[Hiring] Engineering Technical Lead @Fearless

Role Description

At Fearless, we are seeking an Engineering Tech Lead as part of our Senior Consultant, Engineering & Technical Services career path to lead the technical design and delivery of a new student-facing web portal for a public-sector education client. This portal will enable students to securely review college admissions offers, compare financial aid packages, and confirm enrollment, while giving agency staff tools to manage admissions data and securely transmit enrollment decisions to participating institutions. This is a fully remote role with periodic travel to Massachusetts for client working sessions.

• Lead the technical design and architecture of a modular, cloud-native web portal on AWS, built to add new services over time.
• Build and lead full-stack development with TypeScript/Node, React, PostgreSQL, and REST APIs.
• Define and implement infrastructure as code using Terraform, CI/CD pipelines, and automated deployments across development, test, staging, and production environments.
• Design and build integrations with government identity platforms using OpenID Connect (OIDC).
• Build integrations for loading, validating, and reprocessing admissions data files.
• Design secure data exchange with colleges through contract-first API, secure file transfer, or CRM integration.
• Lead the team's AI-assisted development practice, using agentic AI tools to accelerate requirements refinement, prototyping, coding, testing, and documentation with human review and traceability.
• Work with stakeholders to translate high-level business needs into detailed technical requirements and build working prototypes for iterative review.
• Build security and privacy into the platform from the start, including Zero Trust API design, token-based authentication, role-based access control, encryption, audit logging, and secrets management.
• Build automated accessibility checks into the pipeline and work closely with design and QA on manual and assistive technology testing.
• Plan for high availability, resilience, and scale to support traffic spikes during student enrollment periods.
• Identify technical risks, dependencies, and scope issues proactively on a fixed-price engagement.
• Produce architecture and operational documentation and train client technical staff to ensure long-term ownership of the solution.
• Contribute to shaping the product roadmap beyond the MVP and participate in client presentations and demos.

Qualifications

• Minimum of 7 years of experience in software engineering, technical leadership, or related roles.
• Bachelor's degree in Computer Science, Engineering, or related field, or equivalent work experience.
• Demonstrated experience delivering production software using agentic AI coding tools, with tests written first, human-in-the-loop review, traceability, and quality controls.
• Proven technical leadership experience leading development teams, defining architecture, and owning end-to-end technical delivery.
• Strong full-stack development background with TypeScript/Node, React, and REST API design and implementation.
• Experience designing and deploying applications on AWS using containers (ECS Fargate), serverless functions and queues (Lambda, SQS), and managed PostgreSQL (RDS).
• Proficiency in infrastructure as code with Terraform and building CI/CD pipelines for automated deployments.
• Experience with ORM layers such as Prisma or Sequelize.
• Deep knowledge of secure web application development, including single sign-on, token-based API authentication with OIDC, token-based API authentication using JWT and OAuth client credentials, and role-based access control.
• Hands-on background in OWASP Top Ten protections and securing applications handling sensitive personal data.
• Proven ability to deliver accessible web applications meeting WCAG standards and mobile-responsive design requirements.
• Experience with Agile, iterative delivery, and conducting regular stakeholder demos.
• Ability to explain technical trade-offs clearly to non-technical stakeholders and lead live working sessions with client staff.
• Must be based in and work from the United States.
• Must be able to pass a criminal background check.

Requirements

• Hands-on experience designing and shipping agentic AI solutions, not just using AI tools.
• Background in delivering student-facing digital services or education technology platforms.
• Experience building custom software for government, education, or other public-sector clients.
• Track record of delivering public-facing portals or transactional applications at scale.
• Familiarity with FERPA and other student data privacy requirements.
• Knowledge of Zero Trust architecture per NIST SP 800-207, rate limiting, and API traffic management.
• Experience integrating with state or government identity platforms.
• Background in design systems used in government digital services.
• Data integration experience with file processing pipelines, data validation, error handling, or integrations with CRMs or information systems.
• Familiarity with responsible AI frameworks such as the NIST AI Risk Management Framework.

Benefits

• Flexible, life-friendly schedules.
• 100% coverage for our medical HSA plan + HSA contributions.
• Dental & vision covered 100% for you and your dependents.
• Competitive premiums for HMO/PPO and dependent coverage.
• 401(k) with 4% match & immediate vesting.
• Paid Parental Leave and 12 weeks paid FMLA.
• Generous PTO, 11 Federal Holidays, a Birthday Holiday, and Sick Leave.
• Up to 15 days for Jury Duty and Bereavement Leave.
• Education, wellness, and tech allowances.
• Referral bonus: $6K–$12K for each successful referral.
• Pet insurance & discount plans.
• Employee Assistance Program (EAP).
• Legal support, life insurance, disability coverage.
• Performance-Based Bonuses.