Director of Sales Enablement

Director Of Sales Enablement 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.

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