Director of Sales Enablement (Remote)

San Francisco Bay Area

Full Time Executive-level / Director
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At Truepill, we are building the future of healthcare. Through our digital health platform, we empower our partners to deliver world-class patient experiences. With nearly five million prescriptions shipped, we’ve been included on Forbes’ “Next Billion-Dollar Startup” list and are proud to work with many of the world’s largest healthcare organizations. We never settle for how it’s done today. We invent how it will be done tomorrow. 
None of this is possible without the right team driving us forward. We are committed to creating an environment focused on racial and gender equality, inclusion, empowerment and respect. We believe that when our teams feel supported and inspired, they turn that creativity into innovation. The type of innovation that benefits all of our people, our partners and our patients.
We encourage our team members to expand their horizons and bring their passion and curiosity to work, every day. Come join us. Let’s build something great together.#LI-Remote


  • Oversee day-to-day execution of Sales Enablement programs, including program development, content curation, delivery, effectiveness, and ongoing optimization.
  • Be a subject matter expert in our sales processes, sales methodology, and competitive intelligence.
  • Partner with Sales and Solution Consulting leaders in identifying and prioritizing education and resource needs to optimize the sales process.
  • Collaborate cross-functionally with Sales, Solution Consulting, Finance, Marketing, Product Marketing, and Products to create Sales Enablement programs that align to Sales initiatives and go-to-market strategies and readiness.
  • Proactively improve upon existing sales processes or tools in collaboration with other departments.
  • Develop positioning and messaging to be deployed to the Sales organization by market segment, including US markets (Account Management, Growth, Primary, and Corporate), Canada, and Europe.
  • Understand key trends in content and education needs and confirm the content management system stays current for all positioning and messaging.
  • Validate that the appropriate messaging is implemented by Solution Consulting to align positioning for product demonstrations.
  • Attend all cross-functional product and go-to-market readiness meetings.
  • Lead or execute all readiness tasks to educate and arm the Sales and Solution Consulting teams for all releases in the product portfolio with the messaging, training, tools, and support required to position the business value of, demonstrate and sell Applied's solutions.
  • Track and report on key success metrics and key performance indicators (KPIs) specific to Sales Enablement efforts to show return on investment (ROI) and overall impact to Sales.
  • Lead, develop, coach, and manage a high-performing team of Sales Enablement professionals focused on the delivery, effectiveness, and continuous improvement of sales enablement programs and content for global Sales teams.
  • Provide team members clarity of purpose, necessary resources and tools, and an environment conducive to diversity of t thought, innovation, and personal/professional growth.
  • Pursue a program of self-development through the use of selected reading materials and participation in seminars and continuing education.
  • Proactively stay abreast of industry trends, available authoring/publishing technology, and social media resources.
  • Consider how new technology and practices may be successfully implemented within the insurance industry and Sales Enablement team.


  • Bachelor's degree in sales, marketing, business, or related field or equivalent professional work experience.
  • Formal solution sales training (highly preferred).
  • Field-related certification/designation and ongoing continuing education preferred.


  • Minimum of 5 years sales enablement or related experience, including market positioning, program development, delivery, and management.
  • 3-5 years insurance industry or software sales experience ideal.
  • Must have great leadership skills and a strong passion and empathy for driving sales through enablement.
  • Experience successfully creating and implementing a sales process/methodology with sales playbook initiatives.
  • Experience building effective sales onboarding, continuous learning programs, and instructional design.
  • Ability to identify and track metrics that demonstrate improvements in sales productivity.
  • Ability to forge relationships across internal organizations and build consensus amid competing priorities.
  • Have hands-on experience with CRM and sales enablement tools.
  • Must have strong organization, task, time, and project management skills.
  • Able to work collaboratively with others to obtain required information, assess needs, and effectively execute against a project plan.
  • Must have strong knowledge of Microsoft Outlook, Word, Excel, and PowerPoint with CRM experience ideal.
  • Must have strong knowledge of Learning Management Systems and adult learning theory.
  • Maintain excellent written, verbal communication, and presentation skills.
  • Present strong problem-solving and analytical skills, including the ability to eliminate obstacles through creative and adaptive approaches and deal well with ambiguity.
  • Demonstrate an advanced ability to discourse using insurance industry terminology and discuss insurance-specific issues/needs of consumers and the Sales organization.
  • Must be comfortable working with technology and have an understanding of Software as a Service.
  • Able to develop, communicate and teach technical understanding of software architecture and capabilities.
  • Ability to work with and manage confidential data of major importance such as the development of products, new product introductions, and proprietary organization information.
Truepill is proud to be an Equal Employment Opportunity and Affirmative Action employer. We do not discriminate based upon race, religion, color, national origin, gender (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, or other applicable legally protected characteristics.
Job region(s): North America
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