by Terrance Ellis | Jan 26, 2026 | Uncategorized
If you’re the kind of person who likes building clean, repeatable server environments and keeping them healthy under real-world pressure, this role is right in your lane. You’ll own Windows-heavy infrastructure work across on-prem and Azure, with a strong mix of provisioning, patching, monitoring, backup, security hardening, and Tier III support.
About CVS Health
CVS Health is a leading health solutions company working to make care more connected, convenient, and compassionate. This role supports infrastructure operations and projects that keep critical systems stable, secure, and scalable.
Schedule
- Full-time, 40 hours per week
- Remote
- Application window expected to close: 01/27/2026
What You’ll Do
- Engineer and provision infrastructure solutions for project and operational needs
- Install new or rebuild existing servers (on-prem and cloud), including:
- Hardware and peripherals
- Services and system settings
- Directories, storage, and standards-based configurations
- Install and configure systems supporting:
- EMR and cloud infrastructure applications
- Asset management applications
- Develop and maintain installation and configuration procedures
- Contribute to and maintain system standards
- Research and recommend innovative, automated approaches to system administration
- Perform daily monitoring to verify integrity and availability of:
- Hardware
- Server resources
- Systems and key processes
- Logs, backups, and scheduled jobs
- Perform security monitoring to identify possible intrusions
- Perform vulnerability remediation for cloud and on-prem server infrastructure
- Run daily backup operations using Azure Backup
- Create, update, and delete user accounts as requested
- Provide Tier III support, including investigation and troubleshooting
- Repair and recover from hardware or software failures and communicate impacts
- Apply OS patches and upgrades using Azure Patch Management
- Upgrade and configure software supporting EMR, cloud infrastructure, or asset management needs
- Produce performance reporting for capacity planning
- Perform performance tuning, hardware upgrades, and resource optimization
- Configure CPU, memory, and disk partitions as required
- Maintain data center environmental and monitoring equipment
- Handle other duties as assigned
What You Need
- 3+ years of Windows Server administration experience
- 3+ years of DNS and Active Directory management experience
- 2+ years of Microsoft Azure experience deploying resources such as:
- Virtual machines
- Storage accounts
- 2+ years of Microsoft Entra ID experience
- 2+ years of certificate management experience
- Associate’s degree required (Bachelor’s preferred)
Preferred
- Linux server administration experience
- Nerdio experience
- DigiCert experience
- GoDaddy experience
- RMM package deployment experience
- Experience across Windows Server versions: 2016, 2019, 2022
- Azure Virtual Desktop host pool and application configuration experience
- IIS experience
- SQL experience (2016, 2019)
- Experience with tools/tech such as:
- VMware vCenter 6.0+
- VMware vSAN 6.0
- Citrix ADC
- CrowdStrike
- Tenable
- Sumo Logic
- MCSE or MCSA (preferred)
- Strong PC skills (Microsoft Office, Google Docs)
- Ability to evaluate emerging tech and recommend business-friendly solutions
- Knowledge of data center environments, hosting services, networks, and SaaS
- Ability to document server physical and logical topology
Benefits
- Pay range: $64,890–$173,040 (actual offer depends on experience, education, geography, and other factors)
- Eligible for CVS Health bonus, commission, or short-term incentive program in addition to base pay
- Affordable medical plan options
- 401(k) with matching company contributions
- Employee stock purchase plan
- No-cost programs, including:
- Wellness screenings
- Tobacco cessation
- Weight management
- Confidential counseling
- Financial coaching
- Paid time off
- Flexible work schedules (where eligible)
- Family leave and dependent care resources
- Colleague assistance programs
- Tuition assistance and more (depending on eligibility)
One honest note: this is a “keep the lights on and make it better” infrastructure job. If your resume leans more help desk than server admin, you’ll feel exposed fast. If you’ve actually owned patching, backups, AD/DNS, certs, and Azure VM deployments end-to-end, you’ll be solid.
