Staff Security Engineer – Remote

Lead the security foundation powering a mission-driven healthcare platform.


About Pomelo Care

Pomelo Care is a multidisciplinary team of clinicians, engineers, and problem solvers committed to improving outcomes for mothers and babies. Their virtual care platform engages patients early, conducts individualized risk assessments, and delivers coordinated support across pregnancy, NICU stays, and the first postpartum year. They measure success through fewer preterm births, NICU admissions, c-sections, and maternal mortality—transforming lives at scale.


Schedule

  • Full-time
  • Remote
  • High-collaboration role across engineering, compliance, and executive teams
  • Fast-paced startup environment with evolving security needs

Responsibilities

  • Lead and execute critical cybersecurity initiatives across IAM/RBAC, AppSec, Cloud Security, Endpoint Security, CI/CD security, supply chain security, SAST/DAST, penetration testing, bug bounty management, Incident Response, DFIR, and SaaS security
  • Build and implement security frameworks and solutions that proactively mitigate risks and address emerging threats
  • Partner cross-functionally with engineering, product, compliance, and leadership to embed security best practices
  • Own and continuously refine secure SDLC processes, tools, and developer workflows
  • Mentor teams on cybersecurity fundamentals, secure coding, and threat modeling
  • Participate in Incident Response efforts, investigations, and post-incident reviews
  • Contribute to a collaborative, humble, and entrepreneurial engineering culture

Requirements

  • Ten or more years of hands-on cybersecurity experience with strong software engineering fundamentals
  • Expertise in two or more areas: IAM, AppSec, Cloud Security, CI/CD security, Incident Response, etc.
  • Experience working across the full technology stack (GCP, Kotlin, React/Next.js, Swift, Expo, XCode, Android Studio, yarn, npm, CodeBuild)
  • Past cybersecurity experience in healthcare or startups with familiarity in HIPAA, SOC 2 Type 2, and HITRUST
  • Strong technical foundation in system architecture, PKI, SAML, JWT, HMAC, MITRE ATT&CK, D3FEND, and OWASP Top 10
  • Proven ability to adapt in agile environments and handle multiple responsibilities
  • Excellent communication skills with the ability to explain complex security concepts to non-technical audiences
  • Highly preferred: CISSP, CISM, CCSP; OSCP is a major plus

Benefits

  • Competitive healthcare benefits
  • Generous equity compensation
  • Unlimited vacation
  • Membership in the First Round Network
  • Salary range: $220,000–$260,000, with most hires landing mid-range

A foundational role for someone who thrives on securing complex systems and shaping security culture from the ground up.

Happy Hunting,
~Two Chicks…

APPLY HERE

Senior Software Engineer, Core Data – Remote

Build and scale the data backbone powering AI-driven clinical insights.


About Pomelo Care

Pomelo Care is a team of clinicians, engineers, and problem solvers transforming outcomes for mothers and babies. Their virtual care platform engages patients early, conducts individualized risk assessments, and delivers coordinated support throughout pregnancy, NICU stays, and the first postpartum year. They measure success through real, life-changing outcomes: fewer preterm births, NICU admissions, c-sections, and maternal mortality.


Schedule

  • Full-time
  • Remote
  • Cross-functional collaboration across engineering, product, analytics, and clinical teams

Responsibilities

  • Build and maintain scalable, elegant data pipelines that ingest and normalize data from multiple sources
  • Lead the design and development of robust data infrastructure using dbt, Dagster, Beam, and Dataflow
  • Write performant SQL and Python to transform raw datasets into actionable insights for product and clinical teams
  • Architect data models supporting operational analytics and new data-driven product features
  • Mentor engineers, provide thoughtful code reviews, and champion best practices in data engineering
  • Collaborate with product, clinical, and analytics teams to understand needs and unlock high-impact insights
  • Optimize data workflows for performance, reliability, and cost efficiency

Requirements

  • Five or more years of experience building scalable data systems and pipelines
  • Expert proficiency in SQL and Python
  • Hands-on experience with dbt and orchestration tools such as Dagster, Beam, or Dataflow
  • Strong understanding of data modeling, transformation principles, and modern data stack technologies
  • Experience designing data warehouse architecture
  • Proven ability to deliver elegant, maintainable solutions that drive measurable business value

Bonus Skills

  • Experience building infrastructure for AI or machine learning workloads
  • Background in real-time analytics or fast-paced, product-oriented environments
  • Healthcare data experience, including privacy and compliance requirements

Benefits

  • Competitive healthcare benefits
  • Generous equity compensation
  • Unlimited vacation
  • Membership in the First Round Network
  • Salary range: $190,000–$220,000, with most candidates landing near the middle

A chance to shape the future of maternal and infant health by powering the systems that make data meaningful.

