Business Operations Analyst, Pilot
$109.7-148.3k
+ Equity
Bookkeeping services for startups
Open for applications
Bookkeeping services for startups
201-500 employees
Open for applications
$109.7-148.3k
+ Equity
201-500 employees
Company mission
To help small businesses and startups to achieve their commercial goals by taking care of the CFO services, tax preparation and bookkeeping.
Role
Who you are
- Experience: 3-5 years in business operations, analytics, or finance, ideally in a start-up or technology-forward environment, with a track record of actually building and running a system. Experience owning forecasting, billing, or resource-planning is a strong plus
- Technical Proficiency: Expert-level Excel/Sheets (formulas, modeling, automation/scripting), plus working proficiency in SQL and analytics tools (e.g., Looker). Comfort using AI tools like Claude Cowork
- Detail Orientation: A track record of getting the numbers right the first time
- Systems Thinking: Able to see how planning, allocation, forecasting, and billing connect, and to design solutions that account for the whole picture rather than one piece of it
- Project Leadership: Demonstrated experience leading the build or overhaul of an operational system, including the change management needed to get a team to adopt it
- Communication: Strong verbal and written communication skills, with the ability to work directly with senior leadership and translate technical or data-heavy work into clear recommendations
What the job involves
- This role sits at the center of how we plan, allocate, and forecast work across the organization, and increasingly, how we automate that work
- Pilot is moving fast toward agentic, AI-assisted operations, and this person will build and own the systems, models, and reporting that make that shift possible: work orchestration, KPI reporting, resource forecasting, and billing
- This isn't a role for someone who wants to build one dashboard and maintain it
- It's for someone who wants to keep building better systems as the work itself changes
- The role requires real fluency with data and automation tools (Excel/Sheets at an expert level, plus a builder's instinct for where AI and scripts can replace manual work), sharp attention to detail, and good judgment about what results imply for our strategy and performance
- This person works directly with senior leadership
- Work Orchestration: Own the systems and processes that plan and allocate work across the organization. Build and maintain the models that route work efficiently as volume, team capacity, and service lines change
- KPI Reporting: Build and maintain reporting that gives leadership a clear, accurate, real-time view of business performance. Know the data well enough to catch anomalies before they become someone else's problem
- Resource Forecasting: Build and maintain forecasting models that project staffing and capacity needs against demand. Translate forecasts into recommendations leadership can act on
- Billing Operations: Own billing sheet accuracy and process, including the reconciliation and QA that keeps them error-free at scale
- Automation & AI Adoption: Identify where manual, spreadsheet-based, or repetitive work can be automated or AI-assisted. Build these solutions directly rather than just recommending them, using tools like Excel/Sheets scripting, SQL, and emerging AI tooling
- Process Optimization: Identify and implement improvements to the processes, workflows, and systems this role owns, so accuracy and efficiency improve as the business changes. When an improvement requires cross-functional buildout, lead it end to end, including the change management to get it adopted
Our take
Back office operations such as bookkeeping can be an unwelcome distraction and expense for businesses. Pilot is the largest provider of back office services for startups and small businesses in the US, aiming to take care of a company's back office so they can focus on their core activities.
Founded in 2016. Pilot has attracted an impressive range of customers including Bolt, r2c and Pathrise. The company's proposition is more than just bookkeeping software, providing services that would ordinarily be provided by a fractional CFO. This empowers small businesses and startups to make better budgeting and spending decisions without the need of an expensive finance department hire.
The company evidently excels in customer service, with the vast majority of its business driven by customer referrals and organic interest. Going forward, Pilot aims to become to startups and medium-sized firms what AWS is to cloud computing - a comprehensive, easily scalable solution that prevents the need to reinvent a necessary but non-core function from scratch.
Kirsty
Company Specialist at Welcome to the Jungle
Insights
-4% employee growth in 12 months
Company
Funding (last 2 of 5 rounds)
Mar 2021
$40m
SERIES C
Jan 2021
$60m
SERIES C
Total funding: $158.3m
Company benefits
- Development opportunities & employee happiness initiatives
- 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
- Wellness benefits such as Modern Health, Headscape, One Medical, Aaptiv and Rightway
- Parental leave for birthing or non-birthing parents – 100% pay for 12 weeks
- 401(k) plan
Company HQ
Financial District, San Francisco, CA
Leadership
Waseem Daher
(Chair & Co-Founder)They studied at MIT before founding Ksplice, where they spent 3 years as COO, and working at Oracle and Dropbox. Having founded Zulip in August 2012, they co-founded Pilot in January 2017.
Jessica McKellar
(CEO & Co-Founder)Previously, they were the founder and the VP of Engineering for a real-time collaboration startup acquired by Dropbox, where they then served as a Director of Engineering.
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