Sales Director at Greenshades Software – Jacksonville, Florida

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.