Managing Director, Commercial Sales

Element Fleet Management

3d • $200,000 - $275,000 • Remote

About The Position

Element is redefining the fleet management industry to be people-first, then business, delivering a superior client experience. This role involves leading a commercial region as a business, building a high-performing team of Sales Directors, and translating strategy into profitable growth. The Managing Director will be accountable for the final number and the commercial system that produces it, including pipeline creation and quality, conversion, win rate, cycle time, forecast accuracy, deal economics, and sales productivity. They will understand how different segments, solutions, deal sizes, and buying processes create different sales cycles and adjust pipeline coverage, coaching, resource allocation, and leadership intervention accordingly. The expectation is to build the team, build pipeline, improve conversion, grow profitably, and own the result.

Requirements

• Sales leader who gets results through a team, not by being the individual contributor on every important deal.
• Understands the math of sales: can diagnose performance gaps from insufficient pipeline, poor quality, weak conversion, low win rate, long cycle time, execution issues, or a combination.
• Can run a region as a business: comfortable owning a P&L, making resource trade-offs, balancing growth and profitability, and being accountable for the result.
• Understands complex enterprise sales: familiar with multiple stakeholders, sophisticated procurement, financial analysis, long sales cycles, and difficult negotiations.
• Strong coach: can turn pipeline reviews, deal reviews, and one-on-ones into specific actions that improve seller capability and commercial outcomes.
• Builds accountability without creating unnecessary bureaucracy: expectations, ownership, next steps, and consequences are clear.
• Comfortable making talent decisions: invests in strong performers, addresses performance gaps quickly, and builds a credible bench for the future.
• Uses data to make decisions, but stays close enough to the market, customers, and team to understand what the data cannot explain on its own.
• Significant experience leading complex B2B enterprise sales teams.
• Record of acquiring new business in multi-stakeholder environments.
• Experience leading senior sellers.
• Experience owning a meaningful revenue target or P&L.
• Experience using commercial analytics to improve performance.
• Experience influencing C-suite decision makers.
• Strong working understanding of financial statements, deal economics, risk, and commercial structuring.

Nice To Haves

• Experience in fleet management is valuable, but it is not a prerequisite.

Responsibilities

• Regional new client acquisition, profitable revenue growth, and P&L performance - running your region as a business and owning delivery against plan.
• A high-performing team of Sales Directors, including hiring, onboarding, coaching, performance management, development, and succession planning.
• Pipeline health across the region - creation, coverage, quality, aging, stage progression, conversion, and the right balance of opportunities across near-, mid-, and long-term horizons.
• The commercial metrics that drive business outcomes, including pipeline, win rate, cycle time, conversion, forecast accuracy, revenue, margin, and sales productivity.
• Understanding and actively managing different sales cycles by segment, deal size, solution, and buying process, with clear expectations for the level of pipeline coverage and activity required in each.
• Accurate forecasting and a disciplined operating cadence, with strong CRM hygiene, clear deal inspection, and timely intervention when performance is off track.
• Leadership on complex and high-value opportunities, including deal strategy, commercial structuring, pricing, negotiation, risk trade-offs, and executive engagement.
• Cross-functional alignment across Finance, Credit/Risk, Legal, Operations, Product, Pricing, and other partners to remove barriers and improve speed and quality of execution.
• Set a clear regional sales strategy and translate it into territory priorities, pipeline requirements, account focus, and measurable actions for the team.
• Establish a consistent operating rhythm for prospecting, pipeline, forecast, deal, and performance reviews, with a strong bias toward fact-based decision making and action.
• Create a pipeline-building culture in which prospecting and opportunity creation are continuous leadership priorities, not activities that increase only when the forecast is under pressure.
• Coach Sales Directors on prospect strategy, discovery, business-case development, executive engagement, commercial structuring, negotiation, and closing.
• Allocate leadership attention and company resources to the opportunities, territories, and sellers where they can create the greatest business impact.
• Build team capability over time through structured coaching, feedback, development plans, succession planning, and selective external hiring when needed.
• Partner effectively across functions, escalating issues with judgment and helping the organization make timely decisions without losing accountability for the commercial outcome.
• Represent the region with credibility in planning, budgeting, forecasting, and leadership forums, clearly explaining performance, risks, opportunities, and actions.

Benefits

• Comprehensive health and welfare benefits that serve the needs of you and your family and foster a culture of wellness
• Additional benefits and amenities, including paid time-off programs (vacation, sick leave, and holidays)
• health insurance
• tuition reimbursement
• retirement savings plans

What This Job Offers

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