Jobs in Winnipeg, Canada

Workleap builds practical employee experience software that makes work simpler.

Our products include Workleap , a simple employee experience platform to boost engagement, drive performance, and develop teams, and ShareGate by Workleap , a single, trusted out-of-the-box solution for fast and secure migration, adoption, and Copilot readiness—simplifying data management across Microsoft 365.

With over 20,000 happy customers in more than 100 countries, Workleap products are a must-have for businesses looking to create a more engaging and successful workplace.

So, what will your new role look like?

In this role, you'll contribute to product innovation by implementing LLM-driven features, surfacing contextual insights, and helping make Workleap AI a core pillar of the Workleap platform experience. You’ll play a key part in accelerating adoption, driving usage, and scaling AI capabilities across our organization and entire customer base.

Responsibilities:

• Develop new features for our AI assistant and APIs.
• Ingesting new third-party data sources to our knowledge base.
• Collaborate and design to solve tough technical problems.
• Wear many hats, be flexible and proactive enough to tackle the important issues.
• Make sure to maintain a clean architecture and implementation.
• Perform code reviews, coach and mentor teammates.
• Provide great support to our early adopters.

• Python, FastAPI ;
• MongoDB ;

A typical week?

• Developing new value / features: 65%
• Design, architecture, technical feedback: 25%
• Support our early adopters: 5%
• Team meetings and rituals: 5%

What does your future team look like?

You’ll be part of the Product & Innovation team, with a focus on Workleap AI, our cutting-edge solution designed to leverage AI to boost workplace efficiency and engagement. This is a dynamic and fast-paced team that thrives on curiosity, experimentation, and rapid iteration.

What are the next challenges awaiting your team?

• Develop AI-first features that have never been done before
• Adapt our development process to the new AI tools that are completely changing the way we work every day

• You have solid skills in backend software development with Python, FastAPI and uv.
• You have solid skills in cloud infrastructure using Azure, Github actions, Terraform, Kubernetes, Docker, and Helm.
• You have strong experience with databases such as MongoDB, PostgreSQL, and Neo4j.
• You have experience in building AI systems using LLMs, vector embeddings, RAG pipelines, and agentic workflows.
• You’re very comfortable writing unit, integration, and end-to-end tests.
• You apply SOLID, DRY, KISS, and YAGNI principles.
• You can easily break down complex technical concepts, communicate them simply.
• You’re familiar with product, software and design lifecycles, and collaborating closely with designers, engineers, and product managers.
• You're very autonomous, high agency, great to work with.
• You're assisted by AI in your day to day.

We’re a team of curious minds and bold builders, brought together by a shared drive to make work simpler - and better - for everyone. Challenges fuel our creativity, fast-paced environments keep us sharp, and pushing boundaries is just part of how we operate. We believe the best ideas come from experimentation, rapid learning, and even the occasional discomfort - that’s where growth happens.

Since 2006, we’ve been rethinking the way teams work, blending creativity and tech to solve real problems in IT and HR. We move quickly, we learn constantly, and we always keep our customers at the center of what we do. If you're a proactive thinker who takes ownership, loves to collaborate, and isn’t afraid to leap into the unknown - you’ll fit right in.

AtWorkleap, we build together, we trusteach other,and we support each other in success or failure. You will be able to express yourself, evolve and develop your creativity in an environmentthat will adapt to your daily life and your needs.

We strive to create a healthy and inclusive work environment. This is everyone’s business.

Our Candidate Experience Flow atWorkleap:
Phone Screen - Virtual Interview using Microsoft Teams - Work Sample - Job Offer

We are looking forward to getting to know you!

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