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.

About Pilot

About the Role

What You’ll Do

• Understand how franchise systems buy (corporate vs franchisee vs both)
• Identify high-potential segments (e.g., QSR, fitness, home services, multi-unit operators)
• Test different entry points (top-down via franchisor vs bottom-up via operators)

• Launch scrappy tests across channels (events, outbound support, partnerships, content, paid)
• Try different GTM motions (corporate deals, multi-location bundles, pilot programs)
• Use results to determine what scales

• Talk directly to franchise owners, operators, and corporate teams
• Understand operational pain points (unit economics, reporting, cash flow, multi-entity complexity)
• Translate insights into messaging and acquisition strategies

• Build landing pages, write emails, run outreach, and launch campaigns yourself
• Stand up webinars or events tailored to franchise operators
• Move quickly with minimal process or support

• Be accountable for generating qualified opportunities and contributing to revenue
• Partner closely with Sales to refine positioning and improve conversion
• Focus on what drives deals across different buyer types

• Identify and engage franchise ecosystems (POS systems, franchise consultants, associations)
• Run co-marketing or co-selling experiments
• Help Pilot become relevant within franchise networks

What We’re Looking For

• You’re early in your career but have strong business judgment
• You’ve taken ownership of something ambiguous before
• You’re excited to do the work yourself—not just design strategy
• You’re comfortable navigating messy, multi-stakeholder environments

• 2–5 years of experience in consulting, banking, startups, GTM roles, or similar
• MBA or equivalent experience is a plus, not required
• Exposure to SMBs, multi-location businesses, or operations-heavy industries is helpful

• High ownership: you take responsibility for outcomes, not just tasks
• Scrappy: you find ways to get things done with limited resources
• Analytical: you use data to guide decisions and prioritize
• Clear communicator: you can tailor messaging to different audiences (operators vs HQ)

Why This Role

• You’ll own a new growth channel with real revenue impact
• You’ll work across Sales, Partnerships, and Product
• You’ll gain exposure to complex GTM problems (multi-entity buyers, channel strategy)
• You’ll help define how Pilot wins in a large, underpenetrated market

What Success Looks Like (First 6–12 Months)

• Clear signal on whether top-down (franchisor) or bottom-up (operator) motion works best
• 2–3 channels consistently generating qualified pipeline
• Early wins with franchise groups or multi-unit operators
• Initial repeatable plays for acquiring and expanding within franchise systems

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

About Pilot

About the Role

What You’ll Do

• Identify how accounting firms discover, evaluate, and adopt solutions like Pilot
• Run fast, scrappy experiments across channels (events, outbound support, partnerships, content, paid)
• Use results—not opinions—to decide where to double down

• Talk directly to accounting firms to understand their needs, objections, and workflows
• Turn insights into better messaging, targeting, and acquisition strategies

• Write emails, build landing pages, set up campaigns, and run events yourself
• Launch quickly with minimal process or support
• Iterate constantly based on performance

• Be accountable for generating qualified opportunities and contributing to revenue
• Work closely with Sales to improve conversion and close feedback loops

• Identify and engage potential partners (platforms, communities, firm networks)
• Run co-marketing or co-selling experiments
• Help turn early traction into repeatable plays

What We’re Looking For

• You’re early in your career but have strong business judgment
• You’ve taken ownership of something ambiguous before (at work, school, or side projects)
• You’re excited to do the work yourself—not just design strategy
• You move quickly and are comfortable figuring things out as you go

• 2–5 years of experience in consulting, banking, startups, GTM roles, or similar
• MBA or equivalent experience is a plus, not required
• Exposure to B2B, fintech, or professional services is helpful

• High ownership: you take responsibility for outcomes, not just tasks
• Scrappy: you find ways to get things done with limited resources
• Analytical: you use data to guide decisions and prioritize
• Clear communicator: you can write and speak effectively with a professional audience

Why This Role

• You’ll own a real growth problem with revenue impact, not just a slice of a funnel
• You’ll get exposure to Sales, Partnerships, Product, and Marketing
• You’ll build skills across strategy + execution, early in your career
• You’ll help define a new growth channel at Pilot

What Success Looks Like (First 6–12 Months)

• Identified 2–3 channels that generate qualified pipeline
• Launched and iterated on multiple acquisition experiments
• Built early traction with accounting firms and/or partners
• Established initial repeatable plays for the segment

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 Role

Most marketing leaders inherit a playbook. This one gets to write and scale it.

