Staff Software Engineer

Student First Technologies; United States; Remote; USD 190,000 - 235,000; Full time

Benefits offered by this job

Health insurance (HSA/FSA options)

Dental & vision insurance

Life insurance

Short-term disability (fully paid)

Hospital & critical illness coverage

Job summary

Student First Technologies seeks a senior technical leader to set the direction for Theodore, its Rails monolith. You will guide architecture, ensure auditability of payments and ledgers, and modernize the platform while shipping real features for education programs nationwide.

On a small team, you’ll still write substantial code and mentor engineers, define standards for testing, security, and observability, and collaborate with product leadership to translate policy changes into scalable

Qualifications

• 8+ years building and operating production web applications (Rails).
• Lead major technical changes in a large, long-lived codebase without disrupting customers.
• Expert PostgreSQL knowledge: schema design, performance, migrations.
• Experience designing systems where payments, ledgers, or regulated data matter.
• Strong security judgement: PII, encryption at rest, access control, secrets management.
• Experience working on a remote team.

Responsibilities

• Lead the design of large, cross-cutting changes, and write the proposals and decision records that align the team.
• Own the integrity and auditability of financial systems: ledgers, holds, card authorizations, ACH settlement and reconciliation with banking partners.
• Define and drive modernization of a Rails monolith through projects and feature work.
• Set engineering standards for testing, code review, linting, security, observability and release documentation; build easy-to-follow tooling.
• Shape how the team uses AI coding tools to balance speed with ownership of code.
• Partner with product leadership to translate new state programs into technical plans.
• Mentor engineers through pairing, design review and code review.
• Serve as escalation point for the hardest production problems and drive follow-up.

Skills

Rails expertise

Production web apps

Remote team experience

Security and data protection

Communication skills

Payments/ledgers domain

Code review and testing

Tools

PostgreSQL

Heroku

AWS

GitHub Actions

Job description

Reports To: Chief Technology Officer
Location: Remote (United States; Eastern, Central, or Mountain time zone preferred)
Department: IT/Engineering
Classification: Full-Time, Exempt
Salary: $190,000–$235,000

About Student First Technologies

Student First Technologies builds Theodore, the platform behind education funding programs across the country. Scholarship-granting organizations, state agencies and nonprofits use it to run Education Savings Accounts, tax-credit scholarships and family grants, from application and eligibility through disbursement and reporting. Over more than a decade, Theodore has administered over $1.3 billion in education funds for more than 300,000 students and families in 15+ states.

We believe every child is unique and deserves an education tailored to their gifts and talents. Our software makes that possible at scale: it gives programs the guardrails the law requires, and gives families, schools and vendors an easy way to take part. When a family is approved for a scholarship or pays a tutor from their ESA, that runs through our code.

The work is growing. ESA programs are expanding fast, and the new federal scholarship tax credit takes effect January 1, 2027, bringing donor-funded scholarships to every state that opts in. Programs trust us with public funds and family data, so we hold a SOC 2 Type 2 certification and are audited every year. We’re a small engineering team behind a large, mature Ruby on Rails application that’s in active transition toward modern Rails conventions. That makes this a good place for engineers who like improving real systems while shipping real features.

The Role

You’ll set the technical direction for Theodore, our Rails monolith, which moves public education dollars for programs across the country. On a small team, you’ll still write a lot of code. Your biggest impact, though, is in the decisions that shape the next few years: how we model and audit money, how we keep each program’s data and rules separate, how we modernize legacy code, and how we raise the bar for every engineer on the team.

What You’ll Do

• Lead the design of large, cross-cutting changes, and write the proposals and decision records that get the team aligned on them.
• Own the integrity and auditability of our financial systems: ledgers, holds, card authorizations, ACH settlement and reconciliation with our banking partners.
• Define and drive the modernization of a mature Rails monolith, through dedicated projects and alongside feature work.
• Set engineering standards for testing, code review, linting, security, observability and release documentation, and build the tooling that makes them easy to follow.
• Shape how the team uses AI coding tools, so that speed never comes at the cost of human ownership of the code we ship.
• Partner with product leadership to turn new state programs and policy changes into realistic technical plans.
• Mentor engineers through pairing, design review and code review.
• Serve as the escalation point for the hardest production problems, and drive the follow-up so they don’t recur.

What You’ll Bring

• 8+ years building and operating production web applications, ideally with deep Ruby on Rails expertise across several major versions.
• A track record of leading major technical changes in a large, long-lived codebase, such as framework upgrades, data migrations or large refactors, without disrupting customers.
• Expert PostgreSQL knowledge: schema design, query performance, locking and zero-downtime migrations on large tables.
• Experience designing systems where correctness is non-negotiable, such as payments, ledgers, or regulated or audited data.
• Sound judgment on security: handling PII, encryption at rest, access control across many user roles, and secrets management.
• Experience working on a remote team.
• Strong written communication. You can explain a tradeoff to engineers, product managers and executives, and get a decision made.

Nice to Have

• Experience with card issuing, ACH or banking-as-a-service.
• Experience designing multi-tenant SaaS at the data and configuration level.
• Experience with government, edtech or other compliance-heavy domains (audits, SOC 2, FERPA).
• Experience modernizing a legacy front end (Bootstrap, jQuery, React) toward Hotwire and/or ReActionView.
• Experience leading a team’s adoption of AI coding tools while keeping engineers accountable for the code they ship.
• Experience with Heroku, AWS and GitHub Actions.

How We Work

• Every change goes through a pull request with review and a passing CI run.
• Work is tracked in Asana and discussed in Slack; we write things down.
• We ship small, safe changes frequently, and document every release for compliance.
• We use AI coding tools every day, but a person owns every line we ship. Whether an agent wrote the code or you did, you’re expected to understand it, test it and stand behind it.
• Fully remote within the United States. The team meets in person about once a quarter for a few days of team-building. Other travel, such as for a client meeting, is rare. The company pays for all work-related travel.
• Engineers are rarely expected to attend client meetings.
• Primarily computer-based work, including extended periods of reading code and documentation and participating in video meetings.
• We believe that healthy conflict produces great work, and strive to create opportunities for everyone, regardless of role or seniority, to share their knowledge and perspective toward that end.
• Flexible time off with no set cap. We want you to take the time you need to rest and recharge.
• Health insurance, including HSA- and FSA-eligible plan options.
• Dental and vision insurance.
• Life insurance.
• Short-term disability, fully paid by the company.
• Hospital, critical illness and accident insurance.

Student First Technologies is an equal opportunity employer. We do not discriminate on the basis of race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, veteran status or any other protected characteristic. This description reflects the role’s current responsibilities, which may change as the company evolves.