Business Development Representative

Join ExpensePoint 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.

Role Overview

• Individual contributor role focused on outbound prospecting and early-stage engagement with potential customers.
• Support global sales efforts by identifying target companies, engaging the right buyers, and setting high quality meetings for Account Executives.
• Ideal candidate enjoys outbound activity, curious about complex, structured buying organizations and thrives in a high growth remote-first company.

Role Objectives

• Generate qualified outbound meetings with mid-market and enterprise prospects
• Support consistent pipeline of prospect for the Account Executives
• Engage target companies with relevant, personalize outreach
• Develop a strong understanding of the company ICP, buyers and value propositions
• Execute outbound activities with consistency and discipline

Core Responsibilities

Outbound Prospecting and Lead Generation

• Research and identify target companies and buyers in our ICPs
• Execute outbound outreach via email, phone, LinkedIn and other channels
• Personalize messaging based on company research and prospect context
• Book qualified meetings aligned to agreed qualification criteria

Collaborate with Account Executives

• Work closely with Account Executives on ICP targeting and outreach strategies
• Support account based prospecting into mid-market and enterprise organizations
• Share prospect feedback, objections and insights
• Ensure clean handoffs and well-prepared meetings

Qualification and Discovery Support

• Identify prospect pain points, priorities and buying signals
• Confirm ideal fit before passing opportunities to Account Executives

Process and Tool Discipline

• Maintain accurate activity, lead, and account data in the HubSpot CRM
• Follow outbound sequences and continuously improve messaging
• Track outreach performance and contribute ideas for improvement

Required Experience & Profile

Experience

• 1- 3+ years of experience in BDR, SDR or outbound sales role
• Experience working in a small or growth stage software company
• Exposure to mid-market and enterprise selling is a plus
• Comfortable supporting global outbound efforts across time zones

Skills and Attributes

• Strong written and verbal communication skills
• Curious, coachable and motivated to learn
• Organized and consistent with outbound execution
• Resilient and comfortable with rejection
• Able to work independently in a remote-first environment

Preferred Experience (Nice to Have)

• Bilingual (English/French) verbal and written
• Experience with CRM and sales engagement tools
• Familiarity with account based prospecting
• HubSpot fluency

What Success looks like in the first 6 months

• Consistent delivery of qualified meetings
• Strong working relationships with Account Executive
• Improving outreach to meeting conversion rates
• Solid understanding of ICP, buyers and use cases
• Reliable execution and HubSpot CRM hygiene

Tools and Working Environment

• HubSpot 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, collaborative sales organization with direct access to decision-makers

Compensation and Benefits

• Competitive base salary plus variable compensation
• Clear performance targets tied to meetings and pipeline
• Benefits and flexibility aligned with a Canadian-based, remote workforce

Why Join?

• 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 indust