Director, Product Enablement & Operations

Teladoc HealthMcCullom Lake, IL
$165,000 - $187,000Remote

About The Position

The Director, Product Enablement & Operations is responsible for driving operational excellence, AI enablement, and product lifecycle governance across the Product organization. This role leads Product Operations functions that support operational scalability, tooling strategy, cross-functional coordination, and execution consistency across product development activities. The Director partners closely with Product leadership to improve operational effectiveness through process optimization, tooling adoption, AI-enabled workflow improvements, and organizational enablement initiatives that support product delivery and execution quality across a fast-paced, matrixed environment.

Requirements

  • 10+ years of experience in product operations, product management, or a related field at a leading digital health or technology firm.
  • Track record of rolling out AI tools at scale, ideally on product or management teams, with measurable impact on efficiency and quality.
  • Has designed and scaled processes that measurably improved efficiency, accuracy, or performance, backed by solid data analysis and KPI reporting.
  • Deep understanding of the product development lifecycle, specifically in a technology-focused company.
  • Can break down complex problems, find root causes, design solutions, and plan the rollout.
  • Operates independently — sets direction and ships results on high-impact, cross-functional work.
  • Proficient in stakeholder management, relationship building, and communication management across executive levels.
  • Strong written and verbal communication, including executive-level presentations on roadmap updates, quarterly objectives, and org-wide initiatives.
  • Familiarity with tools like Figma, Jira, Confluence, Miro, Airtable, Productboard, and modern AI assistants.
  • Bachelor's degree in a related field. In lieu of a Bachelor's degree, an equivalent combination of education and experience is accepted.

Nice To Haves

  • Experience in a B2B2C software company is preferred; experience in healthcare is a strong plus.

Responsibilities

  • Identify, evaluate, and roll out AI tools across the product development lifecycle — roadmapping, requirements, design, content ops, documentation — with measurable gains in efficiency and quality.
  • Champion AI use across the Product organization, leading adoption and change management to embed AI into workflows and improve business outcomes.
  • Track emerging AI trends in product operations, design and run pilots, measure results, and build the business case for broader rollout.
  • Own the Product organization's tooling strategy, with accountability for efficiency, adoption, and ROI.
  • Lead change management and adoption programs so new tools land cleanly across product teams.
  • Build and scale a training program covering onboarding, skill-building, and ongoing development across product roles.
  • Own onboarding for new hires — set the bar for their first weeks, raise engagement, and shorten time to productivity.
  • Build and maintain a collaborative environment with stakeholders across product, engineering, finance, sales, customer success, and leadership to ensure strategic objectives are met.
  • Build the systems that get product managers the data they need to make better decisions.
  • Define strong communication strategies that provide effective sharing of information, determining the most appropriate communication channels, formats, and frequency.
  • Run the decision-making forums on the product operating cadence — surface risks, shape priorities, and get teams aligned faster.
  • Comfortable leading initiatives and reviews with executive stakeholders.

Benefits

  • performance bonus
  • Flexible Vacation Policy
  • 80 hours of Paid Sick, Safe, and Caregiver Leave annually
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