Director, Strategic Fleet Sales (2120)

Kooner Fleet Management Solutions

2d•$100,000 - $120,000•Remote

About The Position

The Director, Strategic Fleet Sales is responsible for developing and winning Kooner FMS's largest national fleet opportunities. This is a senior individual contributor role focused on a defined portfolio of named strategic prospects. These organizations may operate thousands or tens of thousands of vehicles, trailers, and other fleet assets across hundreds of locations. You will own the opportunity from initial prospecting through executive engagement, solution design, pricing, pilot development, contract negotiation, and national rollout planning. This role requires someone who understands how major fleets buy maintenance services, how complex organizations evaluate suppliers, and how to build a compelling business case for changing an established operating model. You will work closely with Kooner's executive leadership, operations, finance, recruiting, account management, and other internal stakeholders to determine how Kooner can successfully support each opportunity. The ideal candidate brings deep relationships and credibility within the fleet industry and has spent their career selling complex fleet solutions to large national organizations. This is a remote opportunity with travel required up to 50-75%.

Requirements

10+ years of fleet, transportation, automotive, commercial vehicle, fleet maintenance, fleet technology, or related B2B sales experience.
Demonstrated experience selling directly to large national fleets and enterprise organizations.
Existing relationships with leaders responsible for major commercial fleets.
Experience calling on organizations comparable in size and complexity to Walmart, The Home Depot, FedEx, UPS, Amazon, PepsiCo, Coca-Cola, Sysco, Ryder, Penske, major utilities, national rental fleets, or similar organizations.
Proven success navigating complex enterprise sales cycles involving multiple stakeholders.
Track record of winning large strategic accounts with significant annual revenue potential.
Strong understanding of fleet maintenance operations and the economics surrounding fleet uptime, technician productivity, preventive maintenance, repair services, and asset utilization.
Ability to translate operational challenges into financial business cases.
Experience developing customized pricing and commercial models.
Experience designing pilots and phased enterprise rollouts.
Strong executive presence and ability to communicate with senior corporate leaders.
Advanced negotiation, presentation, discovery, and relationship-development skills.
Ability to manage a small number of highly complex opportunities with discipline and persistence.
Strong financial and analytical skills.
Proficiency with CRM platforms, Microsoft Office, and presentation tools.
Willingness to travel up to 50-75% for customer meetings, site visits, conferences, and strategic pursuits.
Valid driver's license and clean driving record.

