Staff Software Engineer – Remote

If you like early-stage “build it, ship it, fix it, improve it” work and you’ve got the range to go from database schema to HIPAA-friendly AWS to a React UI, Wisdom is offering exactly that. This is a high-impact staff-level role where you’ll shape product and engineering culture, not just crank tickets.

About Wisdom
Wisdom combines dental billing expertise with purpose-built technology to help dental practices run smoother, get paid faster, and spend more time with patients. They’re a remote-first company and they’re scaling after a fresh $21M Series A funding round.

Schedule

  • Full-time
  • Remote (US)
  • Reports to: Head of Engineering
  • Compensation: $150K–$180K base + equity

What You’ll Do
⦁ Build and ship software from the ground up, then iterate quickly as products launch and learnings roll in
⦁ Work full stack: design database schemas, build Node.js services, and ship React frontends (all in TypeScript)
⦁ Deploy and maintain HIPAA-compliant cloud infrastructure (AWS)
⦁ Design and implement resilient integrations with dental insurance carriers and practice management systems
⦁ Partner directly with dental billers and clients to understand real workflow pain, then translate that into product solutions
⦁ Take on ambiguous problems and help set engineering best practices, patterns, and team culture

What You Need
⦁ 5+ years of software engineering experience
⦁ Strong proficiency in a web-stack language (TypeScript/JavaScript, Python, or C#) and openness to working in TypeScript
⦁ Experience designing and scaling Postgres (or similar relational databases)
⦁ Cloud infrastructure experience (AWS or GCP)
⦁ Product mindset with strong user empathy (you care how the work actually gets done)
⦁ High ownership, autonomy, and curiosity
⦁ Low ego: you can admit mistakes, learn fast, and collaborate without drama

Benefits
⦁ Equity included
⦁ Fully remote, distributed team
⦁ High ownership and influence in an early-stage product org

My blunt take: this role will reward builders who like ambiguity and can balance speed with correctness (especially around HIPAA and integrations). If you need a highly defined roadmap and tight guardrails, this will feel chaotic. If you like being trusted and moving fast with real-world stakes, it’s a strong fit.

Happy Hunting,
~Two Chicks…

APPLY HERE

Data Integrations Engineer II – Remote

If you’re the “data plumbing” person who makes sure files flow cleanly, ETLs don’t break, and the business stops panicking, HMA wants you. This role is about building and maintaining the ETL and EDI pipelines that keep internal and external systems talking, with a heavy emphasis on SQL, SSIS, and production support.

About Healthcare Management Administrators (HMA)
HMA is a third-party health plan administrator serving the Pacific Northwest and beyond, building customized health plans for medium to large employers. They’re known for strong customer service, a mission-driven culture (“Proving What’s Possible in Healthcare™”), and they’ve been recognized as one of Washington’s Best Workplaces for three years.

Schedule

  • Full-time
  • Remote (US-based)
  • Hires across the US with exclusions: Hawaii and the cities of Los Angeles and San Francisco
  • Flexible schedules supporting multiple US time zones

What You’ll Do
⦁ Design, build, test, deploy, monitor, and run production ETL processes
⦁ Troubleshoot ETL issues in production and lead resolution efforts with clear communication back to the team
⦁ Partner with business users, IT, and vendors to gather requirements and implement or improve database applications and integrations
⦁ Translate business concepts into technical requirements and design (SDLC-driven work)
⦁ Develop, implement, and optimize stored procedures and functions in T-SQL
⦁ Analyze and tune SQL queries for performance (including queries used by front-end apps)
⦁ Create and maintain EDI document mappings for inbound/outbound transactions
⦁ Own SQL development for new products and enhancements to existing systems
⦁ Design ETL/SSIS architecture and build SSIS packages pulling from multiple sources (SQL, flat files, XML) with transformations into target systems
⦁ Evaluate new tools/technologies to modernize existing applications and workflows

