Who We Are & Why We’re Hiring

At Odyssey, we support logistics and freight operations by driving safe, efficient, and accurate movement across our organization. From sales and commercial strategy to warehouse and administrative teams, every role contributes to our success.

As we continue to grow, we’re adding dedicated professionals to support increasing business demands and uphold the high standards our customers and partners expect.

Location:

This is a remote role, based in Chicago, IL, with a primary focus on Eastern Time Zone clients and collaboration.

Schedule:

Full-time, exempt role. Standard business hours with flexibility based on client needs.

Compensation:

Base salary range: $95k – $125k annually, commensurate with experience.

(Incentive/commission structure may apply based on role design.)

About the Job:

The Sales Manager is responsible for generating new revenue by securing enterprise-level clients and expanding opportunities across Odyssey’s SAAS TMS solutions and third-party transportation services. This role requires a strong hunter mentality, deep logistics knowledge, and a consultative approach to uncover client needs and deliver value-driven solutions across multimodal transportation and technology offerings.

Odyssey has different sales levels based on a candidate’s experience, performance history, and the scope of the portfolio they will support. We are hiring at both Sales Manager and Senior Sales Manager levels, and the final title will be aligned to the selected candidate’s background and qualifications.

In This Role, You Will:

• Drive new business development for managed transportation and 4PL solutions.
• Partner with operations and solution design teams to build customized logistics programs aligned with client goals.
• Identify customer pain points and develop compelling solution narratives.
• Manage the full sales cycle from prospecting and consultative selling through negotiation and post-sale transition.
• Build long-term client relationships through renewals, upselling, and cross-selling value-added services.
• Navigate complex procurement, contracting, and legal processes.
• Stay current on transportation trends, technology platforms, and market dynamics to position solutions effectively.

Qualifications:

We recognize not all applicants have every skill or qualification to match a job description exactly. Odyssey values diverse experiences in other industries, and we encourage everyone who meets most required qualifications to apply. While having “desired” qualifications make for a strong candidate, we encourage applicants with alternative experiences to also apply. We are always looking for people who will bring something new to the table!

Requirements:

• 5+ years of experience in managed transportation sales, preferably in a 4PL or managed services environment.
• Proven success selling multi-year managed transportation deals and renewals.
• Strong understanding of domestic road transportation and logistics network design.
• Experience collaborating with operations and technology teams to deliver tailored client solutions.
• Ability to manage complex negotiations and procurement processes.
• Strong consultative selling, communication, and relationship-building skills.

Desired:

• Experience with value-added upselling and post-sale account growth.
• Exposure to port or ocean logistics environments (preferred, not required).
• Strong presentation skills and executive-level communication capabilities.

We offer a comprehensive and competitive compensation and benefits package, including:

• A choice of medical plans with FSA and HSA options

• Dental Insurance

• Vision Insurance

• Company-paid Life and Disability Insurance

• 401(k) Plan with Company Match

• Employee Assistance Program

• Company Health & Wellness Program

• Discounts with Preferred Vendors

No relocation allowance will be considered unless specifically addressed. All applicants must be currently authorized to work in the United States.

Equal Opportunity Employer

Odyssey is proud to be an equal opportunity employer. Qualified applicants are considered for employment and evaluated without regard to mental or physical disability, race, color, religion, gender, national origin, age, genetic information, military or veteran status, sexual orientation, marital status, or any other classification protected under applicable federal, state, or local law.

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