Senior Director of Underwriting Technology Transformation

Highmark

$169K — $286K *
US-Anywhere
+ 51 other locationsRemote
Finance & Insurance
8 - 10 years of experience
Job Overview by Ladders

Qualifications

  • Minimum 10 years in a leadership role managing multi-layer teams
  • At least 7 years leading technology transformation initiatives
  • 5 years experience in underwriting and/or revenue generation
  • Preferred 5 years of actuarial pricing experience
  • Bachelor's degree or equivalent work experience; preferred Master's degree in relevant fields

Responsibilities

  • Lead technological innovation in underwriting transformation alongside cross-functional teams
  • Drive continuous innovation of product technology to replace outdated systems
  • Determine technical direction for technology teams in accordance with product roadmap
  • Manage team operations, including hiring, coaching, and budget oversight
  • Collaborate with senior stakeholders to implement analytics and tools for decision-making
  • Maintain the underwriting technology portfolio and investment governance
  • Establish enterprise standards for underwriting tools and analytics capabilities

Benefits

  • Flexible office-based or remote work options
  • Occasional travel (0% - 25%)
  • Comprehensive support for ongoing professional development
  • Encouragement of cross-functional skills and multi-departmental collaboration
  • Engagement with executive leadership on strategic decision-making
Full Job Description

JOB SUMMARY

This job is responsible for leading the enterprise technology transformation of the underwriting technology operating model, decisioning systems, and technology products that enable a unified, scalable, and data-driven ecosystem.

The role shapes and delivers innovative product technology delivering enterprise-level value, integrating workflow orchestration, advanced analytics, and automation to improve underwriting productivity, pricing accuracy, and margin performance. It directly incorporates analytic insights, tools, and decisioning capabilities into day-to-day underwriting workflows, enabling realization of measurable financial outcomes at scale.

This position operates across a highly matrixed environment, partnering with product management, underwriting, actuarial, finance, sales, and technology leadership, and influencing senior leaders across the enterprise on the technological innovation needed to achieve desired business outcomes.

The role demands a high degree of strategic leadership, independent decision-making, and accountability for innovation and sustained business results, serving as the primary point of contact across technology teams to ensure successful execution of technology product development and deployment . Working with the health plan segments, it establishes enterprise standards for tools, data integration, and decisioning capabilities. The role will work directly with Executive Leadership, Senior Vice Presidents and other senior leaders to develop and influence cross-functional strategy.


ESSENTIAL RESPONSIBILITIES

  • Lead and provide expertise to technological innovation as part of the underwriting transformation, co-led in partnership with Underwriting, Actuarial, Technology and Product Management.

  • Leads the continuous innovation of the product technology, ensuring we are addressing aging technology and embracing new, cutting-edge technology.

  • Sets the technical direction across technology teams to determine what needs to be built and how it will integrate into the broader ecosystem, in alignment with the product roadmap.

  • Perform management responsibilities to include, but not limited to: involved in hiring and termination decisions, coaching and development, rewards and recognition, performance management and staff productivity. Plan, organize, staff, and manage the day-to-day operations of the team; develop and implement policies and programs as necessary; manage to assigned budgets.

  • Partner with senior stakeholders across UW, Actuarial, Finance, IT, Sales, Product Management, Architecture, Analytics, Infrastructure, Platform Operations

  • Drive implementation of analytics, tools, and workflow-integrated decisioning. Oversee development and deployment of tools, applications, and decision support capabilities that translate insight into action and measurable outcomes. Ensure underwriting insights are directly embedded into day-to-day workflows to enable consistent decision-making and performance improvement

  • Collaborate with Product Management, Underwriting, Segment, and other stakeholders in the creation, maintenance and communication of the underwriting technology portfolio, roadmap, and investment governance.

  • Collaborate with Product Management, Underwriting, Segment, and other stakeholders on build/buy decisions, vendor strategy, and platform selection, leading the technical evaluating in each. Provide critical input into the business case, supporting alignment to ROI expectations.

  • Establish enterprise standards for underwriting tools, data integration, and analytics capabilities. Drive implementation of analytics, tools, and workflow-integrated decisioning

  • Provides deep understanding of underwriting, actuarial, and/or technology/analytics functions and uses that expertise to provide critical input into and shape the product technology strategy and roadmap.

  • Other duties as assigned or requested.


EXPERIENCE

Required

  • 10 years with Leadership role multi-layer teams

  • 7 years of experience with Technology transformation leadership

  • 5 years of Underwriting and/or revenue generation experience

Preferred

  • 5 years of Actuarial pricing experience

SKILLS

  • Enterprise transformation leadership (technology and operating model)

  • Underwriting/pricing/risk management domain expertise

  • Deep technology product lifecycle knowledge

  • Actuarial and/or advanced analytics experience

  • Executive communication and stakeholder alignment

  • Vendor and partner management

  • Data, analytics and AI enabled decisioning

EDUCATION

Required

  • Bachelor’s degree or relevant experience and/or education as determined by the company in lieu of bachelor's degree.


Preferred

  • Master Degree in MBA, Actuarial Science, Math, Statistics, Analytics, Technology


LICENSES or CERTIFICATIONS

Required

  • None


Preferred

  • None


Language (Other than English):

  • None

Travel Required:

  • 0% - 25%

PHYSICAL, MENTAL DEMANDS and WORKING CONDITIONS

Position Type

  • Office-Basedor RemotePosition

Physical work siterequired

  • Occasionally

Disclaimer: The job description has been designed toindicatethe general nature and essential duties and responsibilities of work performed by employees within this job title. It may notcontaina comprehensive inventory of all duties, responsibilities, and qualificationsrequired ofemployees to do this job.

Pay Range Minimum:

$169,500.00

Pay Range Maximum:

$286,700.00

Base pay is determined by a variety of factors including a candidates qualifications, experience, and expected contributions, as well as internal peer equity, market, and business considerations. The displayed salary range does not reflect any geographic differential Highmark may apply for certain locations based upon comparative markets.

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