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…
by Terrance Ellis | Oct 9, 2025 | Uncategorized
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…
