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Director of Commercial Contracts | SaaS Specialization


Job Location:

Chicago, IL - USA

Monthly Salary: $ 125000 - 175000
Posted: 31 May 2026 (30+ days ago)
Application Deadline: 28 August 2026
Vacancies: 1 Vacancy
The job posting is outdated and position may be filled

Department:

Legal

Job Summary

Director of Commercial Contracts SaaS Specialization

Reports To: Vice President of Corporate Counsel and Legal

Location: Remote or preferably based out of Chicago IL

Status: Exempt; Salaried

Who We Are:

Recognized by Gartner in their Modern 4PL Market Guide Redwood Logistics is at the forefront of industry innovation. Our cutting-edge supply chain technology pairs with the expertise of our brilliant minds to empower logistics execution across North America and Mexico.

Leveraging a comprehensive range of services data-centric network solutions and a seamlessly integrated platform we have established our prominence as a key player in the mid-market segment within the freight tech industry.

Whether youre just starting your career or are an established professional looking for your next opportunity Redwood inspires innovation across teams to provide transformative solutions for our customers.

Purpose of Your Work/Scope:

As a Director of Commercial Contracts working within shared services for all Redwood Logistics entities you will leverage your legal expertise and play a critical role in reviewing drafting and assessing risk within our commercial engagements.

Responsibilities & How You Make a Difference Every Day:

  • Draft review and negotiate complex commercial agreements including MSAs SaaS subscription agreements SOWs and other strategic partnership contracts
  • Collaborate with our GTM (Sales Marketing and Commercial) teams to facilitate initiatives while protecting companys legal and financial interests
  • Provide legal assistance and review on transportation management services engagements and supply chain agreements
  • Assist with contract strategy and negotiations for high-value multi-year client engagements
  • Collaborate with our security team on regulatory compliance related to transportation logistics data privacy cyber security and cross-border data transfers
  • Support corporate initiatives including vendor contracting technology procurement M&A diligence and internal governance as needed
  • Assist with supervision of a small team of attorneys in the legal department

Experience & Required Skills:

  • J.D. from an accredited law school and active membership in good standing with at least one U.S. state bar
  • 7-10 of relevant legal experience including substantial experience in commercial contracting (firm or in-house)
  • Demonstrated experience drafting and negotiating complex commercial agreements including MSAs SaaS subscription agreements SOWs and vendor agreements
  • Direct experience supporting either SaaS tech or software-enabled services (additional logistics or supply chain experience is a plus)
  • Strong understanding of subscription models data protection terms information security and limitation of liability frameworks
  • Proven ability to manage priorities in a high contract volume environment
  • Strong business acumen with ability to manage risk with commercial objectives in a fast-paced environment
  • Excellent communication and negotiation skills with ability to advise across leadership and cross-functional stakeholders clearly

What We Offer:

  • Access to experts and resources for your Learning & Development journey
  • Opportunity for internal mobility
  • Employee referral bonus program
  • Employee Resource Groups (ERGs)
  • Annual fundraising and volunteer events to give back to communities
  • Paid time off floating holidays time off to volunteer and rollover
  • Paid parental leave
  • Medical dental vision and 401k plans (with match)
  • Flexible spending account mass transit and dependent care plans available
  • Health savings account with a annual company contribution for plan participants
  • Short-term and long-term disability; life insurance policies subsidized by company
  • Additional benefits include pet insurance accident care access to legal advice and more

Work Schedule:

This position is full-time and remote Monday through Friday with general business hours 8:00 AM through 5:00 PM CDT Monday through Friday. Some after-hours work will be expected with peak volume cycles or high priority engagements.

Compensation Range:

Salary Range:

$125000 - $175000

This position is eligible to earn an annual incentive based on individual and company performance.

The estimated pay range reflects an anticipated range for this position. The actual base salary offered will depend on a variety of factors including the qualifications of the individual applicant for the position years of relevant experience specific and unique skills level of education attained certifications or other professional licenses held and the geographical location in which the applicant lives and/or which they will be performing the job.

Redwood is an equal opportunity employer. Employment decisions at the Company are based on individual merit qualifications abilities and the Companys needs and resources. The Company does not discriminate in recruiting hiring compensation promotions discipline termination or any other aspect of employment on the basis of an individuals actual or perceived race color creed religion sex (including pregnancy childbirth and related medical conditions) sexual orientation gender identity national origin ancestry citizenship status age disability marital status military service or status genetic information arrest and conviction record credit history or any other basis protected by applicable law.


Required Experience:

Director


About Company

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Unlock the full potential of your supply chain with Redwood's LPaaS and RedwoodConnect. Build a customized logistics solution that offers optionality, profitability, control, visibility, simplicity, and collaboration. Connect with us today!

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