The motion is enterprise B2B—longer cycles, multiple stakeholders, relationships that close deals. Pilot has that motion working. Your job is to point it at 2 distinct segments and build everything behind it. The segments are distinct:

• Franchisors are corporate buyers whose vendor decisions cascade across entire franchise systems—win one, and you've won dozens of locations. 
• And Mid-market accounting firms adopting Pilot as the platform they run their clients' books on, at scale. 

We’re building a partner-led growth model that scales through relationships rather than ad spend. This role is about extending that model across new segments in a way that drives consistent, measurable pipeline.

This role is ideal for a senior marketing leader who has built and scaled demand programs in complex B2B environments and is ready to take on broader ownership. You’re equal parts strategist and experimenter—excited to unlock new growth channels, test bold ideas, and deepen a partner ecosystem as a meaningful driver of acquisition.

You'll report to the VP of Marketing and manage a direct report: a Partner Marketing and Events Lead. You'll also work with a shared team of senior specialists across lifecycle marketing, marketing operations, product marketing, and content—giving you the support to build full-funnel programs without building a large team from scratch.

This is a hybrid role requiring presence in our San Francisco office on Mondays, Tuesdays, and Thursdays.

What You’ll Own

• Segment strategy. Each segment requires a distinct motion—but they share the same enterprise foundation. You’ll define how we approach each and make that strategy actionable.
• Pipeline. You’re accountable for what these segments produce. In close partnership with sales, you’ll align on account prioritization and build programs that move the right prospects from first impression to signed contract.
• Partner pipeline. You’ll build on and scale our partner-led motion—working with our Partner Marketing and Events Lead to turn relationships into a consistent source of pipeline through referral programs, co-marketing, and field engagement.
• Messaging. You’ll shape how Pilot speaks to each of these audiences—externally and in the materials our sales team uses every day.

What Success Looks Like in Year 1

• A clear, defensible go-to-market strategy across all three segments
• Repeatable demand and partner programs in market
• Growing, measurable pipeline contribution
• A team aligned around a clear roadmap and direction for year 2

 About You

• 10+ years of B2B marketing experience, including time in enterprise or multi-stakeholder sales environments
• Experience managing and developing direct reports
• Strong foundation in demand generation and/or account-based marketing (ABM), including pipeline ownership and conversion metrics
• Experience partnering closely with sales leadership on account prioritization and pipeline goals
• Exposure to partner or channel marketing (direct ownership or close collaboration)
• Writes and communicates clearly
• Ideally, previous experience marketing to franchisors or accounting firms.

About Pilot

Pilot.com provides bookkeeping, CFO, and tax services powered by a combination of expert teams and intelligent software. We work with thousands of startups and growing businesses, giving them the financial clarity and confidence they need to scale. Backed by top investors and loved by founders, we’re on a mission to be the financial back office for every business.

The Role

We're looking for a hands-on Sales Manager to lead and develop a team of 5–8 inside sales reps selling Pilot's suite of accounting and advisory services. This is a player-coach role focused on the fundamentals: daily execution, data-driven coaching, and helping each rep reach their full potential.

You'll sit between the reps and our Director of Sales, translating strategy into day-to-day action. The right person for this role loves being in the details — reviewing call recordings, digging into pipeline data, running tight 1:1s, and rolling up their sleeves to help reps work through tough deals.

What You'll Do

Coach and Develop Your Team

• Run structured weekly 1:1s with each rep focused on skill development, pipeline review, and goal-setting
• Listen to call recordings and provide specific, actionable feedback to improve rep performance
• Identify each rep's strengths and growth areas, and build individualized development plans
• Onboard new hires and ensure they ramp quickly and confidently

Drive Performance Through Data

• Own team-level metrics including activity volume, conversion rates, pipeline health, and quota attainment
• Use CRM and sales analytics data to spot trends, flag risks early, and surface coaching opportunities
• Hold the team accountable to daily and weekly activity targets in a constructive, motivating way
• Deliver clear, consistent reporting to the Director of Sales on team performance and forecast

Execute Day-to-Day Operations

• Lead weekly team meetings that keep the team energized and aligned
• Partner with reps on live deals — provide deal coaching, handle escalations, and help close
• Maintain CRM hygiene standards across the team to ensure data accuracy and pipeline visibility
• Coordinate with Sales Leadership and Marketing on messaging, campaigns, and tooling rollouts

Build a Winning Culture

• Create a team environment that is high-performance and high-care — reps should feel challenged and supported
• Recognize wins loudly and coach through misses constructively
• Advocate for your team's needs: tools, process improvements, and career growth opportunities

