Product Sales Trainer

Role Overview

• Deliver one-on-one and group coaching sessions focused on pipeline development, discovery, objection handling, product demos, and closing techniques specific to Payroll and HCM solutions.
• Shadow live and recorded sales calls; provide structured, actionable feedback tied to measurable outcomes, ensure sellers can effectively position our products as a solution for our clients.
• Conduct personalized training for team based on sales rep feedback and the specific needs of a division or region.
• Travel as needed to conduct in-person training at various sales events and meetings.
• Facilitate training workshops during 2-week new rep training and broader ongoing trainings including selling season.
• Conduct product demo training to ensure sellers can effectively demonstrate the value of our products and link to meaningful discovery with prospects.
• Embed structured, advanced sales methodologies and skills across the sales organization.
• Partner with key stakeholders for cross-functional collaboration to align training objectives with organizational strategies.
• Equip new sellers with critical product knowledge to increase sales activity.
• Design and deliver training programs for sales reps covering product knowledge, competitive positioning, and sales methodology focused on selling to core client categories and selling more than one product per client.
• Develop playbooks, talk tracks, objection-handling guides, and ROI frameworks tailored to Payroll and HCM buyer personas.
• Consult with sales teams and leaders to develop curated and targeted training.
• Track rep performance metrics and use data to identify coaching priorities.
• Partner with Sales Leadership to identify skill gaps at the team and individual level.
• Report on training impact and enablement program effectiveness through defined KPIs.
• Foster a culture of continuous learning, peer accountability, and high performance.
• Facilitate peer learning sessions, deal reviews, and "win/loss" retrospectives.
• Serve as a subject matter expert and go-to resource for complex Payroll and HCM sales scenarios.

Requirements

• 7+ years of B2B sales experience as a trainer or sales representative, with a minimum of 3 years selling Payroll, HCM, HRIS, or HR Tech solutions (e.g., ADP, Paylocity, Paychex, UKG, Ceridian, Paycom, or similar platforms).
• Demonstrated track record of consistent performance as a trainer and meeting deadlines for content creation.
• 2+ years in a formal or informal sales coaching, training, or mentorship capacity.
• Deep fluency in consultative and value-based selling methodologies.
• Strong understanding of the HR and payroll buyer journey, common pain points, and competitive landscape.
• Exceptional facilitation, presentation, and written communication skills.
• Ability to diagnose performance gaps and tailor coaching approaches to different learning styles.
• Comfortable analyzing CRM data (Salesforce, HubSpot) to drive coaching decisions.
• Proficiency with sales enablement tools.
• A genuine passion for developing people — not just hitting numbers.
• High emotional intelligence; able to build trust quickly across diverse personality types.
• Growth mindset with a bias toward continuous improvement.
• Collaborative, patient, and direct.
• Expertise in varied adult learning methodologies.

Benefits

• Comprehensive medical insurance, dental insurance, and vision insurance; life and disability insurance; fertility benefits; wellness resources; and paid sick time.
• Generous paid time off and holidays; Employee Assistance Program (EAP); and a complimentary Calm app subscription.
• Immediate vesting in a 401(k) plan; Health Savings Account (HSA) and Flexible Spending Account (FSA) options; commuter benefits; and employee discount programs.
• Paid maternity leave and paid paternity leave (including for adoptive parents); legal plan options; and pet insurance coverage.