What You Need
⦁ 3–5+ years of MSSQL T-SQL development experience
⦁ 3–5+ years of MSSQL SSIS development experience
⦁ 3–5+ years of Data Warehouse / ETL (Extract, Transform, Load) experience
⦁ Strong ability building and optimizing complex SQL queries and stored procedures
⦁ Understanding of inbound/outbound EDI transactions and protocols (and mapping)
⦁ Proficiency in a programming language like C# and/or Python, plus scripting and data analysis comfort
⦁ Strong communication skills (this role touches business users and vendors)
⦁ Bachelor’s in IT/CS preferred (or equivalent experience)

Benefits
⦁ Base salary range (greater Seattle area): $117,000–$145,000 (varies by geography, skills, experience, and market factors)
⦁ Performance-based incentive bonus eligibility
⦁ 17 days PTO (individual contributors)
⦁ 11 paid holidays
⦁ 2 paid personal days and 1 paid volunteer day
⦁ Company-subsidized medical, dental, vision, and prescription insurance
⦁ Company-paid disability, life, and AD&D insurance
⦁ Voluntary insurance options
⦁ HSA and FSA pre-tax programs
⦁ 401(k) with company match
⦁ Annual $500 wellness incentive and $600 wellness reimbursement
⦁ Remote work and continuing education reimbursements
⦁ Parental leave
⦁ Up to $1,000 annual charitable giving match
⦁ Discount program

Real talk: this is a strong fit only if you’ve actually lived in MSSQL/SSIS land and you’re not scared of production fires. If that’s you, this is a clean remote gig with solid pay and benefits.

Happy Hunting,
~Two Chicks…

APPLY HERE

Senior Software Engineer – Remote

If you’re a senior full-stack engineer who likes building scalable systems with real-world impact, Counterpart Health wants you. You’ll help evolve Counterpart Assistant, a primary care tool that supports physicians in earlier diagnosis and long-term chronic care management, improving outcomes while lowering costs.

About Counterpart Health
Counterpart Health builds Counterpart Assistant, an AI-enabled tool designed to fit directly into primary care workflows. It’s used by thousands of practitioners during patient visits to improve disease management, reduce medical spend, and succeed in value-based care. Counterpart Health is a subsidiary of Clover Health and operates with a mission-first, outcomes-driven mindset.

Schedule

  • Full-time
  • Remote (USA)
  • Pod-based model with cross-functional collaboration (engineering, data science, product, and clinical partners)
  • Remote-first culture with ongoing collaboration and documentation-heavy workflows

What You’ll Do
⦁ Build scalable, efficient systems that reduce complexity and enhance physician workflows
⦁ Partner with product and operational teams to shape and deliver new features
⦁ Maintain strong development practices: tests, documentation, and high-quality implementations that support fast iteration
⦁ Participate in technical discovery, propose durable solutions, and write clear technical design documents for ambiguous problems
⦁ Reinforce effective design patterns to manage complexity and introduce new patterns when needed
⦁ Evaluate new tools and technologies to improve performance, reliability, and developer velocity
⦁ Mentor junior and mid-level engineers, helping raise the team’s technical bar

What You Need
⦁ 5+ years of software engineering experience
⦁ Proficiency in at least one of: Python, Ruby, Go, C, or Java
⦁ Strong systems mindset: scalability, rigor, maintainability, and reliability
⦁ Comfort working across different technical systems and concerns in a full-stack environment
⦁ Experience building and refactoring complex, often distributed systems
⦁ Ability to collaborate smoothly with both technical and non-technical partners and drive discussions toward practical solutions

Benefits
⦁ Base salary range estimate: $185,000–$230,000 (final pay based on internal equity, market data, experience, and qualifications)
⦁ Competitive base salary and equity opportunities
⦁ Performance-based bonus program, 401(k) matching, and regular compensation reviews
⦁ Comprehensive medical, dental, and vision coverage
⦁ Mental health resources, No-Meeting Fridays, monthly company holidays, and flexible time off
⦁ Learning programs, mentorship, and professional development funding
⦁ Employee Stock Purchase Plan (ESPP)
⦁ Office setup reimbursement
⦁ Monthly cell phone and internet stipend
⦁ Paid parental leave for all new parents

This is a premium comp band for a reason. They want someone who can own a slice of a complex product, drive clarity when problems are fuzzy, and ship improvements that actually help clinicians and patients.

