
HR - People Experience Stefanini
- Temporary
- Contractor
| Location | Chicago, IL |
Transcarent is seeking a strategic, technically fluent, and highly collaborative Director, People Technology to lead our People Technology function.
This leader will own the operating model, roadmap, delivery, and performance of our People Technology ecosystem, ensuring our platforms, integrations, data, and workflows are stable, scalable, and aligned to business priorities. This role is accountable for turning People strategy and operational needs into well-run technology solutions that improve employee and manager experience, increase reliability, reduce manual work, and support the company as the function grows in scale and complexity.
This is not a traditional HRIS administration role. The Director, People Technology will lead the team that builds, runs, improves, and governs the People Technology portfolio, while partnering closely with the Architect on future-state design, integrations, data foundations, controls, and major decisions across the company in context of our people and knowledge.
The ideal candidate brings strong People Technology leadership with an AI background for reinventing work. Their approachesfollowa product mindset, demonstratedsound operational judgment, and the ability to lead through complexity, ambiguity, and change. This person knows how to create clarity, align teams around shared priorities, and ensure the function delivers consistency, partnership, and credibility.
What you will do
Lead the People Technology function
Own the day-to-day and strategic leadership of the People Technology function across platform operations, roadmap execution, governance, service delivery, release management, issue resolution, and continuous improvement.
Lead the transition from implementation mode to a durable, scalable operating model that can support business growth, evolving People priorities, and an expanding systems landscape with agentic business process coverage.
Establish clear team goals, roles, responsibilities, decision rights, operating rhythms, and performance expectations.
Build a culture of ownership, follow-through, quality, urgency, and strong cross-functional partnership.
Ensure the team can balance day-to-day support, enhancement delivery, production stability, and longer-term transformation work.
Own the People Technology roadmap and execution
Develop and maintain a clear People Technology roadmap aligned to business priorities, People strategy, employee and manager needs, compliance obligations, and platform capabilities.
Translate business needs into sequenced initiatives, measurable outcomes, and realistic delivery plans.
Build and run strong intake, prioritization, and governance processes for enhancements, defects, projects, and cross-functional requests.
Drive disciplined execution across configuration, integrations, testing, deployment, issue management, and adoption.
Ensure work moves from idea to design to production with clear ownership, practical tradeoffs, and strong stakeholder communication.
Establish transparent status reporting, risk management, and escalation practices so leaders have confidence in delivery.
Improve operational excellence, service reliability, and data quality
Ensure the People Technology environment is reliable, supportable, secure, and well governed.
Create and manage service levels, incident response expectations, release controls, production support practices, and operational metrics.
Improve data quality, workflow integrity, and transaction reliability across the People Technology ecosystem.
Identify and eliminate recurring issues, manual workarounds, unclear handoffs, and avoidable operational risk.
Partner with the People Systems Architect and technical partners to ensure operational realities inform design decisions and architectural priorities.
Establish practical monitoring and performance measures for system health, issue trends, adoption, service quality, and roadmap delivery.
Lead with a product and employee-experience mindset
Ai powered first; meet the people where they work, self-serve operations and coach/grow our culture at scale. Empower all the business to reinvent their operations and talent with the power of Ai.
Treat employees, managers, People teams, and business partners as customers whose needs should shape technology decisions.
Start with the business problem and user need, not only the requested solution.
Improve self-service, simplify processes, and increase usability across the People technology experience.
Balance short-term business needs with long-term platform health, maintainability, and scale.
Build feedback loops that turn stakeholder insight and production learnings into better product decisions.
Partner across the business
Partner closely with People leadership, Employee Experience, People Operations, Total Rewards, Talent Acquisition, Payroll, Finance, IT, Security, Legal, Data, and external vendors.
Translate complex technical issues into clear business implications, options, and recommendations.
Build trust with stakeholders through strong communication, dependable execution, and visible follow-through.
Ensure the right stakeholders are engaged early and that business readiness, change impacts, and operational handoffs are managed well.
Support People Centers of Excellence as they define policy, process, business rules, and employee experience requirements, while ensuring People Technology delivers the technical solution effectively.
Build the next phase of People Technology capability
Help shape a People Technology function that can support platform operations, integrations, data, automation, analytics, and emerging AI-enabled capabilities.
