Sales Enablement - Sr. Manager

CP Payroll, LLC dba ConnectPay • Mansfield, MA

17d • $130,000 - $150,000

About The Position

ConnectPay 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. At ConnectPay, our team members are our greatest asset. We foster a supportive, collaborative environment that values innovative thinking and professional growth. Our team is empowered with the resources, tools and autonomy they need to drive success for our clients and themselves. Every role contributes to building a streamlined, reliable payroll experience for our clients, all while upholding our core values of integrity, excellence and client-centered service in everything we do. Job Details 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 to align enablement initiatives with operational processes, data insights, and channel-driven growth objectives. In a high-growth environment targeting 30% YoY expansion, the Sales Enablement Director 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. Complementing the Sales Operations Manager's emphasis on data hygiene, forecasting, and CRM administration, this role owns the human element of sales effectiveness—ensuring teams are equipped to leverage Zoho CRM, marketing collateral, and product roadmaps to shorten sales cycles (<45 days) and maximize deal velocity in B2B SaaS, payroll, and HR tech markets.

Requirements

• Bachelor's degree in a relevant field (e.g., Business Administration, Marketing, Education, Technology)
• Requires 5–7+ years’ experience in Sales Enablement or related roles (e.g., 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 expertise as a liaison 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 Zoho One, ZoomInfo, content management tools (e.g., Seismic or Highspot), and analytics platforms.
• Advanced skills in instructional design, adult learning principles, and tools like Google Slides/PowerPoint for training materials.
• Experience integrating enablement with CRM systems for personalized learning paths and performance tracking.

Nice To Haves

• Sales Enablement certification (e.g., from Sales Enablement Society or ATD).
• MBA or related graduate degree in Organizational Development or Business.

Responsibilities

• 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 (e.g., 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 (e.g., Zoho CRM features, ZoomInfo 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.

Benefits

• 401(k) with company contributions
• group medical, dental, and vision coverage
• life insurance
• short and long-term disability insurance
• flexible spending accounts
• eligible for an annual bonus with a target of 10% of base salary, based on company and individual performance
• equity

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level