Director of Sales Enablement

Woodmenlife; Omaha (NE); Hybrid; USD 150,000 - 210,000; Full time

Benefits offered by this job

Health, dental, vision benefits

401(k) plan

Life insurance and more

Job summary

WoodmenLife in Omaha, NE seeks a Director of Sales Enablement to steward a comprehensive enablement strategy and multiyear roadmap that supports distribution growth, recruiting, retention and productivity. You will lead with the Manager of Sales Operations and Manager of Sales Training, aligning tools, training and processes for a scalable sales ecosystem.

The role emphasizes strategic leadership, cross‑functional collaboration, AI integration and responsible usage, in a growth‑oriented

Qualifications

• Bachelor’s degree required; advanced degree preferred.
• 10+ years in life insurance sales distribution, operations, training or related.
• Experience leading through managers and cross-functional teams.
• Experience with large-scale technology implementations and change management.
• Knowledge of life insurance distribution, contracting, commissions and retention.
• Experience with IMOs and independent producers and licensing processes.
• Strong strategic planning, budgeting and vendor management.
• Ability to define performance metrics and translate data into improvements.
• Excellent communication and stakeholder influence at all levels.
• Familiarity with AI tools and responsible AI usage.

Responsibilities

• Develop and execute a comprehensive sales enablement strategy and multiyear roadmap aligned with growth objectives.
• Provide strategic leadership through Managers of Operations and Training; set priorities and expectations.
• Continuously evaluate the sales ecosystem to identify gaps and drive solutions.
• Oversee enablement technology strategy, including CRM, contracting, and commissions; lead change management.
• Lead the selection and implementation of a new commission system in partnership with key stakeholders.
• Set standards for CRM usage and needs-based selling across the sales force.
• Collaborate with Directors of Sales and field leaders to enhance onboarding and retention.
• Develop dashboards and KPIs for adoption, cycle times, training effectiveness and productivity.
• Manage budgets, vendor relationships and investments to maximize ROI.
• Lead cross-functional initiatives with IT, HR, Marketing, Finance and Compliance.
• Promote AI-enabled, ethical, and compliant workflows across teams.

Skills

Sales Enablement

Strategic Leadership

Change Management

Cross-functional Influence

AI/GenAI Usage

CRM Familiarity

Vendor Management

Budget Management

Education

Bachelor’s degree in relevant field

Advanced degree preferred

Tools

CRM platforms

Sales enablement tools

Contracting platforms

Microsoft Office

Copilot

Job description

Job Title: Director of Sales Enablement

Location: Omaha, Nebraska

WoodmenLife is looking to hire a Director of Sales Enablement to join our team! In this role, you will develop and execute WoodmenLife’s sales enablement strategy to support long-term distribution growth, recruiting, retention, productivity and sales execution. The Director owns the sales enablement ecosystem, ensuring sales professionals and recruiters have effective tools, technology, training, processes, support and resources. The role provides strategic leadership through the Manager of Sales Operations and Manager of Sales Training, while those managers oversee day-to-day operations. This position aligns commissions, contracting, training, sales technology and field processes; evaluates capabilities; closes gaps; and creates a multiyear roadmap to strengthen the recruiter and representative experience. The Director also maximizes the value of CRM, agent contracting, commission systems and future enablement investments to help grow the sales force from approximately 1,000 to 2,500 career representatives over the next seven to ten years.

WoodmenLife is one of the best places to work in Omaha, with more than 135 years of service rooted in purpose and community. Since 1890, WoodmenLife has been dedicated to helping hardworking Americans secure their families’ financial futures and leave a lasting legacy. As a purpose‑driven, not‑for‑profit life insurance company, our commitment is to our members and the communities they call home.

We offer a comprehensive benefits package including health, dental, vision, 401(k), life insurance, and more.

We are looking for someone to:

