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 to build solutions that completely change how companies of all shapes and sizes manage their 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

Thousands of Canadian small and mid-sized businesses rely on Rise to run payroll, manage HR, and deliver group benefits. There are tens of thousands more who don't know us yet, and that's the opportunity we're hiring for.

We're hiring an Account Executive who's built to hunt. You self-source pipeline, you're fluent in modern sales enablement tools, and you know how to run a territory without waiting for leads to land in your inbox. Cold outreach is where you do your best work, and a lost opportunity is just a deal you haven't closed yet.

You'll own a territory of companies with 50–200 employees, build your book through self-sourced prospecting, and get the Rise platform in the hands of businesses that need it. You'll work alongside other Rise teams: Marketing, Client Onboarding, and Product, to bring on more happy clients.

The day-to-day

• Self-source pipeline through cold outreach, lapsed and lost opportunities, and targeted prospecting into companies with 50–200 employees in your territory.

• Work marketing and SDR-generated inbound leads alongside your outbound pipeline.

• Use HubSpot CRM and other sales enablement and automation platforms to run sequences, track activity, and keep your territory moving.

• Run business case presentations and product demos that get clients engaged and show them what's possible.

• Keep customer, planning, and forecasting data accurate and up to date so you and your manager always know where deals stand.

• Know the product, the competitive landscape, and the trends shaping HR, payroll, and benefits for Canadian SMBs.

About you

• 4+ years of consultative, relationship-based sales experience with a real track record of self-sourced pipeline.

• Experience selling in a high-growth SaaS environment. 2+ years of selling Payroll or HRIS cloud products to small-to-medium businesses is preferred.

• Fluent with modern sales enablement and automation tools (HubSpot, Outreach, Apollo, LinkedIn Sales Navigator, or similar).

• Degree or diploma in Business or a related field, or equivalent experience.

• Results-focused with a strong sense of agency. You don't wait to be told where the next deal is coming from.

• Quick to build rapport with small and mid-sized business owners and the people around them.

• Outstanding communication and presentation skills.

• Resilient and adaptable. You learn fast, adjust fast, and keep selling through change.

• Genuine enthusiasm for the challenges small and mid-sized Canadian businesses face.

• Bonus: Fluent in Canadian French.

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.

• The base salary for this position is $60,000-75,000, based on experience, plus commission, plus stock options. On-target earnings are $140,000-155,000.

• 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. 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.