What We're Looking For

Required:

• 4-6+ years of experience in sales, including at least 2 years managing a team of inside sales reps
• A track record of developing individual reps into consistent quota-attainers
• Strong analytical skills — comfortable digging into sales data, building a forecast, and using metrics to make coaching decisions
• Excellent communication and interpersonal skills; you give direct, caring feedback
• Proficiency with a modern CRM (Salesforce, HubSpot, or similar)
• Organized, detail-oriented, and consistent in following through on commitments to your team

Nice to Have:

• Experience selling professional services, fintech, or SaaS products
• Familiarity with accounting, bookkeeping, or financial services
• Experience with advanced AI tools and processes for sales (Claude Cowork, Codex)
• Prior experience building or iterating on a sales playbook or onboarding program

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 between $163,000 - $214,000 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

What You'll Own

• ABM strategy and programs. You'll define the account-based approach for this segment—target account selection, buying committee mapping, personalized campaigns, and the sequencing that moves multi-stakeholder deals through a longer cycle. You'll test, learn, and build the playbook as you go.
• Pipeline contribution. You're accountable for what this segment produces: SQLs, opportunity value, conversion rates, pipeline velocity. You know what the numbers are telling you and what to adjust when they're not moving.
• Sales alignment. You'll be in pipeline reviews, contributing to account plans, and making sure marketing programs are coordinated with where sales is focused. One unified motion, not two separate ones.
• Partner-sourced pipeline. Working closely with the Partner Marketing and Events Lead, you'll help turn partner relationships into a source of qualified leads for strategic accounts, coordinating on referral programs and ensuring partner-generated opportunities are tracked, nurtured, and converted with the same rigor as any other channel.
• Campaign execution. Working with shared specialists across lifecycle, paid media, content, and marketing ops, you'll design and run full-funnel programs that reach strategic account buyers via paid channels, events, outbound sequences, and direct engagement.

What Success Looks Like in Year 1

• A clear ABM strategy for strategic accounts. 
• Targeted programs running against priority accounts. 
• Partner-sourced leads flowing into the pipeline alongside ABM-generated opportunities.
• Growing, measurable pipeline contribution from the segment. 
• A tight, trusted working relationship with sales.

About You

The Role

What You'll Own

• ABM strategy and programs. You'll define the account-based approach for this segment—target account selection, buying committee mapping, personalized campaigns, and the sequencing that moves multi-stakeholder deals through a longer cycle. You'll test, learn, and build the playbook as you go.
• Pipeline contribution. You're accountable for what this segment produces: SQLs, opportunity value, conversion rates, pipeline velocity. You know what the numbers are telling you and what to adjust when they're not moving.
• Sales alignment. You'll be in pipeline reviews, contributing to account plans, and making sure marketing programs are coordinated with where sales is focused. One unified motion, not two separate ones.
• Partner-sourced pipeline. Working closely with the Partner Marketing and Events Lead, you'll help turn partner relationships into a source of qualified leads for strategic accounts, coordinating on referral programs and ensuring partner-generated opportunities are tracked, nurtured, and converted with the same rigor as any other channel.
• Campaign execution. Working with shared specialists across lifecycle, paid media, content, and marketing ops, you'll design and run full-funnel programs that reach strategic account buyers via paid channels, events, outbound sequences, and direct engagement.

What Success Looks Like in Year 1

• A clear ABM strategy for strategic accounts. 
• Targeted programs running against priority accounts. 
• Partner-sourced leads flowing into the pipeline alongside ABM-generated opportunities.
• Growing, measurable pipeline contribution from the segment. 
• A tight, trusted working relationship with sales.

About You

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

At Pilot, we're on a mission to grow the small business economy — and we're at an inflection point. AI is fundamentally reshaping what's possible in financial services, and this role sits at the center of that transformation.

We're looking for a Staff Product Manager to lead Pilot's Agent driven bookkeeping automation platform. This is one of the highest-impact, highest-visibility roles at Pilot. The future of our business, and frankly, the future of bookkeeping as an industry, will be shaped by what this team builds. We're talking about the kind of foundational work that sets a company up for double and triple-digit growth, and positions Pilot as the definitive AI-native back office for small businesses.

The foundation of financial insights is banking data. This team owns the core automation, including agent pipelines, that ensures bank transaction data is accurate, timely, and actionable. You'll drive Pilot's AI transformation from the product layer, architecting how we apply agentic workflows to achieve near-fully autonomous bookkeeping, and setting the standard for how great agent driven products get built and shipped.

