The Role

Pilot is hiring a Software Engineer to join our Bookkeeping Automation team.

This team builds the systems and tooling that power high-quality bookkeeping, including secure and reliable agentic workflows, integrations with third-party systems, and the infrastructure needed to operate them effectively in production. We focus on improving the accuracy, efficiency, and reliability of bookkeeping at scale.

As a Software Engineer on the team, you’ll build product and platform capabilities that help transform financial data into dependable bookkeeping outcomes. You’ll work closely with engineers, product managers, designers, and operational experts to ship systems that are practical, measurable, and robust.

This is a strong fit for someone who enjoys building real-world automation systems and is excited about the engineering challenges that come with agentic workflows, including orchestration, security, evaluation and observability.

Pilot’s backend is written in fully typed Python, and our frontend stack includes JavaScript, TypeScript, and Vue.js. We use Terraform to manage infrastructure, deploy containerized services on AWS, and rely on Postgres and modern observability tooling in production.

Location: San Francisco, CA (3 days/week in office - Mondays, Tuesdays, and Thursdays).

Key Responsibilities

• Build, test, and deploy software in a continuous manner
• Develop systems that power bookkeeping automation, including agentic workflows and integrations with third-party platforms
• Design and implement reliable workflow orchestration across services, tools, and operational processes
• Build observability into automation systems so teams can understand performance, investigate failures, and improve quality over time
• Contribute to the security and reliability of systems that handle sensitive financial data and operational decisions
• Help design and improve evaluation frameworks that measure workflow quality, correctness, and business impact
• Partner with PMs, designers, and cross-functional stakeholders to turn ambiguous problems into practical solutions
• Write clear technical designs, contribute thoughtful code reviews, and maintain high engineering standards
• Investigate production issues, improve system reliability, and support services as needed
• Ability to work in our San Francisco office Mondays, Tuesdays, and Thursdays

About You

Even if you don’t have experience with every part of our stack, we’d still love to talk.

We’re looking for someone who has:

• 3+ years of experience as a software engineer
• Experience building production software and shipping customer-facing or business-critical systems
• Strong coding fundamentals and the ability to write clean, maintainable, well-tested code
• Good product and systems judgment, especially in ambiguous or evolving problem spaces
• Strong communication skills and comfort working cross-functionally
• Interest in building automation systems that are reliable, observable, and secure
• A thoughtful approach to building systems that are trustworthy, practical, and effective in production

Nice to Have

• Experience with Python in production
• Experience with workflow orchestration, automation platforms, or distributed systems
• Familiarity with agentic or AI-assisted systems in production environments
• Experience building observability, alerting, or operational debugging tools
• Experience with system security, permissions, or handling sensitive data
• Experience building evaluation or quality measurement frameworks
• Experience with fintech, accounting, or financial operations tooling
• Experience integrating with third-party APIs and external systems

Why This Role Matters

The Bookkeeping Automation team is building systems that expand what Pilot can automate while preserving quality, trust, and control. Agentic workflows are only valuable when they are observable, secure, measurable, and reliable in production. This role is an opportunity to shape those foundations and help define how modern automation can improve financial operations at scale.

About Pilot

Pilot launched in 2017 to bring the back office into the modern era. Pilot provides small businesses with dedicated finance experts - which Pilot hires as full-time, U.S.-based employees - who learn the ins-and-outs of their business. Pilot integrates directly with the billing, banking, expense, and payroll systems customers already use. With a special blend of custom software and expert bookkeepers, Pilot delivers accurate, consistent bookkeeping and financial management and tax services that give entrepreneurs the freedom to focus on their business.

Pilot has over 3,000 customers and has raised over $170 million in financing from Sequoia, Index Ventures, Stripe, Bezos Expeditions, and Whale Rock.  Our investors also include a long list of world-class entrepreneurs, including Patrick and John Collison, Drew Houston, and Diane Greene.  Our most recent funding round doubled our valuation to $1.2 billion – Meet Fintech’s Newest Unicorn.

Why Pilot?

• We invest in our employees’ development and happiness because our employees are the keys to our success and ensuring happy customers
• The opportunity to join a seasoned founding team that has led companies through two prior successful startups and acquisitions (by Oracle and Dropbox).
• Flexible vacation/time-off policy
• All federal holidays are observed
• Competitive benefits package including additional wellness benefits
• Parental leave for birthing or non-birthing parents – 100% pay for 12 weeks
• 401(k) plan

The base pay range target for the role seniority described in this job description is $138,000 - $186,000 in San Francisco, CA. Final offer amounts depend on multiple factors such as candidate experience and expertise, geographic location, total compensation, and market data. In addition to cash pay, full-time regular positions are eligible for equity, 401(k), health benefits, and other benefits; some of these benefits may be available for part-time or temporary positions.

Pilot commits to provide a work environment free of discrimination and harassment, as well as equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or Veteran status. We also consider qualified applicants regardless of criminal histories, consistent with legal requirements. You may view all of Pilot’s recruiting notices here, including our EEO policy, information about requesting a reasonable accommodation in the job application process, recruitment agency policy, recruitment scam notice, and important E-Verify information. You may view our job candidate privacy policy here.

