Director, Customer Enablement & Learning

Applied Systems•Chicago, IL

4d•Remote

About The Position

Transforming the insurance industry is ambitious, we know. That’s why at Applied, we’re building a team that shows up every day ready to learn, willing to try new things, and driven to deliver innovative software and services that make us indispensable to our customers – all within a culture built on values that make us indispensable to each other too. With 40+ years of experience in the Insurtech game, we’re not just redefining what’s achievable; we’re creating a place where amazing career moments are made possible. Position Overview We’re searching for a Director, Customer Enablement & Learning to join our Activation Services team in remote location. The Director, Customer Enablement & Learning will lead our customer-facing learning organization. This role owns how customers learn, adopt, and become proficient in Applied’s software through innovative, customer‑centric learning experiences that evolve as new technologies emerge and customer needs, maturity, and product capabilities change. This is a senior leadership role responsible for designing and scaling customer learning experiences that accelerate time to value, reinforce best practices, and drive sustained adoption. We are looking for a leader who understands how adults learn complex software, and who can translate that understanding into learning journeys that meet customers where they are – across roles, maturity levels, and moments in their lifecycle To keep us headed in the right direction, we’re looking for people who understand winning is a team sport, who value and seek to learn from our team’s diverse experiences and backgrounds, who welcome a challenge and take risks in the pursuit of creating better outcomes for our customers, and who can, at any given time, step back to laugh and have some fun.

Requirements

10+ years’ experience in customer enablement, customer education, software training, or professional services within a SaaS or technology environment.
5+ years’ experience leading and developing teams, including senior individual contributors and managers.
Deep understanding of adult learning principles and how people learn complex software in real-world environments.
Proven ability to design learning experiences that drive adoption, proficiency, and behavioral change, not just knowledge transfer.
Curiosity and comfort experimenting with AI and emerging technologies as tools to enhance how customers learn, without losing focus on human-centered design and outcomes.
Strong customer-centric mindset, with a focus on outcomes such as time to value, product usage, and long-term success.
Operational rigor – able to define processes, manage capacity, and scale learning programs without sacrificing quality.
Ability to analyze and demonstrate impact of programs delivered, with a goal of maximizing impact.
Comfort partnering cross-functionally and influencing without direct authority.

Nice To Haves

Familiarity with insurance agency workflows and Applied products.

Responsibilities

Own the strategy and execution for customer enablement and learning across Applied’s software portfolio.
Lead, develop, and evolve a team currently responsible for private, customer-specific training and scalable virtual group learning programs.
Design customer learning journeys that support onboarding, proficiency, advanced usage, and ongoing optimization.
Ensure learning experiences are role-based, workflow-oriented, and outcome-driven, not feature-centric.
Balance tailored private training with repeatable, scalable virtual learning models that meet customers at different stages of maturity.
Partner closely with Onboarding & Success Services leaders, Support, Product, and Sales to align learning experiences to implementation milestones and customer goals.
Establish quality standards and expectations for learning design, delivery, and customer experience.
Use adoption data, customer feedback, and health indicators to continuously refine learning approaches.
Forecast demand and manage capacity to deliver high-quality learning experiences at scale.
Serve as a senior leader within Onboarding & Success Services, shaping how customer learning supports broader adoption and success outcomes.