Director of Business Development

McLenehan and Associates Chartered Professional Accountants • Winnipeg, MB

2d • CA$100,000 - CA$150,000 • Hybrid

About The Position

McLenehan and Associates CPAs is a growing Winnipeg-based accounting firm that helps incorporated Canadian small businesses access the financial leadership they actually need, from monthly bookkeeping to Fractional CFO and Virtual Controller services. This is a ground-floor opportunity for an experienced sales professional to convert inbound inquiries and build a dedicated sales motion. The role involves working directly with the firm's owner, Mike McLenehan, and focuses on selling professional services within a firm that prioritizes work-life balance. The position offers a structured ramp-up period, comprehensive training, and the chance to build something meaningful.

Requirements

• A proven, verifiable track record in B2B sales of professional services: accounting, legal, consulting, financial services, or a closely related field.
• Demonstrated experience selling directly to business owners, operators, or senior executives.
• A history of hitting or exceeding revenue targets, with real numbers you can speak to.
• Comfort and competence running the complete sales cycle: prospecting, discovery, proposal, negotiation, and close.
• A CRM as a daily operating tool, not an afterthought. HubSpot experience is a meaningful advantage.
• The discipline to manage your own pipeline and the self-awareness to know when it is not healthy.

Nice To Haves

• Familiarity with accounting, bookkeeping, or CFO-level financial concepts.
• Experience with LinkedIn Sales Navigator for structured outbound prospecting.
• Working knowledge of CASL compliance for email and digital outreach in Canada.

Responsibilities

• Convert inbound inquiries from referrals and marketing with speed, professionalism, and a consultative approach.
• Build a CASL-compliant outbound prospecting motion on LinkedIn, targeting incorporated business owners in the $2M to $10M revenue range.
• Attend Winnipeg business and professional networking events to develop referral relationships and generate qualified opportunities.
• Run structured discovery conversations to understand each prospect's financial situation, current challenges, growth goals, and readiness to engage.
• Qualify opportunities against the firm's ideal client profile, and disqualify gracefully and professionally when the fit is not right.
• Document every contact, conversation, and committed next step in HubSpot without exception.
• Build tailored proposals for accounting and advisory services with input from Mike and the delivery team.
• Present proposals, handle objections with composure and evidence, and negotiate engagement terms professionally.
• Own the new client onboarding handoff: from a signed engagement to a seamless first deliverable.
• Maintain accurate deal stages, close date forecasts, and complete activity records in HubSpot at all times.
• Report on pipeline health and new revenue progress in weekly 1:1 check-ins with Mike.
• Identify patterns in wins and losses and use them to continuously sharpen messaging, qualification, and approach.

Benefits

• 4-Day Work Week
• Competitive Base $100,000 annual salary
• Uncapped Commission
• Hybrid Remote Work
• Generous Time Off (3 weeks of vacation plus a paid week during the December holidays)
• Paid Training (Firm-funded ramp including Sales Gravy University masterclasses and HubSpot Sales certifications)
• RRSP Matching Contribution
• Comprehensive Benefits (Prescription, dental, and vision coverage)

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed