Sales Manager

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. We know that Smile.io as a business is constantly evolving - the same is true of our people. We're here to support each other in our growth, so we talk openly about our career & personal goals.

Smile.io is a fully remote company looking to hire someone in Canada for this remote role. This is a full-time, remote position. Core hours are Monday to Friday, 9am–5pm Eastern Time (plus or minus 2 hours).

About the Role

This isn't a traditional sales leadership role, and we think that’s what makes it exciting.

You'll start by leading a team of five Account Executives with a range of experience: some are product experts that are newer to selling, while others are seasoned sellers still ramping up on Smile, ecommerce, and loyalty strategy. Regardless of tenure, they all share a hunger to grow, and they’ll look to you for timely, practical coaching that helps them succeed. That might mean helping shape an outbound strategy, reviewing call recordings, joining on live calls, or stepping in to unblock a stuck deal. It is expected that coaching happens in the moment here, not just saved for weekly 1:1s.

We're looking for a Sales Team Manager who's eager to stay close to the work, support a high-potential team, and help shape how we sell at Smile. You won't be quota carrying, but you'll always be running at least one active deal. This helps you stay sharp, relatable, and hands-on; ready to support the team with firsthand insight and jump in when things get complex, especially on higher-value or enterprise opportunities.

We believe sales is a craft and success comes from a mix of grit, curiosity, and care. That’s why our culture emphasizes ownership and long-term value, not short-term wins or leaderboard pressure. At Smile, a deal isn't considered closed until the merchant has launched and gone live. That standard helps us grow sustainably and stay accountable to the brands we serve.

We also run lean. There’s no RevOps or Enablement team to lean on. But for the right person, that's not a limitation, it's an opportunity. You'll be hands-on with forecasting, reporting, and sales operations, and we'll look to you to spot friction in how deals are routed, distributed, or supported. If something isn't working, we want you to play a role in fixing it.

You’re not waiting for someone to hand you a playbook. You’re excited to shape one over time. If you thrive in ambiguity, value humility and teamwork, and want to build something meaningful alongside people who care deeply about their craft, this is a role where you'll have both impact and ownership.

Who you Are

This role is a great fit for someone at a leadership crossroads, equally capable of carrying a bag or growing a team. You want to stay close to the work, and you believe leadership means leading by doing—rolling up your sleeves when needed, not just reporting on the numbers. You're not looking for a role where you manage from afar; you want to make an impact side by side with your team and welcome involvement from senior leadership as we learn in real time, embrace a highly iterative process, and grow this function out collaboratively.

You care deeply about the craft of selling and helping others level up. You know how to coach, guide, and step in when needed. You’re energized by working with talented people at different stages of their careers, and you take pride in helping them get better every day.

You’re excited by the challenge of building in a lean environment, where ownership, initiative, and curiosity matter more than process or polish. You’re not waiting for someone to hand you a playbook. You’re excited to shape one over time, with your team, and do it in a way that reflects your values.

While this role offers strong earning potential through team-based and direct deal contributions, it’s important to know that this is still an early-stage team. We’re in the process of building toward full quota attainment, and your leadership will directly shape how quickly we get there. This is a role for someone energized by the opportunity to turn promise into performance—and who’s motivated to unlock meaningful results, not just inherit them.

We love seeing candidates who’ve done a little homework. If there’s a brand or merchant using Smile that you admire, or would be excited to work with, mention them in your application. If you’re looking to grow something meaningful, take on real responsibility, and work alongside humble, driven teammates who care about doing great work, you’ll feel at home here.

