by Terrance Ellis | Feb 3, 2026 | Uncategorized
If you’re the rare person who can speak “security tooling” and “exec dashboard” without sounding like two different humans, this role is built for you. It’s DevSecOps, but the emphasis is enterprise operations leadership: workforce planning, KPIs, adoption metrics, and making security programs actually run like a business.
About CVS Health
CVS Health is focused on building a more connected, convenient, and compassionate health experience, with large-scale enterprise tech teams supporting millions of members and patients.
Schedule
- Full-time
- Remote
- Application window expected to close: 02/04/2026
What You’ll Do
- Lead security and engineering operations across the enterprise, aligning delivery with business and security goals
- Own workforce management: headcount tracking, capacity planning, and contingent labor oversight
- Optimize productivity and workflows using data-driven decision-making
- Build analytics and insights around tool adoption, remediation velocity, dev experience friction, and resourcing needs
- Translate complex datasets into executive-ready insights, dashboards, and reporting
- Create clear narrative materials and presentations for leadership and engineering stakeholders
- Develop and track KPIs and operational metrics to support strategy and business cases
- Manage and mentor staff (permanent and contingent) and partner closely with engineering, platform, and business teams
- Provide hands-on technical support when needed to enable secure development practices and security tooling adoption
- Identify operational/technical/workforce risks and ensure governance and compliance expectations are met
What You Need
- 7+ years in technology operations, strategy, or engineering (Product, Cybersecurity, or Development context)
- 3+ years direct SDLC security experience (SAST, DAST, MAST, scanning, automation, containers, etc.)
- 3+ years in analytics + executive reporting + strategic storytelling
- 2+ years people management, contingent workforce oversight, and headcount tracking
- Bachelor’s degree or equivalent experience (HS diploma + 4 years relevant experience)
Preferred Qualifications
- Proven work improving developer experience via tooling, automation, data, and reporting
- Track record leading enterprise-scale operational initiatives with measurable improvements
- Strong executive presentation and stakeholder management skills
Benefits
- Pay range: $106,605–$284,280/year (actual offer varies by experience, location, etc.)
- Bonus/short-term incentive eligibility + equity award target
- Medical plan options, 401(k) with match, employee stock purchase plan
- No-cost wellness programs, counseling, and financial coaching
- PTO, flexible schedules, family leave, tuition assistance, and more (eligibility varies)
Real talk, this is not a “pure engineer” DevSecOps job. It’s closer to Ops/Strategy leader who can still go technical when needed. If your background is heavy on dashboards, KPIs, program ops, and you’ve lived inside SDLC security tooling, you’re in the right zip code. If you’re mostly pipeline-building and hands-on engineering with little exec comms, this could feel like death by PowerPoint.
Happy Hunting,
~Two Chicks…
by Terrance Ellis | Feb 3, 2026 | Uncategorized
You’ll help modernize MinuteClinic’s tech stack, building scalable services that support both patient-facing experiences and clinical workflows. This role is for a strong senior engineer who can own problems end-to-end, ship reliable systems in the cloud, and work in a team that’s actively re-platforming and leaning into AI-assisted development.
About CVS Health
CVS Health is working to build a more connected, convenient, and compassionate health experience. This engineering role supports MinuteClinic platforms that serve millions of patients and clinical staff.
