Assistant Software Development Manager Jobs in Ontario

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

We’re looking for a Director, Software Development to lead Engineering for Lightspeed Payments, a key department within Financial Services that has grown 3x in the past couple of years. You will also be a key leader in the Payments group working with cross‑functional leaders & their teams; ensuring alignment of goals across the organization. You will be leading & working closely with a group of talented Engineering Managers, Software Developers; provide clear direction around where the organization must be heading & ensure the teams are delivering quality outcomes. In addition, you will make sure we are growing a diverse, happy and high‑performing organization.

For this role, you can be located in Canada/USA , and able to work within EST/EDT hours. We offer a choice of fully remote, partially remote or fully office‑based work environments (in cities with local offices).

• Navigate ambiguity, bring structure to complex challenges, and drive alignment across teams.

• Work cross‑functionally to bring clarity to priorities and define what needs to be done to drive success.

• Operate closely with the team, wearing multiple hats to ensure critical projects are executed successfully.

• Own the delivery, collaborating closely with Product Managers and business stakeholders to achieve meaningful outcomes.

• Act as a people leader, mentoring and developing engineers into future leaders.

• Hire and grow a high‑performing team, ensuring strong technical and leadership talent.

• Set high standards and elevate the team through coaching, feedback, and hands‑on support.

• Foster a culture of ownership, collaboration, and technical excellence within and beyond the team.

• Extend expertise and influence beyond Payments into the broader Financial Services organization & the Services vertical.

• Ensure clear and concise messaging across stakeholders, particularly around the goals, objectives and priorities.

• Work cross‑functionally with business teams to align on technical and product strategy.

• Influence and drive decision‑making across teams, advocating for best practices in engineering and business execution.

• Architect and scale business systems with a strong understanding of various paradigms, including event‑driven systems.

• Evaluate and guide technical architecture decisions to ensure scalability, reliability, and efficiency.

• Developing a deep understanding of existing systems, guide the teams to continuously evolve their systems/architecture/patterns.

• Drive continuous delivery of value, ensuring high availability and operational excellence.

• Develop quick prototypes to validate ideas or assist with technical spikes.

• Deep knowledge and understanding of software engineering principles, technologies and best practices.

• Has a strong software development background with a history of being an engineer & expertise in multiple mainstream technology stacks (Node, JVM, .NET, etc).

• Expertise in software architecture & design of scalable, maintainable & resilient systems that run on the cloud across regions.

• Expertise in modern software delivery practices (continuous delivery, lean practices, etc).

• Operational Excellence Mindset: Experience running & managing operations of business critical systems on the cloud.

• People management: experience in hiring, performance management, and growth.

• Experience leading other leaders in a software engineering organization.

• Experience working with cross‑functional leaders as one unit & setting organizational goals and objectives.

• Experience owning technology/product for a clear line of business or a complete product.

• Experience working in product engineering and/or SaaS software delivery is a plus.

• The hunger to learn across the core areas of your domain, to synthesize insights from your learnings and to leverage those insights in your team.

• Highly collaborative and effective team member.

We know that people are more than what’s on their CV. If you’re unsure that you have the right profile for the role… hit the ‘Apply’ button and give it a try!

Come live the Lightspeed experience…

• Lots of autonomy, flexible work culture.

• Join a fast‑paced, high‑growth company.

• Work on systems that handle billions of dollars in transactions for our merchants globally.

• Surround yourself with strong talent and enjoy continuous professional growth.

• Develop in a modern and proven technology stack.

• Great benefits and perks, including equity and flexible/hybrid remote work options, in a diverse and inclusive environment.

• Development of very high traffic products, used at the global scale.

• Opportunities to learn and expand your skill set

Become a valued part of the diverse and inclusive Lightspeed family.

… and enjoy a range of benefits that’ll keep you happy, healthy and (not) hungry:

• Lightspeed equity scheme (we are all owners)
• Flexible paid time off policy
• Health and wellness benefit of $500 per year
• Paid leave and assistance for new parents
• Mental health online platform and counseling & coaching services
• Volunteer day

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 to creating an inclusive and barrier‑free workplace. Lightspeed welcomes and encourages applications from people with disabilities. Accommodations are available on request for candidates taking part in all aspects of the selection process.

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.

Powering the businesses that are the backbone of the global economy, Lightspeed’s one‑stop commerce platform helps merchants innovate to simplify, scale, and provide exceptional customer experiences. Our cloud commerce 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.

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