Customer Support Engineer – Remote

Ready to redefine what great technical support looks like? At Files.com, Customer Support Engineers don’t just answer tickets—they solve complex technical challenges, influence product direction, and directly impact customer success.


About Files.com
Files.com is a profitable, founder-led SaaS company powering secure file transfer and automation for over 4,000 global brands including Marc Jacobs, GrubHub, Michelin, and Planet Fitness. With $35M+ in revenue, $46.5M in growth capital, and a lean team of 70, we’ve scaled by hiring smart communicators who act fast and own outcomes. Here, Customer Support is treated as a first-class function—central to product growth and customer loyalty.


Schedule

  • Full-time, remote within the U.S. or in-office (Austin, TX / Scottsdale, AZ)
  • Expect direct customer interaction via phone, email, and Zoom during business hours

What You’ll Do

  • Provide first-class support to enterprise customers through phone, email, and Zoom
  • Troubleshoot issues across networking, API integrations, identity management, and automation workflows
  • Identify and replicate bugs, escalate quickly, and collaborate with Engineering for fast fixes
  • Deliver crisp, empathetic communication that builds trust and confidence
  • Feed customer insights into Product and R&D for continuous improvement

What You Need

  • Technical curiosity with strong problem-solving skills
  • Clear communication skills, especially in phone and video conversations
  • Ability to empathize with customers while staying solution-oriented
  • Comfort working in a fast-moving environment with shifting priorities
  • Strong written documentation skills for internal alignment and customer clarity

Compensation & Benefits

  • Salary: $95,000 – $150,000 (based on qualifications and experience)
  • Equity grants for every employee
  • 100% paid health, dental, and vision (75% for family)
  • 401(k) with 4% company match
  • Paid parental leave
  • 20 PTO days + 11 holidays + full company winter break
  • $1,000 signing bonus, modern Apple laptop, and anniversary gifts
  • Team travel opportunities (NYC, Austin, San Diego, and more)

This isn’t a “support desk” job—it’s a high-impact technical role where you’ll solve real problems, shape the product, and grow your career. If you’re looking for variety, intellectual challenge, and a clear growth path, this is your seat.


Happy Hunting,
~Two Chicks…

APPLY HERE

Senior Product Designer, Access – Remote

Bring clarity to complexity by designing seamless digital experiences that guide members into care. At Included Health, you’ll shape conversion flows and engagement strategies that simplify healthcare and make it accessible for everyone.


About Included Health
Included Health is redefining healthcare by delivering integrated virtual care and navigation. From urgent care to behavioral health and specialty services, we break down barriers so everyone can access high-quality care. Our design team plays a pivotal role in turning complex healthcare systems into intuitive, human-centered experiences.


Schedule

  • Full-time, remote (U.S.-based)
  • Flexible hours with cross-functional collaboration across product, engineering, and marketing teams

What You’ll Do

  • Lead end-to-end design for Growth & Engagement, owning conversion flows and digital entry points
  • Simplify complex authentication and coverage systems into intuitive, frictionless experiences
  • Run A/B tests and rapid iterations using insights and data to refine design strategies
  • Explore new storytelling, motion, and interaction design approaches to elevate member engagement
  • Use AI-powered design tools (e.g., v0.dev, Spline, Cursor, Bolt) for prototyping and iteration
  • Mentor peers, set design direction, and advocate for long-term vision alongside rapid experimentation
  • Collaborate with product, engineering, and marketing to align design with business outcomes

What You Need

  • 6+ years of product design experience (at least 2 years in growth, engagement, or conversion flows)
  • Strong portfolio showcasing high-quality, high-converting experiences
  • Proficiency with AI-powered design and research tools for prototyping and testing
  • Experience with complex flows like authentication, onboarding, or coverage verification
  • Strategic mindset with the ability to connect design decisions to business outcomes
  • Excellent communication and storytelling skills to advocate for design solutions
  • Bonus: Background in healthcare, fintech, or other regulated industries

Compensation & Benefits

  • Base salary ranges by location:
    • Zone A: $128,130 – $180,990
    • Zone B: $140,943 – $199,089
    • Zone C: $153,756 – $217,188
    • Zone D: $166,569 – $235,287
  • Equity package + comprehensive benefits including:
    • Medical, vision, and dental coverage with multiple plan options
    • 401(k) savings plan through Fidelity with company match
    • Generous PTO and Discretionary Time Off
    • 12 weeks 100% paid parental leave + up to $25,000 fertility/family building benefit
    • Compassionate leave for failed pregnancy, surrogacy, adoption, or fertility treatment
    • Paid volunteer time off (24 hours per year)
    • Work-from-home reimbursement for effective setup
    • Access to full suite of Included Health telemedicine services at no cost

Design with impact. Help us transform healthcare journeys and make access effortless for millions of members.