Schedule
- Full-time (40 hours/week)
- Remote
- Application window expected to close: 03/23/2026
What You’ll Do
- Build and ship scalable, cloud-based services that improve patient experience and clinical workflows
- Partner with product managers, architects, and engineers to design and implement new platform capabilities
- Take ownership of ambiguous problems and drive solutions from design to deployment
- Contribute to re-platforming efforts across the stack and adopt modern engineering practices
- Implement CI/CD, automated testing, and observability practices to keep systems stable and maintainable
- Identify opportunities for improvement and proactively address technical risks early
- Model clean, testable, maintainable code and strong engineering habits across the team
What You Need
- 5+ years of software development experience
- Strong programming skills in Java, Kotlin, Python, C#, and/or TypeScript
- Solid fundamentals: system design, distributed systems, and API development
- Hands-on experience building cloud applications (Azure, AWS, or GCP)
- Experience with CI/CD pipelines, automated testing, and observability
- Strong collaboration in an Agile environment
- Ability to own features end-to-end and deliver high-impact solutions
Preferred Qualifications
- Experience building healthcare, clinical, or other regulated enterprise systems
- Microservices, event-driven architecture, and/or cloud-native design experience
- Familiarity with healthcare standards like FHIR or HL7
- Experience mentoring or guiding junior engineers, or contributing to architecture discussions
- Exposure to modern front-end frameworks (React/Angular) or mobile development
- Experience using AI-assisted development and automation tools to improve delivery speed and quality
Benefits
- Pay range: $83,430–$222,480/year (varies by experience, location, and other factors)
- Eligible for bonus/commission/short-term incentives (in addition to base pay)
- Medical plan options, 401(k) with company match, employee stock purchase plan
- No-cost wellness programs + confidential counseling + financial coaching
- PTO, flexible schedules, family leave, tuition assistance, and more (eligibility varies)
Quick gut-check: this role screams “platform rebuild + distributed systems + ownership.” If someone’s resume is mostly front-end UI work or light scripting without real service ownership, it’s probably a reach. If they’ve shipped APIs, lived through production incidents, and can talk tradeoffs, they’re in the pocket.
Happy Hunting,
~Two Chicks…
by Terrance Ellis | Feb 3, 2026 | Uncategorized
You’re leading a small squad of experienced designers, but you’re not hiding behind a calendar. This is a player-coach role: you manage people, you coach hard, and you still ship high-impact, accessible UX across web and mobile in a healthcare/pharmacy context.
About CVS Health
CVS Health is focused on building a more connected, convenient, and compassionate health experience. This UX leadership role sits in Innovation & Technology and helps shape the digital products people rely on to navigate care.
Schedule
- Full-time
- Remote
- Application window expected to close: 02/27/2026
What You’ll Do
- Coach and develop experience designers and content strategists through frequent, hands-on feedback and growth plans
- Balance people leadership with individual contributor ownership of key design initiatives
- Build strong partnerships with Product, Engineering, and Research; communicate status, risks, and needs early
- Negotiate priorities and timelines while balancing user needs with business and technical constraints
- Integrate user research, analytics, and accessibility best practices into daily design decisions
- Run and participate in design reviews, giving actionable feedback on craft, consistency, and accessibility
- Assign work based on strengths and skill-building while keeping delivery on track
- Address bias/exclusion and ensure team processes and meetings are inclusive and accessible
- Manage workload and resourcing so the team ships quality work on schedule
- Advocate for user-centered, human-first design thinking across roadmaps and execution
What You Need
- 7+ years professional experience
- 5+ years leading design teams (people leadership + technical/design leadership)
- 5+ years hands-on design for both mobile and web (retail/pharmacy domain preferred)
- 3+ years advanced proficiency with tools like Figma and accessibility standards (WCAG), plus using research to inform delivery
- Bachelor’s degree or equivalent experience (HS diploma + 4 years relevant experience)
Preferred Qualifications
- Strong coaching track record with accessible, user-centered healthcare work (portfolio helps)
- Strong facilitation, project management, and cross-functional collaboration skills
- Experience leading through change while protecting team health and delivery
- Strong storytelling, feedback, and stakeholder communication
- Agile experience
Benefits
- Pay range: $106,605–$284,280/year (varies by experience, location, and other factors)
- Eligible for bonus/commission/short-term incentives (in addition to base pay)
- Includes an equity award program target
- Medical plan options, 401(k) with company match, employee stock purchase plan
- No-cost wellness programs + confidential counseling + financial coaching
- PTO, flexible schedules, family leave, tuition assistance, and more (eligibility varies)
Here’s the honest filter: this job is heavier on coaching + accessibility leadership than pure “big-idea design.” If someone loves crafting, but hates giving feedback, managing feelings, and pushing standards through cross-functional friction, they’ll burn out fast. If they love developing talent and raising the bar while still designing, it’s a strong seat.