Happy Hunting,
~Two Chicks…
by Terrance Ellis | Jan 26, 2026 | Uncategorized
This role is for someone who can run security operations like a business and still speak fluent engineering. You’ll drive enterprise-wide security and engineering ops, build the metrics and narratives leadership needs, and remove friction from secure development practices through smarter tooling, process, and analytics.
About CVS Health
CVS Health is a leading health solutions company focused on building more connected, convenient, and compassionate health experiences. This role sits in Innovation & Technology within Enterprise Information Security and helps align secure development operations with business outcomes at scale.
Schedule
- Full-time, 40 hours per week
- Remote
- Application window expected to close: 01/28/2026
What You’ll Do
- Lead enterprise security and engineering operations, aligning people, processes, and priorities with business and security objectives
- Manage workforce operations, including:
- Headcount tracking
- Capacity planning
- Contingent labor oversight
- Improve productivity and execution by:
- Streamlining workflows
- Pivoting operational strategy when needed
- Driving continuous improvement using data
- Deliver analytics-driven insights on:
- Tool adoption
- Remediation velocity
- Developer experience friction points
- Resourcing needs and investment priorities
- Turn complex datasets into executive-ready insights, dashboards, and reporting that show:
- Risk posture
- Program effectiveness
- Operational performance
- Build crisp strategic communications and presentations that translate technical complexity into leadership-ready narratives
- Manage, mentor, and develop a mix of permanent and contingent staff
- Partner closely with engineering, platform, and business stakeholders to drive adoption and operational alignment
- Provide technical support for operations by:
- Enabling adoption of security tooling
- Solving complex engineering challenges
- Advising on automation, process improvements, and secure development standards
- Identify and address operational and technical risks, ensuring governance and compliance expectations are met
What You Need
- 7+ years of experience in technology operations, strategy, and/or engineering in a Product, Cybersecurity, or Development context
- 3+ years of direct SDLC security experience, including areas such as:
- SAST
- DAST
- MAST
- Scanning
- Automation
- Containers
- 3+ years of strong analytics and communication work, including:
- Executive reporting
- Strategic storytelling
- 2+ years of people management experience, including:
- Managing teams
- Contingent workforce oversight
- Headcount tracking
- Bachelor’s degree or equivalent experience (High School Diploma + 4 years relevant experience)
Preferred
- Proven experience improving developer experience through:
- Tooling implementation
- Automation
- Data and reporting
- Proven ability to lead enterprise-scale operational initiatives with measurable results
- Strong executive presence, presentation skills, and stakeholder management
Benefits
- Pay range: $106,605–$284,280 (actual offer depends on experience, education, and geography)
- Eligible for bonus, commission, or short-term incentive program in addition to base pay
- Equity award program participation with an award target included
- Affordable medical plan options
- 401(k) with matching company contributions
- Employee stock purchase plan
- No-cost wellness and support programs, including:
- Wellness screenings
- Tobacco cessation
- Weight management
- Confidential counseling
- Financial coaching
- Paid time off
- Flexible work schedules (where eligible)
- Family leave and dependent care resources
- Tuition assistance (where eligible)
- Additional benefits may apply depending on eligibility
Real talk: this is not a “hands-only DevSecOps” job. It’s an ops leader role that also expects you to be technically credible. If your superpower is building pipelines and scanners but you hate headcount, KPIs, and exec storytelling, this will grind you down. If you like owning the whole system (people + process + metrics + security outcomes), this is a power seat.
Happy Hunting,
~Two Chicks…
by Terrance Ellis | Jan 26, 2026 | Uncategorized
This is a hands-on data engineering role for someone early-to-mid in their journey who can build clean cloud pipelines and make analytics usable. You’ll help create datasets for analytics and data science, working alongside Data Engineers and Sr. Data Engineers to design, implement, and test pipelines that actually hold up in the real world.
About CVS Health
CVS Health is one of the nation’s largest health solutions companies, focused on building a more connected, convenient, and compassionate health experience. This role sits in Innovation and Technology (Data & Analytics) and supports enterprise analytics and data science workloads.
