Jobs › Wheels

Manager, Strategic Sales

Wheels · Schaumburg, IL · Remote available · Full time

Posted Sep 11, 2026 · We last checked this listing on Oct 6, 2026

Apply at Wheels

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 a complex, multi-level sale you won. Who were the decision-makers and how did you reach each one?

What they are checking: Whether they can manage a multi-stakeholder sales cycle, which fleet deals require.

Tell me about a sales proposal you wrote that won. What made it work?

What they are checking: Whether they write proposals that address the prospect's real needs, not generic pitches.

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

What they are checking: Whether they take ownership of results and adjust their approach.

What would you do

A deal has stalled for two months with no clear reason. How do you create urgency without being pushy?

What they are checking: Whether they can keep momentum by tying action to the buyer's own costs or deadlines.

Half your time is in the field with day trips and several overnights a month. How do you plan your week to make that productive?

What they are checking: Whether they can manage travel and a home office independently and efficiently.

A prospect's CFO only cares about price, while their fleet manager cares about service. How do you handle both?

What they are checking: Whether they can balance different stakeholder priorities within one deal.

How do you work with internal teams like credit, pricing, and implementation to close a deal?

What they are checking: Whether they collaborate internally to build sales strategies that actually get delivered.

About the work

Walk me through how you'd build a target list of mid-size fleet companies in a new territory.

What they are checking: Whether they can prospect methodically and prioritize accounts most likely to buy.

How would you assess a prospect's creditworthiness before investing heavy time in them?

What they are checking: Whether they qualify deals on financial strength, which the posting lists as part of the job.

How do you negotiate pricing and contract terms so the deal works for both sides?

What they are checking: Whether they protect margin while building a lasting relationship with a new client.

What would you need to learn about fleet leasing to be seen as a knowledgeable industry resource?

What they are checking: Whether they understand that credibility in consultative selling comes from real industry knowledge.

Practice this interview out loud.

Offer builds a real interview for this exact role at Wheels from your resume and this job description, asks the questions one at a time, and tells you what landed. The first one is free.

Practice this out loud

The full job description

As published by Wheels.