• Develops, communicates and executes a comprehensive sales enablement strategy and multiyear roadmap aligned with organizational growth, recruiting, retention, productivity and distribution objectives.
• Provides strategic leadership and direction through the Manager of Sales Operations and the Manager of Sales Training; establishes priorities, decision rights, performance expectations and cross-functional alignment while preserving each manager’s day-to-day operational leadership.
• Continuously evaluates the sales ecosystem, field feedback, competitive environment and emerging capabilities to ensure recruiters and sales professionals have highly capable tools, complete offerings, effective training and efficient support; identifies gaps and leads solutions.
• Owns the strategy, governance, adoption and continuous optimization of sales enablement technology, including the CRM, agent contracting platform, commission systems and future tools; leads business readiness and change management for major implementations.
• Leads the business strategy, selection and implementation of a new commission system and ensures the agent contracting platform operates at its full potential, in partnership with Sales Operations, Information Technology, Finance, Compliance and other stakeholders.
• Establishes standards, measures and reinforcement practices that drive consistent use of the organization’s sales process, CRM and needs-based selling approach across the sales force.
• Partners with Directors of Sales, the Director of Recruiting Sales Manager Development, recruiters and field leaders to strengthen the recruiting value proposition, improve onboarding, accelerate time to productivity and support representative retention.
• Develops dashboards and key performance indicators for system adoption, contracting cycle time, training effectiveness, sales‑process execution, field productivity, recruiting support, representative retention and other enablement outcomes; reports results and recommendations to executive leadership.
• Builds business cases, manages budgets and vendor relationships, prioritizes investments and allocates resources to achieve sales enablement objectives and maximize return on organizational investments.
• Leads cross-functional initiatives with Information Technology, Human Resources, Marketing, Product, Operations, Finance, Legal and Compliance to deliver coordinated, scalable solutions that support distribution growth.
• Demonstrates ability to leverage AI technologies to streamline workflows, promote fair and unbiased work practices, and coach teams on safe, ethical, and effective AI use.
• Meets attendance and punctuality expectations in accordance with supervisor and WoodmenLife policy requirements.
• Performs other duties as assigned by management.

We need someone who has:

• Bachelor’s degree from an accredited college or university required; advanced degree preferred.
• 10+ years of progressive experience in the life insurance industry, including demonstrated experience in sales distribution, sales operations, sales training, recruiting support, field leadership, sales technology or a related discipline.
• Proven experience leading through managers and influencing cross‑functional teams in a complex organization.
• Demonstrated experience leading large-scale technology implementations, process transformation, organizational change and user adoption efforts.
• Comprehensive knowledge of life insurance distribution, career sales force operations, representative recruiting and retention, agent contracting, commissions, training and sales processes.
• Experience working with independent marketing organizations (IMOs) and independent producers, with specific expertise in licensing, contracting, commission administration and distribution hierarchy management.
• Proven strategic planning, business case development, budget management, vendor management, project governance, problem‑solving and decision‑making skills.
• Ability to define meaningful performance measures, analyze quantitative and qualitative data, identify trends and translate insights into practical recommendations and operating improvements.
• Excellent written, verbal, presentation and persuasion skills, with the ability to communicate effectively with executives, managers, associates, field leaders, sales professionals, vendors and other stakeholders.
• The ability to craft clear, concise, and effective prompts to get accurate results from generative AI tools like Copilot or ChatGPT.
• Familiarity with AI‑powered work tools (e.g. Copilot) for content creation, data analysis, automation, and design.
• Understanding the responsible use of AI, including identifying and mitigating algorithmic bias and ensuring data privacy and security.
• Working knowledge of CRM platforms, sales enablement technologies, commission systems, contracting platforms, Microsoft Office applications and Copilot.
• Ability to manage aggressive deadlines, competing priorities and multiple internal and external stakeholders with available resources.
• Knowledge and understanding of applicable insurance laws, regulations, compliance requirements and internal controls.
• Demonstrated ability to provide seamless, trustworthy, attentive and resourceful (S.T.A.R.) customer service and a commitment to an exemplary customer and field experience.

If you're ready to make an impact in your community, we’d love to hear from you.

WoodmenLife will not sponsor applicants for work visas for this position. Applicants must be currently authorized to work in the United States on a full‑time basis.

Please ensure your resume includes your current contact information, including:

• Full name
• Phone number
• Email address
• Current city and state of residence

As part of WoodmenLife’s employment process, candidates will be required to complete a criminal background check, credit check (when required for position), fingerprint check (when required for position), drug screen and reference checks. Any offer of employment will be contingent upon successfully passing the above.

WoodmenLife is welcoming to all regardless of background and beliefs. WoodmenLife respects every associate’s unique perspective and contribution. We are committed to creating an environment that values differences, and creates opportunities for growth, leadership and service. This commitment includes providing equal opportunity in recruitment, employment and promotion, training and community outreach. WoodmenLife is also dedicated to strengthening the communities in which its employees live.

APPLICANTS WITH DISABILITIES SHOULD ADVISE THE HUMAN RESOURCES DEPARTMENT AT THE TIME OF APPLICATION IF SPECIAL ACCOMMODATIONS ARE NEEDED. Woodmen of the World Life Insurance Society (WoodmenLife) is an equal opportunity employer.