Landscape Maintenance Estimator

Outerland; Mashpee (MA); On-site; USD 75,000 - 100,000; Full time

Job summary

Outerland in Mashpee, MA is seeking a Landscape Maintenance Estimator. You’ll be the client’s first experience with us, blending consulting, sales and horticultural problem solving to read a property, understand goals, and design a maintenance plan that fits budget and values.

You’ll own inbound leads from handshake to signed proposal, walk sites with clients, build tailored plans, present precise estimates, lead initial meetings, and hand off to account managers.

Qualifications

• 3+ years in sales or account management; landscaping experience preferred but not required.
• Knowledge of landscape maintenance or drive to learn quickly.
• Consultative style with strong questions, listening, and value communication.
• Self-directed, detail-oriented, highly organized.

Responsibilities

• Own inbound leads from first handshake to signed proposal and follow-up.
• Walk properties with prospective clients, assess priorities and communicate value.
• Build tailored maintenance plans around site conditions, goals, and budgets.
• Prepare accurate, detailed estimates and present proposals you stand behind.
• Lead initial client meetings, set expectations, answer follow-ups, close the sale.
• Onboard new clients and hand off to account managers with complete notes.
• Identify upsell opportunities during site visits and relay to account management.
• Manage sales pipeline in our CRM and track performance against budget.
• Track and manage sales performance against the sales budget.

Skills

Sales experience

Account management

Consultative selling

Attention to detail

Organizational skills

Tools

CRM

Job description

Description

As the Landscape Maintenance Estimator, you’ll be a prospective client’s first experience with Outerland, and the person who earns their business. The estimator role blends consulting, sales, horticultural problem-solving and customer service: you’ll read a property, understand what the client values, design a maintenance plan that fits their landscape and their goals, and hand off a relationship our account managers are excited to inherit. New clients will walk away with the impression that we communicate, we care, and they’re a big deal to us.

Requirements

• Own inbound leads from first handshake to signed proposal, with follow-up that never leaves anyone wondering
• Walk properties with prospective clients — listen to their priorities, assess conditions, and communicate our value
• Build tailored maintenance plans around site conditions, takeoffs, client goals, company service offerings, and real budgets
• Put together accurate, detailed estimates and present proposals you can stand behind
• Lead the initial client meeting, set clear expectations, answer the follow-up questions, and close the sale
• Onboard new clients and hand off cleanly to their account manager — site notes, scope, and preferences all in one place
• Catch enhancement and upsell opportunities during site visits and pass them to the account management team
• Accurately, consistently, and proactively manage the sales pipeline within our CRM
• Track and manage sales performance against the sales budget

Qualifications

• 3+ years in sales or account management. Landscaping or green industry experience is preferred, but not required
• A working knowledge of landscape maintenance, plant material, and the problems properties tend to have — or the drive to learn it fast
• A consultative style: you ask good questions, listen more than you pitch, and communicate our value clearly to clients.
• Self-direction, ruthless attention to detail, and exceptional organizational skills

Compensation & Benefits

• $75,000 – $100,000 base salary based on experience
• Performance-based bonus opportunity
• Company vehicle, phone, and laptop
• Health, dental, vision, and supplemental insurance
• 401(k) with company match