Account Executive

Reports to

VP of Revenue and Customer Experience

Join Expense Point at an inflection point! Fresh off new investment with ex-Google and Microsoft leadership, we're a nimble Canadian fintech taking on Fortune 500 clients and major banks. We're seeking a driven Account Executive to capitalize on our momentum - combining inbound lead conversion with aggressive outbound prospecting to fuel our explosive growth.

• Primary focus on outbound prospecting, new logo acquisition and closing in mid-market and enterprise accounts
• Requires comfort operating in a high growth environment with evolving go-to-market motion
• Experience selling into more complex, structured buying organizations
• Remote-first role with collaboration across time zones

• Independently generate and close a predictable pipeline through outbound efforts
• Win new business in target segments through consultative, technical selling
• Serve as trusted advisor to prospects throughout complex sales cycles
• Represent the company professionally with senior buyers in mid-market and enterprise segments.

• Own the full sales cycle from outbound prospecting through close
• Identify, research and engage target accounts globally
• Develop personalized outbound approaches for mid-market and enterprise buyers
• Maintain accurate pipeline and forecasting discipline
• Lead discovery, demonstrations and solution discussions
• Manage multi-stakeholder buying processes
• Navigate longer sales cycles, including procurement and security reviews where required
• Negotiate commercial terms and close new logo deals

• Develop strong product and industry knowledge
• Confidently engage both business and technical stakeholders
• Translate product capabilities into business outcomes

• Collaborate with Marketing, Product and Customer teams as needed
• Share market and customer insights to support continuous improvement
• Follow defined sales processes while contributing practical feedback

• 5-10+ years of B2B software sales experience
• Experience working in a small or growth stage software company
• Proven success selling outbound into mid-market and enterprise customers
• Experience selling globally or across multiple regions/time zones

• Strong hunter mindset with disciplined outbound execution
• Comfortable working independently in a remote environment
• Strong discovery, qualification and closing skills
• Clear, concise communicator with executive presence
• Highly organized with strong CRM and pipeline management habits

• Experience with finance/accounting/payment SaaS or products selling into the CFO’s office
• Experience selling with or through partners (Banks, Resellers, Referral partners etc.)
• Hub Spot fluency
• Familiarity with global selling considerations (time zones, procurement norms, cultural nuances)

• Consistent self-sourced outbound pipeline
• Closed won new logo revenue in mid-market and enterprise segments in targeted ICPs
• Predictable deal progression and accurate forecasting
• Strong grasp of customer use cases and buying processes
• Reliable execution as a senior individual contributor

• Hub Spot CRM and sales engagement tools (Lemlist, Apollo)
• Access to AI business accounts (ChatGPT, Claude, Gemini)
• Remote-first, distributed team environment headquartered in Winnipeg in a modern, fun space
• Lean organization with direct access to decision-makers

• Competitive base salary with commission
• OTE aligned to mid-market and enterprise sales cycles
• Benefits and flexibility aligned with a Canadian-based, remote workforce

• Exceptional leadership team - founders and senior team from Google, Microsoft, and other top-tier companies
• Backed by reputable private equity with recent investment fueling rapid growth
• Product transformation - exciting time to join as we revamp our platform with cutting-edge technology
• Punch above our weight - small Canadian team selling to Fortune 500 companies and major financial institutions
• Career growth opportunity - break into the exciting world of software sales with mentorship from industry veterans
• Competitive compensation with uncapped commission potential