Entrepreneurial Managing Director / Operating Partner

This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for an Entrepreneurial Managing Director / Operating Partner based in Canada.
We are seeking an established entrepreneur ready to scale an existing business-building track record into a larger, sustainable company. In this remote opportunity, you will lead the commercial launch and growth of a digital marketplace dedicated to pre‑owned recreational vehicles and powersports equipment. You will combine your industry expertise, commercial relationships, and revenue‑generation capabilities with shared infrastructure and strategic support to accelerate business development. As the venture transitions from beta to launch and scale, you will shape its strategy, oversee operations, build partnerships, and establish repeatable systems for long‑term growth. This role offers significant autonomy and direct accountability for commercial results, operational performance, and marketplace development. It is designed for a proven operator who wants to move beyond working independently and build enterprise value through a performance‑based partnership rather than a conventional salaried position.
Accountabilities
Lead the venture's overall strategy, commercial execution, marketplace development, partnerships, and day‑to‑day operating performance.
Drive the transition from beta to commercial launch, assessing platform readiness and prioritizing the improvements required to deliver a focused market entry.
Develop and execute the operating plan, including market positioning, pricing, revenue models, customer acquisition strategies, and go‑to‑market priorities.
Build acquisition channels and establish relationships with buyers, sellers, dealers, distributors, advertisers, strategic partners, and relevant enthusiast communities.
Use customer feedback, market insights, and performance data to inform product priorities, release plans, and measurable business outcomes.
Coordinate technical teams and external vendors, overseeing product roadmap delivery, quality assurance, releases, customer support, uptime, and service levels.
Manage budgets, financial forecasts, operating costs, vendor relationships, commercial risks, and cash flow with a strong focus on financial discipline.
Develop a lean, high‑performing team across product, technology, sales, partnerships, customer success, and operations as business performance supports expansion.
Establish clear KPIs, project plans, risk registers, decision records, and reporting processes to maintain accountability and transparent communication with group leadership.
Lead the initial 90‑day validation and planning phase by assessing existing business activities, relationships, capabilities, intellectual property, and potential conflicts, and determining what may be integrated under a separate written agreement.
Validate the marketplace's commercial assumptions, strengthen buyer and seller engagement, and improve trust, retention, conversion, and overall marketplace activity.
Deliver a practical 6‑ to 12‑month growth plan covering product development, revenue, marketing, staffing, operating costs, and scaling priorities.
Build a scalable business that can grow beyond the direct involvement of a single individual, with progress measured against agreed commercial, operational, and strategic milestones.
Requirements
A proven entrepreneurial track record as a founder, business owner, independent consultant, operator, Managing Director, General Manager, or senior leader in a startup, marketplace, e‑commerce business, SaaS company, automotive business, powersports venture, or related industry.
An active consulting practice, operating business, brokerage, dealership network, marketplace, or comparable venture in powersports, automotive, recreation, e‑commerce, or a closely related field.
Demonstrated ability to generate revenue, acquire customers, develop partnerships, and deliver commercial results without relying on a fixed salary.
Established industry relationships, an existing customer base, audience access, qualified opportunities, domain expertise, or other commercial assets that can accelerate marketplace growth.
Strong commercial acumen and a proven understanding of customer acquisition, sales conversion, retention, partnership development, and revenue growth.
Experience developing business strategies, operating plans, repeatable processes, and scalable systems that enable growth beyond a solopreneur model.
Product and technical fluency, including the ability to collaborate effectively with software developers, technical teams, contractors, and external vendors.
Strong financial management skills, including budgeting, forecasting, cost control, cash flow, KPI analysis, and performance monitoring.
Experience with commercial negotiations, contracts, vendor management, risk assessment, and operational decision-making.
Excellent leadership, communication, and relationship‑building skills, supported by sound judgment, transparency, resilience, and personal accountability.
Comfort working in a performance‑driven environment where results are assessed through revenue, gross margin, cash flow, marketplace activity, and delivery against agreed milestones.
Experience with digital marketplaces, trading platforms, dealer networks, fundraising, contractor‑led teams, or performance‑based compensation structures is an advantage.
Willingness to participate in an initial 90‑day mutual validation and operating‑plan period and collaborate on clearly defined objectives and written commercial terms.
An entrepreneurial mindset and a genuine interest in building long‑term enterprise value through shared capabilities, strategic collaboration, and performance‑based economic participation.
Benefits
Remote opportunity: Work remotely from Canada while leading the venture's commercial and operational development.
Entrepreneurial autonomy: Take meaningful ownership of strategy, execution, partnerships, and business growth.
Strategic support: Access leadership guidance, structured planning, accountability processes, and collaboration with other Managing Directors within the broader group.
Shared business infrastructure: Potential access, as agreed in the operating plan, to finance and administration, marketing, technology, systems, business development, and other operational resources.
Commercial collaboration: Opportunities for referrals, cross‑business partnerships, and shared expertise where strategically appropriate.
Performance‑based earning potential: Compensation may include agreed commissions, revenue share, gross‑margin participation, project or delivery fees, profit participation, or milestone‑based payments.
Potential ownership participation: An opportunity to earn equity or another ownership interest through a milestone‑based arrangement, subject to performance, mutual fit, formal approvals, and definitive written agreements.
Business‑building opportunity: Help transform an early‑stage digital marketplace into a scalable company with long‑term commercial potential.
Structured initial phase: A 90‑day mutual validation period to assess strategic fit, define priorities, and establish an actionable operating plan.
Potential for long‑term partnership: The opportunity to develop an ongoing operating relationship based on demonstrated results and agreed terms.
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