Pilot.com

Account Executive, Mid-Market

Pilot.com$240K — $320K *
Business Services
Less than 5 years of experience
Job Overview by Ladders

Qualifications

  • 3-8 years of B2B sales experience with a demonstrated history of meeting quotas
  • Understanding of consultative sales cycles, particularly in technical products
  • Ability to develop and maintain relationships with senior-level clients
  • Strong written and verbal communication skills, especially for digital platforms
  • Proficiency in using Salesforce for pipeline management

Responsibilities

  • Own and manage the entire sales cycle from prospecting to closing
  • Conduct discovery calls and demos with firm leadership
  • Oversee client evaluations and ensure success metrics are met
  • Expand client accounts as firms adopt Meridian for more customers
  • Deepen knowledge of the product and understand clients' business economics
  • Provide market feedback to refine the sales strategy
  • Collaborate with implementation teams to ensure client success

Benefits

  • Opportunity to be among the first sales team members at a rapidly growing company
  • Sell a proven product with a solid client base and backing from reputable investors
  • Work in a niche market with unique solutions that stand apart from competitors
  • Potential to shape new sales processes and strategies within the organization
  • Access to equity options and comprehensive health benefits
  • 401(k) plan and other supportive workplace benefits
Full Job Description
The Role

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.

Key Responsibilities

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

About You

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.


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. You may view our job candidate privacy policy here.

About Pilot.com

Pilot is a financial services company that provides online bookkeeping, tax, and CFO services to startups and small businesses. The company was founded in 2017 and is headquartered in San Francisco, California. Pilot's mission is to help businesses focus on their core competencies by taking care of their financial needs. The company's services include bookkeeping, tax preparation, and CFO services. Pilot's bookkeeping service is powered by proprietary software that automates many of the tasks associated with bookkeeping, such as data entry and reconciliation. The company's tax preparation service is designed to help businesses save money on taxes by identifying deductions and credits that they may be eligible for. Pilot's CFO service provides businesses with financial planning and analysis, budgeting, and forecasting.
Learn more about Pilot.com
Size
200 employees
Industry

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