Jobs at Pilot.com (Now Hiring) — 12 open

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

Why This Role

• 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.

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