Director, Strategic Sales - Managed Services

Director, Strategic Sales - Managed Services

Reports To: Vice President, Strategic Sales Managed Transportation

Location: Remote or Chicago, IL

Environment:Remote, with ability to travel as needed

Status: Exempt; Salaried

Work Schedule:

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

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 Director of Strategic Sales, Managed Transportation working within Redwood Supply Chain Solutions (one of our entities),you will be responsible for leading and developing the Redwood Managed Transportation business development efforts to meet to exceed quarterly and annual goals.You will possess a proven operations, solutions and sales background that allows you to engage with businesses from C-level to ground floor operations, think strategically, manage complex negotiations, build polished business cases, and build relationships to grow Redwood’s Managed Transportation practice. You will represent our team in front of leaders of all levels across logistics organizations and educate prospects on what we have built and its representative value.

How You Make a Difference Everyday:

• 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

You’ve Got This?

• 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
• Radical thinking paired with strong execution
• This position requires travel to customers and partners
• Previous sales process and methodology training
• Bachelor’s degree or higher

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

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.