Director of Sales Enablement & Performance

Heartland Business Systems, LLC.

Lisle (IL)

On-site

USD 180,000 - 220,000

Full time

3 days ago

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Benefits offered by this job

Competitive Compensation

Growth Opportunities

Community Involvement

Personal Development

Work Life Balance

401k package

Paid Time Off

Recognition and Awards

Job summary

Heartland Business Systems, LLC is seeking a Director of Sales Enablement to lead strategy, onboarding, playbooks and the adoption of sales technology to improve seller productivity. You will partner with Sales, Revenue Operations, Marketing and HR to translate GTM priorities into measurable outcomes.

The role requires 8+ years in sales enablement or related fields, plus a degree in Business/Marketing/Communications or related area.

Qualifications

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

Responsibilities

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.