The Role

Pilot is a successful startup hiring a senior engineer on our Infrastructure team.

All of our teams have unique charters to collectively build the software, services and systems that enable Pilot to deliver a high-quality experience, profitably, at scale. The Infrastructure team accelerates the rest of R&D by providing scalable, efficient, and high-quality building blocks for product development, while also ensuring we can support business growth in a secure and reliable way. The team is responsible for building simple, scalable abstractions and owns the full Infrastructure stack from the AWS infra that our systems run on to the product platform that our product engineers use. 

Pilot’s aim is to provide our customers with the same superpowers as large companies with full finance teams — superpowers that include having a deep understanding of financial health of the business, the machinery to constantly improve it, and the predictive abilities to thoughtfully plan for the future. We do this at a fraction of the cost a large company would pay for this, by delivering these capabilities through powerful software. 

Pilot’s backend is written in fully typed modern Python, and our frontend is JavaScript, TypeScript, and Vue.js. We use Terraform to manage our production infrastructure, and deploy Docker containers to ECS. AWS CodeDeploy powers our deployments and we rely on Honeycomb for our monitoring and Postgres as our database.

We're looking for senior infra engineers who are generalists comfortable working across the full infrastructure stack, with a product platform bent and full stack familiarity.

Key Responsibilities 

• Building, testing and deploying software in a continuous manner (we deploy daily or more often).
• Creating and contributing to technical specs and testing/rollout plans.
• Working with internal customers and stakeholders to ensure we’re solving the right problems.
• Mentoring and sponsoring your teammates to help them grow.
• Working across teams to shape the future of engineering at Pilot.
• Supporting your software and services as required.

About you

Even if you don’t have experience with the specific technologies in our stack, we’d love to talk to you! Our requirements are:

• 5+ years of experience as a software engineer
• Experience with Python in production
• Experience with common infrastructure tooling such as Terraform, AWS
• Familiarity with the frontend ecosystem and frontend infrastructure tools
• Able to work collaboratively across functions
• Strong written, verbal, and technical communication skills
• Able to write well-structured, well-tested, and maintainable code
• Demonstrated ability to mentor and teach others
• This position is only available for remote employment in the United States in the following states: CA, GA, NY, NC, TN, TX, and WA

About Pilot

Pilot launched in 2017 to bring the back office into the modern era. Pilot provides small businesses with dedicated finance experts - which Pilot hires as full-time, U.S.-based employees - who learn the ins-and-outs of their business. Pilot integrates directly with the billing, banking, expense, and payroll systems customers already use. With a special blend of custom software and expert bookkeepers, Pilot delivers accurate, consistent bookkeeping and financial management and tax services that give entrepreneurs the freedom to focus on their business.

Pilot has over 3,000 customers and has raised over $170 million in financing from Sequoia, Index Ventures, Stripe, Bezos Expeditions, and Whale Rock.  Our investors also include a long list of world-class entrepreneurs, including Patrick and John Collison, Drew Houston, and Diane Greene.  Our most recent funding round doubled our valuation to $1.2 billion – Meet Fintech’s Newest Unicorn.

Why Pilot?

• We invest in our employees’ development and happiness because our employees are the keys to our success and ensuring happy customers
• The opportunity to join a seasoned founding team that has led companies through two prior successful startups and acquisitions (by Oracle and Dropbox).
• Flexible vacation/time-off policy
• All federal holidays are observed
• Competitive benefits package including wellness benefits such as One Medical, Calm, Carrot Pro and Fetch
• Parental leave for birthing or non-birthing parents – 100% pay for 12 weeks
• 401(k) plan

The base pay range target for the role seniority described in this job description is $133,000 - $240,000 in most remote locations, and between $166,000 - $267,000 in San Francisco, CA and New York City, NY. Final offer amounts depend on multiple factors such as candidate experience and expertise, geographic location, total compensation, and market data. In addition to cash pay, full-time regular positions are eligible for equity, 401(k), health benefits, and other benefits; some of these benefits may be available for part-time or temporary positions.

Pilot commits to provide a work environment free of discrimination and harassment, as well as equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or Veteran status. We also consider qualified applicants regardless of criminal histories, consistent with legal requirements. You may view all of Pilot’s recruiting notices here, including our EEO policy, information about requesting a reasonable accommodation in the job application process, recruitment agency policy, recruitment scam notice, and important E-Verify information. You may view our job candidate privacy policy here.

As part of Pilot’s commitment to fair and transparent remote hiring, Pilot uses light identity verification steps, such as briefly waving on camera and/or recording interviews, to confirm that candidates are representing themselves. For some roles, we may also invite finalists to our San Francisco office for onsite interviews.  By clicking “Submit Application” below you consent to our recording of interviews with you if your application goes to the interviews stage.

