Director of Sales Enablement

Heartland Business Systems•Lisle, IL

About The Position

The Director of Sales Enablement leads the strategy, programs, and operating rhythm that improve seller effectiveness, accelerate ramp time, and increase sales productivity across HBS. The role partners with Sales leadership, Marketing, Revenue Operations, Services, Human Resources, and other stakeholders to translate go-to-market priorities into practical seller capabilities, repeatable sales motions, and measurable business outcomes. The Director owns the sales enablement roadmap, onboarding and continuous learning, sales methodology and playbooks, frontline manager enablement, content and communications, and adoption of sales technology. Success is measured by seller execution, time to productivity, pipeline conversion and forecast discipline, adoption of priority sales motions and tools, and consistency across the sales organization.

Requirements

Eight years of experience across sales enablement, sales leadership, sales operations, learning and development, or related B2B sales functions.
Demonstrated experience building and scaling sales enablement programs for a complex B2B sales organization.
Experience creating onboarding, continuous learning, sales methodology, playbook, and manager coaching programs.
Experience defining enablement metrics and using performance data to identify needs and demonstrate business impact.
Experience driving adoption of CRM, sales enablement, learning, or sales productivity technology.
Experience partnering directly with senior sales leaders and cross-functional executives.
Bachelor’s degree in Business, Marketing, Communications, Education, or a related field, or an equivalent combination of education and experience.
Strong understanding of B2B sales processes, pipeline management, opportunity management, and seller productivity.
Ability to design and facilitate effective virtual and instructor-led learning for sellers and sales leaders.
Strong analytical skills and ability to translate data into actionable enablement priorities.
Proficiency with Salesforce, Microsoft 365, and sales enablement or learning platforms.
Excellent executive communication, presentation, writing, and stakeholder-management skills.
Maintain an outcome-focused mindset.
Strong prioritization skills.
Team-player approach.
Professional attitude and respectful demeanor.

Responsibilities

Build and own a 12–18-month Sales Enablement strategy and roadmap aligned with HBS revenue, gross profit, services growth, and go-to-market priorities.
Partner with Sales leadership and Revenue Operations to identify productivity gaps, set enablement priorities, and define measurable success metrics tied to seller performance and business outcomes.
Design and continuously improve onboarding and ramp programs, with clear milestones, certifications, and measures of time to productivity.
Own ongoing learning curricula for sellers and sales leaders, including sales methodology, discovery, value-based selling, account planning, opportunity management, negotiation, storytelling, presentation skills, and HBS solutions and services.
Develop and maintain role-based sales playbooks, sales plays, messaging, tools, and field-ready content with Marketing, Services, and subject-matter experts.
Create a frontline manager enablement program to help sales leaders coach consistently, inspect opportunities, reinforce methodology, and improve seller performance.
Lead enablement for strategic growth initiatives, including services, recurring revenue, cross-sell and attach motions, and other priority offers.
Establish a sales competency framework and assessment approach to identify skill gaps and inform development plans by role and tenure.
Partner with Revenue Operations to reinforce Salesforce adoption, pipeline and forecast discipline, data quality, and effective use of sales technology.
Evaluate and optimize the sales enablement technology ecosystem, including learning, content, coaching, and productivity platforms; drive adoption and demonstrate investment value.
Create a disciplined cadence for clear, relevant, and actionable sales communications.
Measure enablement effectiveness using indicators such as onboarding completion, ramp time, certification, tool adoption, pipeline conversion, sales cycle, win rate, and seller productivity.
Gather structured feedback from sellers and sales leaders and use performance data to improve enablement programs and content.
Lead and develop Sales Enablement team members and manage external training partners and vendors as appropriate.
Perform other duties as assigned in support of company objectives.

Benefits

Competitive compensation package, potentially including bonus, incentive, commission, fair wage, retirement plans, and benefits with HSA-compatible plans.
Growth opportunities.
Community involvement.
Personal development.
Employee and family celebrations.
Green initiatives.
Personal time off.
Work-life balance.
Recognition and awards.
Eligibility to participate in the employee benefit plan and earn a performance-based bonus.
Health insurance.
Dental insurance.
Vision insurance.
Company-paid long-term disability.
Paid time off.
401(k) package.