---
title: 'Staff Software Engineer, Takeoff at Pilot.com'
canonical: 'https://feeny.ai/job/staff-software-engineer-takeoff-pilot-com-remote-ewbjnqz9yddw'
type: 'job'
last_seen: '2026-09-08'
---

# Staff Software Engineer, Takeoff at Pilot.com

- **Company:** Pilot.com
- **Location:** Remote
- **Work type:** remote
- **Posted:** 2026-08-19
- **Last confirmed live:** 2026-09-08
- **Apply:** https://job-boards.greenhouse.io/pilothq/jobs/8729123002

## Job description

## The Role

Pilot is hiring a Staff Software Engineer to join our Takeoff team.

The Takeoff team owns core accounting systems behind Pilot's bookkeeping: how transactions get categorized, how revenue from platforms like Stripe and Shopify gets recognized over the right periods, and how it all ties back to accurate financials. What we ship shows up directly in our customers' books.

As a Staff Engineer, you'll take on the largest and most ambiguous problems in this space: setting technical direction for systems that sit at the core of Pilot's product, and driving outcomes that span multiple teams.

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.

## Key Responsibilities

- Lead projects with high levels of ambiguity from problem definition through delivery
- Set technical strategy and make architectural decisions for systems that span teams and surface areas
- Identify cross-team gaps and missed opportunities, and drive the strategy to address them
- Build, test, and deploy software in a continuous manner (we deploy daily or more often)
- Create and review technical specs, and hold Engineering to high quality standards
- Work with PMs, Designers, internal customers, and stakeholders to ensure we're solving the right problems
- Mentor and sponsor engineers across the organization
- Investigate production issues, improve system reliability, and support services as needed

## 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:

- 7+ years of experience as a software engineer
- Experience with Python in production
- A track record of leading complex, multi-team technical projects to successful outcomes
- The ability to set technical direction and get buy-in across teams and functions
- 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
- Experience working effectively on a remote team, including strong async and written communication habits
- Demonstrated ability to mentor, sponsor, and uplevel other engineers
- This position is only available for remote employment in the United States in the following states: CA, GA, NY, NC, TN, TX, and WA

Additionally, we're interested in engineers with specialties or backgrounds in accounting as well as fintech and related fields.

## Nice to Have

- Experience with Vue in production
- Experience with accounting systems, double-entry bookkeeping, or revenue recognition
- Familiarity with agentic or AI-assisted systems in production environments
- Experience integrating with third-party APIs and external systems (e.g. payment processors)

## 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](https://pilot.com/blog/pilot-unicorn-bezos-expeditions-whale-rock/).

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 $200,000 - $240,000 in most remote locations, and between $230,000 - $280,000 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](https://pilot.com/recruiting-notices), 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](https://pilot.com/terms/privacy-job-candidate).

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.

## About Pilot.com

## Company Overview
- **One-liner**: Pilot provides bookkeeping, tax preparation, CFO, and COO services for startups and small businesses, combining software with a team of US-based finance experts.
- **Entity Type**: Private (Series C; total funding of $212.1M)
- **Headquarters**: San Francisco, California, United States (with a second HQ in Nashville, Tennessee)
- **Founded**: 2016
- **Founders**: Jessica McKellar (Founder & CEO)

## Core Business
- **Primary industry**: Accounting / Financial Services / Fintech
- **Target customers**: B2B – startups and small-to-medium businesses (SMBs) that are growth-oriented (from 2 to 20+ employees through to exit preparation)
- **Mission/purpose**: “Build the future of the financial back office to help small and medium sized businesses grow and flourish.”

## Products & Services
- **Bookkeeping**: Full-service bookkeeping with IRS-ready books, real-time expense tracking, and intelligent dashboards.
- **Tax Services**: Year-round tax compliance and strategy to maximize deductions and minimize liabilities.
- **CFO Services**: Strategic guidance from former CFOs and operators, including cash flow modeling, fundraising support, profitability optimization, and exit planning.
- **COO Services**: Operational advisory for scaling businesses, including financial operations consulting.
- **Meridian (AI Operating System)**: An AI-powered platform that automates book closing and provides analytics, designed to help accounting firms and internal teams work more efficiently.

