Director of Sales Enablement

WoodmenLIfe•Omaha, NE

1d•Onsite

About The Position

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. As a member of the WoodmenLife family, you’ll join others who share a commitment to family, community, and country.

Requirements

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.

Nice To Haves

Advanced degree preferred.

Responsibilities

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.