Staff Cloud Engineer – Remote

Bring your expertise in cloud infrastructure, DevOps, and secure system design to a mission-driven company reshaping estate planning. This is a high-impact role where you’ll architect resilient platforms, mentor teams, and drive innovation—including AI integration—across engineering.

About Trust & Will
Founded in 2017, Trust & Will is the leading digital estate planning platform, trusted by over one million users. As a certified B Corporation, the company provides modern, accessible solutions that help families protect their legacies with attorney-approved documents, while partnering with advisors and institutions to make legacy planning more inclusive and affordable.

Schedule

  • Remote-first role, U.S. based (CA, CO, FL, GA, ID, IL, MD, NJ, NY, NC, PA, TX, VT)
  • Full-time position with cross-functional collaboration
  • Flexible schedule with family-friendly environment

What You’ll Do

  • Serve as the center of excellence for cloud infrastructure, DevOps, and DevSecOps practices
  • Architect and evolve secure, scalable, and self-healing AWS platforms
  • Build and maintain CI/CD pipelines, cloud tooling, and developer enablement systems
  • Lead resilience engineering, incident readiness, and observability culture across teams
  • Mentor engineers in cloud architecture, infra-as-code, and performance optimization
  • Influence technical vision, shaping how AI integrates into development processes

What You Need

  • 7+ years in software engineering, with strong cloud-native and infrastructure automation experience
  • 2+ years contributing to product features, not just infra tools
  • Deep AWS expertise and Infrastructure-as-Code skills (Terraform, CDK, etc.)
  • Proven track record building secure, cost-efficient, and observable platforms
  • Experience scaling CI/CD pipelines, testing strategies, and monitoring systems
  • Strong grasp of platform security, IAM, and threat modeling

Benefits

  • Salary range: $187,000–$220,000 + equity package
  • Medical, dental, vision, life insurance, and generous parental leave
  • Employer-matched 401k, financial wellness coaching, equity & tax advisory support
  • Flexible PTO, holidays, and volunteer time off
  • Monthly “friends & family” day + family-friendly work culture
  • $500 home office stipend + Apple gear, plus optional company events and travel

Applications are open—step into a role where your cloud expertise shapes the future of a high-growth, mission-driven platform.

Scale impact, secure systems, and mentor teams—all while helping families protect their legacies.

Happy Hunting,
~Two Chicks…

APPLY HERE

Cybersecurity Engineer – Remote

Protect critical data and infrastructure while shaping enterprise security strategies. Modivcare is hiring a Cybersecurity Engineer III to lead security initiatives, monitor threats, and safeguard systems across the organization.

About Modivcare
Modivcare is transforming healthcare access with non-emergency medical transportation, personal care, and home care solutions. Their mission is to connect underserved populations to care, improve outcomes, and protect the systems that make this work possible.

Schedule

  • Full-time, remote role (occasional business travel may be required)
  • Posted 16 days ago – applications are reviewed as received
  • Collaboration across IT, operations, and leadership teams

What You’ll Do

  • Lead development and execution of cybersecurity strategies
  • Implement and oversee advanced security controls and policies
  • Monitor, troubleshoot, and respond to security incidents using threat intelligence
  • Conduct regular risk assessments and compliance checks (ISO 27001, NIST, etc.)
  • Provide expert-level troubleshooting for complex network/security issues
  • Oversee change management processes tied to security measures
  • Lead projects, enhance reporting, and mentor team members

What You Need

  • Bachelor’s degree in Computer Science, IT, or related field (or equivalent experience)
  • 5+ years of experience in cybersecurity roles
  • Advanced knowledge of security technologies, cloud security, and virtualization
  • Familiarity with compliance frameworks (ISO 27001, NIST)
  • Relevant certifications (CompTIA Security+, CEH, CISSP) a plus
  • Strong analytical, communication, and leadership skills
  • Proven ability to manage projects and respond to complex security challenges

Benefits

  • Salary range: $81,000–$111,400 annually
  • Medical, Dental, and Vision insurance
  • Employer-paid life insurance & AD&D
  • 401(k) with company match
  • Paid Time Off + Paid Parental Leave
  • Short- and Long-Term Disability
  • Tuition reimbursement & employee discounts

This opportunity will close quickly—early applications encouraged.

