Landscape Maintenance Estimator

Outerland Holdings•Mashpee, MA

5d•$75,000 - $100,000

About The Position

As the Landscape Maintenance Estimator, you’ll be a prospective client’s first experience with Outerland and the person who earns their business. The role blends consulting, sales, horticultural problem-solving, and customer service. You’ll assess properties, understand what clients value, design maintenance plans that fit their landscapes and goals, and hand off new client relationships to account managers. The goal is for new clients to feel that Outerland communicates, cares, and values their business.

Requirements

At least 3 years of experience in sales or account management.
Working knowledge of landscape maintenance, plant material, and common property problems, or the ability and drive to learn quickly.
A consultative approach, including asking good questions, listening more than pitching, and clearly communicating value to clients.
Self-direction, strong attention to detail, and exceptional organizational skills.

Nice To Haves

Landscaping or green industry experience.

Responsibilities

Own inbound leads from the initial contact through signed proposal, with consistent follow-up.
Walk properties with prospective clients, listen to their priorities, assess site conditions, and communicate the company’s value.
Build tailored maintenance plans using site conditions, takeoffs, client goals, company service offerings, and budgets.
Prepare accurate, detailed estimates and present proposals.
Lead initial client meetings, set clear expectations, answer follow-up questions, and close sales.
Onboard new clients and provide account managers with complete site notes, scope, and client preferences.
Identify enhancement and upsell opportunities during site visits and pass them to the account management team.
Manage the sales pipeline accurately and proactively in the CRM.
Track and manage sales performance against the sales budget.