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…