Step into a leadership role that strengthens security and supports access to life-saving care.

Happy Hunting,
~Two Chicks…

APPLY HERE

Graphic Designer – Remote

Bring creative ideas to life while shaping visuals that make a real impact. Modivcare is hiring a Graphic Designer III to produce compelling, brand-aligned graphics for proposals, reports, websites, and marketing initiatives.

About Modivcare
Modivcare connects people with care through non-emergency medical transportation, personal care, and home care services. Their mission is to transform access to healthcare for underserved communities, reducing barriers and improving outcomes nationwide.

Schedule

  • Full-time, remote role
  • Cross-functional collaboration with marketing, creative, and operations teams
  • Posted 7 days ago – applications reviewed as received

What You’ll Do

  • Design technical and non-technical visuals for proposals, reports, websites, and presentations
  • Create original graphics and refine existing layouts to meet brand standards
  • Partner with subject matter experts to conceptualize and render custom visuals
  • Maintain the company’s image library and ensure consistency across deliverables
  • Support marketing and proposal initiatives with layouts, infographics, and web content

What You Need

  • Bachelor’s degree in Graphic Design
  • 5+ years of experience in business proposal graphics, web design, and marketing communications
  • Advanced proficiency in Adobe Creative Suite (Photoshop, InDesign, Illustrator) and HTML
  • Strong understanding of web media (audio, video, animation) and content management systems
  • Proven success designing healthcare service proposals (Medicaid/managed care a plus)
  • Excellent communication, attention to detail, and ability to work independently

Benefits

  • Salary range: $69,900–$94,400 annually
  • Medical, Dental, and Vision insurance
  • Employer-paid life insurance & AD&D
  • 401(k) with company match
  • Paid Time Off + Paid Parental Leave
  • Short- and Long-Term Disability
  • Tuition reimbursement & employee discounts

This position will only remain open for a limited posting window—early applications encouraged.

Use your design expertise to elevate proposals and campaigns that help people access essential care.

Happy Hunting,
~Two Chicks…

APPLY HERE

Intermediate Platform Developer – Remote

Help build and scale platform infrastructure for a global technology provider. ScanSource is looking for an Intermediate Platform Developer to design, develop, and maintain microservices and cloud systems that support reliable, secure business operations.

About ScanSource
ScanSource delivers top-tier technology solutions while supporting the teams that power them. With a focus on scalability, innovation, and teamwork, ScanSource builds robust platforms that drive success across industries. Their commitment extends equally to customers and employees—ensuring reliable systems and a supportive workplace.

Schedule

  • Full-time, remote role based in Canada
  • Locations: Ontario (Toronto) and additional provinces
  • On-call rotations required for system support

What You’ll Do

  • Design, develop, and maintain platform infrastructure and applications in T-SQL, C#, Python, and PowerShell
  • Administer AWS services (EC2, Lambda, ECS, ECR, VPC, Redshift, CloudFormation, CloudWatch, EventBridge, and more)
  • Diagnose and resolve system and security issues promptly
  • Automate tasks with shell scripts, TypeScript, and GitHub Actions
  • Collaborate with cross-functional teams to improve scalability and reliability
  • Participate in code reviews, document operations, and share best practices
  • Maintain application observability and performance

What You Need

  • 3+ years of hands-on development experience
  • Fluent in T-SQL with strong PowerShell skills
  • Proficient in AWS, Git/GitHub, C#, Python, and JavaScript/TypeScript
  • Knowledge of web application security best practices
  • Familiarity with Agile methodologies

Benefits

  • Salary range: $94,000–$104,000 CAD annually (based on experience and skills)
  • Medical, dental, and vision coverage
  • Life insurance and 401(k) with matching provision
  • 128 hours paid time off per year + 10 paid company holidays

This role is in high demand—applications are reviewed as they come in.

Shape the future of cloud platforms with ScanSource and take your career to the next level.

Happy Hunting,
~Two Chicks…

APPLY HERE

Senior Platform Engineer – Remote

Build the infrastructure powering life-saving virtual mental health care. Charlie Health is hiring a Senior Platform Engineer to design, optimize, and scale the systems that keep care accessible and reliable for clients nationwide.