Happy Hunting,
~Two Chicks…

APPLY HERE

Senior Data Scientist, Care Intelligence – Remote

Drive AI innovation that improves real maternal and infant health outcomes.


About Pomelo Care

Pomelo Care is a team of clinicians, engineers, and problem solvers transforming care for pregnant people and babies. Their virtual platform enables early engagement, individualized risk assessment, and coordinated support throughout pregnancy, NICU stays, and the first postpartum year. They measure success through meaningful outcomes, including reductions in preterm births, NICU admissions, c-sections, and maternal mortality.


Schedule

  • Full-time
  • Remote
  • Cross-functional collaboration with clinical, engineering, and product teams

Responsibilities

  • Become an expert in Pomelo’s business model and patient experience to identify opportunities for AI product development
  • Conduct exploratory analyses to support AI features such as topic categorization and patient journey segmentation
  • Contribute to AI-powered product development including content generation, clinical decision support, and automated workflows
  • Define metrics and measurement frameworks for evaluating AI-generated content and clinical workflows
  • Run detailed analyses to measure performance, conduct A/B tests, and quantify the impact of AI-driven features
  • Scope and deliver solutions across multiple domains in a fast-moving environment

Requirements

  • Six or more years of experience in data science with a strong product focus
  • Three or more years working in healthcare or regulated industries
  • Expert-level proficiency in SQL and Python
  • Proven experience with LLMs, model evaluation, and AI product prototyping
  • Strong ability to solve ambiguous problems and communicate across technical and non-technical teams
  • Passion for improving maternal health outcomes through innovative AI solutions

Bonus Skills

  • Experience with fine-tuning, prompt engineering, and building production AI applications
  • Background in healthcare AI, clinical decision support, or medical NLP
  • Familiarity with dashboarding and visualization tools such as Tableau, Looker, or Metabase
  • Experience with modern data stack tools such as dbt, Airflow, or Snowflake

Benefits

  • Competitive healthcare benefits
  • Generous equity compensation
  • Unlimited vacation
  • Inclusive, mission-driven culture focused on transforming maternal and infant health
  • Salary range: $160,000–$190,000, depending on experience and location

Build intelligent systems that shape the future of clinical care.

Happy Hunting,
~Two Chicks…

APPLY HERE

Product Operations, AI Content – Remote

Help shape the knowledge backbone that powers clinicians and AI at Pomelo Care.


About Pomelo Care

Pomelo Care is a team of clinicians, engineers, and problem solvers dedicated to improving outcomes for pregnant people, babies, and families. Their virtual care platform enables early engagement, individualized risk assessment, and coordinated support throughout pregnancy, NICU stays, and the first postpartum year. They measure success through real-world results, including reductions in preterm births, NICU admissions, c-sections, and maternal mortality.


Schedule

  • Full-time
  • Remote
  • Cross-functional collaboration with product, clinical, and engineering teams

Responsibilities

  • Organize clinical guidelines, operational workflows, and product documentation into structured, AI-friendly formats
  • Build taxonomies, tagging systems, and metadata to improve searchability and modularity
  • Partner with engineering teams to prepare knowledge for LLM-powered tools, including RAG pipelines, embeddings, and structured content
  • Break down existing content into smaller, referenceable units optimized for clinician and AI use
  • Maintain version control, accuracy, and consistency across all knowledge sources
  • Conduct regular audits and update content with clinical and operational stakeholders
  • Translate clinical workflows into structured schemas for technical teams
  • Gather and manage feedback from clinicians using AI tools and internal documentation
  • Align with the Clinical Education team to ensure consistency across onboarding and clinician-facing materials

Requirements

  • Five or more years of experience in product operations or similar roles supporting technical teams
  • Demonstrated interest or experience with AI/LLMs, including prompt engineering, RAG, embeddings, or knowledge graphs
  • Strong information organization skills and ability to design structured knowledge systems
  • Comfortable working with structured content formats like Markdown, JSON, or SQL basics
  • Curiosity and willingness to learn healthcare and clinical workflows
  • Strong communication skills and ability to bridge technical and clinical conversations

Bonus Skills

  • Background in healthcare or clinical operations
  • Experience with knowledge management platforms such as Confluence, Notion, or Guru
  • Exposure to AI tools such as LangChain, vector databases, or annotation systems

Benefits

  • Competitive healthcare benefits
  • Generous equity compensation
  • Unlimited vacation
  • Salary range: $110,000–$140,000, depending on experience and location
  • Mission-driven environment focused on improving maternal and infant health outcomes
  • Inclusive culture welcoming candidates from diverse backgrounds

Craft the knowledge foundation that fuels next-generation clinical care and AI.

Happy Hunting,
~Two Chicks…

APPLY HERE

Product Manager – Remote

Build AI-powered clinical tools that help clinicians deliver exceptional care at scale.


