Remote VP Engineering job at

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Are you looking to join a rapidly-growing, profitable company and help them continue to scale? Have you successfully led and optimized an engineering team 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. We 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. Smile 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 lead a 20-person remote engineering organization, while working closely with the product management, data/infrastructure, and customer success teams to ensure effective delivery. This involves expanding the existing product + building in new areas.

As an inspiring technology leader, you’ll continue to build and motivate the engineering team and culture. It’s a team that is hungry to learn, where the focus is on following a product-led philosophy, building simple solutions, and distilling the most important priorities. You’ll be a key member of the executive leadership team and you will participate in company-wide strategic planning. You’ll be working with leaders across the business to ensure customer and business success.

Success in this role looks like:
  • Solving bottlenecks within the product lifecycle such as technical planning and architecture.
  • Guiding the engineering team to release new features quickly & reliably.
  • Reduce the time to developer escalations significantly to close the merchant feedback loop as quickly as possible.
  • Ensuring our product can scale & grow to support rapid growth of users into the future.
  • Developing a team structure, and a hiring plan for 2021 & beyond based on our objectives.

Does this sound like you?

On the management front, you'll:
  • Mentor, develop, and guide your engineering directors, engineering managers, and engineers so they can do their best work.
  • Help guide the team on important architectural and long-term engineering decisions, as well as shorter-term tradeoffs.
  • Participate in all steps of the recruiting process to build the engineering team.
  • Lead with compassion and make the tough calls when needed.
  • Listen to first understand and build consensus.
  • Be pragmatic, learn about the product, process, and tools, and evaluate what can be done to build faster and better products, and maintain acceptable SLOs and system operations.
  • Work as an effective leader across the organization, and collaborate with other leaders to translate the business priorities of the company into a technical agenda.
As a manager of engineers and a technology leader, you'll:
  • Be a key contributor to strategic and tactical roadmap planning and product definition.
  • Guide our engineering design and architecture decisions.
  • Be intimately familiar with our product, languages, and our tech stack to make decisions about vendors and frameworks.
  • Focus on delivery, execution, and our tactical engineering approach.
  • Be on top of the latest technologies, tools, methodologies, and frameworks for software engineering and engineering management.
  • Ensure our systems are scalable, development is reproducible, tested, and that we have efficient deployment processes.
  • Ensure the team is building simple, elegant solutions in an iterative way by coaching on best practices and how/when to make trade-offs.

  • Experience in a senior leadership role in a scale-up environment (ideally you’ve seen the 10-50M growth stage).
  • You have managed a team of 20 or more engineers, and managed engineering managers or directors of engineering.
  • You've built highly scalable, highly reliable, and low-latency systems.
  • Strong communication skills (both oral and written).
  • Demonstrated business and technical acumen. Ability to convey complex technical issues to a non-technical audience.
  • Comfort and experience working in a completely remote environment (as a result, the location is flexible for this role).