Rise to the challenge

Rise is Canada’s complete people management solution that gives employers everything they need to build loyal and productive teams—all in one place. We collaborate and co-create solutions that fundamentally change how companies of all sizes manage payroll, scheduling, time tracking, group benefits, recruitment, onboarding, and more.

At Rise, we’re changing how work happens and how people work. We’d love for you to join us and experience the most positive, challenging, and transformative part of your career.

About the role

Rise is looking for a Vice President of Sales to take our revenue engine to the next level. You'll own the strategy and execution for scaling our sales organization through a mix of inbound, outbound, channel, and upsell motions.

Reporting directly to the Co-CEO, you'll grow and lead a talented sales team, develop a high-performance playbook, and create a culture where top performers thrive. As a member of the senior leadership team, you’ll partner closely with executives in every other function, from Product and Marketing, through Client Experience and Finance.

This isn’t a job for a hands-off “sales strategist.” You’re a driver and a builder who rolls up their sleeves, coaches reps through deals, and uses data and AI tools to move faster and close smarter.

The day-to-day

• Build, coach, and retain a high-performing sales team through active deal reviews, call coaching, and one-on-ones.

• Develop and refine a sales playbook that drives consistent results across inbound, outbound, and account expansion motions.

• Turn inbound leads into qualified pipeline and get reps self-sourcing some of their own opportunities.

• Scale the reseller partner channel, targeting accountants, bookkeepers, and HR consultants as key distribution partners.

• Use data to accurately forecast and improve the performance of campaigns, sequences, and overall sales execution.

• Design compensation plans and incentives that maximize individual and team productivity.

• Create compelling sales messaging, sequences, and scripts.

• Drive urgency and rigour to close deals today, not tomorrow.

About you

• You have a proven track record of hitting targets and winning in fast-paced, quick-cycle sales environments.

• You know how to hire, motivate, and retain top performers.

• You're hands-on with coaching: deal reviews, call replays, and role-plays are part of your routine.

• You're fluent in CRM, prospecting tools, and AI-powered sales technology.

• You know your numbers inside and out and use data to forecast and optimize.

• You can build sales enablement assets (emails, sequences, etc.) without heavy reliance on other teams.

• You're ambitious, highly motivated, and energized by building something great.

• Bonus: Experience in HR, Payroll, or Accounting Tech.

What Rise offers

Rise is all about creating a positive company culture, both for our clients and our employees. We believe that happiness isn’t the cause of employee engagement, it’s the result.

• This position offers $150,000-200,000 in base salary, based on experience, plus commission, plus stock options.

• We offer a remote work environment. On occasion, we may meet as a team or one-on-one in person.

• Rise believes that time off is just as important as time spent working. We offer 3 weeks of paid vacation, flexible personal wellness days, as well as one day off for your birthday and your work anniversary.

• We support your growth with a personal $1,000 learning and development budget to take courses, attend conferences, webinars, you name it!

• We offer no-wait benefits. This means that starting your first day, you have access to our comprehensive benefits package, which includes dental, eye care, and $2,000 in counselling coverage, among many other great health benefits.

At Rise, we care more about where you’re headed, not where you’ve been. We encourage people of all ages, backgrounds, identities, and orientations to apply.