Head of Insurance Sales

Flex Dental offers a modern software platform that helps dental practices streamline communication, reduce administrative workload, improve treatment acceptance, and increase payment collection. We provide a full suite of patient engagement and workflow tools, including online scheduling, automated reminders, mobile forms, two-way texting, digital payments, reputation management, and insurance verification — all designed to deliver a better experience for both patients and dental practices.

The Senior Enablement Manager will own the strategy, development, and execution of Flex Dental's customer enablement program. This role is responsible for creating scalable learning experiences that help customers successfully adopt and grow with Flex—from onboarding and product adoption to new feature education and ongoing training.

This is a highly cross-functional role that partners closely with Product, Customer Success, Support, Onboarding, Marketing, and Engineering to ensure customers have access to timely, engaging, and effective learning resources.

This position will also provide leadership for our internal documentation efforts, overseeing our Technical Writer and helping establish processes and standards for internal knowledge management. While internal enablement is an important responsibility, the primary focus of this role will be building and scaling customer-facing education.

We're looking for someone who thrives in a fast-paced startup environment, enjoys building programs from the ground up, and is excited to make a measurable impact on customer success..

Customer Enablement Develop and execute Flex Dental's overall customer enablement strategy.

Design scalable learning programs that improve customer onboarding, product adoption, and long-term success.

Create engaging customer education through written documentation, interactive learning paths, videos, webinars, and self-service resources.

Measure learning effectiveness and continuously improve content using customer feedback, analytics, and adoption metrics.

Design, build, and maintain in-app guidance using Pendo, including walkthroughs, guides, announcements, and contextual help.

Partner with Product and Engineering to identify opportunities to improve customer adoption through digital enablement.

Monitor Pendo analytics to optimize customer engagement and identify knowledge gaps.

Training & Education Help develop customer webinars, group training sessions, and other one-to-many educational programs.

Partner with the Onboarding and Customer Success teams to identify training opportunities and create scalable solutions.

Produce high-quality video tutorials, walkthroughs, and product demonstrations.

Documentation & Knowledge Management Oversee customer-facing documentation, knowledge base articles, FAQs, and user guides.

Lead documentation standards, style guides, and content governance.

Manage and mentor the Technical Writer, providing direction, feedback, and prioritization.

Help develop internal documentation, processes, and training materials using Confluence and other knowledge management tools.

Cross-Functional Collaboration Partner closely with Product, Engineering, Customer Success, Support, Onboarding, and Marketing to deliver high-quality enablement experiences.

Support product launches through training materials, release documentation, webinars, and customer communications.

Identify opportunities to improve customer education through automation, self-service resources, and scalable processes.

Additional Responsibilities Contribute to strategic initiatives that improve customer experience, operational efficiency, and product adoption.

What You Bring 5+ years of experience in customer enablement, technical training, instructional design, technical writing, or a related SaaS enablement role.

Experience building and administering content within a Learning Management System (LMS).

Hands‑on experience designing and maintaining Pendo guides, walkthroughs, and digital adoption experiences.

Experience producing written documentation, video tutorials, webinars, and interactive learning content.

Strong project management and organizational skills with the ability to manage multiple priorities in a fast‑paced environment.

Experience collaborating across Product, Engineering, Customer Success, Support, and Marketing teams.

Experience leading projects, influencing cross-functional stakeholders, and driving initiatives from concept through execution.

Experience managing or mentoring team members is preferred.