Sales Enablement Manager

Wagepoint is a small-but-mighty fintech on a mission to make payroll simple (and maybe even delightful). Our online software takes care of the “ugh” stuff — like wage calculations and tax reporting — so 30,000+ small businesses, accountants, and bookkeepers across North America can get back to doing literally anything else. Since 2012, we’ve been making payroll magic happen with the world’s friendliest team: always supportive, never stuffy, refreshingly human.

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’re looking for a talented Sales Enablement Manager who doesn’t shy away from building programs from scratch and enabling sales teams to thrive. In this role, you’ll design, deliver, and optimize the enablement strategy that helps our reps — and their managers — sell smarter, faster, and more effectively. You’ll report directly to our VP, Sales.

The salary range for this role is $90,000 - $100,000 CAD + $20,000K variable.

What You'll Be Expected To Own:

• Designing and implementing our sales enablement function from the ground up.

• Building scalable onboarding, documentation, and training programs that improve consistency and performance across our growing sales team.

• Creating content like playbooks, talk tracks, wikis, and coaching tools that reinforce best practices.

• Leveraging tools like Gong to extract insights and improve rep and manager performance.

• Enabling product releases and ensuring the sales team is always up to speed on what’s new.

• Creating the structures and rhythms (calendars, certifications, LMS usage) that ensure enablement is consistent and impactful.

What You Bring To The Table:

• 3+ years of sales enablement experience in a fast-growing, SaaS-focused environment.

• Deep knowledge of modern sales methodologies and frameworks, with the ability to translate theory into action.

• Hands-on experience with Gong or similar conversation intelligence tools.

• Strong communication and project management skills — you know how to prioritize and get things done.

• A track record of building onboarding programs, enablement content, and training calendars that actually get used.

• A collaborative mindset and ability to work cross-functionally with Sales, Product, and Marketing.

Bonus points if:

• You’ve worked directly in sales before — even better if it was SaaS or partner/channel sales.

• You have experience supporting accounting/bookkeeping ecosystems.

• You’ve built enablement for a partner-led motion.

• You bring a systems mindset and enjoy creating structure, templates, and processes from scratch.

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!

This job posting is for an existing vacancy.

As part of our hiring process, AI-based tools are used to support the initial review of applications. Rest assured, our People Ops team carefully reviews all applications and makes the final decisions on candidate progression.