Sales Enablement - Sr. Manager

ConnectPay Payroll Services; Mansfield (MA); On-site; USD 130,000 - 150,000; Full time

Benefits offered by this job

401(k) with company contributions

Group medical, dental, and vision coverage

Annual bonus plan

Job summary

A payroll technology firm located in Mansfield, Massachusetts is seeking a Sales Enablement - Sr. Manager. This role focuses on empowering the sales organization with essential knowledge, tools, and training to accelerate revenue growth. Candidates should have 5-7+ years of experience in Sales Enablement within B2B SaaS or HR tech. The position offers competitive compensation and benefits, including equity and an annual bonus plan. Join a company that values innovation and collaborative growth.

Qualifications

• 5-7+ years of experience in Sales Enablement or related roles.
• Proven track record showing improvement in win rates by 15%+.
• Experience in developing sales training materials.

Responsibilities

• Design and implement comprehensive sales enablement programs.
• Create high-impact sales content tailored to buyer personas.
• Lead sales training initiatives for Account Executives.

Skills

Sales Enablement Program Development

Content Creation

Training Delivery

Cross-Functional Collaboration

Sales Technology Proficiency

Education

Bachelor’s degree in Business Administration, Marketing, Education, Technology

Tools

Zoho CRM

ZoomInfo

Seismic

Job description

Job Title

Sales Enablement - Sr. Manager

Company

ConnectPay Payroll Services

About the Company

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. 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.

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. 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.

Primary Duties and 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 (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, 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.

Qualifications

• 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 Zoho One, ZoomInfo, content management tools (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.

Compensation and Benefits

Base salary: $130,000–$150,000 annually (actual salary depends on education, training, experience, location, and internal equity). All team members receive equity, an annual bonus plan with a target of 10% of base salary, and a role‑based sales incentive plan. Benefits include 401(k) with company contributions; group medical, dental, and vision coverage; life insurance; short‑term and long‑term disability insurance; and flexible spending accounts.

Equal Opportunity Employer

CP Payroll is an equal‑opportunity employer. We are committed to a work environment free from discrimination and harassment. All employment decisions are made without regard to race, color, religion, gender, sexual orientation, gender identity or expression, national origin, age, disability, marital status, veteran status, or any other protected characteristic under applicable law.

Seniority Level

Mid‑Senior level

Employment Type

Full‑time

Job Function

Sales, General Business, and Education

Industries

Wireless Services, Telecommunications, and Communications Equipment Manufacturing