Director of Business Development
4-Day Work Week | Hybrid Remote | Winnipeg, Manitoba
McLenehan and Associates Chartered Professional Accountants
$100,000 Base Salary | Uncapped Commission | OTE $150,000+
WHY YOU'LL LOVE WORKING HERE
- 4-Day Work Week Four 8-hour days. In a sales role. Yes, really.
- Competitive Base $100,000 annual salary. Yours for hitting a clear, measurable target.
- 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. Real training, not a binder.
- RRSP Matching Contribution matching to support your long-term financial security.
- Comprehensive Benefits Prescription, dental, and vision coverage.
THE OPPORTUNITY
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.
WHAT YOU'LL EARN
You will not be expected to hit $500,000 in revenue in your first week. Your first 90 days are a structured ramp: learning the services, configuring your tools, building your pipeline, and closing your first engagements, with Mike present for every major deal conversation until you are ready to run them independently.
WHAT YOU'LL SELL
McLenehan and Associates serves incorporated Canadian small businesses across three service lines. You will sell them in this priority order:
1. Fractional CFO and Virtual Controller Services
Our highest-priority service. Weekly retainer engagements for owner-managed businesses doing $2M to $10M in revenue. These clients need strategic financial leadership but cannot afford to hire a full-time CFO. Retainer engagements typically range from $900 to $2,000 per week, or $46,800 to $104,000 annually per client.
2. Monthly Bookkeeping and Financial Reporting
Recurring retainer engagements for smaller businesses typically under $2M in annual revenue. High volume, predictable lifetime value, and a natural entry point that frequently converts to higher-value advisory services. Retainer engagements typically range from $190 to $600 per week, or $9,880 to $31,200 annually.
3. Year-End Financial Statements and Corporate Income Tax
Project-based engagements with fees ranging from $2,900 to $15,000 annually, depending on the size and complexity of the business and the number of entities in a group of corporations. These engagements often serve as relationship-builders that convert to ongoing monthly services over time.
The buyer:
The owner or operator of an incorporated Canadian small business. They are running a growing company, feel underserved by their current accounting situation, and are open to help, if they trust the firm they are working with. Your job is to build that trust and earn that decision.
The sales motion:
Primarily inbound in the early months: referrals and marketing inquiries that you will convert with consultative discovery. As you build your pipeline, you will layer in a CASL-compliant outbound prospecting motion using LinkedIn. You own the full sales cycle: from first conversation to signed engagement letter.
Your tools:
HubSpot Sales Hub Professional (your daily operating system), LinkedIn Sales Navigator (outbound prospecting), and Sales Gravy University (structured skill development throughout your first 90 days). If it is not in HubSpot, it did not happen.
WHAT YOU'LL DO
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
WHAT SUCCESS LOOKS LIKE — YOUR FIRST 90 DAYS
Month 1: Oriented and Active (Days 1–30)
In your first month, you are getting fully grounded in the firm, the services, and the sales motion. You understand all three service lines well enough to run a credible, confidence‑building discovery conversation with a business owner. HubSpot is fully configured and in daily use, with contacts, deals, task queues, and your calendar kept current. Sales Gravy University and HubSpot training modules are underway, and learning is actively applied in real conversations. You have participated in your first discovery calls with Mike present and are sharing thoughtful, honest observations about what you are hearing from prospects.
Month 2: Independent and Building (Days 31–60)
By month two, you are running discovery calls independently and qualifying opportunities with real discipline. A live, well‑maintained pipeline exists in HubSpot, with multiple active deals progressing through defined stages. Follow‑up is consistent, timely, and reliable, with nothing slipping through the cracks. You are building proposals with Mike’s input and confidently presenting them to qualified prospects. Initial closed and won engagements are possible during this stage.
Month 3: Fully Operational (Days 61–90)
By the end of your third month, you are managing the full inbound‑to‑close sales cycle independently. A compliant outbound LinkedIn prospecting motion is in place and actively generating conversations. Your pipeline and activity levels indicate a credible trajectory toward the $500,000 annual new‑revenue target. Mike’s involvement has shifted from hands‑on coaching to reviewing deal strategy and providing high‑level guidance as needed.
WHAT WE'RE LOOKING FOR
You must have:
- 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
You will stand out if you have:
- 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
WHO YOU ARE
Top performers in this role will recognize themselves in this list:
- You ask better questions than you give answers. Your discovery process is genuinely curious, not scripted.
- You treat follow-up as a competitive advantage, not an inconvenience
- You are driven by your numbers and honest with yourself when your pipeline is not healthy
- You represent a firm the way you would represent yourself: with warmth, professionalism, and credibility
- You can distinguish a tough prospect from a bad fit, and you have the judgment and discipline to act on the difference
- You can build a relationship patiently over months and close it decisively when the moment arrives
- You want to be part of building something, not just filling a seat
This is not a role for someone who needs to be pushed. It is a role for an experienced, self-directed professional who wants structure, the right tools, direct access to firm leadership, and the freedom to perform.
OUR VALUES
Profit Minded: We do work that is profitable and allows our firm to grow.
Quality Focused: We review each other's work and make sure we get it right.
Value Driven: We give great advice to clients, which makes us valued partners.
We believe everyone deserves the chance to thrive, personally and professionally. Our clients are small business owners who are building something meaningful, and we are here to give them the financial leadership they need to succeed. If you want to sell something that genuinely helps people, and do it within a firm that respects your time and your life, we would love to hear from you.
HOW TO APPLY
Apply directly through our careers page on BambooHR, or send your resume and a brief note on why this role is the right fit for you to [email protected].
We review applications on a rolling basis. Here is what to expect:
Step 1 A 20-minute introductory call with our Director of People and Culture.
Step 2 A deeper conversation about your sales experience and your approach to selling professional services.
Step 3 A short discovery call role-play: a chance for both of us to evaluate fit.
Step 4 Final conversation, reference check, and offer.
