Director of Sales

Location: Greater Burlington, Vermont
Job Type: Full-Time
Work Arrangement: On-Site
Reports To: Owner

Position Overview

We are seeking a strategic, results-driven Director of Sales to lead business development efforts while building a scalable sales organization. This is a unique player-coach opportunity for a senior sales leader who thrives on generating new business while coaching and developing a high-performing sales team.

This role combines hands-on selling with sales leadership. The successful candidate will focus on expanding commercial maintenance and snow contracts, developing relationships that generate design-build opportunities, implementing sales processes and CRM systems, and creating the infrastructure needed to support long-term growth.

Key Responsibilities

Business Development

• Develop and close new commercial maintenance and snow contracts.
• Build relationships with architects, custom builders, general contractors, developers, property managers, and facilities leaders.
• Generate new residential and commercial design-build opportunities.
• Sell design agreements and collaborate with estimating and design teams throughout the sales process.
• Lead RFP responses, proposal development, contract negotiations, and closing activities.
• Maintain an active sales pipeline and consistently meet revenue goals.

Sales Leadership

• Establish and manage weekly pipeline reviews and forecasting meetings.
• Coach and mentor account managers and sales professionals.
• Implement consistent sales processes, accountability, and performance standards.
• Improve sales execution through ongoing training and coaching.
• Collaborate with ownership on strategic growth initiatives.

Sales Operations

• Evaluate, recommend, and implement a CRM platform.
• Develop reporting dashboards to track:
  • Lead activity
  • Pipeline stages
  • Conversion rates
  • Sales cycle performance
  • Forecast accuracy
• Improve lead management and follow-up processes.
• Partner with marketing to align lead generation with sales objectives.

First 90 Days

• Gain visibility into current opportunities and sales pipeline.
• Develop and begin executing a personal business development strategy.
• Implement weekly sales meetings and forecasting cadence.
• Evaluate current sales team, technology, reporting, and workflows.
• Recommend a CRM implementation plan.

First Year Objectives

• Generate significant personal revenue across commercial maintenance, snow, and design-build markets.
• Successfully implement and drive adoption of a CRM platform.
• Establish standardized sales processes and coaching programs.
• Build the foundation for future sales team expansion.
• Improve forecasting accuracy and pipeline visibility.

Success Metrics

• Growth in commercial maintenance and snow contract revenue.
• Increased design-build opportunities generated through strategic relationships.
• Successful CRM implementation with strong team adoption.
• Improved sales performance through coaching and accountability.
• Reduced dependence on ownership for day-to-day business development.

Qualifications

Required

• Proven success originating, negotiating, and closing B2B sales.
• Experience developing new business and managing complex sales cycles.
• Strong negotiation and relationship-building skills.
• Demonstrated leadership experience coaching or mentoring sales teams.
• Experience managing CRM platforms and sales reporting.
• Strong organizational, communication, and presentation skills.
• Ability to manage multiple opportunities simultaneously.

Preferred

• Experience within landscaping, construction, field services, facilities management, or related industries.
• Existing relationships with contractors, architects, builders, developers, property managers, or facilities professionals.
• Familiarity with AI-enabled sales tools and modern CRM platforms.
• Strong knowledge of the Greater Burlington, Vermont market.

Compensation & Benefits

Base Salary: $95,000 to $110,000 annually

Incentive Compensation

• Performance-based commission structure
• Bonus opportunities tied to personal production and team performance
• Significant earning potential

Benefits

• Profit sharing
• Comprehensive benefits package
• Additional benefits discussed during the interview process

Ideal Candidate

The ideal candidate is a high-performing sales professional who enjoys both winning business and building teams. They possess executive presence, are highly relationship-driven, comfortable using data to drive decisions, and capable of creating repeatable sales systems that support long-term organizational growth.