• Stay Close to the Work: Run at least one active deal at all times to stay sharp and relevant. Step in when reps are away, whether picking up a warm lead or pushing a deal across the line. You're hands-on and happy to help.
• Guide Full-Cycle Success: Support reps through outbound, closing, onboarding, and launch. At Smile, a deal is only closed once the merchant is live. You'll help reinforce that standard and support clean handoffs after 90 days.
• Coach in the Moment: Shadow calls, review messaging, and offer timely feedback. You meet reps where they're at and help them build skill, confidence, and autonomy.
• Drive to Quota: Own the team's collective performance; $3.6M (USD) in new ARR annually, with individual targets of $60K ARR/month.
• Lead Pipeline Reviews: Run weekly 1:1s and team reviews to uncover blockers and drive progress. You flag risks early and help shape the path forward.
• Own the Ops: Take on CRM updates, commissions reporting, lead assignments, and list uploads. We are a lean organization and expect you to help keep things moving.
• Support Rep Growth: Help reps fully own their pipelines and grow into high-performing, well-rounded sellers.
• Champion Fairness: Keep an eye on deal routing and lead allocation. Raise and address concerns when needed and advocate for clarity and balance.
• Partner Across the Business: Collaborate with teams across Smile to surface merchant feedback, identify product gaps, align on roadmap priorities, and contribute to broader GTM strategy. You’ll be a voice for what’s happening on the front lines and a connector between teams.
• Model the Culture: Celebrate team wins, encourage peer feedback, and set the tone for a collaborative, accountable team culture. No one wins alone here.
• Spot and Solve: See the patterns others miss, from process gaps to enablement needs, and take initiative to fix what's broken.

• Experience selling within the Shopify ecosystem, ideally at Shopify or a Shopify app partner. You understand how Shopify merchants evaluate and adopt tools, and you've navigated their buying journey before, specifically the $10M-$100M GMV segments.
• 5 to 10 years of B2B SaaS sales experience, including full-cycle ownership and consistent performance.
• 3 to 5 years in a sales leadership or coaching role, ideally in a startup or lean environment where you created your own enablement resources and took on multiple roles.
• Experience in a hybrid product-led growth (PLG) and sales environment, with a clear understanding of how to support self-serve paths rather than disrupt them.
• A track record of developing talent, especially where enablement resources were limited and reps needed support in both skills and confidence.
• Comfort balancing execution with development; you're willing to step in when needed, and you lead by doing.
• Tech-Savvy: Familiarity with sales tools (ZoomInfo), CRM systems (Pipedrive), and design tools (Canva) as well as an understanding of the AI-driven market landscape to help the team level up or break through the noise when connecting with prospects.
• A strong sense of deal quality, with a focus on long-term value and fit over short-term wins.
• Operational confidence, including forecasting, pipeline management, CRM hygiene, and performance reporting.
• Values Alignment: A shared commitment to Smile’s ethos of helping businesses grow sustainably and putting customers first.
• Empathy, grit, and low ego; you know how to push people to grow while staying collaborative and grounded.

• Base Salary: $145,000 CAD
• OTE: $235,000 CAD, tied to team performance with individual deal upside
• Personal Deal Compensation: You'll be compensated at the full rep commission rate for any deals you close directly
• Team Scope: To start, you'll directly support a team of five Account Executives (scaling may vary slightly based on ramping and future team expansion). Down the line, we expect to grow a second AE team, and you’ll work closely with your peer leader as the org grows.

Our Commitment to Candidates:

At Smile, we understand that finding a new role is challenging and that self-doubt or imposter syndrome can prevent you from applying to a role, don’t let it! You have a ton to offer and we want you to feel encouraged to apply, even if you don’t check all of the boxes. If you are passionate about eCommerce and helping merchants grow through loyalty and reward, connect with us. 

At Smile, we rely on a range of backgrounds, experiences, and ideas. We value diversity, and we’re proud to be an inclusive, equal opportunity workplace. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. Smile welcomes and encourages applications from people with disabilities. Accommodations are available on request for candidates taking part in all aspects of the selection process.

AI Disclaimer: At Smile, we’re strong advocates for using AI to help speed up iteration, increase productivity, and save our human brainpower for the really challenging problems. While we’re happy for AI to help you generate or tailor your resume, we’d ask that you please refrain from using AI to answer any of the questions on this application form, or to answer questions during the interview process itself.