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 OverviewIndividual 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 ObjectivesGenerate qualified outbound meetings with mid-market and enterprise prospectsSupport consistent pipeline of prospect for the Account ExecutivesEngage target companies with relevant, personalize outreachDevelop a strong understanding of the company ICP, buyers and value propositionsExecute outbound activities with consistency and disciplineCore ResponsibilitiesOutbound Prospecting and Lead GenerationResearch and identify target companies and buyers in our ICPsExecute outbound outreach via email, phone, LinkedIn and other channelsPersonalize messaging based on company research and prospect contextBook qualified meetings aligned to agreed qualification criteriaCollaborate with Account ExecutivesWork closely with Account Executives on ICP targeting and outreach strategiesSupport account based prospecting into mid-market and enterprise organizationsShare prospect feedback, objections and insightsEnsure clean handoffs and well-prepared meetingsQualification and Discovery SupportIdentify prospect pain points, priorities and buying signalsConfirm ideal fit before passing opportunities to Account ExecutivesProcess and Tool DisciplineMaintain accurate activity, lead, and account data in the HubSpot CRMFollow outbound sequences and continuously improve messagingTrack outreach performance and contribute ideas for improvementRequired Experience & ProfileExperience1- 3+ years of experience in BDR, SDR or outbound sales roleExperience working in a small or growth stage software companyExposure to mid-market and enterprise selling is a plusComfortable supporting global outbound efforts across time zonesSkills and AttributesStrong written and verbal communication skillsCurious, coachable and motivated to learnOrganized and consistent with outbound executionResilient and comfortable with rejectionAble to work independently in a remote-first environmentPreferred Experience (Nice to Have)Bilingual (English/French) verbal and writtenExperience with CRM and sales engagement toolsFamiliarity with account based prospectingHubSpot fluencyWhat Success looks like in the first 6 monthsConsistent delivery of qualified meetingsStrong working relationships with Account ExecutiveImproving outreach to meeting conversion ratesSolid understanding of ICP, buyers and use casesReliable execution and HubSpot CRM hygieneTools and Working EnvironmentHubSpot 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 spaceLean, collaborative sales organization with direct access to decision-makersCompensation and BenefitsCompetitive base salary plus variable compensationClear performance targets tied to meetings and pipelineBenefits and flexibility aligned with a Canadian-based, remote workforceWhy Join?Exceptional leadership team - founders and senior team from Google, Microsoft, and other top-tier companiesBacked by reputable private equity with recent investment fueling rapid growthProduct transformation - exciting time to join as we revamp our platform with cutting-edge technologyPunch above our weight - small Canadian team selling to Fortune 500 companies and major financial institutionsCareer growth opportunity - break into the exciting world of software sales with mentorship from industry veteransCompetitive compensation with opportunities for career progression #J-18808-Ljbffr
Job Title
Business Development Representative