Director, Customer Enablement & Learning

Job Description

Amazing Career Moments Happen Here

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 a 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.

What You’ll Do

• 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.

We’re Excited To Learn More About You

Your experience may include:

• 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.

Other skills or credentials you may have include:

• Familiarity with insurance agency workflows and Applied products.

We know that talent comes from all backgrounds and experience levels. We encourage military members and their spouses as well as candidates without a degree or a background in tech to apply!

When You Join Team Applied, You Can Expect:

A culture that values who you are and recognizes that you aren’t just an employee; you are a teammate, and you matter. We thrive on the benefits of our different experiences and celebrate the uniqueness our teammates bring to work with them every day.

We flex our time together, collaborating remotely and in‑person to empower our teams to work in the ways that work best for them.

A comprehensive benefits and compensation package that centers our teammates and helps them to bring their best to work every day:

• Medical, Dental, and Vision Coverage
• Holiday and Vacation Time
• Health & Wellness Days
• A Bonus Day for Your Birthday

Our targeted starting base salary in the United States for this position ranges from $140,000 - $175,000 USD. To determine a new team member’s starting pay, we consider a variety of factors, including someone’s depth, breadth, and variety of experience, skills, and responsibilities. Depending on the role, team members may also be eligible to participate in additional compensation plans such as bonus and commission.

Your Security Matters:

Our candidates’ personal information and online safety are top of mind for us. At Applied, we proactively protect your personal information and only communicate with candidates via a secure @appliedsystems.com email or through our official careers portal. Recruiters will never request payments, ask for financial account information or sensitive information like social security numbers.

AI Utilization

We leverage AI tools to streamline parts of our recruitment workflow (such as resume parsing and interview scheduling). However, candidate screening, interviews, and final decisions are conducted by real humans.

EEO Statement

Applied Systems is proud to be an Equal Employment Opportunity Employer. Diversity and Inclusion is a business imperative and is a part of building our brand and reputation. At Applied, we don’t discriminate, and we are committed to recruit, develop, retain, and promote regardless of race, religion, color, national origin, sexual orientation, gender identity, disability, age, veteran status, and other protected status as required by applicable law.