Landscape Client Representative

Woodlawns Landscape Company is seeking a confident, motivated, and relationship-focused Landscape Client Representative to manage a portfolio of commercial landscape clients throughout the City of Chicago.

The Client Representative serves as the primary point of contact for assigned clients and works closely with our Operations team to understand client expectations, communicate property priorities, resolve concerns, and ensure our teams are set up to deliver high-quality work.

The primary focus of this position is building strong client relationships that lead to client retention, contract renewals, and enhancement sales.

This is a strong opportunity for someone who enjoys developing relationships, solving problems, evaluating properties, preparing proposals, and recommending solutions that improve the client’s landscape.

What You Will Do

• Serve as the primary point of contact for a portfolio of commercial landscape clients.
• Build trusted, long-term client relationships through proactive communication, property visits, and consistent follow-through.
• Understand each client’s expectations, priorities, property standards, and upcoming needs.
• Partner with Operations Management to communicate client expectations and set field teams up for success.
• Address client questions and concerns promptly and coordinate with Operations through resolution.
• Follow up with clients to confirm concerns have been addressed satisfactorily.
• Conduct regular property visits and identify landscape improvement opportunities.
• Prepare accurate estimates, proposals, and contract documents.
• Present recommendations to clients and follow up consistently on open proposals.
• Lead the annual contract-renewal process for assigned clients.
• Maintain accurate client notes, opportunities, proposals, and follow-up activity in Aspire.
• Assist the Accounts Receivable team when client involvement is needed to resolve outstanding balances.
• Occasionally respond to time-sensitive client or property needs outside normal business hours, including limited weekend or snow-event support.

What Success Looks Like

• Strong, trusted client relationships
• Client retention and contract renewals
• Positive client satisfaction and NPS results
• Consistent enhancement sales
• Professional and timely issue resolution
• Accurate estimates, proposals, and account information
• Clear communication and a strong partnership with Operations

What We Are Looking For

• Experience in client relationship management, sales, hospitality, property management, facilities services, construction, or another high-touch service environment
• Strong written and verbal communication skills
• Excellent organization and consistent follow-through
• Ability to manage multiple clients, proposals, priorities, and deadlines
• Confidence discussing pricing, contracts, budgets, and service expectations
• Ability to identify client needs and recommend appropriate solutions
• Strong problem-solving skills and professional judgment
• Ability to prepare accurate estimates and professional proposals
• Ability to work independently while collaborating closely with Operations and administrative teams
• Comfort learning CRM and estimating software
• Aspire experience is a plus
• Previous landscaping or horticultural experience is helpful but not required
• Valid driver’s license and reliable personal transportation
• Willingness to travel regularly throughout the City of Chicago

Why Woodlawns: Woodlawns is known for the quality of our seasonal color, the quality of our operations teams and the work they deliver. Our Client Representatives are supported by experienced Operations leaders and crews that take pride in maintaining and improving our clients’ properties.

This allows the Client Representative to focus on understanding the client, communicating expectations clearly, developing thoughtful recommendations, and building lasting relationships.

Successful Client Representatives may have opportunities to advance into Senior Client Representative, sales leadership, client service leadership, or branch leadership roles.

The Perks 

• 401(k) plan with company match  

• Medical insurance  

• Dental insurance  

• Vision insurance  

• FSA/HSA  

• PerkSpot  

• Long-Term Disability and Life Insurance 

• Paid time Off  

• Tuition Reimbursement (after one year of service) 

This position is also eligible for commission and performance-based bonus opportunities.