Bookkeeper Pilot Jobs (NOW HIRING)

Pilot spent 10 years building the software that powers its own bookkeeping operation — running it on thousands of clients, at software margins, with a fully US-based team. Meridian is that software, now available to other accounting firms.

The pitch is simple: every other tool reduces your time to close. Meridian eliminates it. The full month-end close — reconciliation, categorization, accruals, tick-and-tie — runs automatically. Controllers walk in on the first to review finished books, not build them.

We’re early. The motion is being built right now. This is the role that builds it with us.

You’ll own a territory of outsourced accounting firms, CPA firms, and fractional CFO shops — the kinds of firms that live and die by the quality of their month-end close. Your job is to get them in the door, run a rigorous evaluation, and close them into a full Meridian engagement. This isn’t a post-PMF, run-the-playbook sales job. The playbook is still being written. You’ll be talking to firm founders, managing directors, controllers, and heads of technology — senior buyers who have seen every AI pitch and aren’t impressed by any of them. What impresses them is knowing what you’re talking about and having proof behind it. We have both. You’ll carry a quota. You’ll own your accounts for at least a year and expand them. You’ll be accountable for revenue, not just activity.

Own the full sales cycle

• Prospect and build your own pipeline through outbound, network, and inbound leads
• Run discovery calls, demos, and evaluation kickoffs with firm leadership and their teams
• Manage active client evaluations — weekly syncs, implementation support, tracking toward success metrics
• Close new logos and expand accounts over time as firms roll out Meridian to more clients

Know the product and the buyer

• Get deep on how Meridian works — the close process, the QBO integration, the agent workflows
• Understand the economics of running an accounting firm well enough to have a real conversation with a founder about margins
• Build relationships across the firm — founders, MDs, heads of tech, controllers. Multi-thread every account.

Build the motion with us

• Feed back what you’re hearing in the market — objections, competitive intel, what’s resonating
• Help sharpen the playbook as it’s being built
• Work closely with our implementation team to make client evaluations successful and convert

The profile we’re hiring for is specific. You’re probably 3–8 years into your career. You’ve closed real deals against real quotas. You know what it feels like to have a pipeline problem and fix it yourself. You’re not waiting for leads to show up — you go get them.

You don’t need to have sold to accounting firms before, but if you have, that’s a meaningful edge. The buyer is sophisticated and the sales cycle is long enough that domain fluency pays off fast.

You’re a strong fit if

• You have 3–8 years of B2B sales experience with a track record of hitting quota
• You’ve sold a technical product into a professional services buyer before — or you’re confident you can learn the domain fast
• You’re comfortable running a long, consultative sales cycle — our evaluations run 2–3 months, not a 30-day free trial
• You write well and communicate clearly. Most of your first impressions happen over email or LinkedIn.
• You’re the kind of person who updates Salesforce because you actually want to know what’s in your pipeline, not because someone tells you to
• You want to be part of building something, not just running a motion someone else already figured out

Bonus if you have

• Sold to accounting firms, CPA firms, or professional services buyers
• Experience at a fintech or accounting software company
• Worked at an early-stage company before and know what ‘figuring it out’ actually looks like

• You’re not the 50th AE at a company that’s already figured everything out. You’re one of the first. That has real upside.
• The product has 10 years of proof behind it. You’re not selling vapor. You’re selling something that runs on thousands of real clients right now.
• The competitive line is clean: every other tool reduces time to close. Meridian eliminates it. That’s a conversation worth having.
• Pilot has $170M raised, 3,000+ customers, and investors including Sequoia, Index, and Stripe. The foundation is real.
• You’ll be part of building a channel that doesn’t exist yet. If it works — and we think it will — you’ll have built it.

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.

• 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 on-target earnings (OTE) range target for the role seniority described in this job description is $240k - $320k in New York, NY (base pay is 50% of OTE). 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.

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