## Market Standing
- **Valuation**: Not publicly disclosed (private company).
- **Key Metric**: Annual revenue of $20.0M (estimated) and total funding of $212.1M across 6 rounds.
- **Notable Investors**: Sequoia, Index Ventures, Stripe, Bezos Expeditions (Jeff Bezos’s investment company), Whale Rock Capital Management, and Akkadian Ventures. Also includes angel investors Patrick and John Collison, Drew Houston, and Diane Greene.
- **Growth Signals**:
  - Headcount grew 15.3% YoY to ~220 employees.
  - Trusted by 3,000+ growth-driven startups and small businesses.
  - Active job postings increased 167.9% year-over-year (75 open roles as of mid-2026).
  - Expanding into franchise and accounting firm verticals (dedicated marketing leads hired).

## Competitive Advantages
- **Human + Software Model**: Combines automated tools with a dedicated team of US-based CPAs, CFOs, and operators – providing both efficiency and strategic insight.
- **Deep Startup Expertise**: Specializes in complex financial needs like fundraising, cap table management, international expansion, and exit preparation – areas where generic bookkeepers fall short.
- **Meridian AI Platform**: Proprietary AI operating system that automates book closing, giving Pilot a technology moat in the accounting space.
- **Strong Investor Backing**: Backed by top-tier VCs and influential operators, providing credibility and a network effect.

## Strategic Focus
- **Vertical Expansion**: Targeting accounting firms and franchise businesses with dedicated marketing and sales teams.
- **Product Innovation**: Continued development of Meridian AI to serve both internal clients and external accounting firms.
- **Scaling the Team**: Aggressively hiring across engineering, marketing, sales, and operations to support growth.
- **Geographic Reach**: Maintaining dual headquarters (San Francisco and Nashville) while offering remote roles to access broader talent.

## Why Work Here
- **Culture & Values**: Emphasizes ownership, focus, quality, trust, teamwork, collaboration, and justice. Described as a high-performance, respectful environment where “everyone takes personal responsibility to treat each other with respect, fairness, and dignity.”
- **Work Model**: Hybrid – offices in San Francisco (FIDI with Bay views) and Nashville (Music Row). Many roles are listed as remote (e.g., Senior Software Engineer, Infrastructure), and some are location-flexible.
- **Growth Opportunity**: Rapidly growing company with increasing headcount and job postings; opportunity to work on impactful financial products for thousands of businesses.
- **Engineering Culture**: Focus on building resilient systems, root cause analysis, and shipping frequently. “If you like to build things and watch them ship, this is your office.”
- **Diversity & Inclusion**: Committed to equal employment opportunity and building a diverse, inclusive team.

## Sources
1. [pilot.com](https://pilot.com/) – Official website
2. [pilot.com/about](https://pilot.com/about) – About page (investors, locations, mission)
3. [pilot.com/careers](https://pilot.com/careers) – Careers page (values, culture, office locations)
4. [linkedin.com/company/pilothq](https://www.linkedin.com/company/pilothq) – LinkedIn company page (headcount, revenue, funding, employee breakdown)
5. [job-boards.greenhouse.io/pilothq](http://job-boards.greenhouse.io/pilothq) – Greenhouse job board (open roles, departments)

## Other roles at Pilot.com

- [Senior Manager, Revenue Accounting](https://feeny.ai/job/senior-manager-revenue-accounting-pilot-com-san-francisco-1zx15xdteyak) — San Francisco, CA
- [Senior Accountant, General Ledger](https://feeny.ai/job/senior-accountant-general-ledger-pilot-com-san-francisco-wabt8m1mgeb9) — San Francisco, CA
- [Sr. Software Engineer, Takeoff](https://feeny.ai/job/sr-software-engineer-takeoff-pilot-com-remote-kjgqfjfgegeb)
- [Engineering Manager, Infrastructure](https://feeny.ai/job/engineering-manager-infrastructure-pilot-com-remote-047nzzw2yzec)
- [Consultant, Payroll Operations](https://feeny.ai/job/consultant-payroll-operations-pilot-com-nashville-a1zzxf81myk9) — Nashville, TN
- [Manager, Business Operations](https://feeny.ai/job/manager-business-operations-pilot-com-san-francisco-nb5ef5kbqw3x) — San Francisco, CA
- [Manager, Business Operations](https://feeny.ai/job/manager-business-operations-pilot-com-nashville-20em5cskwhc6) — Nashville, TN
- [Sr. Software Engineer, Bookkeeping Automation](https://feeny.ai/job/sr-software-engineer-bookkeeping-automation-pilot-com-san-francisco-bxty312j22bm) — San Francisco, CA
- [Sr. Software Engineer, Infrastructure](https://feeny.ai/job/sr-software-engineer-infrastructure-pilot-com-remote-2s8fp7m6bbzr)
- [Founding Account Executive](https://feeny.ai/job/founding-account-executive-pilot-com-austin-z11vc8dfv20q) — Austin, TX