Director, Strategic Sales – Managed Transportation

Redwood Logistics

Director of Strategic Sales responsible for Managed Transportation business development at Redwood Logistics. Leading sales strategy and building customer relationships in the logistics industry.

Posted 5/23/2026full-timeRemote • Illinois • 🇺🇸 United StatesLead💰 $90,000 - $150,000 per yearWebsite

About the role

Key responsibilities & impact

Build and manage a customer pipeline, revenue growth targets and global go-to-market strategies for Managed Transportation opportunities though 100% hunting activities
Coordinate onsite industry events with certain partners and customer prospects
Lead strategies and contribute to market facing material aimed at establishing the Redwood brand as the top Managed Transportation option within the industry
Support and scale the Managed Transportation practice as a SME
Consistently meet quarterly and annual targets
Develop proposals and negotiate/close complex contracts
Work across functional groups within Redwood to ensure the Managed Transportation product is meeting customer demands and requirements to close deals
Build scalable Sales/GTM motions and programs
Identify new markets, verticals, and partners to help scale within those segments
Summarize product feedback gathered from customer and prospect meetings and act as advocate for our customers with internal development and product teams
Conduct Agile Sales where a consistent sales process is followed along with constant improvement day by day, week by week
Develop Land and Expand strategies to meet the needs of the customer while allowing for future growth of Redwood Logistics products and services
Be proficient in Salesforce to update leads, opportunities and real time status of customers
Ensure a smooth transition from Sales to Account Management
Analyze data and collaborate with customers, partners and stakeholders to capture feedback understand business needs and build consensus
Set and measure KPIs that drive key product and business decisions forward
Maintain up-to-date knowledge of emerging technologies, industry trends, best practices and change management to improve performance and increase profitability
Work in partnership with other executives regarding cost, value and risk-potential of new projects and products
Represent Redwood Logistics as a domain and product expert during customer interactions

Requirements

What you’ll need

A proven hunter, with 10+ years experience in a sales role with experience in logistics/supply chain
5+ years experience in a SaaS, technology, or managed transportation discipline
Previous 3PL solutions and/or operations experience
Proven track record of delivering on quota
Ability to be strategic, but still roll up your sleeves to accomplish what needs to be done
Strong communication skills and ability to thrive in a team environment
Have a good understanding of both business needs and technology capabilities plus be capable of translating that knowledge in plain terms
Excellent analytical and problem-solving skills
Strong interpersonal skills; ability to rapidly develop and cultivate relationships with peers, partners and key influencers
Experience presenting to executive leadership, participating in the sales cycle and handling sensitive customer escalations
Growth mindset and positive can do attitude
Exceptional written and verbal communication skills, including presentation skills
Entrepreneurial drive and demonstrated ability to achieve stretch goals in an innovative and fast-paced environment
Previous sales process and methodology training
Bachelors degree or higher

Benefits

Comp & perks

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 including pet insurance, accident care, access to legal advice and more

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

salesnegotiationdata analysisproposal developmentcontract managementAgile SalesKPI measurementmanaged transportation3PL solutionsSaaS

Soft Skills

communicationinterpersonal skillsanalytical skillsproblem-solvingstrategic thinkingteam collaborationrelationship buildingpresentation skillsgrowth mindsetentrepreneurial drive

Certifications

Bachelor's degree