The Role

Pilot’s mission is to be the back office for every small business in America, and we’re hiring a Staff Design System Engineer to help make this future a reality. 

We are giving every SMB the superpowers of a full finance team at a fraction of the cost. These superpowers include having a deep understanding of the financial health of the business, the machinery to constantly improve it, and the predictive abilities to thoughtfully plan for the future. We do this at a fraction of the cost a large company would pay for this, by delivering these capabilities through powerful software. 

All of our teams have unique charters to collectively build the software, services and systems that enable Pilot to deliver a high-quality experience, profitably, at scale. The Infrastructure team accelerates the rest of R&D by providing scalable, efficient, and high-quality building blocks for product development, while also ensuring we can support business growth in a secure and reliable way. The team is responsible for building simple, scalable abstractions and owns the full Infrastructure stack that our systems run on to the product platform that our product engineers use. 

We’re looking for a Design Systems Engineer who bridges design and engineering, owns component quality across Figma, Storybook, and code, and builds scalable, production-ready UI systems.

What You Will Own

• Ownership of our design system across Figma, Storybook, and production code, and supporting the design team in fast prototyping with AI tools
• Stewardship of Storybook as the source of truth for UI components and usage
• Tight alignment between design intent and shipped UI 
• Component quality, consistency, and scalability across the product, and great interfaces that accelerate frontend development

What You Will Do

• Expand the design system to support product, marketing, and AI-ready experiences from a single, shared foundation
• Partner daily with product designers to shape components early, not after the fact
• Partner with frontend engineers to ensure components are easy to adopt and extend
• Build and maintain reusable, accessible UI components in Vue
• Translate design system decisions into clean, documented, production-ready components
• Keep Figma, Storybook, and code in sync and actively close gapsEvolve the design system to be AI-ready, enabling design to prototype faster

What You Bring

• 7+ years of experience as a software engineer
• Strong frontend skills including modern CSS
• Deep experience working with or owning a design system
• Hands-on experience with Storybook in a production environment
• Strong design sensibility and ability to read and challenge design decisions
• Comfort acting as the bridge between design and engineering
• Experience with vibecoding tools or AI-assisted design and development workflows
• Familiarity with MCP or intent-driven UI concepts is a big plus
• Clear communication and a bias toward practical solutions
• This position is only available for remote employment in the United States in the following states: CA, GA, NY, NC, TN, TX, and WA

Why This Role Matters

• You shape how the product UI is built, not just how it looks
• You reduce friction between design and engineering
• You make the design system faster, safer, and easier to scale

About Pilot

Pilot launched in 2017 to bring the back office into the modern era. Pilot provides small businesses with dedicated finance experts - which Pilot hires as full-time, U.S.-based employees - who learn the ins-and-outs of their business. Pilot integrates directly with the billing, banking, expense, and payroll systems customers already use. With a special blend of custom software and expert bookkeepers, Pilot delivers accurate, consistent bookkeeping and financial management and tax services that give entrepreneurs the freedom to focus on their business.

Pilot has over 3,000 customers and has raised over $170 million in financing from Sequoia, Index Ventures, Stripe, Bezos Expeditions, and Whale Rock.  Our investors also include a long list of world-class entrepreneurs, including Patrick and John Collison, Drew Houston, and Diane Greene.  Our most recent funding round doubled our valuation to $1.2 billion – Meet Fintech’s Newest Unicorn.

Why Pilot?

• We invest in our employees’ development and happiness because our employees are the keys to our success and ensuring happy customers
• The opportunity to join a seasoned founding team that has led companies through two prior successful startups and acquisitions (by Oracle and Dropbox).
• Flexible vacation/time-off policy
• All federal holidays are observed
• Competitive benefits package including additional wellness benefits
• Parental leave for birthing or non-birthing parents – 100% pay for 12 weeks
• 401(k) plan

The base pay range target for the role seniority described in this job description is $185,000 - $313,000 in most remote locations, and between $231,000 - $313,000 in San Francisco, CA and New York City, NY. Final offer amounts depend on multiple factors such as candidate experience and expertise, geographic location, total compensation, and market data. In addition to cash pay, full-time regular positions are eligible for equity, 401(k), health benefits, and other benefits; some of these benefits may be available for part-time or temporary positions.

Pilot commits to provide a work environment free of discrimination and harassment, as well as equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or Veteran status. We also consider qualified applicants regardless of criminal histories, consistent with legal requirements. You may view all of Pilot’s recruiting notices here, including our EEO policy, information about requesting a reasonable accommodation in the job application process, recruitment agency policy, recruitment scam notice, and important E-Verify information. You may view our job candidate privacy policy here.

As part of Pilot’s commitment to fair and transparent remote hiring, Pilot uses light identity verification steps, such as briefly waving on camera and/or recording interviews, to confirm that candidates are representing themselves. For some roles, we may also invite finalists to our San Francisco office for onsite interviews.  By clicking “Submit Application” below you consent to our recording of interviews with you if your application goes to the interviews stage.