Happy Hunting,
~Two Chicks…

APPLY HERE

IT Engineer – Remote

Help shape the future of IT in mental health care. Alma is looking for an IT Engineer 2 who thrives on problem-solving, empowering employees, and building scalable systems to support a growing remote-first workforce.


About Alma
Alma’s mission is to simplify access to high-quality, affordable mental health care. By helping therapists accept insurance with ease, Alma empowers providers to grow their practices while offering in-network care to clients. Available in all 50 states, Alma supports a nationwide network of over 20,000 therapists. Backed by $220.5M in funding from leading investors, Alma has been named one of Inc’s Best Workplaces in 2022 and 2023.


Schedule

  • Remote-first (U.S., contiguous states)
  • Full-time role on Alma’s internal IT team
  • Cross-functional collaboration with Security, Operations, and company-wide stakeholders

What You’ll Do

  • Administer best-in-class hardware and software tools to empower Alma employees
  • Own and drive iterations of IT domains such as Requests, MDM, Patching, or Employee Lifecycle
  • Provide technical support across the organization for hardware and software issues
  • Educate employees on IT security and best practices
  • Collaborate with Security team on SOC 2 audits and HITRUST certifications
  • Participate in team meetings and contribute to ongoing IT process improvements

What You Need

  • 3+ years of experience in Technical Support, IT Infrastructure, or SaaS Operations
  • Strong troubleshooting skills in mixed-platform environments
  • Proficiency in administering company-wide SaaS tools (Google Workspace, Microsoft Office 365, Slack, Zoom, etc.)
  • Familiarity with MDM, APIs, GenAI, and cloud infrastructure (AWS, Azure, GCP)
  • Experience with procurement and supply chain for IT hardware
  • Curiosity about applying AI technologies to IT solutions
  • Passion for Alma’s mission of improving mental health access

Benefits

  • Remote-first company
  • Health, dental, and vision insurance (Aetna, MetLife), plus FSA and HSA plans
  • 401(k) with ADP
  • Monthly therapy, wellness, co-working, and WFH stipends
  • Financial wellness benefits through Northstar and BenefitHub
  • Pet discount program
  • One-time home office stipend
  • Comprehensive parental leave
  • 12 paid holidays plus 1 Alma Give Back Day
  • Flexible PTO
  • Salary range: $95,000–$120,000

Grow your IT career while helping Alma’s mission-driven team expand access to care nationwide.


Happy Hunting,
~Two Chicks…

APPLY HERE

Backend Engineer, Claims Reconciliation – Remote

Help build software that directly impacts mental health providers and the clients they serve. Alma is looking for a Backend Engineer to join the Claims Reconciliation team, where you’ll design and implement features that make insurance processing easier and more reliable.


About Alma
Alma’s mission is to simplify access to high-quality, affordable mental health care. By making it easy and financially rewarding for therapists to accept insurance, Alma supports over 20,000 providers across all 50 states. Providers gain access to tools that streamline business operations and improve client care. Alma has raised over $220M in funding and was named one of Inc’s Best Workplaces in 2022 and 2023.


Schedule

  • Remote-first (U.S., contiguous states)
  • Full-time engineering role
  • Collaborative work with Product, Design, and Operations teams

What You’ll Do

  • Build and scale backend features that support claims reconciliation at Alma
  • Gain a deep understanding of provider workflows and pain points
  • Design and implement maintainable systems using Python, Django, MySQL, and Linux
  • Collaborate with PMs, designers, and engineers to solve real-world problems
  • Develop and maintain automated testing for reliability
  • Ensure performance, scalability, and security across applications

What You Need

  • 1–3 years of backend engineering experience with proven history building products at scale
  • Proficiency in at least one common web framework (language-agnostic interviews)
  • Experience with Git and version control best practices
  • Strong understanding of automated testing platforms and unit tests
  • Collaborative, customer-focused approach to building software
  • Comfort with experimentation, iteration, and data-driven decision making

Benefits

  • Remote-first company
  • Health, dental, and vision insurance (Aetna, MetLife), plus FSA and HSA plans
  • 401(k) with ADP
  • Monthly therapy, wellness, co-working, and WFH stipends
  • Financial wellness benefits through Northstar and BenefitHub
  • Pet discount program
  • Comprehensive parental leave
  • 12 paid holidays plus 1 Alma Give Back Day
  • Flexible PTO
  • Salary range: $105,200–$150,200

Shape the technology that helps providers focus on care, not paperwork.

