by Terrance Ellis | Oct 10, 2025 | Uncategorized
Lead a high-performing engineering squad shipping secure, scalable web apps used by families and financial advisors nationwide. If you balance hands-on coding with people leadership—and you’re excited about AI-accelerated workflows—this remote role is built for you.
About Trust & Will
Founded in 2017, Trust & Will is the leading digital estate planning platform, trusted by 1M+ users. As a certified B Corporation, the team makes legacy planning accessible with attorney-approved documents and advisor partnerships that put families first. The company is remote-first and growing quickly across the U.S.
Schedule
- Remote-first within the U.S. (CA, CO, FL, GA, ID, IL, MD, NJ, NY, NC, PA, TX, VT)
- Full-time; cross-functional collaboration with Product and Design
- Flexible hours with a family-friendly culture
What You’ll Do
- Manage and mentor a team of 3–5 engineers; run 1:1s, feedback loops, growth plans, and onboarding
- Drive delivery within a product squad: set goals/roadmaps, balance IC work (up to ~50%) with leadership
- Own technical strategy and architecture aligned to long-term business goals
- Champion secure-by-design practices, observability, performance, and reliability
- Implement AI tooling and automation to improve developer velocity and code quality
- Lead code reviews, pair programming, and continuous improvement on CI/CD and testing
- Track and improve engineering metrics (quality, velocity, reliability) to guide decisions
What You Need
- 7+ years software development; 2+ years in an engineering leadership/management role
- Advanced React, TypeScript, API design, and data modeling (relational + NoSQL)
- Experience building and maintaining cloud-native applications
- Strong secure coding, threat modeling, and compliance awareness (GDPR, SOC2)
- DevOps mindset with CI/CD pipelines and modern testing frameworks
- Proficiency with AI-assisted development (e.g., GitHub Copilot, Cursor, RooCode, RooCline)
- Proven ability to mentor, align stakeholders, and deliver in fast-moving environments
Bonus Points
- Infrastructure-as-code (CloudFormation, AWS CDK, Pulumi, or Terraform)
- High-growth startup leadership experience
- Docker/Kubernetes or other orchestration tooling; pair programming practices
- Open-source contributions or active developer community involvement
Benefits
- Salary range: $171,000–$220,000 + equity
- Medical, dental, vision, life insurance, generous parental leave
- Financial wellness (equity & tax advisory, financial coach, employer-sponsored 401k)
- Flexible PTO, company holidays, monthly friends & family day, volunteer time off
- $500 home office stipend + Apple accessories; optional events & travel; learning reimbursements
Roles like this move quickly—raise your hand and get in the mix.
Build the team, shape the platform, and help families protect their legacies.
Happy Hunting,
~Two Chicks…
by Terrance Ellis | Oct 10, 2025 | Uncategorized
Build high-impact products at the intersection of React/Next.js, TypeScript/Node.js, and AWS—while shaping how AI powers a modern estate-planning platform. You’ll lead system design, mentor engineers, and ship secure, scalable features that elevate the advisor experience.
About Trust & Will
Founded in 2017, Trust & Will is the leading digital estate planning platform, trusted by 1M+ users. As a certified B Corporation, the team makes legacy planning accessible and affordable with attorney-approved documents and advisor partnerships that put families first.
Schedule
- Remote-first within the U.S. (CA, CO, FL, GA, ID, IL, MD, NJ, NY, NC, PA, TX, VT)
- Full-time with cross-squad collaboration
- Flexible hours; family-friendly culture
What You’ll Do
- Build and enhance the advisor-facing platform: integrations, AI features, and document ingestion/parsing
- Own reliability and security for sensitive operations (member data deletion, pen-test remediations, access reviews)
- Integrate the advisor platform with Planning, Admin, and Consumer squads for a unified experience
- Drive Platform Expansion initiatives that boost satisfaction, engagement, retention, and revenue
- Lead system design and implementation: secure, scalable applications and services with strong test coverage
- Champion observability, performance, CI/CD, and code quality; reduce technical debt with ongoing refactors
- Apply AI strategically to improve developer efficiency, automate workflows, and strengthen reliability
- Mentor engineers; communicate complex topics clearly to technical and non-technical stakeholders
What You Need
- 7+ years on high-performing engineering teams
- Advanced frontend expertise (React, TypeScript), API design, and data modeling (MongoDB, Postgres)
- AWS experience with IaC (CloudFormation, CDK); strong DevOps/TDD and CI/CD practices
- Proficiency in secure-by-design principles; compliance awareness (GDPR, SOC2)
- Strength in debugging, performance tuning, distributed tracing, and log correlation
- Hands-on with AI coding assistants (e.g., GitHub Copilot, Cursor, RooCode, RooCline) and metrics-driven decision-making
Benefits
- Salary range: $166,000–$215,000 + equity
- Medical, dental, vision, life, generous parental leave
- 401k with employer match; equity & tax advisory; financial coaching
- Flexible PTO, holidays, monthly friends & family day, volunteer time off
- $500 home office stipend + Apple accessories; optional events & travel; learning reimbursements
Roles like this move quickly—signal interest and get on the radar.
Lead with impact, scale what matters, and help families protect their legacies.
Happy Hunting,
~Two Chicks…
by Terrance Ellis | Oct 10, 2025 | Uncategorized
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…
by Terrance Ellis | Oct 9, 2025 | Uncategorized
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…
by Terrance Ellis | Oct 9, 2025 | Uncategorized
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…
