Team Lead, Software Development (Java OR Python), AI

Hi there! Thanks for stopping by

Are you actively looking for a new opportunity? Or just checking the market? Well… you might be in the right place!

We\’re looking for a talented Software Development Team Lead to guide and grow our Agent OC Squad —a new team focused on building and scaling AI-powered systems using LLMs, agent frameworks, and related technologies. The team works on a mix of internal tools, product-facing AI features, and enablement efforts that help other teams adopt AI across Lightspeed.

You’ll play a key leadership role while staying hands-on. You’ll guide a team of backend engineers, work directly on backend systems (Java or Python), and help define and deliver practical AI solutions. As a leader, your focus will be to grow your team, support clear delivery, and bring solid engineering practices to an evolving and fast-moving domain.

This is a hands-on leadership role. We’re looking for someone with strong engineering leadership experience who has also applied LLMs or AI technologies in real-world systems—whether building user-facing AI features or integrating intelligent capabilities into backend services.

Your Mission

Under your guidance, the Agent OC Squad will design and build intelligent tools, services, and features that support internal teams and extend Lightspeed’s product capabilities. You’ll shape the squad’s technical direction, lead delivery, and help team members grow their impact.

What you’ll be responsible for

• Be the trusted lead and partner of a development team of 5–6 engineers, supporting their growth and day-to-day work
• Guide the design and delivery of AI-powered tools, APIs, and services that use LLMs and agent frameworks
• Stay hands-on: review code, contribute to system design, and lead by example
• Foster a collaborative, supportive, and inclusive team culture
• Ensure high-quality, maintainable backend systems—primarily in Java (Spring Boot) or Python
• Collaborate closely with product managers, designers, and other engineering leaders to align strategy and execution
• Drive technical decision-making and help define the squad’s roadmap in an emerging domain
• Continuously improve delivery processes, development practices, and team health
• Contribute to hiring by identifying and attracting strong engineering talent

What you’ll be bringing to the team

• Proven experience leading software engineers in a team setting
• Strong backend development skills in either Java (Spring Boot) or Python (FastAPI, Flask)
• Solid understanding of system design, scalable services, and API development
• Experience working with CI/CD, Docker, Kubernetes, and cloud platforms (AWS preferred)
• Excellent communication skills and the ability to collaborate across roles and regions
• Ability to manage complexity, make trade-offs, and keep teams focused
• Professional experience building or integrating AI-powered features using LLMs (e.g. OpenAI, Claude, open source) or agent frameworks
• Practical understanding of how to deploy, evaluate, and improve LLM-based systems in production

Even better if you have hands-on experience with (but not necessary):

• Building SaaS products at scale or in a multi-tenant architecture
• Developer productivity or internal enablement tooling
• Observability, performance monitoring, and security best practices
• Vector databases, embeddings, or retrieval-augmented generation (RAG)

Who you are:

• You care deeply about helping engineers grow and succeed
• You enjoy solving complex problems through clean, maintainable code
• You thrive in environments that are still taking shape and aren’t afraid of ambiguity
• You’re passionate about AI and excited to explore its practical impact
• You’re calm under pressure and able to lead with clarity

What’s in it for you?

Come live the Lightspeed experience!

• Lots of autonomy, flexible work culture with the option of working remotely or from one of our beautiful offices
• Genuine career growth opportunities within a company that\’s continuously expanding
• Make a meaningful impact by shaping how Lightspeed adopts and scales AI
• Be part of a team large enough for growth yet agile enough for real impact
• Work on high-traffic products with a global user base
• Opportunities to learn, develop new skills, and expand your expertise

… and enjoy a range of benefits that’ll keep you happy and healthy:

• Lightspeed share scheme (we are all owners).
• Flexible working policy.
• Mental health online platform and counseling & coaching services.
• Health and wellness benefits.
• LinkedIn Learning license (learning is always ongoing).
• Volunteer day to be able to give back to society!

To all recruitment agencies: Lightspeed does not accept unsolicited agency resumes. If we have not directly engaged your company in writing to supply candidates for a specific vacancy, Lightspeed will not be responsible for any fees related to unsolicited resumes.

Lightspeed is a proud equal opportunity employer and we are committed tocreating an inclusive and barrier-free workplace. Lightspeed welcomes andencourages applications from people with disabilities. Accommodations areavailable on request for candidates taking part in all aspects of theselection process.

Where to from here?
Obviously, this has to be mutually beneficial: we want you to step into a role you love, and we want to offer you a place you’re proud to come to every day. For a glimpse into our world check out our career page here .

Lightspeed is building communities through commerce, and we need people from all backgrounds and lived experiences to do that. We were founded in 2005, in Montreal’s gay village and our original members were all part of the LGBTQ+ community. The ethos of our business has been about inclusion from the very beginning, and we strive to provide a workplace where everyone belongs.

Who we are:
Powering the businesses that are the backbone of the global economy, Lightspeed\’s one-stopcommerce platform helps merchants innovate to simplify, scale, and provide exceptional customer experiences. Our cloudcommerce solution transforms and unifies online and physical operations, multichannel sales, expansion to new locations, global payments, financial solutions, and connection to supplier networks.

Founded in Montréal, Canada in 2005, Lightspeed is dual-listed on the New York Stock Exchange (NYSE: LSPD) and Toronto Stock Exchange (TSX: LSPD). With teams across North America, Europe, and Asia Pacific, the company serves retail, hospitality, and golf businesses in over 100 countries.

Lightspeed handles your information in accordance with ourApplicant Privacy Statement .

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