Head of Sales (B2B) (Remote)

The Sales Manager is responsible for managing and coaching Green Leaf's Sales and Client Support teams and plays a key role in driving day-to-day sales execution and supporting our commercial growth strategy. The Sales Manager oversees pipeline development, ensures consistent sales processes, and partners closely with Implementation, HR Tech, and Operations teams to deliver seamless customer experience. This is a hands-on leadership role-responsible for motivating the team, refining sales tactics, tracking performance, and fostering a strong culture of accountability and results. As Green Leaf continues to grow, this role contributes directly to building scalable sales practices and developing future sales leaders.
Lead a team of Sales Account Executives and Client Success Specialists to achieve new revenue goals across the SMB and Mid-Market segments

• Manage day-to-day sales operations, including pipeline reviews, forecasting, talent development, and activity tracking
• Own the achievement of annual revenue targets through strategic sales planning and execution.
• Drive consistent use of sales tools, CRM hygiene, and reporting accuracy to maintain visibility into team performance
• Coach and develop team members through regular 1:1s, skill development plans, and performance feedback
• Support recruiting, onboarding, and training of new Sales Account Executives to ensure successful ramp-up and productivity
• Collaborate with product, implementation, and support teams to ensure smooth handoffs and strong client onboarding experiences
• Oversee pipeline quality across inbound, outbound, and referral sources to maintain predictable deal flow
• Monitor team KPIs-such as conversion rates, sales cycle time, and forecast accuracy-and act quickly on performance gaps
• Participate in deal strategy for complex or strategic accounts, offering hands-on coaching and support
• Build and maintain relationships with referral and channel partners to support lead generation and market visibility
• Identify process improvements in sales execution, reporting, and communication across teams
• UKG Ready System and Training Responsibilities
• Participate in ongoing UKG Ready training and certifications as required
• Support internal enablement by sharing product knowledge and demo best practices with sales staff
• Stay current on release notes and new functionality to ensure accurate representation in the sales cycle

5+ years of B2B sales leadership experience with prior supervisory experience of Sales and/or Client Success individual contributors

• Bachelor's degree in business, technology, or a related field, and/or equivalent combination of education and work experience
• Experience selling complex, multi-product solutions (payroll, HR, SaaS, compliance, or professional services preferred)
• Hiring, coaching, and performance management capabilities
• Experience working with referral partners and channel-based sales models
• Experience with HCM and payroll platforms such as UKG Ready is a plus
• Experience in payroll, HCM, PEO, or HR technology environments
• Knowledge of compliance considerations in payroll and HR systems
• CRM and sales enablement tool familiarity
• Experience with data migrations and system integrations

Remote or hybrid depending on business needs
• Travel will be required for key presentations, conferences, or client meetings
Reasonable accommodations may be made to enable individuals with disabilities to perform the functions. All duties and responsibilities are essential functions and requirements and are subject to possible modification to reasonably accommodate individuals with disabilities. Some requirements may exclude individuals who pose a direct threat or significant risk to the health or safety of themselves or others. The requirements listed in this document are the minimum levels of knowledge, skills, or abilities. This document does not create an employment contract, implied or otherwise, other than an "at will" relationship.