Director of Sales Operations

Director of Sales Operations

HeartLand | Remote | Reports to the Chief Commercial Officer Base salary: $130,000–$150,000

Bring the experience to lead sales transformation.

HeartLand brings together local landscape businesses with the support of a national organization. Our approach is centrally guided, locally executed—and this role will help strengthen how our sales teams operate across local markets.

We’re seeking an experienced sales operations leader who has personally led sales transformation in a decentralized, field service delivery model. You know how to establish consistent processes, turn sales data into practical decisions, and work directly with sales professionals and local leaders to improve performance.

Reporting to the Chief Commercial Officer, you’ll serve as a hands-on individual contributor, mentor, and coach to our Business Development Managers (BDMs). You’ll own the processes, systems, and reporting that support sales execution while taking an active role in BDM onboarding, training, and performance management in partnership with local leaders.

This remote role requires an established leader who brings sound judgment, analytical depth, and the credibility to influence teams across a decentralized organization.

What You’ll Own

Sales Transformation & Process Leadership

• Lead implementation of enterprise sales priorities, drawing on experience delivering sales transformation from design through adoption and measurable results. • Establish consistent sales stages, opportunity requirements, handoffs, and operating standards across local operating companies. • Partner with the CCO and local leaders to identify barriers, implement improvements, and sustain accountability for execution.

BDM Onboarding, Training & Coaching

• Work directly with BDMs as a mentor and coach, reinforcing effective sales practices and consistent execution. • Partner with local leaders and Training & Development to deliver structured onboarding, ongoing training, and CRM education. • Track onboarding milestones and ramp performance, identify development needs, and provide targeted support to improve productivity.

Sales Metrics & Performance Management

• Build and maintain scorecards covering sales against goals, pipeline health, activity, proposals, conversion, and win rates. • Analyze performance trends to distinguish activity, skill, process, and pipeline gaps—and recommend specific actions. • Work with BDMs and local leaders to establish improvement actions, monitor results, and maintain follow-through.