Sales Enablement - Sr. Manager

Job Title

Sales Enablement - Sr. Manager

Connect Pay Payroll Services

Connect Pay is a rapidly growing, forward‑thinking company dedicated to transforming payroll for small businesses across the United States. We deliver innovative cloud‑based technology through direct solutions and trusted partnerships, empowering business owners to streamline operations, reduce complexity, and focus on growth. Our team members are our greatest asset; we foster a supportive, collaborative environment that values innovative thinking and professional growth.

Every role contributes to building a streamlined, reliable payroll experience while upholding our core values of integrity, excellence, and client‑centered service.

The Sales Enablement Senior Manager is responsible for developing and executing strategies to empower the sales organization with the knowledge, tools, content, and training needed to accelerate revenue growth and enhance seller productivity. This role reports directly to the VP of Sales and collaborates closely with the Sales Operations Manager. In a high‑growth environment targeting 30% YoY expansion, the Sr. Manager will focus on building scalable programs that drive adoption of best practices, improve win rates, and support seamless onboarding and ongoing development for Account Executives (AEs), channel partners, and sales leaders.

• Design and implement comprehensive sales enablement programs, including onboarding, continuous training, certification paths, and skill‑building workshops to boost seller confidence and performance.
• Create and curate high‑impact sales content (playbooks, battle cards, case studies, demo scripts, objection‑handling guides) tailored to buyer personas, ICPs, and channel partners, in partnership with Marketing and Product teams.
• Lead sales training initiatives, including role‑playing sessions, product knowledge deep‑dives, and channel partner enablement, to ensure consistent messaging and effective use of sales tools.
• Measure and optimize enablement ROI through KPIs such as ramp time to productivity, win rates, content utilization, and training completion rates, using insights from Sales Operations analytics.
• Foster cross‑functional collaboration by acting as a bridge between Sales, Marketing, Product, and Operations to align on go‑to‑market strategies, feedback loops, and enablement needs.
• Drive adoption of sales technologies (Zoho CRM features, Zoom Info for prospecting, proposal automation tools) through targeted training and change management.
• Conduct regular needs assessments, sales audits, and feedback sessions to identify skill gaps and refine enablement strategies for organic and inorganic growth.
• Develop and maintain a sales enablement portal or knowledge base for easy access to resources, ensuring integration with CRM for real‑time updates.
• Support sales leadership in coaching and mentoring programs, including performance reviews tied to enablement outcomes.
• Stay ahead of industry trends in payroll, HR tech, and B2B SaaS to evolve enablement content and tactics for competitive advantage.

• Bachelor’s degree in a relevant field (Business Administration, Marketing, Education, Technology).
• 5–7+ years of experience in Sales Enablement or related roles (Sales Training, Revenue Enablement) within B2B SaaS, payroll, or HR tech environments.
• Proven track record building and scaling sales enablement programs that improved win rates by 15%+ and reduced ramp time by 20%+.
• Experience in content creation and management, including sales collateral aligned with buyer journeys and ICPs.
• Demonstrated success in training delivery, including virtual/in‑person sessions for AEs, managers, and channel partners.
• Cross‑functional liaison experience between Sales, Marketing, Product, and Operations to drive alignment on enablement initiatives.
• History of measuring enablement impact using metrics like adoption rates, content efficacy, and revenue attribution.
• Experience in high‑growth, matrixed organizations (30%+ YoY) with a focus on people development and process adoption.
• Proficiency in sales tech stacks, including…