Grow your engineering career while making an impact in mental health access nationwide.


Happy Hunting,
~Two Chicks…

APPLY HERE

Senior Data Scientist – Remote

Join the team powering the largest health data network in the U.S. and help shape the future of machine learning in healthcare. Work on real NLP problems with tens of millions of patient records—all from the comfort of your home.

About Datavant
Datavant is the industry leader in health data exchange. Our platform enables secure, privacy-compliant data collaboration across hospitals, clinics, researchers, and government agencies. Trusted by over 350 real-world data partners, Datavant is on a mission to ensure every healthcare decision is informed by the right data at the right time.

Schedule

  • Remote
  • Full-time
  • U.S. based only
  • No visa sponsorship available

What You’ll Do

  • Build and deploy NLP and machine learning models using large-scale healthcare datasets
  • Drive the entire ML lifecycle: ideation, experimentation, deployment, and monitoring
  • Collaborate with product managers, engineers, and other data scientists across verticals
  • Perform data cleaning, error analysis, and pipeline optimization
  • Define performance metrics and develop continuous learning systems

What You Need

  • Advanced degree or equivalent experience in data science, statistics, or computer science
  • 4+ years of professional experience with ML in industry
  • Expertise in Python, PyTorch (preferred), TensorFlow, SQL, Numpy, Pandas
  • Strong background in NLP techniques (e.g., classification, NER, dependency parsing)
  • Familiarity with production ML workflows and deployment best practices
  • Self-driven with excellent time management and team collaboration skills

Benefits

  • Salary range: $136,000–$170,000/year
  • Company-provided equipment and remote flexibility
  • Medical, dental, vision, and 401(k) with match
  • Paid time off, parental leave, wellness benefits
  • Mission-driven team solving real problems with real data

If you’re excited about cutting-edge AI and want to impact lives through data, this is where your work will matter.

Help shape the future of healthcare—model by model.

Happy Hunting,
~Two Chicks…

APPLY HERE

Senior Software Engineer – Remote

Looking to lead meaningful projects in healthcare while working remotely with cutting-edge tech? Join Datavant as a Senior Software Engineer and help connect the world’s health data.

About Datavant
Datavant is the leading health data platform in the U.S., trusted by top healthcare providers, life sciences companies, and government agencies. We enable the secure, seamless exchange of over 60 million health records, helping power data-driven decisions that improve patient care. With offices across the globe and a mission-first mindset, Datavant engineers tackle some of healthcare’s most complex challenges every day.

Schedule

  • Remote
  • Full-time
  • U.S. based only
  • No employment sponsorship available

What You’ll Do

  • Lead design, development, and implementation of core health data products
  • Translate product requirements into robust technical solutions
  • Own multiple projects and guide other engineers through mentorship and code reviews
  • Collaborate with cross-functional teams to shape a scalable data ecosystem
  • Work with modern tech: Python, Java, React, TypeScript, Spark, AWS, Azure (bonus: Scala, Elasticsearch)

What You Need

  • 5+ years of experience writing production-level code across the full stack
  • Proven ability to design and scale data-driven systems and applications
  • Experience leading migrations, projects, or architecture-level decision-making
  • Strong communication and collaboration skills in fast-paced teams
  • Passion for healthcare innovation and improving patient outcomes

Benefits

  • Compensation range: $150,000–$285,000/year
  • Bonus eligibility and performance-based incentives
  • Medical, dental, vision, and 401(k) with employer match
  • Paid parental leave, generous PTO, and wellness support
  • High-impact projects in a mission-driven, inclusive culture

Make your next engineering move count—in a role that delivers both technical challenge and real-world impact.

This is where high-performing engineers come to drive change in healthcare.

Happy Hunting,
~Two Chicks…

APPLY HERE