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 industry veterans

Competitive compensation with opportunities for career progression

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