Landscape Maintenance Estimator

Outerland Holdings, LLC•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 client priorities, design maintenance plans suited to each landscape and the client’s goals, and hand off new client relationships to account managers. The position aims to ensure clients feel that Outerland communicates, cares, and values them.

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 drive to learn quickly.
Consultative communication style, including asking effective questions, listening, and clearly communicating value.
Self-direction, strong attention to detail, and exceptional organizational skills.

Nice To Haves

Landscaping or green industry experience is preferred, but not required.

Responsibilities

Own inbound leads from the first handshake through a signed proposal, with consistent follow-up.
Walk properties with prospective clients, listen to their priorities, assess conditions, and communicate Outerland’s value.
Build tailored maintenance plans based on 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 hand them off to their account manager with organized site notes, scope, and 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.