Outside Sales Manager at Midwest Groundcovers LLC – Saint Charles, Illinois

OBJECTIVE / ACCOUNTABILITY

In this role, the Outside Sales Manager is a hands-on leader who drives growth, energy, and accountability across the sales organization. You will lead, coach, and inspire a team of both employed and independent Outside Sales Representatives, helping them win in their territories while delivering an exceptional customer experience every step of the way.

You’ll be at the center of turning strategy into action—aligning territory plans to company sales goals, reinforcing strong and consistent selling habits, and creating a performance-driven culture through regular coaching, feedback, and development. Partnering closely with the Vice President of Sales & Marketing and the Inside Sales Manager, you’ll ensure tight alignment across teams and seamless customer handoffs that strengthen relationships and fuel long-term growth.

This role is built for someone who thrives on results and leadership. Success is measured by achieving 7–10% annual sales growth, accelerating new business, retaining and growing key customer relationships, elevating sales rep performance, and driving disciplined CRM adoption. The Outside Sales Manager plays a critical role in shaping how we sell, how we show up for customers, and how we build a winning sales team for the future.

KEY RESPONSIBILITIES

• Leadership & Management of Outside Sales Team
  1. Coach a team of 8–10 Outside Sales Reps and Account Managers, adapting support to experience level.
  2. Set clear expectations for sales activity, responsiveness and follow-through, drive consistency without micromanaging.
  3. Build a collaborative, high-performance culture focused on customer satisfaction, team results, and individual growth.
  4. Provide targeted in-field coaching as needed (ride-alongs, joint calls, skill-building, role-play).
  5. Address performance gaps early with clear feedback and coaching plans; recognize and scale best practices.
• Drive Territory Execution & Annual Sales Growth
  1. In partnership with the VP of Sales & Marketing and Inside Sales Manager, align territory plans to company sales goals and drive 7–10% annual growth across all territories.
  2. Establish territory priorities (key accounts, prospecting focus, seasonal initiatives) and ensure consistent execution.
  3. Review territory results and pipeline with Sales leadership; adjust coaching, focus, coverage to improve outcomes.
  4. Support expansion initiatives in developing markets as prioritized by leadership.
  5. Represent Midwest Groundcovers at trade shows and key industry events; set follow-up expectations
  6. Stay informed on competitor activity and customer needs; share insights that improve strategy and messaging.
• Improve Customer Retention & Customer Experience
  1. Reinforce a customer-first approach that delivers a 98% customer retention rate and long-term relationships.
  2. Support reps in resolving escalations and time-sensitive customer needs quickly and consistently.
  3. Provide decision support on exceptions within guidelines (pricing/discounts, freight, special logistics) in collaboration with the VP of Sales & Marketing, Inside Sales Manager, and Shipping Manager.
• Build & Manage CRM Adoption & Outside Sales Best Practices
  1. Champion consistent CRM usage and reinforce simple habits that improve follow-up, visibility, and forecasting.
  2. Define and document CRM best practices (minimum activity expectations, notes, stages, pipeline hygiene).
  3. Coach reps to use the CRM effectively without creating unnecessary administrative burden.
  4. Partner with Sales leadership to improve CRM workflows and team adoption over time.
• Collaborate with Inside Sales & Cross-Functional Teams
  1. Partner tightly with the Inside Sales Manager to ensure smooth handoffs, consistent messaging, and service standards.
  2. Communicate field insights to leadership to strengthen programs, policies, and seasonal execution.
  3. Maintain clear team communication rhythms (updates, priorities, follow-up expectations).

QUALIFICATION REQUIREMENTS

• Proven ability to lead, coach, and influence a field-based sales team, including both employed and independent/contract reps.
• Strong customer-first mindset with a practical, relationship-based approach to selling and problem solving.
• Comfortable making timely decisions and providing clear guidance in fast-moving, seasonal sales environments.
• Working knowledge of CRM systems and ability to build adoption through simple, effective processes and coaching.
• Ability to travel within territories and attend trade shows as needed; flexibility to work extended hours during peak season.

EDUCATION AND / OR EXPERIENCES

• Bachelor’s degree in business, marketing, horticulture, or related field.
• 7+ years of sales experience. Experience in wholesale, horticulture/agriculture, or a related field preferred but not required.
• 3+ years of experience leading and coaching sales representatives with responsibility for performance and development.

SKILLS AND ABILITIES

• Leadership & Coaching: Adapts leadership style to rep experience levels; balances empathy, accountability, and results.
• Responsiveness & Decision-Making: Reliable communicator who can make or facilitate quick decisions to keep sales moving.
• Relationship Building: Builds trust with reps, customers, and internal teams; communicates with confidence and positive intent.
• Organization & Prioritization: Plans across seasons, focuses on what moves the needle.
• Collaboration: Works seamlessly with the Inside Sales Manager, VP of Sales & Marketing, and key departments to improve execution and customer experience.
• Adaptability: Thrives in seasonal peaks and troughs; maintains a steady, solution-oriented presence during high-pressure periods.

BENEFITS

• Medical, Dental and Vision insurance options
• Employer paid life and short term disability insurance
• 401k
• Paid time off and paid holidays
• Employee discounts

ABOUT THE COMPANY

Proudly ranked as a 2024 + 2025 Top Work Place in several categories, including Woman-Led companies and Cultural Excellence for Professional Development. Midwest Groundcovers has been growing and propagating over 20 million of the finest wholesales plants in the Midwest. Although Groundcovers are our specialty, Midwest Groundcovers’ plant offerings include Evergreens and Broadleaves, Deciduous Shrubs, Perennials, Ornamental Grasses, Vines and Native Prairie, Wetland and Woodland species. We are leaders in the Green Industry in partnering with landscape architects, landscape designers, green roof and plant professionals to create inspiring planting combination solutions. Experts in plants for Midwestern durability and sustainability for over five decades.