Director of Sales Enablement

HEARTLAND BUSINESS SYSTEMS LLC; Lisle (IL); On-site; USD 180,000 - 220,000; Full time

Benefits offered by this job

Competitive compensation package

Growth opportunities

Work-life balance

Employee recognition

Job summary

Heartland Business Systems seeks a Director of Sales Enablement to lead strategy, onboarding and ongoing learning for the sales organization. You will partner with Sales, Marketing and Revenue Operations to translate priorities into practical seller capabilities, repeatable motions and measurable outcomes.

The role oversees a comprehensive enablement roadmap, frontline manager programs and adoption of sales technology to improve productivity, time-to-productivity and forecast discipline.

Qualifications

• 8 years of experience across sales enablement, sales leadership, operations or related B2B functions.
• Experience building and scaling enablement programs for complex B2B sales organizations.
• Experience defining enablement metrics and using performance data to drive decisions.
• Proficiency with Salesforce, Microsoft 365 and enablement/learning platforms.

Responsibilities

• Build and own a 12-18 month Sales Enablement strategy and roadmap.
• Partner with Sales leadership and Revenue Operations to identify productivity gaps and define success metrics.
• Design onboarding and ramp programs with milestones and measures of productivity.
• Own ongoing learning curriculum for sellers and sales leaders, including methodology and playbooks.
• Develop and maintain role-based sales playbooks, messaging and tools in partnership with Marketing and Services.
• Create a frontline manager enablement program to coach consistently.
• Lead enablement for growth initiatives like services and cross-sell motions.
• Establish a sales competency framework and assessment approach.
• Partner with Revenue Operations to reinforce Salesforce adoption and data quality.
• Evaluate and optimize enablement tech ecosystem and drive adoption.

Skills

Sales enablement

Sales leadership

CRM adoption

Analytics

Executive communication

Program design

Coaching

Learning platforms

Education

Bachelor's degree in Business/Marketing/Communications/Education or related field

Tools

Salesforce

Microsoft 365

Job description

Description

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. This role partners closely with Sales leadership, Marketing, Revenue Operations, Services, Human Resources and other stakeholders to translate HBS 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 stronger seller execution, faster time to productivity, improved pipeline conversion and forecast discipline, higher adoption of priority sales motions and tools, and increased consistency across the HBS sales organization.

Roles and Responsibilities/ Essential Functions:

• Build and own a 12-18 month Sales Enablement strategy and roadmap aligned to HBS revenue, gross profit, services growth and go-to-market priorities.
• Partner with Sales leadership and Revenue Operations to identify productivity gaps, establish enablement priorities and define measurable success metrics tied to seller performance and business outcomes.
• Design and continuously improve onboarding and ramp programs for new sales team members, with clear milestones, certifications and measures of time to productivity.
• Own the ongoing learning curriculum 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 in partnership with Marketing, Services and subject‑matter experts.
• Create a frontline manager enablement program that equips sales leaders to coach consistently, inspect opportunities, reinforce methodology and improve individual seller performance.
• Lead enablement for strategic HBS growth initiatives, including services, recurring revenue, cross‑sell/attach motions and other priority offers, ensuring sellers understand when, where and how to position them.
• Establish a sales competency framework and assessment approach that identifies skill gaps and informs targeted 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 value from investments.
• Create a disciplined cadence for sales communications so sellers receive clear, relevant and actionable information without unnecessary noise.
• Measure enablement effectiveness through leading and lagging 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 continuously 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.

Requirements

How to qualify:

• 8 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 equivalent combination of education and experience.
• Strong understanding of B2B sales process, 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
• Have strong prioritization skills
• Always be a team player
• Carry a professional attitude and respectful demeanor

Why HBS?

Heartland Business Systems is one of THE LARGEST technology VARs or Value‑Added Resellers in the Midwest. Anything that happens with computers – we do it! We PRIDE ourselves on our Core Values of:

Performance – HBS is driven to achieve exceptional results in all aspects of our business.

Respect – HBS Team Members demonstrate personal integrity and professionalism when dealing with all internal and external contacts.

Innovation – HBS is passionate to serve our internal and external customers with innovative solutions to enhance their success.

Development – HBS is committed to developing ourselves and each other in ways that support and improve the performance of ourselves and our business.

Excellence – HBS takes great pride in all we do and strive for excellence always.

What you can expect from HBS:

• Competitive Compensation Package (May include but not limited to: Bonus, Incentive, Commission, Fair Wage, Retirement Plans, 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

Day in and day out, you will be a part of a collaborative, innovative and award‑winning team that will make you a better professional. Choose HBS today!

Heartland Business Systems is an Equal Opportunity Employer - Including Disabled and Veterans.

The salary for this position is $200,000, plus eligibility to participate in the employee benefit plan and earn a performance based bonus. The employee benefit plan includes health, dental, vision insurance, company paid long term disability, paid time off, and 401k package. The base pay offered will take into account the candidate’s job‑related knowledge, skills, education, certifications and experience among other factors as well as internal equity.