Schedule
- Full-time, 40 hours per week
- Remote
- Application window expected to close: 02/06/2026
What You’ll Do
- Design and build ETL/ELT pipelines to ingest, process, and transform datasets from multiple sources
- Apply performance best practices to improve query speed and efficiency, including:
- Performance tuning
- Partitioning
- Clustering
- Follow data quality standards and support:
- Data governance frameworks
- Security policies for data storage and access
- Develop and optimize data models and schemas for:
- Analytics and reporting
- Machine learning requirements
- Collaborate with data scientists and analysts to integrate data solutions with:
- BI tools
- Machine learning models
- Create clear documentation for pipelines, workflows, and processes
- Work with other Data Engineers and Sr. Data Engineers on designing, implementing, and testing pipelines
What You Need
- 2+ years of applicable work experience
- Python proficiency focused on ETL pipelines
- Strong SQL skills, including complex queries
- Experience deploying data pipelines in a cloud environment, including:
- Strong communication skills and ability to collaborate with data scientists and analysts
- College degree or certification in a related field
Preferred
- Healthcare data experience, especially Epic
- BigQuery experience
- Knowledge of cloud data governance best practices
- Experience working with machine learning processes
Benefits
- Pay range: $64,890–$173,040 (actual offer depends on experience, education, and geography)
- Eligible for bonus, commission, or short-term incentive program in addition to base pay
- Affordable medical plan options
- 401(k) with matching company contributions
- Employee stock purchase plan
- No-cost wellness and support programs, including:
- Wellness screenings
- Tobacco cessation
- Weight management
- Confidential counseling
- Financial coaching
- Paid time off
- Flexible work schedules (where eligible)
- Family leave and dependent care resources
- Tuition assistance (where eligible)
- Additional benefits may apply depending on eligibility
Quick positioning: this one is basically the “build and ship pipelines” role, while the Sr. Data Engineer version expects more ownership, deeper architecture decisions, and heavier mentoring. If someone’s got 2–4 years and wants to level up fast, this is a clean target.
Happy Hunting,
~Two Chicks…
by Terrance Ellis | Jan 26, 2026 | Uncategorized
If you like building the plumbing that makes analytics possible, this is that role. You’ll design and ship cloud-based ETL/ELT pipelines, keep queries fast and costs sane, and turn business needs into reliable datasets for finance and analytics.
About CVS Health
CVS Health is one of the nation’s largest health solutions companies, serving millions through local and digital care channels. This role sits in Innovation and Technology (Data & Analytics) and supports large-scale analytic and financial data workloads.
Schedule
- Full-time, 40 hours per week
- Remote
- Application window expected to close: 01/27/2026
What You’ll Do
- Design and build ETL/ELT pipelines to ingest, process, and transform large datasets from multiple sources
- Optimize performance and cost using best practices such as:
- Performance tuning
- Partitioning
- Clustering
- Establish and enforce standards for:
- Data quality
- Data governance
- Security policies for data storage and access
- Develop and optimize data models and schemas for:
- Analytics and reporting
- Machine learning requirements
- Collaborate with data scientists and analysts to integrate data solutions with:
- BI tools
- Machine learning models
- Create documentation for pipelines, workflows, and processes
- Share best practices and mentor junior data engineers
- Design and architect data infrastructure for analytical workloads
What You Need
- 5+ years of applicable data engineering experience
- Strong Python skills focused on ETL pipelines
- Strong SQL skills, including complex query development
- Familiarity with at least one of the following:
- PySpark
- dbt
- Similar data transformation frameworks
- Experience deploying pipelines in a cloud environment, such as:
- Strong understanding of:
- Data warehousing concepts
- Dimensional modeling
- Building data marts
- Strong communication and collaboration skills across data, analytics, and product teams
- College degree or certification in a related field
Preferred
- Cloud data governance best practices
- BigQuery data design experience
- Experience with the Epic data model
- Experience with healthcare data, including:
Benefits
- Pay range: $83,430–$222,480 (actual offer depends on experience, education, and geography)
- Eligible for bonus, commission, or short-term incentive program in addition to base pay
- Affordable medical plan options
- 401(k) with matching company contributions
- Employee stock purchase plan
- No-cost wellness and support programs, including:
- Wellness screenings
- Tobacco cessation
- Weight management
- Confidential counseling
- Financial coaching
- Paid time off
- Flexible work schedules (where eligible)
- Family leave and dependent care resources
- Tuition assistance (where eligible)
- Additional benefits may apply depending on eligibility
Quick gut-check: if your sweet spot is “I build pipelines and datasets” more than “I run the platform,” this is the better fit compared to the Platform Engineer role. Platform is governance, uptime, cost controls, and firefighting. This one is building and optimizing the data products themselves.