This is a generalist PM role at its core, but one that requires deep fluency in AI, not just familiarity. You'll work shoulder-to-shoulder with our engineering and technical teams, speak their language, and make hard technical and product tradeoffs with confidence.

Key Responsibilities 

• Own and drive Pilot's AI transformation for a critical product area, defining the roadmap for how agent orchestration becomes the engine of automated bookkeeping
• Ship outstanding features to drive Pilot’s product feature set, and be responsible for that product delivering substantial impact for both our customers and our business
• Partner deeply with technical teams software engineers to design, build, and ship AI-powered features at high quality
• Audit and evaluate system system quality: assess product quality, pipeline reliability, output performance, and data fidelity; push the bar on what "production-ready" means
• Set the strategic vision for how agent-native bookkeeping evolves at Pilot, influencing company-level decisions about technology investment, product direction, and competitive positioning
• Talk to customers, understand their pain points, and translate those insights into customer solutions they didn't know were possible
• Make smart prioritization decisions informed by customer feedback, data, and a clear-eyed view of technical feasibility and business impact
• Serve as the internal and external ambassador for your product, keeping leadership, cross-functional partners, and customers excited and aligned on what's being built and why

About You

• A proven track record of shipping AI, financial, or data-driven products that have moved meaningful business metrics, not just launched, but delivered
• 7+ years building products, ideally with significant time in B2B and/or data-intensive domains
• Deep familiarity with the agent toolchains, model evaluation frameworks, evaluation/orchestration tools (e.g., Arize, LangChain, Prefect, Airflow)
• Outstanding analytical and problem-solving skills: you can break down complex systems, identify failure modes, and make high-quality decisions with incomplete information
• Exceptional ability to learn complex domains quickly and communicate them simply to customers, executives, and the board

Bonus Points

• Experience as a founder or operator running a business yourself
• A background in finance, accounting, or fintech
• Hands-on experience building or deploying AI, agentic, or LLM based products

Why This Role Matters

Pilot is at a once-in-a-generation moment. AI is enabling us to reimagine what bookkeeping looks like, moving from human-heavy workflows to intelligent automation that gives small business owners real-time, accurate financial clarity with minimal friction. The PM who leads this area will have direct influence on our growth trajectory, our technical architecture, and our positioning in the market.

This is not a supporting role. It's a defining one, for Pilot, and for the category.

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 $197,000 - $313,000 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.

GTM & Revenue Analytics

• Maintain and optimize core revenue funnel reporting across channels and segments
• Build and maintain dashboards in Salesforce and BI tools (e.g., Looker or similar)
• Develop GTM efficiency reporting (CAC, payback, win rates, sales cycle)
• Conduct recurring analyses on pipeline health, funnel performance, and win/loss trends
• Analyze segment-level profitability and performance
• Evaluate pricing and discount impact on win rate and lifetime value
• Support ICP refinement with data-backed insights
• Build and measure campaign performance across channels by first-touch, last-touch, and multi-touch attribution
• Measure campaign ROI and blended CAC by channel
• Deliver ongoing ad hoc strategic analyses

Retention, Expansion & Churn

• Support expansion pipeline reporting and upsell insights
• Conduct churn analysis by segment, timing, and drivers
• Identify churn signals and contribute to risk scoring models
• Run cohort-based retention analysis

Financial & Efficiency Insights

• Analyze operating expense performance vs. budget
• Support LTV/CAC modeling and forecasting
• Assist with commission and incentive analysis as needed

Required

• 2-3+ years of experience in RevOps, SalesOps, Marketing Analytics, Data Analytics, or Business Intelligence roles
• Experience working with Salesforce, Marketo, Clay, and BI tools such as Looker (or similar)
• Strong proficiency in Excel / Google Sheets
• Experience partnering cross-functionally with Marketing, Sales, Data, Finance, and Customer Success
• Strong analytical rigor with the ability to translate data into clear, actionable business insights

Nice to Have

• Experience writing SQL queries
• Experience building or refining attribution models
• Familiarity with product-led growth or hybrid sales motions
• Exposure to forecasting, commission modeling, or revenue planning

Who You Are

• Highly analytical and structured in your thinking
• Comfortable working with ambiguous or messy datasets
• Curious and proactive in investigating metric shifts
• Able to balance depth with speed
• Strong communicator who can translate insights for non-technical stakeholders
• Interested in how revenue systems work end-to-end

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 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.