ConnectPay Payroll Services · 1 month ago
Sales Enablement - Sr. Manager
Mansfield, MA
Full-time
Onsite
Senior Level
$130K/yr - $150K/yr
5+ years expConnectPay Payroll Services is a rapidly growing, forward-thinking company dedicated to transforming payroll for small businesses across the United States. 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.
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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
Qualification
Required
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
Preferred
Sales Enablement certification (e.g., from Sales Enablement Society or ATD)
MBA or related graduate degree in Organizational Development or Business
Benefits
401(k) with company contributions
Group medical, dental, and vision coverage
Life insurance
Short and long-term disability insurance
Flexible spending accounts
Company
ConnectPay Payroll Services
ConnectPay empowers small businesses across America through hassle-free payroll processing.
201-500 employees
Funding
Current Stage
Growth StageTotal Funding
$8.36M2019-04-05Series Unknown· $3M
2016-11-15Series Unknown· $5.36M
Leadership Team
Michael Young
CEO & Co-Founder
Drew Schildwachter
Partner and COO
Recent News
2025-07-02
2025-06-16
Company data provided by crunchbase