Happy Hunting,
~Two Chicks…
by Terrance Ellis | Jan 26, 2026 | Uncategorized
This is a hands-on platform engineering role for someone who likes owning the “health of the machine.” You’ll keep Azure Databricks stable, secure, and cost-efficient, while helping teams ship scalable data products and migrating legacy platforms into a clean cloud future.
About CVS Health
CVS Health is one of the nation’s largest health solutions companies, focused on building a more connected and compassionate health experience. This role sits in Innovation and Technology (Data & Analytics) and supports enterprise-grade data platforms that power reporting, operations, and decision-making.
Schedule
- Full-time, 40 hours per week
- Remote
- Application window expected to close: 02/04/2026
What You’ll Do
- Maintain day-to-day operational health of the Azure Databricks platform, including:
- Monitoring system performance
- Managing upgrades
- Ensuring stability and availability
- Support current platforms during migration, including:
- On-prem MS SQL Server
- Palantir Foundry
- Optimize performance and cost by:
- Fine-tuning jobs
- Optimizing cluster configurations
- Identifying cost-saving opportunities
- Build and maintain KPI dashboards and reporting across areas like:
- Reliability and stability
- Performance and scalability
- Innovation and enablement
- Cost and utilization monitoring
- Data quality and governance
- Strengthen security and governance within Databricks, with emphasis on Unity Catalog for:
- Access controls
- Lineage
- Compliance
- Provide advanced troubleshooting for escalations, including:
- Root cause analysis (RCA)
- Platform-level fixes to prevent repeat incidents
- Maintain and enhance automation, scripts, and CI/CD pipelines for platform deployment and admin efficiency
- Contribute to platform roadmap and enhancements by partnering with internal data teams on:
- Best practices
- New features and services
- Improved user experience
What You Need
- 5+ years of hands-on experience in platform engineering, data engineering, or DevOps with cloud data platforms
- Strong Azure Databricks experience operating and managing production environments
- Experience with Databricks core components, including:
- Delta Lake
- Unity Catalog
- Apache Spark
- Solid Azure ecosystem knowledge, including:
- Azure Data Lake Storage (ADLS)
- Azure Active Directory (AAD)
- Cloud networking concepts
- Strong understanding of distributed systems and troubleshooting in distributed environments
- Strong programming and scripting skills, including:
- Terraform
- Python
- Apache Spark / PySpark
- SQL
- Shell scripting
- Proven Infrastructure as Code and CI/CD experience for platform and data deployments
- Strong operational mindset focused on uptime, performance, and stability
- Strong communication, documentation, and presentation skills with ability to influence technical and business stakeholders
- Bachelor’s or Master’s degree in Computer Science, Engineering, or related field
- Certifications are a plus, including:
- Microsoft Certified: Azure Solutions Architect Expert
- Databricks Certified Data Engineer Professional
- Databricks Certified Platform Administrator
Benefits
- Pay range: $83,430–$222,480 (actual offer depends on experience, education, and geography)
- Bonus, commission, or short-term incentive eligibility may apply
- Affordable medical plan options
- 401(k) with matching company contributions
- Employee stock purchase plan
- No-cost wellness and support programs, including:
- Wellness screenings
- Tobacco cessation
- Weight management
- Confidential counseling
- Financial coaching
- Paid time off
- Flexible work schedules (where eligible)
- Family leave and dependent care resources
- Tuition assistance (where eligible)
- Additional benefits may apply depending on eligibility
This is not a “build a pipeline and bounce” data engineering gig. It’s platform ownership: governance, performance, cost, incident response, and migration support. If you’ve got Databricks scars and you like being the person everyone calls when the cluster’s on fire, this is your seat.
