Sales Manager

Summary

Join Smile.io, a leading loyalty program provider, as a Sales Team Manager in a fully remote role based in Canada. Lead and coach a team of five Account Executives, supporting their growth and success through hands-on mentorship and timely feedback. Maintain active involvement in sales processes, contributing to deal closure and shaping sales strategies. This role requires a blend of sales leadership, coaching, and operational skills, with a focus on long-term value and sustainable growth. You will be responsible for driving team performance towards a $3.6M annual new ARR goal, while also contributing directly to deal closure. The ideal candidate possesses extensive B2B SaaS sales experience, proven leadership skills, and a deep understanding of the Shopify ecosystem.

Requirements

• 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

Responsibilities

• 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

Benefits

• 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