Product Sales Trainer

This is a fully remote position, open to applicants in Oklahoma.

📋 Description

• Provide individualized and group coaching sessions aimed at pipeline development, discovery, objection handling, product demonstrations, and closing techniques specifically related to Payroll and HCM solutions.

• Observe live and recorded sales calls; deliver organized, actionable feedback linked to measurable results, ensuring that sales representatives can effectively position our products as solutions for clients.

• Tailor training sessions for the team based on feedback from sales representatives and the distinct requirements of a division or region.

• Travel as necessary to offer in-person training at various sales events and meetings.

• Lead training workshops during two-week new representative training and ongoing training sessions, including those during the selling season.

• Provide product demonstration training to ensure sales representatives can effectively showcase the value of our products and connect to significant discovery with prospects.

• Integrate structured, advanced sales methodologies and skills throughout the sales organization.

• Collaborate with key stakeholders for cross-functional alignment of training goals with organizational strategies.

• Equip new sales representatives with essential product knowledge to enhance sales activity.

• Design and implement training programs for sales representatives focusing on product knowledge, competitive positioning, and sales methodologies aimed at selling to core client categories and promoting multiple products per client.

• Create playbooks, talk tracks, objection-handling guides, and ROI frameworks tailored to the Payroll and HCM buyer personas.

• Consult with sales teams and leadership to develop focused and targeted training initiatives.

• Monitor sales representative performance metrics and utilize data to establish coaching priorities.

• Partner with Sales Leadership to identify skill gaps at both team and individual levels.

• Report on the impact of training and the effectiveness of enablement programs through defined KPIs.

• Promote a culture of continuous learning, peer accountability, and high performance.

• Facilitate peer learning sessions, deal reviews, and "win/loss" retrospectives.

• Act as a subject matter expert and primary resource for complex Payroll and HCM sales scenarios.

⛳️ Requirements

• Over 7 years of B2B sales experience as a trainer or sales representative, including at least 3 years of selling Payroll, HCM, HRIS, or HR Tech solutions (e.g., ADP, Paylocity, Paychex, UKG, Ceridian, Paycom, or similar platforms).

• Proven history of consistent performance as a trainer and meeting deadlines for content development.

• Minimum of 2 years in a formal or informal coaching, training, or mentorship role.

• Profound understanding of consultative and value-based selling methodologies.

• Strong comprehension of the HR and payroll buyer journey, common pain points, and the competitive landscape.

• Excellent facilitation, presentation, and written communication abilities.

• Capacity to identify performance gaps and customize coaching methods to suit various learning styles.

• Comfortable with analyzing CRM data (Salesforce, HubSpot) to inform coaching decisions.

• Proficient in using sales enablement tools.

• A genuine enthusiasm for developing individuals — not solely focused on achieving numbers.

• High emotional intelligence; capable of quickly building trust across diverse personality types.

• Growth mindset with a focus on continuous improvement.

• Collaborative, patient, and straightforward.

• Expertise in a variety of adult learning methodologies.

🏝️ Benefits

• Comprehensive medical, dental, 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; options for Health Savings Account (HSA) and Flexible Spending Account (FSA); commuter benefits; and employee discount programs.

• Paid maternity and paternity leave (including for adoptive parents); legal plan options; and coverage for pet insurance.