Happy Hunting,
~Two Chicks…

APPLY HERE

Senior Software Developer – Remote

If you like building real products that change real outcomes, this one’s got purpose. Counterpart Health is looking for a senior full-stack engineer to help scale Counterpart Assistant, a primary care tool that supports physicians in earlier diagnosis and long-term chronic care management.

About Counterpart Health
Counterpart Health is transforming healthcare through Counterpart Assistant, an AI-enabled tool designed to fit directly into primary care physicians’ workflows. It’s used by thousands of practitioners during patient visits to improve disease management, reduce medical expenses, and drive value-based care. Counterpart Health is a subsidiary of Clover Health.

Schedule

  • Full-time
  • Remote (Canada)
  • Remote-first culture with collaboration across technical and clinical teams
  • Pod model with empowered, cross-functional teams

What You’ll Do
⦁ Build scalable, efficient systems that support physicians and simplify complex healthcare workflows
⦁ Collaborate with developers, data scientists, healthcare professionals, and product managers to ship impactful features
⦁ Help define and maintain development practices that enable fast iteration with quality (tests, documentation, durable patterns)
⦁ Participate in technical discussions, propose solutions for ambiguous problems, and write clear technical design documents
⦁ Reinforce proven design patterns to manage complexity, and introduce new ones when needed
⦁ Evaluate and adopt new tools and technologies that improve reliability, performance, and developer velocity
⦁ Mentor junior and mid-level engineers and raise the team’s technical capabilities

What You Need
⦁ 5+ years of software development experience
⦁ Proficiency in at least one of: Python, Ruby, Go, C, or Java
⦁ Mature approach to building and maintaining scalable systems (rigor, reliability, long-term thinking)
⦁ Comfort working across multiple systems and concerns in a full-stack environment
⦁ Experience building and refactoring complex, often distributed systems
⦁ Ability to collaborate well with both technical and non-technical partners

Benefits
⦁ Competitive base salary and equity opportunities
⦁ Performance-based bonus program and regular compensation reviews
⦁ Comprehensive group medical coverage (hospitalization, outpatient, optical, dental)
⦁ Mental health support, No-Meeting Fridays, company holidays, and generous annual leave
⦁ Remote-first flexibility and office setup reimbursement
⦁ Learning programs, mentorship, and professional development funding
⦁ Paid parental leave for all new parents
⦁ And more

This is a strong fit if you want senior-level ownership with mission impact: building software that helps doctors act earlier, manage chronic conditions better, and ultimately improve patient lives.

Happy Hunting,
~Two Chicks…

APPLY HERE

Back End / Full Stack Software Engineer (Senior) – Remote

If you’re a senior engineer who loves owning the backend and can still jump into the front end when needed, Worth AI is looking for you. You’ll build scalable products that support AI-driven decision-making, working in a culture that leans hard on ownership, tight teamwork, and shipping fast without breaking trust.

About Worth AI
Worth AI is a software company focused on using artificial intelligence to improve how businesses make decisions. They emphasize collaboration, adaptability, and “extreme ownership,” with a goal of creating raving fans for both customers and employees. The work lives at the intersection of engineering, product, and real-world risk-focused industries.

Schedule

  • Fully remote (US)
  • Full-time
  • Agile/Scrum sprint environment
  • Remote hires must travel to Orlando, Florida at least twice per year for town halls and team collaboration, plus orientation in Orlando

What You’ll Do
⦁ Design, develop, and maintain scalable, high-performing web applications with a backend-first focus
⦁ Collaborate cross-functionally to turn user needs into clear technical specs and shipped features
⦁ Build and improve front-end interfaces and user experiences when needed (React/TypeScript)
⦁ Write clean, secure, efficient code with strong testing and debugging practices
⦁ Participate in code reviews and raise the quality bar through constructive feedback
⦁ Own sprint deliverables and be transparent during planning and retrospectives
⦁ Support releases, patches, revisions, and troubleshooting in existing codebases
⦁ Research new technologies and recommend best-fit solutions for tough problems
⦁ Improve and modernize codebases to keep products current and maintainable