Happy Hunting,
~Two Chicks…
by Terrance Ellis | Feb 3, 2026 | Uncategorized
This is a true senior technical leadership role for someone who can steer architecture, raise engineering standards, and help modernize a massive clinical platform used by millions. You’ll be central to MinuteClinic’s multi-year re-platforming push, with a strong emphasis on cloud modernization and AI-enabled development.
About CVS Health / MinuteClinic
CVS Health is reimagining healthcare with connected, convenient, and compassionate experiences. MinuteClinic supports clinical and patient-facing platforms at huge scale, and this role helps shape what that next generation looks like.
Schedule
- Full-time
- Remote
- Application window expected to close: 03/23/2026
What You’ll Do
- Lead architecture and engineering decisions for large-scale clinical and patient-facing platforms
- Drive a multi-year re-platforming initiative: cloud modernization, delivery acceleration, and long-term system health
- Design and guide development of complex distributed systems
- Establish engineering standards and best practices (API design, security, scalability, observability, test automation, operational excellence)
- Partner with Product, Architecture, and engineering teams to influence roadmaps and execution
- Identify strategic opportunities, convert vision into actionable solutions, and deliver through ambiguity
- Mentor engineers and elevate overall technical maturity
- Evaluate and integrate emerging tech, including AI/ML tools, LLMs, and automation, into engineering workflows
What You Need
- 10+ years software engineering experience, including designing/building large-scale distributed cloud-native systems
- Deep expertise in modern languages (Java, Kotlin, Python, C#, TypeScript)
- Strong cloud experience (Azure, AWS, or GCP)
- Demonstrated ability to set technical strategy and lead complex initiatives end-to-end
- Strong ownership and bias for action, able to break down complex problems and deliver outcomes
- Strong cross-functional communication and stakeholder influence
- Proven mentoring/technical leadership experience
Preferred Qualifications
- Healthcare/regulated industry experience
- Familiarity with interoperability standards (FHIR, HL7)
- Experience modernizing legacy systems into cloud architectures
- Microservices, event-driven architectures, and/or domain-driven design experience
- Experience participating in enterprise architecture councils or technical working groups
- Ability to influence product strategy through technical insight
Education
- Bachelor’s degree in Computer Science/Software Engineering (or equivalent experience)
- Master’s degree preferred, not required
Benefits
- Pay range: $144,200–$288,400/year (based on experience, location, and other factors)
- Eligible for bonus/commission/short-term incentives (in addition to base pay)
- Includes an award target in CVS Health’s equity award program
- Medical plan options, 401(k) with company match, employee stock purchase plan
- No-cost wellness programs + confidential counseling + financial coaching
- PTO, flexible schedules, family leave, tuition assistance, and more (eligibility varies)
One real note: this isn’t a “great coder” job. It’s a “build the freeway system while traffic is still moving” job. If you don’t enjoy influencing, aligning people, and making tough architectural calls with imperfect info, it’ll be miserable. If you do, it’s a strong lane.
Happy Hunting,
~Two Chicks…
by Terrance Ellis | Feb 3, 2026 | Uncategorized
This is a senior, high-impact engineering seat for someone who can lead big technical initiatives and keep systems reliable at scale. You’ll build and operate distributed, enterprise-grade services that directly support value-based care and the “home as the health hub” model.
About Signify Health (CVS Health)
Signify Health, part of CVS Health, is transforming the home into a healthcare hub through data, technology, and people. Their unified platform for value-based care helps improve outcomes and reduce costs by coordinating care and linking payments to patient results.
