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Director Business Development - Dedicated Transportation

Ryder · Chicago, IL · Full time

Posted Sep 13, 2026 · We last checked this listing on Oct 6, 2026

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Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

Tell me about the largest new logistics contract you closed. What was your plan of attack from first contact to signature?

What they are checking: Whether they have run a full complex sales cycle themselves rather than riding along on someone else's deal.

You lead a cross-functional pursuit team of pricing, operations and engineering people who don't report to you. How do you keep them aligned on deal strategy?

What they are checking: Whether they can direct team selling through influence and clear direction rather than authority.

Tell me about a year you missed your quota. What happened and what did you change?

What they are checking: Whether they own their results honestly and adjust their approach, since they will carry a quota here.

How do you build a pipeline in a new territory where you don't have relationships yet?

What they are checking: Whether they have a repeatable prospecting habit and an industry network rather than relying on inbound leads.

What would you do

How would you explain the value of dedicated transportation to a company that runs its own private fleet today?

What they are checking: Whether they can make a consultative case around risk, cost and service instead of just quoting a rate.

A prospect says a competitor is 8 percent cheaper. What do you do?

What they are checking: Whether they defend value and margin with substance instead of cutting price to win at any cost.

After you close a deal, how do you hand the account to operations without losing the customer's trust?

What they are checking: Whether they protect the relationship during transition and stay involved in looking for cross-sell openings.

About the work

Walk me through how you'd build a pricing strategy for a dedicated transportation deal with a new shipper.

What they are checking: Whether they understand the cost drivers of dedicated fleets, like drivers, equipment and lanes, well enough to price profitably.

How do you decide whether a prospect is worth pursuing or whether you should walk away early?

What they are checking: Whether they qualify leads with discipline so quota time goes to deals that can actually close and make money.

Which industry vertical do you know best, and how does a dedicated fleet solve a real problem for companies in it?

What they are checking: Whether they have the vertical depth this role expects for consultative selling in one business unit.

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The full job description

As published by Ryder.

Job Seekers can review the Job Applicant Privacy Policy by clicking here . Job Description : Summary The Director Business Development, Dedicated Transportation (DTS) is responsible for leading the pursuit of new business and expansion/renewal business as applicable. A successful DBD will coordinate the complete sales cycle process including lead generation, prospect qualification, and leading the cross-functional pursuit team by providing clear direction on deal strategy: pricing, service, value proposition and presentation message and medium. The focus for this position is on new sales contracts, team selling, and solution selling. The individual will be issued a sales quota, for which they will be held responsible. Essential Functions • Lead deal pursuit Create deal and pricing strategy. o Proposal plan of attack o Prospect new brands and develop industry network to build pipeline o Explore cross sell opportunities where applicable o Negotiate contracts and close deals • Continued commercial support on accounts closed DBD. o Explore cross-selling opportunities for existing clients • Further education on vertical for consultative selling Additional Responsibilities • Focus in one vertical/business unit – can work other deals at sales leader’s discretion. Understand how Ryder’s solutions can be customized to meet customer’s needs. Transition new accounts to combo after 24 months unless otherwise decided by Sales & Operations management. Transition new business to Director of Key Accounts to further develop after 24 months unless otherwise decided by Sales & Operations management. • Propose $100 million over 5-year period. • Sign 1 cross sell opportunity SCS /DTS. • Adhere to Ryder’s Policies and Procedures including Travel and Expense Policy • Performs other duties as assigned. Skills and Abilities • Ability to listen, write, and speak effectively Inform, explain, and give instructions. • Develops and delivers effective presentations. • Effective interpersonal skills • Effective negotiation skills • Demonstrates customer service skills. • Demonstrates problem solving skills. • Ability to manage multiple assignments and tasks, set priorities, and adapt to changing conditions and work assignments. • Ability to effectively think, speak and act without preparation. • Ability to create and maintain professional relationships within all levels of the organization (peers, work groups, customers, supervisors) • Ability to influence internal and/or external constituents. • Ability to maintain confidential information. • Ability to work independently and as a member of a team. • Ability to work within tight timeframes and meet strict deadlines. • Demonstrates time management and priority setting skills. • Flexibility to operate and self-driven to excel in a fast-paced environment. • Understanding of services, costs, pricing and value expert required Qualifications • Bachelor's degree required business administration, finance, or related field. • Master's degree preferred business administration (MBA) • Five (5) years or more sales experience: 3 years at quota and 2 years at 75% of quota required. • Five (5) years or more in selling supply chain solutions and/or achieve quota attainment more than 3 times within a 60-month period required. • Understanding of services, costs, pricing and value. expert required. • Noncommercial Driver License CLASS E Travel - 40-50% (Remote otherwise) Salary - Base salary plus commission Job Category Outside Sales Our Culture & Commitment : At Ryder, you’re trusted to make an impact—while enjoying room to grow and having a voice that’s heard. Our culture is built on respect, collaboration, and shared pride in doing great work rooted in innovation and safety. Your Voice. Your Success. The Future We Build Together. Compensation Information : The compensation offered to a candidate may be influenced by a variety of factors, including the candidate’s relevant experience; education, including relevant degrees or certifications; work location; market data/ranges; internal equity; internal salary ranges; etc. The position may also be eligible to receive an annual bonus, commission, and/or long-term incentive plan based on the level and/or type. Compensation ranges for the position are below: Pay Type : Salaried Minimum Pay Range : 140,000 Maximum Pay Range : 165,000 Benefits Information : For all Full-time positions only : Ryder offers comprehensive health and welfare benefits, to include medical, prescription, dental, vision, life insurance and disability insurance options, as well as paid time off for vacation, illness, bereavement, family and parental leave, and a tax-advantaged 401(k) retirement savings plan. For more information about benefits, click here to download the comprehensive benefits summary. Ryder is proud to be an Equal Opportunity Employer and Drug Free workplace . All qualified applicants will receive consideration for employment without regard to race, religion, color, national origin, sex, sexual orientation, gender identity, age, status as a protected veteran, among other things, or status as a qualified individual with disability. Important Note : Some positions require additional screening that may include employment and education verification; motor vehicle records check and a road test; and/or badging or background requirements of the customer to which you are assigned. Security Notice for Applicants : Ryder will only communicate with an applicant directly from a [@ryder.com] email address and will never conduct an interview online through a chat type forum, messaging app (such as WhatsApp or Telegram), or via an online questionnaire. During an interview, Ryder will never ask for any form of payment or banking details and will never solicit personal information outside of the formal submitted application through www.ryder.com/careers . Should you have any questions regarding the application process or to verify the legitimacy of an interview or Ryder representative, please contact Ryder at careers@ryder.com . Current Employees : If you are a current employee at Ryder, please click here to log in to Workday to apply using the internal application process. Job Seekers can review the Job Applicant Privacy Policy by clicking here .

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