What You Need
⦁ Proven experience as a senior full stack engineer with heavy backend ownership
⦁ Strong JavaScript plus backend proficiency in Node.js (and/or Python)
⦁ React + TypeScript experience for front-end work
⦁ Experience with Node.js/Express and relational databases (MySQL and/or PostgreSQL)
⦁ Cloud and containerization experience (AWS or Azure, plus Docker/Kubernetes)
⦁ Familiarity with tools like Argo CD and Kafka (or similar event and deployment tooling)
⦁ Strong understanding of security principles and architecture
⦁ Comfortable working in Agile/Scrum with Git-based workflows
⦁ Strong written and verbal communication skills
⦁ Bonus: Risk, underwriting, and/or payments industry experience

Benefits
⦁ Medical, dental, and vision coverage
⦁ Retirement plan options (401k, IRA)
⦁ Life insurance
⦁ Unlimited vacation
⦁ Work from home
⦁ Wellness resources
⦁ Free food and snacks (in office)

If you want a backend-heavy senior role where you can still flex full stack skills, modernize systems, and ship in a high-ownership culture, this is a strong match.

Happy Hunting,
~Two Chicks…

APPLY HERE

Front-End Developer (Senior or Lead) – Remote

If you’re a React-heavy front-end builder who cares about performance, clean architecture, and pixel-level polish, Esprow wants you. You’ll own the UI layer for financial web applications, improve existing interfaces, and help lay the foundation for new products in a small-team, high-autonomy environment.

About Esprow
Esprow is a fast-growing tech company with global clients in high-profile financial environments. Their Enterprise Testing Platform (ETP) supports automated certification, testing, and simulation of financial trading solutions. With teams across New York, Singapore, Tokyo, and India, they ship serious software with minimal bureaucracy and a lot of ownership.

Schedule

  • Full-time, permanent
  • Remote (or onsite option)
  • Five-day work week
  • Core hours listed as 9:00am–6:00pm with flexitime

What You’ll Do
⦁ Build functional, responsive, and polished web interfaces for Esprow’s web products
⦁ Solve challenging UI/UX problems tied to real client use cases
⦁ Collaborate closely with back-end and core developers to ship end-to-end features
⦁ Add new features to existing products while reviewing and improving legacy front-end code
⦁ Help design and build new products from scratch, bringing strong front-end patterns and structure
⦁ Contribute to front-end testing to meet functional and non-functional requirements
⦁ Ensure cross-browser and cross-platform compatibility
⦁ Document your code and decisions, and share knowledge with the team

What You Need
⦁ 3–6 years of modern front-end development experience across the SDLC
⦁ Strong HTML5, CSS, and JavaScript (ES6+), plus TypeScript experience
⦁ Strong React experience
⦁ Familiarity with Redux / Redux Toolkit, styled-components, and immutability libraries (ex: Immer)
⦁ Practical experience with REST + WebSocket APIs and data formats like JSON/XML
⦁ Experience testing front-end code and web UIs
⦁ Understanding of UI/UX principles and design thinking
⦁ Comfort with modern IDEs, build tools, deployment tools, and monitoring tools
⦁ Familiarity with jQuery and Bootstrap for supporting or migrating legacy code
⦁ Ability to work independently, take ownership, and deliver under deadlines
⦁ English proficiency (basic or higher)
⦁ Bachelor’s/College degree in CS/IT or equivalent

Benefits
⦁ Full-time permanent position with remote flexibility
⦁ Flexitime within a standard weekday schedule
⦁ Competitive remuneration package
⦁ Training and professional growth support
⦁ Friendly, efficient team and clear career path in a global, fast-growing tech company
⦁ Complimentary coffee/tea and snacks (onsite only)

If you’re ready to own the front end, tighten the codebase, and ship clean UI work that holds up in serious production environments, this one’s worth your shot.

Happy Hunting,
~Two Chicks…

APPLY HERE