Director of Business Development

McLenehan and Associates Chartered Professional Accountants

6d • $100,000 - $150,000 • Hybrid

About The Position

Most sales roles are built to burn people out. Long hours. Vague targets. Thin margins on a product you can barely believe in. A manager who has never actually sold anything. This one is different. 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. We serve hundreds of clients. Our team genuinely enjoys its work. And our 4-day work week has proven, for years, that you can maintain high standards and still have a life. Until now, our growth has come from referrals and the owner's personal network. That changes with this hire. This is the ground-floor opportunity that experienced sales professionals talk about but rarely find: a firm with a proven service, an excellent reputation in its market, a steady stream of inbound inquiries, and no dedicated salesperson to convert any of it. You will work directly with Mike McLenehan, the firm's owner, who will be as invested in your success as you are. We are not looking for someone to train into sales. We are looking for someone who has already proven they can sell professional services to business owners, and who wants to do it within a firm that takes work-life balance seriously. Some networking and business development events will fall outside standard hours, but that is the exception, not the expectation. If that describes you, keep reading.

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. You do not need to be an accountant, but you need to speak credibly about financial leadership with a business owner.
• Experience with LinkedIn Sales Navigator for structured outbound prospecting
• Working knowledge of CASL compliance for email and digital outreach in Canada

Responsibilities

• Pipeline Development and Prospecting
• Convert inbound inquiries from referrals and marketing with speed, professionalism, and a consultative approach that earns trust before it asks for a decision
• 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
• Discovery and Qualification
• 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
• Proposals and Closing
• 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
• Pipeline Hygiene and Performance Reporting
• 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 $20,000 for every $100,000 of new revenue above your target. No ceiling. No politics.
• Hybrid Remote Work from home most days, with in-person time in Winnipeg for client meetings and networking events when it counts.
• 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 matching to support your long-term financial security.
• Comprehensive Benefits Prescription, dental, and vision coverage.

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed
• Number of Employees: 1-10 employees