Senior Director, Marketing

Reports To: Chief Commercial Officer

Location: Anywhere within the U.S. (Chicago preferred)

Environment: Remote

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 you’re 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:

As a Senior Director, Marketing at Redwood Logistics, you’ll help lead Redwood into its next phase of growth – strengthening our market position, sharpening how we tell our story, and building a modern, measurable marketing engine that consistently drives revenue. You’ll modernize how we work using data, automation, and AI-enabled tools to move faster, personalize at scale, and continuously improve performance.

This is a highly visible leadership role where you’ll set the vision, drive execution, and lead the team to deliver it. You’ll connect the dots between market insight, brand narrative, demand creation, and sales outcomes – turning what we know about our customers and category into programs that move the business forward.

You’ll operate as a true cross-functional partner across Sales, Business Development, Revenue Operations, Product, and Client Success – aligning priorities, clarifying the story, and creating momentum.

The goal is simple: make Redwood easy to understand, easy to trust, and easy to choose – turning awareness into demand, and demand into pipeline, bookings, and long-term customer growth.

How You Make a Difference Everyday:

Marketing Strategy & Leadership

• Own Redwood’s end-to-end marketing strategy and annual/quarterly planning—setting clear priorities, goals, and success metrics aligned to company growth targets.
• Establish the marketing operating cadence (planning, performance reviews, pipeline inspection, campaign retros) to keep teams aligned and execution moving.
• Lead, mentor, and grow a high-performing marketing team—hiring and developing talent, setting clear expectations, and building a culture of accountability and collaboration.

GTM Alignment & Partnership

• Partner closely with Sales, Business Development, Revenue Ops, Product, and Client Success to align priorities, messaging, and integrated GTM plays across the funnel.
• Serve as the “connector” across teams—bringing clarity to what we’re doing, why it matters, and how we’ll measure success.
• Ensure tight handoffs and shared accountability across marketing + sales motions (targeting, follow-up, pipeline progression, and customer expansion programs).

Integrated Demand Creation

• Build and run a fully integrated demand engine across ABM, intent, web/digital, paid/organic, email nurtures, content, partners, and field programs/events—driving predictable pipeline and bookings.
• Define campaign strategy and messaging frameworks for key segments—value props, themes, proof points, and content experiences that resonate with target buyers and support sales conversations.
• Lead the field and events strategy across key customer and industry moments (CAB, customer events, industry conferences, Redwood-hosted experiences, partner activations)—ensuring each investment has clear objectives, tight cross-functional alignment, and measurable outcomes.
• Optimize conversion across the funnel (inquiry - MQL/SQL- pipeline - bookings) using data to refine targeting, offers, channel mix, and field plays over time.

Measure What Matters

• Own marketing performance reporting and ROI—partnering with RevOps to ensure clean attribution, dashboards, and insight-driven decisions on budget allocation.
• Manage the marketing budget and vendor ecosystem (agencies, contractors, event partners), ensuring alignment to strategy, timelines, and performance expectations.
• Advance Redwood’s marketing tech and AI roadmap—partnering with RevOps to strengthen data quality, attribution, lifecycle automation, and experimentation so we can scale what works.
• Build a test-and-learn culture—using rapid iteration (A/B testing, message testing, channel experiments) and AI-assisted insights to improve performance and efficiency over time.

You’ve Got This?

• 10+ years of B2B marketing experience spanning demand generation, integrated campaign strategy, or digital marketing; enterprise SaaS and/or supply chain logistics experience is a plus
• Proven track record building and scaling integrated marketing programs that drive pipeline, revenue, and measurable ROI
• Experience leading, hiring, and developing high-performing teams
• Exceptional communicator with executive presence—strong collaboration, influence, and presentation skills across stakeholders
• Strong GTM instincts: ability to shape positioning, messaging, and campaign narratives
• Demonstrated success partnering cross-functionally to align on priorities, improve funnel performance, and drive shared accountability
• Highly analytical and data-driven; comfortable using insights to adjust strategy
• Comfortable using AI + automation + modern martech to scale impact (personalization, speed, and measurable performance)
• Strong program management and operational rigor; able to manage multiple workstreams with high quality and follow-through
• Thrives in a fast-paced, metrics-oriented environment
• Some travel required

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

Work Schedule:

This position is full-time and remote Monday through Friday from 8:00 AM to 5:00 PM with an hour break, but flexibility is available based on coverage.

Compensation Range:

Salary Range:

$175,000 - $215,000

This position is eligible to earn annual incentives 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 Company’s 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 individual’s 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.