Heartland, LLC

Compensation

Full Description

About Heartland Heartland, LLC is a leading provider of commercial landscaping services in the U.S., headquartered in Kansas City, Missouri and founded in 2016. Heartland is a $600M+ company that operates a multi-brand, locally led model with centralized support—serving commercial customers across 20+ states through 60+ branches and 4,000 employees, and supporting more than 15,000 customers across its footprint. Heartland is private equity–backed, having partnered with Pritzker Private Capital in December 2023, and operates with the performance cadence and metrics discipline expected in a PE-sponsored environment. Position Summary Heartland is seeking a Senior Vice President, Sales Operations & Marketing to build and lead a scalable, disciplined, and data-driven commercial organization. This executive will be responsible for professionalizing Heartland’s sales engine—operating with the rigor, cadence, and metrics discipline expected in a private equity–backed environment—while respecting the regional nuances and entrepreneurial spirit that have fueled the company’s growth. This role provides enterprise-level sales leadership, strategy, systems, and standards while reinforcing that day-to-day sales management and execution remain vested locally within Heartland’s branch and regional operating model. This role is not about being the top salesperson. It is about leading salespeople, building systems that drive accountability, and creating the infrastructure required for sustainable, profitable growth across a multi-region, multi-site organization. This leader will own enterprise sales strategy, sales infrastructure, marketing alignment, pricing frameworks, and talent development - ensuring consistency, visibility, and performance across the organization. Reporting The Senior Vice President, Sales Operations & Marketing reports directly to the Chief Operating Officer. Position Responsibilities Build the Enterprise Sales Foundation • Design and implement an enterprise-wide platform to support sales execution, forecasting, and performance management • Establish standardized sales processes, KPIs, and reporting across regions • Create visibility and predictability in the sales pipeline while enabling local teams to execute effectively Lead Performance Through Data, Discipline, and Accountability • Leverage data and analytics to evaluate sales effectiveness, identify gaps, and inform strategy • Champion the adoption and effective use of AI-enabled tools across sales and marketing to improve pipeline quality, forecasting accuracy, customer targeting, pricing insight, and BDM productivity. • Lead change management across commercial functions, enabling sales teams to adopt new systems, tools, and performance expectations with clarity, confidence, and consistency • Use sales data, customer insights, and frontline feedback to guide commercial initiatives, refine go-to-market strategy, and prioritize growth opportunities • Develop and execute strategies to address performance gaps across people, process, and market coverage • Establish and lead a consistent sales cadence that reinforces accountability, execution, and results Develop and Lead Sales Talent Operating Model & Reporting: Business Development Managers will continue to report directly to their local and regional leaders. This role maintains a dotted-line leadership relationship to BDMs, focused on capability development, performance standards, tools, training, and enterprise consistency—without disrupting Heartland’s local reporting structure. • Mentor and develop Business Development Managers, with particular focus on Year 1–3 BDM effectiveness • Partner with the Training team to design and deploy sales training and enablement content that reinforces consistent processes, builds capability, and accelerates BDM effectiveness • Lead, motivate, and influence experienced sales professionals with strong personalities and diverse selling styles • Create a culture of coaching, performance management, and continuous improvement Balance Regional Flexibility with Enterprise Consistency • Understand regional and market differences and tailor commercial strategies accordingly • Maintain consistent processes, expectations, and accountability across all regions • Partner closely with Operations to ensure alignment between sales commitments and execution capability Own Broader Commercial Strategy • Lead the marketing function and establish clear priorities aligned to sales and growth objectives • Develop and implement pricing frameworks and strategies that support profitable growth • Review and refine sales compensation strategies to align incentives with desired behaviors and outcomes • Support strategic and national account opportunities as needed, while maintaining focus on enterprise leadership Qualifications & Competencies Experience & Education • Bachelor’s degree required (business, marketing, or related field) • Advanced degree (MBA or similar) preferred but not required • Experience leading both commercial functions and operational teams, with a demonstrated ability to translate sales strategy into executable, scalable operations • 12+ years of progressive leadership experience in sales, commercial operations, or related roles, with at least 5 years leading senior sales or commercial leaders in a multi-site or regional environment through periods of growth and change • Experience supporting significant revenue growth within a complex, multi-region organization • Proven ability to scale sales organizations while maintaining accountability and consistency • Experience aligning sales, marketing, pricing, and operations in support of enterprise objectives Leadership & Skills • A proven sales leader who builds systems, not silos • Low ego, high credibility, and comfortable leading strong, experienced sales professionals • Process-oriented, tech-forward, and highly disciplined in execution • Experienced in sales software selection, implementation, and adoption • Data-driven decision maker who uses insight to drive performance • Able to step into high-impact deals when needed without being the “hero seller” • Comfortable operating in a fast-paced, multi-site, and regionally diverse environment Success Metrics (Within 12-18 Months): • Consistent sales processes, KPIs, and cadence in place nationwide • Regional and branch leaders actively participating in standardized pipeline reviews that focus on deal quality • BDMs demonstrate consistent use of defined sales stages, opportunity qualification standards, and system hygiene (Within 18–24 Months): • Enterprise sales system strategy developed and executed, resulting in successful implementation and adoption across regions • Improved visibility and accuracy of sales forecasting • Increased effectiveness and retention of Business Development Managers, particularly in years 1–3 • Clear alignment between sales, marketing, pricing, and operations • Measurable improvement in sales productivity and disciplined growth Note: HeartLand is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. This job description is not designed to cover or contain a comprehensive listing of activities, duties, or responsibilities required of the employee. Duties, responsibilities, and activities may change at any time with or without notice.