About Charlie Health
Charlie Health delivers personalized, virtual behavioral healthcare for people facing complex mental health needs. Their mission is to break down barriers to care by combining evidence-based treatment, community connection, and innovative technology. Over 90% of clients report improvement in their most challenging symptoms.

Schedule

  • Remote U.S.-based role (hybrid required if within commuting distance of NYC office)
  • Core collaboration hours: 12pm–5pm EST
  • Teams work in Scrumban-style 2-week sprints

What You’ll Do

  • Design, build, and maintain AWS infrastructure using Terraform/OpenTofu and Terragrunt
  • Develop core services in Python, Golang, and Typescript
  • Improve CI/CD pipelines with GitHub Actions for faster, more reliable deployments
  • Automate provisioning, monitoring, and scaling across systems
  • Implement security best practices (IAM, networking, HIPAA compliance)
  • Mentor engineers and drive improvements in scalability, reliability, and developer experience
  • Participate in on-call rotation to ensure system availability

What You Need

  • 3+ years in Platform, DevOps, SRE, or Cloud Engineering
  • 2+ years writing production-level backend code
  • Strong AWS expertise (ECS Fargate, Lambda, Aurora, SQS, etc.)
  • Proficiency with infrastructure as code (Terraform/OpenTofu)
  • Experience with CI/CD tools (GitHub Actions, GitLab CI, Jenkins)
  • Hands-on experience with Docker, monitoring tools (Datadog, Prometheus, Grafana), and troubleshooting distributed systems
  • Ability to deliver incremental value while planning for long-term improvements

Nice-to-Have

  • Experience with cloud migrations or monolith-to-microservices transitions
  • Linux system administration and security best practices
  • Familiarity with AI-enabled developer productivity tooling

Benefits

  • Base compensation: $150,000–$200,000 annually (location and experience considered)
  • Stock options and discretionary bonuses
  • Comprehensive health and wellness benefits

Opportunities at this level don’t last long—apply while the role is open.

Help reshape the future of mental healthcare with scalable, secure technology that makes care possible.

Happy Hunting,
~Two Chicks…

APPLY HERE

Software Engineer – Remote

Help build the platform powering digital onboarding for banks and financial institutions worldwide. This role gives you the chance to tackle massive-scale engineering challenges while shaping the infrastructure millions rely on.

About Prelim
Prelim is a remote-first fintech startup revolutionizing how banks onboard and serve their customers. From deposit accounts to treasury services, our platform powers financial institutions of every size. We’re doubling revenue year-over-year while staying profitable, offering engineers the opportunity to build meaningful systems in a fast-paced, growth-driven culture.

Schedule

  • Full-time, remote-first role
  • Based in the U.S. (locations: New York, San Francisco, Atlanta, Austin, Boston, Chicago, Seattle)
  • Must be legally authorized to work in the United States

What You’ll Do

  • Architect and build features across the stack: React, Node.js, and PostgreSQL
  • Design onboarding flows for deposits, loans, treasury services, credit cards, and emerging products
  • Integrate with core banking systems, compliance tools, and legacy infrastructure
  • Solve challenges around multi-tenant architecture, real-time processing, and reliability at scale
  • Work directly with banks to translate complex requirements into technical solutions
  • Build both customer-facing applications and internal tools for bank employees
  • Own performance, scalability, and reliability for millions of transactions

What You Need

  • Experience with modern web tech (React, Node.js, PostgreSQL preferred)
  • Strong system design skills and familiarity with scalable architectures
  • Ability to balance technical excellence with business impact
  • Clear communication skills for technical and non-technical stakeholders
  • Willingness to work directly with customers and iterate fast
  • Passion for solving complex problems and shaping technical strategy

Compensation & Benefits

  • Salary range: $110K – $140K
  • Equity offered
  • Remote-first company with career growth and promotion from within
  • Inclusive, mission-driven culture focused on accessibility in banking

Applications are reviewed on a rolling basis—early applications encouraged.

Join Prelim and help engineer the future of digital banking accessibility.

Happy Hunting,
~Two Chicks…

APPLY HERE