About Pomelo Care

Pomelo Care is a team of clinicians, engineers, and problem solvers dedicated to improving outcomes for pregnant people, babies, and families. Their virtual care platform enables early engagement, individualized risk assessment, and coordinated support throughout pregnancy, NICU stays, and the first postpartum year. Pomelo measures success by real-world outcomes such as reduced preterm births, NICU admissions, c-sections, and maternal mortality.


Schedule

  • Full-time
  • Remote
  • Highly cross-functional role supporting internal clinical operations

Responsibilities

  • Build and launch features that enhance clinical decision-making, reduce administrative burden, and improve clinician efficiency
  • Drive measurable improvements in business metrics such as quality gap closure, patient engagement, and workflow adoption
  • Shadow clinicians, conduct interviews, and analyze data to understand pain points and uncover opportunities
  • Translate clinical protocols and operational needs into intuitive, user-centered product experiences
  • Prioritize, scope, and ship high-impact features using rapid testing and iteration
  • Partner closely with product, engineering, design, clinical, and operations to deliver cohesive solutions
  • Ensure internal tools also elevate the patient journey and strengthen the overall care experience

Requirements

  • Two or more years of product management experience building products from scratch
  • Strong user empathy and passion for improving workflows for expert users
  • Ability to craft clear value propositions that drive adoption and behavior change
  • Skilled at influencing across clinical, operational, and technical teams
  • Strong instincts for practical AI applications in workflow improvement
  • Bias for action, comfort with MVP approaches, and ability to iterate toward a long-term vision
  • Ability to prototype using AI-enabled tools (Figma Make, Claude Code, etc.)
  • Exceptional communication and collaboration skills across all levels
  • Strong product and design sense, with a focus on creating consumer-grade experiences

Bonus Skills

  • Experience with hybrid digital and human-delivered products
  • Experience building workflow platforms for expert users
  • Healthcare technology experience, especially in value-based care
  • Founder or early-startup experience

Benefits

  • Competitive healthcare benefits
  • Generous equity compensation
  • Unlimited vacation
  • Salary range: $155,000–$180,000, depending on experience and location
  • Mission-driven culture focused on improving maternal and infant health outcomes
  • Inclusive workplace that values diverse backgrounds and perspectives

Empower clinicians with intelligent tools that transform patient care.

Happy Hunting,
~Two Chicks…

APPLY HERE

Data Scientist, Care Intelligence – Remote

Build AI-powered healthcare products that improve pregnancy and postpartum outcomes nationwide.


About Pomelo Care

Pomelo Care is a multidisciplinary team of clinicians, engineers, and problem solvers dedicated to improving care for pregnant people, babies, and families. Their technology-driven virtual care platform engages patients early, identifies risk, and delivers coordinated, evidence-based support through pregnancy, NICU stays, and the first postpartum year. Pomelo measures success by real clinical outcomes: fewer preterm births, fewer NICU admissions, fewer c-sections, and improved maternal health.


Schedule

  • Full-time
  • Remote
  • Fast-paced, cross-functional AI product environment

Responsibilities

  • Become an expert in Pomelo’s business model and patient experience to identify high-value AI product opportunities
  • Conduct exploratory data analyses to support AI features such as topic categorization, segmentation, and patient engagement insights
  • Develop and refine AI-powered features, including content generation, clinical support tools, and automated workflows
  • Define quantitative metrics to measure AI-generated content and system performance
  • Lead A/B tests, performance evaluations, and impact assessments for AI products
  • Translate complex findings into actionable insights for product, clinical, and engineering teams

Requirements

  • Six or more years of experience as a data scientist with strong product focus
  • Three or more years in healthcare or regulated industries
  • Expert proficiency in SQL and Python
  • Proven experience building and evaluating AI-driven products using LLMs and modern model evaluation techniques
  • Ability to scope, design, and execute solutions for complex ambiguous problems
  • Strong communicator who can bridge technical and non-technical teams
  • Passion for improving maternal health outcomes through AI innovation

Bonus Skills

  • Experience fine-tuning models, prompt engineering, or developing production AI systems
  • Background in healthcare AI, medical NLP, or clinical decision support
  • Experience with visualization tools like Looker, Tableau, or Metabase
  • Familiarity with dbt, Airflow, Snowflake, or modern data stack tools

Benefits

  • Competitive healthcare benefits
  • Generous equity compensation
  • Unlimited vacation
  • Salary range: $140,000–$160,000, dependent on experience and location
  • Mission-driven culture centered on improving outcomes for families
  • Inclusive environment welcoming diverse backgrounds and perspectives

Use your AI expertise to shape clinical intelligence and deliver life-changing healthcare at scale.

Happy Hunting,
~Two Chicks…

APPLY HERE