Element Fleet Management

Managing Director, Commercial Sales

Element Fleet Management • $200K — $275K *
Business Services
8 - 10 years of experience
Job Overview by Ladders

Qualifications

  • 5+ years of experience leading B2B enterprise sales teams
  • Proven track record in new business acquisition
  • Strong understanding of financial statements and deal economics
  • Exceptional coaching and talent development skills
  • Ability to own a P&L and make resource allocation decisions

Responsibilities

  • Drive regional client acquisition and profitable revenue growth
  • Lead and develop a high-performing team of Sales Directors
  • Manage pipeline health and metrics across the region
  • Forecast accurately and uphold disciplined operational standards
  • Execute leadership on complex deals and negotiations

Benefits

  • Innovative and empowered company culture
  • Comprehensive health and welfare benefits
  • Paid time-off programs including vacation and sick leave
Full Job Description
THE OPPORTUNITY

Element sits at the intersection of fleet, capital, technology, and operations.

We manage some of the world's largest and most complex commercial fleets, and the breadth of what we can bring to clients continues to expand - from financing and fleet management to technology, data, connected vehicles, payments, and emerging mobility solutions.
That creates a significant leadership opportunity.

We are looking for a Managing Director who can lead a commercial region as a business, build a high-performing team of Sales Directors, and translate strategy into profitable growth. You will be accountable not only for the final number, but for the commercial system that produces it - pipeline creation and quality, conversion, win rate, cycle time, forecast accuracy, deal economics, and sales productivity.

You will know how different segments, solutions, deal sizes, and buying processes create different sales cycles, and you will adjust pipeline coverage, coaching, resource allocation, and leadership intervention accordingly.

The expectation is straightforward: Build the team. Build pipeline. Improve conversion. Grow profitably. Own the result.

WHAT YOU WILL OWN

  • 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.


YOU SHOULD CONSIDER THIS ROLE IF:

  • You are a sales leader first. You know how to get results through a team, not by becoming the individual contributor on every important deal.
  • You know the math of sales. You can diagnose whether a performance gap comes from insufficient pipeline, poor quality, weak conversion, low win rate, long cycle time, execution issues, or a combination of them.
  • You can run a region as a business. You are comfortable owning a P&L, making resource trade-offs, balancing growth and profitability, and being accountable for the result.
  • You understand complex enterprise sales. Multiple stakeholders, sophisticated procurement, financial analysis, long sales cycles, and difficult negotiations are familiar territory.
  • You are a strong coach. You can turn pipeline reviews, deal reviews, and one-on-ones into specific actions that improve seller capability and commercial outcomes.
  • You build accountability without creating unnecessary bureaucracy. Expectations, ownership, next steps, and consequences are clear.
  • You are comfortable making talent decisions. You invest in strong performers, address performance gaps quickly, and build a credible bench for the future.
  • You use data to make decisions, but stay close enough to the market, customers, and team to understand what the data cannot explain on its own.


HOW YOU WILL LEAD

  • 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.


YOU SHOULD BE ABLE TO TELL US

  • The size and scope of the business, revenue target, or P&L you were accountable for
  • How you built pipeline coverage and improved pipeline quality across a team
  • How you used win rate, cycle time, conversion, and forecast accuracy to diagnose and improve performance
  • How you improved the performance of a sales team, including examples of coaching, talent development, and difficult performance decisions
  • The most complex or significant deal you helped your team win and the specific role you played
  • How you allocated resources or changed priorities when a region, territory, or forecast was off plan
  • How you balanced growth, profitability, client value, and risk in an important commercial decision


Successful candidates will typically bring significant experience leading complex B2B enterprise sales teams, with a record of acquiring new business in multi-stakeholder environments. You should have experience leading senior sellers, owning a meaningful revenue target or P&L, using commercial analytics to improve performance, and influencing C-suite decision makers. A strong working understanding of financial statements, deal economics, risk, and commercial structuring is important for this role.

Experience in fleet management is valuable, but it is not a prerequisite. We can teach fleet; building leaders who can create pipeline, diagnose performance, coach teams, and own a business is harder to teach.

LOCATION AND TRAVEL

  • Location: U.S. - based within assigned region
  • Working arrangement: Remote
  • Travel: Significant travel across the assigned region and for key prospect, client, and team engagements


COMPENSATION

The hiring base salary range for this position is $200,000 - $275,000 annually. This range represents the Company's good-faith estimate of the expected base salary at the time of posting. Salary ranges may vary based on the geographic location where the work is performed. The salary range listed in this posting applies only to the location identified. Actual compensation will be determined based on several factors, including the successful candidate's qualifications, knowledge, skills, experience, internal pay equity, and relevant market data. In addition to base salary, eligible employees may participate in annual incentive programs, including bonuses, commissions, or other incentive compensation, as applicable to the role. Element also offers a comprehensive benefits package, which may include health insurance, tuition reimbursement, and retirement savings plans.

What's in it for You
• A culture of innovation, empowerment, decision-making, and accountability
• 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)

Applicants will be required to undergo a background check only if and after a conditional offer of employment has been extended.

About Element Fleet Management

Element Fleet Management is a global provider of fleet management services. The company was founded in 2011 and is headquartered in Toronto, Canada. Element Fleet Management's services include vehicle acquisition and financing, maintenance and repair, fuel management, and driver safety programs. The company serves a wide range of industries, including transportation, construction, healthcare, and government. Element Fleet Management aims to help its clients reduce costs, increase productivity, and improve safety and sustainability.
Learn more about Element Fleet Management
Size
5,000 employees
Industry

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