Happy Hunting,
~Two Chicks…
by Terrance Ellis | Jan 26, 2026 | Uncategorized
This is a senior leadership seat for someone who can run multiple engineering teams, ship enterprise-grade software in regulated environments, and keep the org moving without burning people out. You’ll own execution, team health, technical direction, and delivery outcomes across one to two product areas.
About One Call
One Call helps injured workers get the care they need when they need it, powered by teams that deliver secure, scalable technology behind the scenes. They’re remote-first and guided by values like Think Big, Go Fast, Deliver Awe, Win Together, and Care Deeply. This role sits in Shared Services (Technology) and supports globally distributed teams.
Schedule
- Full-time, remote
- Globally distributed teams
- Ongoing applications (no posting deadline)
What You’ll Do
- Lead multiple engineering teams delivering scalable, secure, high-quality software products
- Drive adoption of modern engineering practices, including:
- Agile delivery
- DevOps
- CI/CD
- Test automation
- Partner with Product, Design, and Architecture to define roadmaps and deliver with speed and quality
- Align engineering work to business outcomes and measure success using KPIs, including:
- Velocity
- Quality
- Availability
- Customer impact
- Build and maintain a high-talent, high-accountability culture through:
- Hiring
- Coaching
- Performance management
- Career development
- Champion engineering excellence through:
- Code quality
- Technical reviews
- Observability
- Continuous improvement
- Manage offshore teams and ensure alignment to standards and delivery expectations
- Own operational health of applications, including:
- Uptime
- Incident response
- Compliance (SOC2, HIPAA)
- Drive strategic initiatives, including:
- Platform modernization
- Technical debt reduction
- Automation
- Resolve cross-functional challenges and deliver integrated solutions across teams
- Manage resource allocation and capacity planning
What You Need
- Bachelor’s degree in Computer Science, Engineering, or equivalent experience
- 5+ years of engineering leadership experience managing multiple teams and product areas
- Proven experience leading cloud-native teams in:
- Experience working in remote-first, globally distributed environments
- Track record delivering enterprise software in regulated settings, including:
- Strong leadership and communication skills with the ability to influence across levels
- Deep understanding of modern SDLC practices, including Agile, DevOps, and CI/CD
- Familiarity with tools such as:
- Ability to drive technical strategy, architecture decisions, and platform evolution
- Working knowledge of both cloud-based and on-prem applications
- Comfort using engineering metrics and data to guide decisions
- Ability to juggle multiple priorities in a fast-paced environment
- Commitment to DEI and belonging standards
Benefits
- Salary range: $138,568–$221,709 (based on experience, skills, and business needs)
- Remote-first flexibility
- Minimum 18 days of paid time off
- 8 company holidays
- 2 personal days each year
- Medical, dental, and vision insurance
- Pet insurance
- 401(k) with matching
- Company-paid life insurance
- Short-term and long-term disability
- Colleague Assistance Program (free counseling and financial services)
- One Call Foundation support for colleagues facing unexpected hardships
Real talk: this is not a “keep the lights on” manager job. It’s a “build the machine, modernize the platform, hit outcomes, and protect compliance” job. If you’ve led multiple teams through delivery in a regulated environment, you’ll be right at home.
Happy Hunting,
~Two Chicks…
by Terrance Ellis | Jan 23, 2026 | Uncategorized
Build the data engine behind patient growth, engagement, and retention for a women’s and children’s healthcare company that actually moves outcomes. If you love owning strategy, partnering cross-functionally, and shipping data-backed product wins, this role is built for you.
About Pomelo Care
Pomelo Care delivers evidence-based virtual healthcare for women and children, supporting patients across pregnancy/postpartum, infant care and pediatrics, and perimenopause/menopause. Their tech-enabled, multidisciplinary model improves outcomes while expanding access through partnerships with payers, employers, and providers.
