Director, Sales Development

Reports To: SVP of Revenue Operations and Strategy

Location: Chicago, IL

Environment: Hybrid (2 days on-site per week)

Work Schedule:

This position is full-time and hybrid Monday 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, Sales Development working within Redwood Supply Chain Solutions (one of our entities), you will be responsible for supporting the sales development strategy which includes working closely with sales, sales operations and marketing to ensure strategic alignment for lead generation, opportunity velocity, and professionalism. The successful candidate will be a highly organized sales professional who has experience defining and running initiatives that focus on sales strategy to generate new business, messaging, and positioning.

How You Make a Difference Everyday:

• Team Leadership: Manage and mentor a team of SDRs, providing guidance, training, and support to enhance performance

• Lead Generation Strategy: Develop and implement strategies to optimize lead generation processes and improve outreach effectiveness

• Performance Metrics: Establish KPIs and monitor team performance against targets, providing regular feedback and coaching

• Collaboration: Work closely with marketing and sales teams to align goals, share insights, and ensure a seamless handoff of qualified leads

• Training & Development: Design and conduct training sessions for SDRs to improve skills in prospecting, cold calling, and email outreach

• Reporting: Analyze team performance data and present findings to upper management to inform strategic decisions

• Recruitment: Participate in the hiring process to build a high-performing SDR team

You’ve Got This?

• Experience: Proven experience in sales development or a related role, with a track record of success

• Leadership Skills: Strong leadership and coaching abilities, with a focus on team development

• Analytical Skills: Proficiency in data analysis and the ability to interpret metrics to drive performance improvements

• Communication Skills: Excellent verbal and written communication skills, with the ability to motivate and inspire others

• Tech Savvy: Familiarity with CRM software and sales engagement tools

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.