smile is the largest provider of loyalty programs in the world. We power the loyalty programs for over 40,000 eCommerce merchants, which have rewarded over 100 million people. These user numbers are growing rapidly, especially with the recent acceleration of eCommerce worldwide.

Smile exists to help businesses make their customers happy. Our product helps eCommerce businesses create fun, on-brand, and easy-to-use loyalty programs. They integrate with eCommerce platforms like Shopify, Wix, and Bigcommerce to create the world’s most engaging loyalty programs for any entrepreneur.

The results are in - and it’s working. is helping small companies thrive and run sustainable businesses by increasing customer lifetime value, increasing repeat purchases, and fostering a community around their brands.

Smile was ranked 28th on Deloitte’s Top 50 list of the fastest-growing tech companies in Canada. We have exciting and aggressive scaling plans for 2021 and beyond as we evolve our vision.

We’ve built our app, business, and culture around our values that are the driving force behind everything we do:
  • Be Humble - think of the team before thinking of yourself. There’s no room for massive egos.
  • Be Hungry - set hard goals, ask lots of questions, and learn every day.
  • Be Human - show empathy towards others, consider the impact of your decisions on other teams.

How will you make an impact?

You will own the direction and execution of the product in the short-to-medium term, along with working with the CTO and CEO on the long-term vision.

Success in the role looks like:
  • Identifying the key areas of improvement to the product, and building & communicating a strong roadmap to drive our growth in the future.
  • Working in partnership with the CTO and establishing strong communication, collaboration, and alignment of company goals & the product team’s goals.
  • Building strong rapport and trusting relationships, ensuring the product team members are supported across the company.
  • Developing a data-informed measurement framework to monitor the health of the product and ensure this data is actionable (working with our current data team).
  • Ensuring our roadmap addresses merchants’ needs, shoppers’ needs, and company goals.

Does this sound like you?
  • You pride yourself on building strong and motivated teams with great morale and promoting a positive employee experience.
  • You value simple-yet-effective products, and are able to make tradeoffs when deciding what to build - and what not to build.
  • You promote a positive product culture of continuous innovation, learning, driven by data and testing, as well as intuition informed by familiarity with our industry.
  • You understand that great products are the result of true collaboration of engineers & designers, and working in conjunction with our merchant-facing support teams.
  • You love to communicate (often repeatedly!), your product strategy, vision and guiding principles company-wide.
  • You are a master at resource planning & managing trade-offs.
  • You ensure that your teams are supported and levelling up to do the best work of their careers.
  • You enjoy meticulously digging deeper into the data and to define how to measure success for projects and initiatives.
  • You set an ambitious product delivery pace with clear expectations and high standards.
  • You enjoy creating delightful experiences and delivering value for merchants & shoppers.
  • You love solving optimization problems: solving difficult expectations of user growth, increasing revenue, subscription health, brand reputation, and pricing.

  • Experience in a senior leadership role in a scale-up environment (ideally you’ve seen the 10-50M growth stage).
  • Product management background in a high-volume business (B2C or SMB focus) is an asset.
  • Proven analytical and decision-making skills - both data-informed & intuition-informed.
  • Strong communication skills (both oral and written) in remote environments.
  • Demonstrated business and technical acumen. Ability to work with technical analysts to make sure the right data is being collected to answer the right questions.
  • Comfort and experience working in a completely remote environment (as a result, the location is flexible for this role).

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