Program Manager

Full job description
Description

Who We are:

At Wagepoint, we’re good people. Sure, maybe we’re biased. But that’s only because Wagepointers bring the best versions of ourselves to do some of the best work in our careers.

We’re an authentic team who bring our diverse backgrounds, ideas, experiences and cultures together to make payroll magic. Speaking of, we “pull rabbits out of hats” for thousands of small business owners across Canada who rely on our payroll software to pay their employees and process their payroll taxes. And we’re just getting started.

We’re growing and looking for more awesome people to join our merry band of misfits. We are looking for people who share our understanding that when it comes to our commitment to our customers: we mean business. Especially given that the consequences of getting payroll wrong can sometimes be dire.

If you are the kind of person who has always wanted to make a difference and be heard at work, Wagepoint will give you plenty of opportunity to do just that.

The Role at High Level:

We are seeking an experienced and proactive Program Manager to join our Product team at Wagepoint. This role is critical to driving operational excellence during a period of significant platform evolution. You’ll lead the coordination of key cross-functional initiatives, including the migration of customers from our legacy 1.0 platform to the new 2.0 experience, incident management, and product launch processes.
At the core of this role is our company-wide goal of delivering a frictionless migration experience for our customers. We’re looking for someone who is not only highly organized and execution-focused, but also deeply passionate about effective change management — someone who can bring people along through complex transitions with clarity, empathy, and precision.
This is a high-visibility role with significant impact across Product, Engineering, Customer Success, and Marketing. You will report directly to the VP of Product and work closely with leaders across the organization to ensure alignment, momentum, and strong delivery.

What You'll Be Expected To Own:

Migration Coordination:
Own the cross-functional planning and execution of our migration from the 1.0 to 2.0 platform — ensuring that each cohort of customers is transitioned successfully and that internal teams are prepared to support them.
Work with Product Management, Engineering, CS, Marketing, and other stakeholders to align timelines, dependencies, and risk mitigation plans.
Provide regular communication to senior leadership and other stakeholders on migration progress, risks, blockers, and learnings.
Establish and maintain tools and dashboards to track migration progress and customer readiness.
Proactively identify process gaps and surface opportunities for smoother customer and internal team experiences.
Incident Management:
Serve as the primary liaison between Customer Support and Engineering during high-severity production incidents.
Coordinate incident response efforts, ensuring timely resolution and clear communication to stakeholders.
Develop and maintain incident management protocols and post-incident review processes.
Product Launch Coordination:
Work closely with Product Managers, Marketing, Sales, and Customer Support to ensure readiness across all functions.
Establish and manage launch checklists, timelines, and communication plans.


What You Bring To The Table:

Bachelor's degree in Business, Computer Science, or a related field.
5+ years of experience in program or project management within a software development environment.
Certification in Project Management (e.g., PMP, PMI-ACP)
Proven track record of managing complex, cross-functional programs.
Strong understanding of software development lifecycle (SDLC) and Agile methodologies.
Familiarity with incident management frameworks and tools.
Excellent communication, leadership, and interpersonal skills.
Ability to navigate ambiguity and drive results in a fast-paced environment.
Proficiency in project management tools such as Jira, Confluence, or similar platforms.
Bonus Points If
You’ve worked in a remote environment and know how to keep distributed teams aligned and motivated
You have experience in the fintech or payroll space
You’re familiar with the unique needs of small businesses and how technology can help solve them

What We Bring To The Table:

Impact: Roll up your sleeves and directly contribute to the growth and success of Wagepoint by shaping our workforce.
Culture: The opportunity to work with the world’s friendliest team, solving interesting problems together with an endless amount of laughter (We work hard, but we always have time for a bad joke or two).
Growth: Opportunities for professional development and career advancement - we are always, always learning with a growth oriented mindset.
Innovation: Work in an environment that encourages creativity and new ideas.
Remote: The ability to work from home, forever! Wagepoint is a remote company, so you don’t have to worry about commuting to an office. Plus, more time with your pets is always a bonus!
Ready to embark on an exciting journey with us? Apply now and help us build the future of Wagepoint!

About Wagepoint
Wagepoint is a simple and fast online payroll app, backed by the world's friendliest team.

The app is ideal for small businesses across North America (US Canada) who are looking to pay their employees easily and quickly.

Next Steps:
If all the above feels right and proper, please don’t feel like you need to send us an uninspired cover letter. Just send us your updated resume and perhaps a few lines on what excites you about the job - we really want to get to know who you are, not just about how we can work together. If we believe you’re a good match, someone from our team will reach out to schedule a call.

Psssst!
Wagepoint is an equal opportunity employer. We welcome and appreciate all applicants with diverse backgrounds, races, religions, genders, identities, ages, experiences (the list goes on!). We are committed to making not only our workplace safe and inclusive for everyone, but also ensuring our recruitment process reflects that. We are a remote company, so there's no need to travel to an office for an interview, but if you require any special accommodation during our recruitment process, please let us know. We are more than happy to assist! Read more