Schedule
Remote (United States)
Cross-functional role spanning Growth, Patient Experience, Marketing, Product, Clinical, and Engineering
High ownership role with leadership-facing reporting and metric stewardship
What You’ll Do
- Own the data strategy and roadmap for Growth and Patient Experience, focused on enrollment and retention
- Build and optimize multi-channel enrollment strategy with Marketing, including attribution models and funnel conversion analysis
- Define and iterate on core business health metrics (enrollment, engagement, retention) and present insights to leadership
- Run exploratory analyses to inform enrollment and engagement features (e.g., topic categorization, journey segmentation)
- Build data pipelines and analytics infrastructure connecting marketing, external, and product usage data into a unified patient journey view
- Lead A/B testing across marketing and product initiatives to accurately measure impact
- Partner with Product, Clinical, and Engineering to translate patient insights into product improvements and new capabilities
What You Need
- 6+ years of professional experience in data science, product analytics, or data engineering
- 2+ years in healthcare, consumer health, or high-touch consumer products
- Expert SQL and Python, with ability to work across the full data stack
- Strong product sense: prototyping, experimentation, and user behavior analysis
- Proven track record delivering data-driven solutions to ambiguous problems with real business impact
- Confidence leading cross-functional initiatives and influencing stakeholders as a strategic partner
- Strong communication skills and ability to tailor insights for different audiences
- Experience with dashboards/visualization tools (Looker, Tableau, Metabase)
- Experience with modern data stack tools (dbt, Airflow, Snowflake)
Benefits
- Competitive healthcare benefits
- Generous equity compensation
- Unlimited vacation
Roles like this don’t stay open long, especially when they sit at the center of growth and product. If you’re ready to own the funnel and the journey, take your shot.
Happy Hunting,
~Two Chicks…
by Terrance Ellis | Jan 23, 2026 | Uncategorized
Build real product that helps real people. Pomelo’s platform powers virtual care for women and children, and this role sits right in the engine room shipping features, improving systems, and helping their AI tools make clinicians faster and more present with patients.
About Pomelo Care
Pomelo Care delivers evidence-based virtual healthcare across reproductive care, pregnancy and postpartum, infant care and pediatrics, and perimenopause and menopause. Their 24/7 multispecialty model combines clinical care + tech to improve outcomes and reduce cost, partnering with payers, employers, and providers to expand access.
Schedule
- Remote (U.S.)
- Collaborative, cross-functional work with product, design, and clinical teams
- Production-focused environment where shipping and learning happen fast
What You’ll Do
- Write clean, elegant code to ship features and keep the platform stable
- Help design and implement systems that enable personalized, data-driven clinical care
- Contribute to AI-powered tools and agents that increase clinician efficiency
- Improve the mobile experience so families feel supported and connected
- Work closely with PMs, designers, and clinical staff to translate real user needs into technical solutions
What You Need
- Strong CS foundation (degree or equivalent professional experience)
- 2+ years shipping high-quality software in languages like Java, C#, Kotlin, Python, Go, etc.
- Experience with React or Vue
- Experience operating and maintaining production systems
- You keep up with LLM coding agents and use them to multiply your output
- You like solving hard problems without overengineering them
Nice to Have
- AI/ML, NLP, or agent-based systems experience
- Startup or fast-moving product environment experience
Benefits
- Competitive healthcare benefits
- Generous equity compensation
- Unlimited vacation
- First Round Network membership
- Estimated salary range: $135,000–$190,000 (plus equity and benefits)
Backbone moment: this posting says “mid-level” but wants someone who can ship in production, collaborate across disciplines, and not get lost in complexity. If your resume doesn’t show shipped outcomes (not just “worked on”), you’ll want to tune it before applying.
Happy Hunting,
~Two Chicks…
by Terrance Ellis | Jan 23, 2026 | Uncategorized
Build the core tech behind Pomelo’s virtual care platform, and help push AI-powered clinician tools from “cool idea” to “daily essential.” This is a senior, product-minded engineering role for someone who likes ambiguity, talks to users, and ships systems that actually matter.
