Director, Sales Enablement

Company OverviewCanopy is an integrated tree care service company dedicated to building the leading tree care platform in North America. We acquire high-performing local brands and accelerate their growth through proven best practices, scalable playbooks, and centralized services that ease administrative burdens—empowering local leaders to focus on exceptional service and lasting customer relationships.

Founded in 2022, Canopy has grown rapidly to ~ with 18 partner companies operating across 9 states and 3 time zones. Backed by Alpine Investors, a private equity firm known for its people-first approach, Canopy is redefining partnership in the arboriculture industry through investment in people, operational excellence, and sustainable growth.

Position Summary

The Director, Sales Enablement (DSE) is a hands-on, results-driven leader responsible for driving revenue growth and sales excellence across assigned partner companies in their region. This role combines strategic leadership with in-field execution—rolling out Canopy’s standardized sales playbook, building a high-performance sales culture, and leading training, coaching, and performance management for sales teams.

Reporting directly to the Regional President and partnering closely with the Chief Revenue Officer, the DSE ensures that sales strategies are executed with consistency, that teams are equipped and motivated to win, and that performance is continuously improved through data-driven insights.

Key Responsibilities

· Sales Playbook Implementation & Optimization
· Lead the rollout of Canopy’s standardized sales process across partner companies, ensuring consistent adoption and execution.
· Partner with leadership to refine the playbook based on performance data and field insights.
· Sales Culture & Mindset
· Establish a culture of accountability, continuous learning, and ethical, customer-focused value selling.
· Facilitate regular sales meetings, role-play sessions, and peer learning opportunities to reinforce best practices.
· Training & Enablement
· Own the development and delivery of training programs for new and existing sales arborists, including onboarding, certification, and ongoing skills development.
· Provide in-field coaching through ride-alongs, shadowing, and real-time feedback to improve conversion and customer experience.
· Performance Management
· Define and track KPIs at the rep and branch level, leveraging CRM and Power BI dashboards to drive accountability.
· Analyze performance trends, identify skill gaps, and create targeted improvement plans.
· Collaborate with leadership to design and implement sales incentive programs aligned with company goals.
· Change Management & Integration
· Support post-acquisition sales team integration, assessing capabilities and deploying tools, training, and processes to elevate performance.
· Lead the adoption of CRM systems and standardized sales tools to ensure efficiency and data accuracy.
· Cross-Functional Collaboration
· Work closely with marketing, operations, and other regional leaders to align sales efforts with lead generation, operational capacity, and customer experience goals.
· Share field insights to influence marketing campaigns, service offerings, and operational improvements.

Qualifications & Experience

· 7–10+ years of progressive sales leadership experience, ideally in residential services, field services, or home improvement; tree care or green industry experience a plus.
· Proven track record of building high-performing sales teams and driving revenue growth.
· Expertise in sales enablement, training, and coaching with measurable results.
· Strong analytical proficiency in KPI-driven management, excel, CRM systems, and dashboard reporting.
· Experience designing and optimizing sales incentive/compensation programs.
· Exceptional communication, interpersonal, and coaching skills.
· Entrepreneurial, adaptable, and comfortable leading through change and ambiguity.
· Willingness to travel extensively across the region for in-field coaching and team support.

Why Join Canopy?

· High-Growth Platform: Backed by Alpine Investors, with a proven track record of scaling service businesses.
· Impact & Visibility: Direct influence on revenue performance and sales culture across multiple companies.
· Professional Growth: Clear pathways to expanded leadership responsibilities as the business scales.
· Mission-Driven Culture: A people-first philosophy, exceptional service standards, and a commitment to sustainable growth.
· Competitive Compensation and Benefits
· Base salary + performance bonuses aligned to regional sales targets and revenue growth
· 401k match
· Comprehensive benefits including health, vision, dental, LTD, STD etc. along with generous PTO package