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Trail of Bits

•
125 employees
Fully Remote

Trail of Bits is a security engineering firm that audits code for some of the world's most targeted organizations and approaches the work the way an attacker would. Founded in 2012 by three people with no investment capital, the firm publishes research and builds open-source security tools across software security, reverse engineering, cryptography, blockchain and AI/ML.

Trail of Bits's Remote Policy

Trail of Bits is remote-first. Its team page says: "Remote first, always. While the rest of the industry calls people back to the office, we believe the best work happens where people work best." The careers page FAQ adds: "All roles are remote-friendly and we work across multiple time zones. Some positions list a primary city for tax or in-person reasons, but day-to-day work is remote."

On working hours, the same FAQ says: "Flexible, with enough overlap across time zones for teams to collaborate. Core hours are set per role and team, and we discuss them during the interview."

Benefits & Perks

Health & Wellness

7

Health Insurance

Health insurance is fully company-paid, with no monthly premiums for employees. The health package also includes access to HealthAdvocate, Teladoc and One Medical.

Dental Insurance

Trail of Bits pays the full premium for employee dental insurance.

Vision Insurance

Trail of Bits covers vision insurance in full, alongside its health and dental plans.

Life Insurance

Life insurance is provided at no cost to employees.

Disability Insurance

Disability coverage is part of the fully company-paid insurance package.

Flexible Spending Account (FSA)

A flexible spending account is available through ConnectYourCare.

Fitness Stipend

Fitness stipends help employees cover the cost of staying active.

Financial

5

401(k) / Retirement Plan

US employees can save for retirement through a 401(k) plan that includes a company match.

401(k) Match

Trail of Bits provides a 401(k) match of 5% of base salary.

Performance Bonus

Trail of Bits pays end-of-year performance bonuses, plus ongoing bonuses for work such as public presentations, blog posts and continuing education.

Relocation Assistance

US employees who choose to move to New York City receive $10,000 in relocation assistance. Relocating is optional; the team is remote-first.

Commuter Benefits

Trail of Bits offers commuter benefits alongside its FSA and fitness stipends.

Time Off

3

PTO / Vacation

Employees receive 20 days (four weeks) of paid vacation a year, with flexibility to take more.

Paid Holidays

Trail of Bits observes 15 paid company holidays each year.

Flexible Schedule

Working hours are flexible, with core hours set per role and team so there is enough overlap across time zones to collaborate.

Remote & Equipment

2

Company Offsites / Retreats

Annual off-sites bring the team together to build and learn, and company-sponsored all-team celebrations include travel and accommodation.

Home Office Stipend

Employees receive a $1,000 work-from-home stipend to create a comfortable and productive home office.

Family & Care

2

Fertility Benefits

Employees have access to Kindbody for gynecology and fertility care.

Parental Leave

New parents receive four months of paid parental leave.

Professional Growth

3

Learning & Development Budget

Employees receive an annual $750 learning and development stipend and dedicated time for internal research and tool-building. Trail of Bits also runs training sessions, bi-weekly lunch-and-learns and a paper reading group.

Conference Attendance

Trail of Bits supports employees attending conferences, and its culture rewards visible public output such as talks and publications.

Mentorship Program

Trail of Bits' apprenticeship pairs new engineers one-on-one with a senior mentor on real audits.

Culture & Perks

3

Employee Referral Bonus

Employees earn bonuses for referring candidates and helping with recruiting.

Team Events & Social Budget

Company and team outings run alongside virtual events for the distributed team.

Charity Matching

Trail of Bits matches employees' charitable contributions up to $2,000 a year.

Tech Stack

JavaScript & Libraries

TypeScript
JavaScript
React
Astro
Styled Components
Sentry

Frameworks

Python
Cpp
C
Go
Rust
Kotlin
Solidity
Haskell

Databases

PostgreSQL
RocksDB
SQLite

Infrastructure

AWS
Linux
GitHub
fly.io

CMS & Content

Hugo
Webflow

Hosting

Microsoft Azure
Vercel

Sales & CRM

HubSpot

Integrations

PyTorch
LangChain
OpenAI
Anthropic
Slack
DocuSign
1Password

Media

Google Meet
36 technologies detected

Why Trail of Bits

Trail of Bits took the $3M second-place prize at the DARPA AIxCC finals in 2025, and it works with OpenAI on Patch the Planet, an open-source security initiative. CEO and co-founder Dan Guido describes how the firm chooses its engagements: "We take real pride in only accepting work we find genuinely interesting, engaging, and hard."

Client audits are only part of the job. The firm says it runs "lower utilization than the industry so engineers get dedicated time to build tools and research, with bi-weekly lunch-and-learns and a paper reading group." Its apprenticeship program pairs new engineers one-on-one with a senior mentor on real audits. In the company's words, its culture "rewards curiosity, deep technical work, and visible public output," and annual off-sites bring the whole team together.

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