About Pomelo Care
Pomelo Care delivers evidence-based virtual healthcare for women and children, spanning reproductive care, pregnancy and postpartum support, infant care and pediatrics, and perimenopause and menopause care. Their model is designed to improve outcomes through coordinated, 24/7 multispecialty support, partnering with payers, employers, and providers to expand access.
Schedule
- Remote (U.S.)
- Cross-functional collaboration with product and clinical leadership
- Fast-moving, startup environment with high ownership and broad scope
What You’ll Do
- Ship new features with clean, maintainable code and keep the platform reliable at scale
- Design and build scalable systems that help clinicians deliver personalized, data-driven care
- Build and improve AI-powered tools and agents that increase clinician efficiency and effectiveness
- Enhance the mobile experience so patients and families feel supported throughout their journey
- Mentor engineers through code reviews, technical guidance, and strong engineering standards
- Partner with product and clinical leaders to shape the roadmap and prioritize the highest-impact problems
What You Need
- 5+ years building and shipping scalable software systems
- Strong skills in system design, relational database design, and at least one backend language (Java, C#, Kotlin, Python, Go, etc.)
- Experience with modern front-end frameworks like React or Vue
- Comfort with ambiguity and a product mindset: you’d rather understand the user than blindly follow a spec
- Interest in agentic tooling and using modern AI capabilities to speed delivery and increase impact
- Track record of delivering elegant, maintainable solutions to complex problems
Nice to Have
- AI/ML experience, NLP exposure, or building agent-based systems
- Experience in fast-paced, product-driven environments
Benefits
- Competitive healthcare benefits
- Generous equity compensation
- Unlimited vacation
- First Round Network membership
- Estimated salary range: $190,000–$220,000 (plus equity and benefits)
Quick gut-check: this role screams “senior product engineer with real production chops.” If someone’s resume is mostly tickets and not outcomes, they’ll drown here. If they ship, own, and talk to users, they’ll thrive.
Happy Hunting,
~Two Chicks…
by Terrance Ellis | Jan 23, 2026 | Uncategorized
Help Pomelo cut the busywork and build the “autopilot” layer for how the company runs. This is a senior, high-impact role focused on spotting repetitive operational pain points and turning them into AI-powered internal tools that create immediate productivity wins across teams.
About Pomelo Care
Pomelo Care delivers evidence-based, virtual care for women and children, supporting patients through pregnancy and postpartum, infant care and pediatrics, and hormonal health through perimenopause and menopause. Their 24/7 multispecialty model is built to improve outcomes and expand access across the healthcare system.
Schedule
- Remote (U.S.)
- Cross-functional role partnering with teams across the business
- Startup pace: rapid prototyping, fast deployment, visible impact
What You’ll Do
- Build and maintain internal automation tools that eliminate manual work and boost employee productivity using AI
- Use AI heavily in your own build process to speed up delivery and iteration
- Partner with stakeholders to identify the highest-leverage process bottlenecks, then ship solutions that get adopted and deliver obvious value
- Rapidly prototype AI-enabled utilities and push them into production quickly
- Make architecture and tooling decisions for automation systems and step in to debug hard problems when AI falls short
- Own systems that may touch sensitive data or business-critical logic, with a security-first mindset
What You Need
- Strong CS foundation and 2+ years shipping high-quality software
- Hands-on experience with AI/ML tooling, LLMs, and API integrations for automation
- Ability to build both front-end interfaces and back-end services using modern frameworks
- High-trust ownership mindset for systems handling sensitive data and critical workflows
- Curiosity and practical awareness of new AI models and tools, and the ability to apply them to real operational needs
Bonus Points
- Built AI agents, workflow automation, or process optimization tooling
- Experience in healthcare, startups, or similarly fast environments where automation moves the needle
- Familiarity with low-code/no-code or RPA tools and business process automation
Benefits
- Competitive healthcare benefits
- Generous equity compensation
- Unlimited vacation
- First Round Network membership
- Salary range: $190,000–$220,000 (plus equity and benefits)
If you love taking messy, manual workflows and turning them into clean, reliable systems that make people’s days easier, this role is your lane.
Happy Hunting,
~Two Chicks…
