Lead Director, Software Product Management

CVS Health is a healthcare organization focused on creating a more connected and compassionate health experience. The Lead Director, Software Product Management leads strategy, roadmap, adoption, and lifecycle management for the Security Automation portfolio while building and developing a product management team. The role partners with engineering and senior stakeholders to drive discovery, outcome measurement, financial planning, and product management practice maturity.

Responsibilities:

• Owns product strategy, vision, and the multi-year roadmap for the Security Automation portfolio in partnership with the Lead Director, Security Automation; frames the problems worth solving, sequences investment against enterprise security priorities, and maintains a defensible, communicable position on why the portfolio is working on what it is working on and what it has deliberately chosen not to do
• Leads, builds, and develops the product management team, treating the coaching and development of product managers as the core of the job rather than personally managing products; hires and levels PMs, sets the standard for product craft, runs a structured development approach, and leads by context rather than by control
• Owns product discovery for the portfolio including direct, continuous contact with the security practitioners and CVS Health colleagues whose work the portfolio is meant to change; workflow and pain-point analysis, opportunity sizing, assumption testing before build, and validation that a proposed automation solves a problem the users actually have
• Owns adoption and the full product lifecycle for everything the portfolio ships including internal launch and go-to-market, enablement, documentation and training, onboarding of new user groups, support and feedback channels, iteration based on real usage, and the decision to sunset or replace solutions that are not earning their keep
• Defines and instruments the outcome measures for each product and for the portfolio as a whole including adoption and active-usage measures, manual-effort and cycle-time reduction, support deflection, and risk-reduction proxies; establishes baselines before delivery, reports honestly against them afterward, and treats shipped features as inputs rather than results
• Owns requirements definition and the delivery partnership with engineering including problem statements, user stories and acceptance criteria, backlog health, release planning, scope and tradeoff decisions during delivery, and clear division of decision rights between product and engineering
• Partners on build-versus-buy and commercial evaluation, bringing market scanning, competitive and vendor landscape analysis, requirements definition for proofs-of-concept, and total-cost-of-ownership and licensing analysis to decisions about whether a capability should be built, bought, or assembled on an existing enterprise platform
• Serves as the primary product-facing voice to stakeholders and senior leadership including security function owners, Technology and Digital partners, and executive sponsors; communicates roadmap, tradeoffs, progress, and outcomes in language appropriate to each audience and secures the sponsorship the portfolio depends on
• Owns the business case and financial framing for portfolio investments including benefit quantification, ROI and payback analysis, license and vendor cost modeling, and the value narrative used to defend and grow investment in the function
• Establishes and matures the product management practice for the function including intake and prioritization mechanisms, discovery and requirements standards, roadmap and release communication cadence, product documentation standards, and the tooling that supports them

Requirements:

• 12+ years of experience in technology roles, including 8+ years in software product management
• 4+ years leading product managers, including hiring, coaching, performance management, and career development — with demonstrated understanding that leading PMs is a different job from managing products personally
• candidates from internal-platform or enterprise-IT-only backgrounds should be able to demonstrate equivalent product rigor
• Demonstrated ownership of product strategy and multi-year roadmaps for a software product or portfolio, including the ability to articulate what was deliberately not built and why
• Strong product discovery practice: direct user research and workflow analysis, opportunity sizing, assumption and risk testing before committing to build, and evidence-based decision making rather than requirements collection
• Demonstrated ability to define, instrument, and report on outcome measures — adoption, active usage, effort and cycle-time reduction, support deflection, retention of usage over time — including establishing baselines before delivery
• Track record of driving adoption of software products, with specific, quantified examples including at least one case where adoption stalled and what the candidate changed in response
• Demonstrated prioritization judgment under real constraint, including examples of telling significant stakeholders no and managing the relationship afterward
• Experience owning requirements definition and the delivery partnership with engineering: problem statements, user stories and acceptance criteria, backlog health, release planning, and in-flight scope and tradeoff decisions
• Technical fluency sufficient to earn the trust of engineers and to participate credibly in architecture, integration, and feasibility discussions — including comfort with APIs, data models, and software delivery practice
• Experience with build-versus-buy analysis and commercial software evaluation, including vendor and market assessment and total-cost-of-ownership reasoning
• Demonstrated ability to influence peers, senior stakeholders, and executives without direct authority, and to build genuine co-ownership with partner teams rather than transactional requirements relationships
• Financial acumen: business case construction, benefit quantification, ROI and payback analysis, and budget and license cost management
• Strong written communication — product briefs, strategy narratives, and roadmap communication that hold up without a presenter — and strong verbal communication across engineer-to-executive audiences
• Experience operating in agile delivery models and with modern product and delivery tooling (e.g., Jira, product analytics, roadmap and discovery tools)
• Bachelor's Degree (technical or business: CS, engineering, or related preferred) or equivalent work experience
• Product management experience gained in a commercial software or SaaS organization
• Experience as a product manager or product leader for developer-facing, platform, or internal-facing software products, where users must be won rather than acquired
• Experience in a security, risk, compliance, or IT operations product domain, or demonstrated ability to learn a technical operational domain quickly and credibly
• Experience with workflow automation, integration, or data platform products, including products whose value is measured in effort avoided rather than revenue generated
• Experience with AI-enabled or agentic product management: defining human-in-the-loop experiences, evaluating model accuracy and failure modes, and setting user expectations for probabilistic systems
• Experience with product-led adoption motions — self-service onboarding, in-product guidance, documentation as a product surface, and community or champion programs
• Experience partnering with a peer engineering leader in a formal dual-leadership model, with clear and healthy division of decision rights
• Experience managing a portfolio that mixes custom-built software, third-party commercial products, and platform-based configuration
• Experience sunsetting or consolidating products, including managing the stakeholder consequences
• Experience in a highly regulated industry, ideally healthcare, with familiarity with HIPAA, PCI DSS, HITRUST CSF, SOX, or audit and evidence requirements
• Experience establishing or maturing a product management practice where none previously existed
• Advanced degree or MBA; recognized product management or agile credentials
• Master's Degree or MBA preferred