Schedule
- Full-time
- Remote role
- Application window expected to close: 02/05/2026
What You’ll Do
- Lead technical initiatives solving complex, enterprise-wide problems with a focus on maintainability, performance, and scalability
- Design, build, and maintain distributed, business-critical systems using modern engineering practices
- Deliver value through iterative, customer-focused releases and continuous improvement
- Drive long-term platform improvements with an emphasis on simplicity and maintainability
- Collaborate cross-functionally to meet needs across teams and the broader organization
- Research, propose, and adopt leading-edge technologies when they create real impact
- Mentor others and help raise the technical bar through learning and coaching
What You Need
- 7+ years of software development experience
- Strong fundamentals: data structures, algorithms, concurrency, and design patterns
- Polyglot development experience (more than one of: C++, C#, Java, Go, JavaScript/TypeScript, Python, or similar)
- Full-stack experience shipping and operating large-scale systems
- Strong SQL skills and experience with RDBMS (SQL Server, PostgreSQL, etc.)
- Proven distributed systems design/implementation/operations experience at scale
- Cloud experience (Azure, AWS, or GCP)
- Clear, effective communication skills
Benefits
- Pay range: $106,605–$284,280/year (based on experience, location, and other factors)
- Eligible for bonus/commission/short-term incentives (in addition to base pay)
- Includes an award target in CVS Health’s equity award program
- Medical plan options, 401(k) with company match, and employee stock purchase plan
- No-cost wellness programs plus confidential counseling and financial coaching
- Paid time off, flexible work schedules, family leave, tuition assistance, and more (eligibility varies)
If you’ve been wanting a role where you’re trusted to lead, not just code, and you’ve got real distributed-systems chops, this is the lane.
Happy Hunting,
~Two Chicks…
by Terrance Ellis | Feb 3, 2026 | Uncategorized
This is for the builder who can take messy business requirements and turn them into clean, scalable data pipelines that leadership can trust. You’ll design and architect datasets for financial and analytic workloads, improve performance and cost, and mentor others along the way.
About CVS Health
CVS Health is building a more connected, convenient, and compassionate health experience for individuals and communities. Their data and analytics teams power reporting, insights, and decision-making at scale across healthcare and enterprise operations.
Schedule
- Full-time (40 hours/week)
- Remote role
- Collaborative environment with data engineers, analysts, data scientists, and product owners
What You’ll Do
- Design and build ETL/ELT pipelines to ingest, process, and transform large datasets from multiple sources
- Optimize performance and reduce costs through tuning, partitioning, clustering, and best-practice engineering
- Establish and enforce data quality standards, governance frameworks, and security policies
- Develop and optimize data models and schemas for analytics, reporting, and machine learning needs
- Integrate datasets with BI tools and ML workflows in partnership with analysts and data scientists
- Document pipelines, workflows, and processes and share best practices across the team
- Mentor junior data engineers and help elevate overall engineering standards
- Design and architect data infrastructure to support analytical workloads
What You Need
- 5+ years of applicable work experience
- Strong Python experience building ETL pipelines
- Strong SQL skills, including complex query development
- Familiarity with PySpark, dbt, or similar frameworks
- Experience deploying data pipelines in a cloud environment (Azure, AWS, or GCP)
- Understanding of data warehousing concepts, dimensional modeling, and building data marts
- Strong communication skills and ability to partner across technical and business stakeholders
- College degree or certification in a related field
Benefits
- Pay range: $83,430–$222,480/year (based on experience, location, and other factors)
- Eligible for a CVS Health bonus, commission, or short-term incentive program (in addition to base pay)
- Medical plan options, 401(k) with company match, and employee stock purchase plan
- No-cost wellness programs plus confidential counseling and financial coaching
- Paid time off, flexible work schedules, family leave, tuition assistance, and more (eligibility varies)
This posting is expected to close 02/10/2026, so don’t wait if you want it.
If you’re strong in pipelines, modeling, and cloud delivery, and you can lead by example without being precious about it, this is a great lane.
Happy Hunting,
~Two Chicks…