Job Description: JOB OVERVIEW The Strategic Sales Manager is a highly visible position that is responsible for developing new business for our mid-size prospects. The Manager will target companies with mid-size fleets and employ consultative selling skills to win new accounts in the region. He or she will execute business development strategies and manage all aspects of a multi-level sales cycle. The Strategic Sales Manager may be based in a major metropolitan area within a given territory; working from a home office with 50% of the time is spent out in the field. Most of the travel involves day trips by car, plus six or seven nights out-of-town per month. KEY RESPONSIBILITIES - ESSENTIAL FUNCTIONS • Successfully win new business to increase sales. Negotiate contract terms and product pricing to attain mutually beneficial business relationships with new clients. • Identify key decision-makers and stakeholders and develop multi-level relationships within target companies. Establish credibility as a knowledgeable industry resource. • Determine credit worthiness of target accounts and establish priority prospects. • Manage the sales process to maintain momentum, create a sense of urgency, and motivate decision makers to act. • Collaborate with internal resources to develop and execute effective sales strategies. • Prepare and present winning sales proposals that address the specific needs of the prospective client and differentiate the unique service solutions that are offered. • Support the new account integration process and partner with the designated Account Team to ensure new clients receive the full benefit of the established contract. • Maintain an accurate, up-to-date database on all prospects. Report relevant information regarding potential new accounts, target companies, and competitor’s practices. • Achievement of sales goals and annual plans. LEADERSHIP RESPONSIBILITIES • Analytic skills – effectively coach prospective clients through the complex financial issues and value economics of $100 million+ sourcing decisions. • Manage the sales process to maintain momentum, create a sense of urgency, and motivate decision makers to act. COMPETENCIES - SKILLS • To perform this job successfully, an individual must be able to perform each essential duty satisfactorily. The requirements listed below are representative of the knowledge, skill, and/or ability required. Comfortable working in a collaborative fashion with the VP of Strategic Sales and other functional leaders. Must know when and how to bring in senior management to enhance the sales process. • Experience selling value versus price, excellent solution selling skills. • Enthusiasm – stay positive and be a port in the storm during the most difficult situations. • Strategic thinking –navigate complex deals with complex issues and relationships. • Versatility – function skillfully across a wide variety of issues and people. • Personality – build relationships with key decision influencers across prospective clients and with key resources within the company. • Strong negotiation and influence management skills, excellent customer relationship skills. Extraordinarily strong customer service orientation. • Excellent presentation and facilitation skills, superb written, verbal, and people skills. • Able to pursue multiple customers at once, high organization and prioritization skills. • Experience and comfortable with 50% travel. • Passion for winning - winning new business is in the end the performance metric that really matters. • Able to demonstrate self-discipline to work without direct supervision. • Valid driver's license with good record. EDUCATION AND EXPERIENCE • Bachelor's degree (BA) or related experience. • Five (5) plus years of sales experience in industry with similar characteristics. CORE VALUES At Wheels, we believe in fostering a culture that is built on our Core Values and Guiding Principles. We cultivate a culture of excellence and innovation by upholding these values, driving our collective success and growth. • Integrity – Always act with integrity and honesty. • One Team – Treat others with dignity and respect; act as a cohesive, inclusive and accountable team that is making a difference. • Innovation – Drive continuous improvement, spark creativity and embrace next generation thinking. • Customer Success – Ensure that customer and driver success is at the heart of everything we do. CULTURAL ATTRIBUTES At Wheels, our culture guides us how we work every day, and we look for team members who show these behaviors: • Discipline Drives Quality – Plan the Trip: Think proactively, hold a high bar, follow through by leveraging experience and systems. To produce quality outcomes, we must be intentional and deliberate in everything we do, from big bets to daily execution. • Intellectually Curious – Fuel Your Minds: Be bold, challenge assumptions, think differently, look outside the box. Strive to unlock your own thinking and create new possibilities. • Commit and Deliver – Own It: Take responsibility for your work, from start to finish, and be accountable for the results. Think and act like an owner of the business. • Relationships Matter – Share the Ride: Trust is central, both with key internal and external stakeholders. Relationships are not a side effect of work but a driver of success. JOB SPECIFICATIONS, PHYSICAL DEMANDS AND WORK ENVIRONMENT Work Environment: The job is based on a virtual home office set up Position Type/Standard Schedule: This is a full-time position, Monday through Friday. Travel: 50% Travel Physical Demands: While performing the duties of this job, the employee must regularly talk and hear, and use hands and fingers to operate call center tools. DISCLAIMER Please note this job description is not designed to cover or contain a comprehensive listing of activities, duties, or responsibilities that are required of the employee for this job. Duties, responsibilities, and activities may change at any time with or without notice. Our Benefits Wheels recognizes benefits are a significant part of your employee experience, and we've created a robust benefits package that is market-leading, competitive offerings so you and your family can receive outstanding care. Please click here for an overview of the benefits available to you and your family. Pay Range: 97,600-$136,600 The base salary range for this position is listed above. This position is eligible to participate in the annual incentive plan which is based on company performance and individual performance. Compensation ranges are based on several factors including geographic location. Final offer amounts are determined by factors including, but not limited to, experience, credentials, education, certifications, skill level required for the position, the scope of the position, and geographic location. Actual pay offered will be determined on a case-by-case basis. EEO Statement Wheels is a Drug-Free Workplace. All employment is contingent on successful completion of drug and background screening. Wheels is an equal opportunity affirmative action employer and administers all personnel practices without regard to race, color, religion, sex, age, national origin, sexual orientation, gender identity or expression, marital status or domestic partnership status, disability, protected veteran status or military status, genetic information, or any other category protected under applicable law. Wheels is committed to taking affirmative steps to promote the employment and advancement of minorities, women, persons with disabilities and protected veterans. Wheels applies AI-based analysis to application materials to help assess fitness for hire for the specific job being applied for and to recommend job postings that align with the candidate’s skills, by comparing the candidate’s skills to the characteristics and qualifications listed in job postings and/or criteria established by Wheels’ hiring team.

Apply at Wheels