Partner on opportunities to automate repetitive work, improve reporting, strengthen controls, and enable more scalable service delivery.
Contribute to a practical roadmap for AI-enabled People operations, with appropriate attention to data quality, privacy, security, governance, and measurable value.
Build team capability in operational excellence, vendor management, release discipline, systems thinking, and technology-enabled process improvement.
What you bring
Leadership and operating discipline
Significant experience leading HRIS, People Technology, HR Technology, or related enterprise technology teams.
Experience leading managers, individual contributors, vendors, or blended delivery models in a fast-moving environment.
A track record of strengthening team performance, accountability, execution quality, and stakeholder trust.
Strong judgment, low ego, and a willingness to go deep when needed to unblock the work and raise the standard.
The ability to bring structure to ambiguity and create clarity when priorities, ownership, or decisions are not yet well defined.
People Technology and business fluency
Strong understanding of how People processes, systems, data, compliance, and employee experience connect.
Ability to translate business priorities into practical technology plans, operating practices, and delivery decisions.
Experience partnering with senior leaders and influencing across functions without relying only on formal authority.
Agentic coverage of the employee lifecycle, reimaging over augmentation.
Delivery and transformation experience
Experience leading major HRIS implementations, post-implementation stabilization, optimization, or transformation work.
Strong program and project leadership, including prioritization, dependency management, risk management, testing discipline, and change coordination.
Experience running technology work that spans multiple systems, stakeholders, and operational handoffs.
A track record of moving from strategy to execution and delivering against commitments.
Technical and product mindset
Technical fluency sufficient to work credibly with architects, engineers, system administrators, data partners, vendors, and security teams.
Strong understanding of integrations, workflows, data quality, controls, reporting, and production support in a People Technology environment.
Experience operating with a product mindset, including roadmap thinking, user-centered problem solving, prioritization, and continuous improvement.
Familiarity with automation, analytics, or AI-enabled capabilities in an enterprise setting.
Preferred qualifications
Bachelor's degree in Human Resources, Business, Information Technology, Computer Science, or a related field.
Advanced degree or relevant certifications are a plus.
Experience in healthcare, regulated environments, or organizations managing sensitive workforce data is a plus.
Experience supporting modern HR platforms and a connected ecosystem of downstream systems, integrations, and vendors is preferred.
Who we are
Transcarent is the One Place for Health and Care, bringing medical, pharmacy, and point solutions together with the WayFinding experience, the first and only generative AI-powered health and care platform for health consumers.
Our WayFinding experience, paired with transparent and consumer-driven pharmacy care, 2nd.MD expert medical opinions, and virtual primary care, works seamlessly with comprehensive Care Experiences - Cancer Care, Surgery Care, and Weight Health - to support people with all of their health needs, simple or serious. More than 1,700 employers and health plans rely on us to provide information, guidance, and care, empowering health consumers with more choice, an experience they love, access to higher-quality care, and lower costs for 21 million Members. For more information, visit transcarent.com, and follow us on LinkedIn.
At Transcarent, our values guide everything we do:
People First: We prioritize our Members, clients, and each other in every decision
Care: Every decision starts with improving health and care for our Members
Resilience: We push boundaries and take the uncharted path to change an industry
Results: We take ownership, solve with speed, and deliver for our people and each other
Humble and Human: We lead with humility, bring fun to tough moments, and go further together
Total Rewards
Individual compensation packages are based on a few different factors unique to each candidate, including primary work location and an evaluation of a candidate's skills, experience, market demands, and internal equity. Salary is just one component of Transcarent's total package. All regular employees are also eligible for the corporate bonus program or a sales incentive (target included in OTE) as well as stock options.
Our benefits and perks programs include, but are not limited to:
Competitive medical, dental, and vision coverage
Competitive 401(k) Plan with a generous company match
Flexible Time Off/Paid Time Off, 13 paid holidays
Protection Plans including Life Insurance, Disability Insurance, and Supplemental Insurance
Mental Health and Wellness benefits
Transcarent is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. If you are a person with a disability and require assistance during the application process, please don't hesitate to reach out!
Research shows that candidates from underrepresented backgrounds often don't apply unless they meet 100% of the job criteria. While we have worked to consolidate the minimum qualifications for each role, we aren't looking for someone who checks each box on a page; we're looking for active learners and people who care about disrupting the current health and care with their unique experiences.

