Sales Director

Greenshades Software Jacksonville, Florida, United States Full-Time Sales

About this position

Summary 

Sales Director drives predictable net-new ARR growth and leads a high-performing team focused on acquiring new customers within the Payroll, HCM, and Workforce Management markets. This leader will play a central role in scaling our growth engine, elevating sales execution, and bringing a modern, process-driven GTM mindset to the organization. 

This position owns the new-logo motion, guides a team of AEs, partners cross-functionally across Marketing, RevOps, Product, and CS, and helps shape our operating rhythm as we execute against our FY26 goals focused on growth, profitability and scale. 

Responsibilities 

Lead and scale a high-impact new business sales team 

  • Hire, coach, and develop AEs to consistently achieve quota and pipeline targets 
  • Bring a process-centric mindset to forecasting, deal inspection, pipeline management, and account planning 
  • Establish a disciplined operating cadence aligned to our Revenue Architecture and GTM production lines 
  • Leverage a strong ecosystem of partners, resellers and alliances to drive demand, accelerate deal velocity and improve win rates 

Drive predictable new customer acquisition 

  • Own monthly, quarterly, and annual new-logo ARR targets 
  • Build and refine repeatable sales motions that follow the Bowtie and SPICED frameworks 
  • Ensure consistent execution across discovery, mutual action plans, customer impact mapping, and competitive positioning 

Partner cross-functionally 

  • Work closely with Demand Gen to shape ICP, messaging, and targeted campaigns 
  • Collaborate with Product to ensure field feedback informs the roadmap 
  • Partner with Customer Success to ensure seamless handoffs that drive fast time-to-impact and long-term retention 
  • Align with RevOps on territory design, compensation insights, forecasting models, and performance analytics 

Elevate execution 

  • Drive a culture of accountability, urgency, and continuous improvement 
  • Model excellence in enterprise sales fundamentals, SPICED-style qualification, and value-based storytelling 
  • Identify bottlenecks in the revenue production line and work with GTM leadership to improve throughput, win rates, and cycle times 

Qualifications 

Required 

  • 8+ years of SaaS sales experience with at least 3 years leading quota-carrying teams 
  • Proven success scaling new-logo business in Payroll, HCM, HRIS, WFM, or adjacent enterprise software 
  • Strong command of sales methodology (SPICED, MEDDIC, Command of the Message, or similar) 
  • Demonstrated ability to create predictable pipeline and consistently hit ARR targets 
  • Excellent at coaching, talent development, leading through data, and creating high-trust/high-performance cultures 
  • Experience operating within a multi-product environment and selling to CFOs, HR leaders, and operational buyers 

Preferred 

  • Experience selling into mid-market and enterprise segments 
  • Background working with PE-backed SaaS companies in transformation or scale-up phases 
  • Familiarity with revenue models, GTM motions, and the principles behind the Revenue Factory 

Success Looks Like 

  • Team hitting or exceeding quota within first two quarters 
  • Clear, repeatable sales motions established and adopted 
  • Improved AE productivity, win rate lift, cleaner pipeline discipline 
  • Shorter cycle times and reliable forecasting 
  • Strong cross-functional alignment with Marketing, CS, Product, and RevOps 
  • Meaningful contributions to our FY26 growth plan and the long-term revenue architecture of the company 

This is a remote position.

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