About Smile

At Smile, we don’t just build loyalty programs - we create growth engines for ecommerce merchants. With over 100,000 merchants worldwide, we’re already the largest loyalty program provider on the planet. But we’re just getting started.

Our team is globally distributed but closely connected. Collaboration isn’t just a buzzword here; it’s our way of doing business. If you’re looking to be part of a culture where growth for customers, the company, and for you - is the goal, you’re in the right place.

About the Role

As an Account Executive, you will represent Smile, the best-in-class loyalty expert in the space, and work quickly to be viewed as an expert advisor yourself. This isn’t a typical sales job. You won’t just be closing deals; you’ll be building partnerships that help merchants thrive. You conduct sales using a consultative approach, bringing value to your prospect's decision-making process, and are not above walking away from a deal if it's not the right fit. We’re looking for a sales professional who’s as passionate about helping businesses grow as we are.

We believe in fostering genuine partnerships with our clients, ensuring their success aligns with our mission to help businesses grow sustainably. If you’re motivated, collaborative, and passionate about delivering value to customers, Smile offers an exciting opportunity to join a dynamic team at a pivotal stage in our growth journey. Our sales team works directly with brands to develop effective loyalty strategies for merchants spanning ecommerce and retail operations, and this role offers a unique opportunity to drive our growth through the incredibly rewarding work of helping merchants grow their businesses.

With uncapped earning potential and the chance to work closely with high-performing teammates, you’ll help shape the future of Smile - and the businesses we serve. Smile.io is a remote company looking to hire within Canada for this full-time, remote role. Overlap with core EST working hours is required.

Everyone at Smile is driven by these core values:

Be Humble - think of the team before thinking of yourself. We have no room for massive egos.
Be Hungry - set hard goals, ask lots of questions and learn every day.
Be Human - show empathy towards others, consider the impact of your decisions on other teams.

Salary: $75,000 CAD Base, $165K CAD OTE with uncapped commissions

Requirements & Skills

Hit Sales Targets: Consistently meet or exceed monthly sales targets through proactive pipeline building, including prospecting, event engagement, and strategic follow-ups.
Advise like an Expert: Serve as a trusted advisor to prospects, focusing on Smile’s value while personally overseeing successful program launches.
Engagement and Collaboration: Build genuine connections with merchants and contribute to team success by sharing insights, best practices, and enablement resources.
Tailor Your Approach: Experiment with creative solutions and outreach strategies to effectively engage diverse prospects.
Keep Things Organized: Respond promptly and personally to inquiries and maintain accurate updates on all sales activities.

What We’re Looking For:

Proven Success: At least 3 years of experience in SaaS or B2B sales, with a track record of hitting or exceeding quotas.
Grit and Adaptability: A willingness to pick up the phone, send tailored emails, or explore alternative communication channels to engage prospects effectively.
Empathy and Communication: You can connect authentically, ask great questions, and build rapport fast.
Tech Know-How: Familiarity with tools like ZoomInfo, Pipedrive, and a willingness to leverage AI for efficiency.
Values Alignment: A shared commitment to Smile’s ethos of helping businesses grow sustainably and putting customers first.
Creative Thinker: Ability to problem-solve and iterate on strategies to maximize impact.

Bonus if you have:

Selling in ecommerce or retail industries
Selling a SaaS offering on a month-to-month contract
PLG + sales environment
Post-sales experience (eg. account management, customer success, implementation)

If you’re ready to bring your expertise and passion to a values-driven company poised for its next big chapter, we’d love to hear from you!