Responsibilities

Own a defined list of Kooner's highest-value strategic fleet prospects.
Develop account plans for each named prospect, including organizational structure, fleet profile, current maintenance model, buying process, decision-makers, influencers, existing vendors, and competitive landscape.
Identify and develop relationships across multiple levels of each organization.
Build relationships with fleet, transportation, procurement, operations, finance, safety, maintenance, and executive leadership.
Use industry relationships, research, referrals, conferences, outbound outreach, and other methods to create access within target accounts.
Build multi-threaded relationships that reduce dependence on any single contact.
Maintain a long-term pursuit strategy for accounts that may require extended sales cycles.
Create strategic outreach plans tailored to senior fleet and corporate decision-makers.
Secure meetings with leaders responsible for fleet maintenance, transportation, procurement, operations, sourcing, and asset management.
Engage prospects around business outcomes instead of leading with individual services.
Position Kooner as a strategic fleet maintenance partner capable of supporting complex regional and national programs.
Develop credibility as a knowledgeable advisor who understands large-fleet operating challenges.
Lead comprehensive discovery across each strategic account.
Understand fleet size, asset types, locations, maintenance practices, internal staffing, outsourced services, downtime challenges, service-level expectations, technology requirements, and procurement processes.
Quantify the operational and financial impact of the prospect's current maintenance model.
Identify locations and use cases where Kooner can create immediate value.
Determine the best entry point for each relationship, including pilots, regional programs, specific asset classes, overflow maintenance, preventive maintenance, inspections, repair programs, or dedicated technician models.
Develop a clear opportunity strategy before advancing major prospects through the sales process.
Build customized value propositions for each strategic prospect.
Translate Kooner's capabilities into measurable customer outcomes such as: Reduced vehicle downtime, Increased asset availability, Lower maintenance administration burden, Improved preventive maintenance compliance, Reduced transportation of assets to repair facilities, Improved technician availability, Better maintenance cost visibility, More consistent service across multiple locations.
Develop financial and operational business cases supporting the customer's decision to change its current maintenance model.
Work with customers to establish measurable success criteria for pilots and larger deployments.
Lead development of pricing models for large, complex opportunities.
Work with finance and operations to understand technician economics, travel requirements, service density, customer locations, expected work volume, asset mix, and margin requirements.
Develop pricing structures that create customer value while supporting Kooner's financial objectives.
Evaluate different commercial structures, including: Hourly mobile service, Guaranteed service windows, Dedicated technician programs, Regional programs, National agreements, Pilot programs, Volume-based pricing, Location-specific pricing.
Develop proposals, presentations, pricing schedules, business cases, and executive-level recommendations.
Design pilot programs that allow large fleets to validate Kooner's capabilities before broader deployment.
Identify pilot markets based on customer need, Kooner capacity, fleet density, service volume, and likelihood of measurable success.
Establish pilot objectives, timelines, service levels, reporting requirements, and success metrics.
Create a defined process for reviewing pilot performance and determining expansion opportunities.
Develop phased rollout strategies for regional and national fleet deployments.
Work with operations, recruiting, and leadership to determine where Kooner has existing capacity and where additional technicians or infrastructure may be required.
Help customers create realistic implementation plans for large-scale fleet maintenance programs.
Own the full enterprise sales cycle from first engagement through contract execution.
Navigate procurement, sourcing, legal, operational, IT, finance, and executive approval processes.
Lead formal presentations, RFP responses, pricing negotiations, contract discussions, and executive business reviews.
Coordinate internal resources required to advance strategic opportunities.
Maintain momentum through long enterprise sales cycles involving multiple stakeholders.
Identify risks that could delay or prevent an opportunity from closing and develop strategies to address them.
Serve as the internal commercial leader for assigned strategic opportunities.
Bring the voice of the customer into discussions with Kooner's leadership and operations teams.
Clearly communicate what the customer needs, why they need it, and what Kooner must deliver to win the business.
Partner with operations to validate service capability before making customer commitments.
Partner with recruiting when strategic opportunities require incremental technician capacity.
Partner with finance to validate pricing, profitability, and commercial structures.
Partner with account management to establish a transition strategy before broader customer rollout.
Provide recommendations to executive leadership regarding major commercial opportunities.
Maintain accurate opportunity information within Kooner's CRM.
Develop realistic revenue forecasts for large, multi-stage opportunities.
Create strategic account plans and document next steps for each named prospect.
Track pilot opportunities, expansion potential, estimated annual revenue, decision timelines, and probability of close.
Provide regular updates to executive leadership on strategic account progress.
Maintain disciplined follow-up across sales cycles that may extend for many months.
Represent Kooner FMS at national fleet conferences, customer meetings, industry events, and strategic partner meetings.
Maintain strong relationships throughout the fleet, transportation, maintenance, and logistics industries.
Monitor competitor capabilities, industry trends, fleet outsourcing strategies, and changes in customer buying behavior.
Identify emerging market opportunities that could shape Kooner's future service offerings.
Help strengthen Kooner's reputation among the largest commercial fleets in North America.

Benefits

Competitive base salary $100,000-$120,000, plus uncapped commissions paid quarterly
Company car allowance
401(k) with company match
Medical, dental, and vision insurance
Life and disability insurance
Employee assistance program
Employee referral program
Remote work flexibility
Direct exposure to Kooner's executive leadership
Opportunity to help shape Kooner's national strategic account strategy
Significant career growth opportunity within a rapidly expanding organization