Director of Sales Operations
About The Position
HeartLand is seeking a sales operations leader to strengthen sales practices across local landscape businesses supported by a national organization. The role leads sales transformation in a decentralized, field service delivery model by establishing consistent processes, turning sales data into practical decisions, and working with sales professionals and local leaders to improve performance. Reporting to the Chief Commercial Officer, the Director is a hands-on individual contributor, mentor, and coach to Business Development Managers (BDMs). The role owns the processes, systems, and reporting that support sales execution, and actively supports BDM onboarding, training, and performance management in partnership with local leaders. This remote position requires sound judgment, analytical depth, and the ability to influence teams across a decentralized organization. The role oversees sales process standards, BDM onboarding and coaching, performance metrics, CRM workflows and adoption, pipeline and forecasting, commercial reviews, cross-functional initiatives, and sales capacity planning. Success includes more consistent onboarding and sales execution, improved CRM adoption and data quality, more accurate forecasts, and measurable improvements in BDM ramp, conversion, sales efficiency, and productivity.
Requirements
- 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 and advanced Excel skills.
- Hands-on experience building CRM workflows, dashboards, and sales reporting.
- Ability to turn findings into clear recommendations and drive implementation across leaders and teams outside the reporting line.
Nice To Haves
- Experience supporting decentralized, field-based sales teams.
- HubSpot experience.
- Familiarity with Aspire and Power BI.
Responsibilities
- Lead implementation of enterprise sales priorities, from transformation 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.
- Mentor and coach BDMs, 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.
- Build and maintain scorecards covering sales against goals, pipeline health, activity, proposals, conversion, and win rates.
- Analyze performance trends to identify 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.
- Serve as 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.
- 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.
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What This Job Offers
Job Type
Full-time
Career Level
Director
Education Level
No Education Listed
