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.

CRM, Pipeline & Forecasting

• Serve as the CRM business owner, overseeing workflows, data quality, user support, and adoption while coordinating configuration and integrations with IT and implementation partners.
• Consolidate sales forecasts, evaluate pipeline sufficiency, flag stalled opportunities, and improve forecast accuracy.
• Partner with Marketing and Analytics to strengthen prospect data, lead assignment, follow-up, and analysis by opportunity source and customer segment.

Commercial Execution & Capacity Planning

• Lead structured sales reviews that translate reporting into decisions, clear commitments, and action.
• Coordinate commercial initiatives across functions, manage milestones and dependencies, and escalate unresolved issues.
• Analyze BDM staffing, vacancies, tenure, targets, production, and ramp performance to inform hiring, territory coverage, and sales support decisions.

What You Bring

• An established track record leading sales operations for a business with approximately $300–$500 million in revenue or comparable operating complexity.
• Direct ownership of sales transformation, including designing improvements, leading implementation, gaining adoption, and demonstrating measurable results.
• Experience coaching and developing sales professionals through onboarding, training, performance analysis, and ongoing feedback.
• Strong analytical judgment, advanced Excel skills, and hands-on experience building CRM workflows, dashboards, and sales reporting.
• The ability to turn findings into clear recommendations and drive implementation across leaders and teams outside your reporting line.
• Experience supporting decentralized, field-based sales teams is preferred.
• HubSpot experience is preferred; familiarity with Aspire and Power BI is helpful.

What Success Looks Like

BDMs receive consistent onboarding, practical training, and coaching that helps them build productivity. Local leaders have reliable reporting, clear performance expectations, and actionable plans to address gaps.

CRM adoption and data quality improve. Forecasts become more accurate, sales processes are consistently applied, and commercial commitments translate into completed actions. In partnership with local leaders, your work produces measurable improvements in BDM ramp, conversion, sales efficiency, and productivity.