About

• Base: $200k | OTE: $300k+
• Location: Toronto, Ontario (Hybrid)
• Type: Full-time
• About the Role
• TapMango is seeking a Principal / Strategic Enterprise Account Executive to lead our largest and most complex enterprise opportunities across thrift, retail, and restaurant midmarket/enterprise.
• This is a highly visible role combining enterprise sales leadership with internal orchestration. You will not only close flagship deals, but also mobilize Product, Customer Success, Implementation, and Leadership to continuously evolve TapMango’s platform and success strategies in support of our biggest customers.
• This role directly influences TapMango’s enterprise roadmap.
• What You’ll Do
• Own the full enterprise sales cycle—from prospecting through close—targeting thrift, retail, and restaurant organizations (typically 20–500+ locations)
• Lead discovery, demos, and stakeholder presentations across complex buying groups including Operations, Marketing, IT, and Executive teams
• Drive executive-to-executive relationships and develop multi-year enterprise partnerships
• Negotiate contracts and structure complex, multi-product enterprise agreements and customized deal models
• Design tailored rollout and expansion strategies by vertical and account size
• Build relationships with enterprise customers and continuously identify expansion and upsell opportunities
• Open new vertical segments and national enterprise accounts
• Operate autonomously across multiple enterprise sales motions and verticals
• Act as the enterprise quarterback across Product, Customer Success, Implementation, Marketing, and Leadership
• Partner cross-functionally to support onboarding, scalable rollouts, long-term success, and expansion frameworks
• Translate evolving customer needs into actionable internal priorities and roadmap input
• Partner closely with Product to influence packaging, feature prioritization, and roadmap direction
• Lead internal account planning and executive business reviews
• Identify cross-vertical patterns to refine messaging, GTM strategy, and enterprise playbooks across retail and restaurant environments
• Manage deals with strong organization, communication, and follow-through
• Mentor junior AEs and contribute to deal and account strategy
• Represent the company at enterprise conferences and industry events, with travel up to ~20
• What We’re Looking For
• 8–10+ years enterprise SaaS sales experience
• Proven success closing complex multi-stakeholder deals ($250k–$1M+ ARR)
• Experience selling into both retail and restaurant environments strongly preferred
• Strong cross-functional leadership skills (ability to influence without authority)
• Track record of shaping product and customer success strategy via enterprise feedback
• Exceptional executive presence and negotiation skills
• Comfort operating in ambiguity and building structure where it doesn’t yet exist
• About TapMango
• At TapMango, we provide companies with one of the highest quality customer engagement platforms on the market. We’re currently powering thousands of merchants across Canada, the US and Europe, and we have just begun! Our mission is to empower businesses to do 3 things; retain customers, upsell to existing customers, and acquire new customers. We provide merchants with all the necessary tools to run their very own loyalty program including an integrated suite of customized consumer facing technology, easy-to-use merchant tools, and automation algorithms, all aimed to enhance the customer experience.
• Why Join our Team?
• Our platform is truly a game changer in the small business arena and we need your help to empower as many vendors as possible. TapMango helps merchants compete with larger chains, so you can feel good about supporting local businesses and a diverse economy. Join a fun team with an amazing culture, tons of opportunities for growth and development, competitive pay and lots more!
• What We Offer
• Generous time off plan
• $200k base / $300k+ OTE
• Fully remote work & support to assist with making your home office space as comfortable as possible!
• Continuous virtual coaching and support
• Comprehensive health benefits
• Subsidized gym membership
• Performance recognition
• Professional development program
• Growth opportunities (we really mean it!)
• TapMango welcomes and encourages applications from people with disabilities. Accommodations are available on request for candidates taking part in all aspects of the selection process.
• Notice Regarding Automated Decision-Making
• We may use artificial intelligence and automated tools to assist in reviewing job applications. These tools support our hiring team, but all final decisions are made by human reviewers.