Head of Finance

About Pylon

Pylon is the AI-Native Support Platform for B2B companies. We consolidate ticketing, account management, knowledge base, AI agents, analytics, and chat into one product. Over 1000 customers use Pylon to run their post-sales motion. We are a well-funded company ($51M total raised from Y Combinator, General Catalyst, a16z, and Bain), and we are growing our pipeline at a rate of 15% month-over-month. We are seeking an individual who can scale with us from 10M ARR to 100M ARR and beyond.

What You'll Do

• Be the expert in the room. Challenge our decisions and add rigor to how we plan for the company.
• Proactively identify the unknown unknowns. You will be the finance expert, bringing your knowledge to the table.
• Work closely with GTM as a RevOps-leaning Head of Finance. Ensure we maintain and accelerate our sustainable growth.
• Take the numbers and weave them into a story. Transition us from a vibe-based to an evidence-based decision-making process.
• Build the entire finance function from scratch. Own our accounting firm, implement FP&A, and establish real-time visibility into burn and spending.
• Be a strategic partner to leadership. Challenge headcount decisions, evaluate sales targets, negotiate major contracts, and provide the financial rigor behind every big decision.
• Leverage modern finance tooling to scale operations without building a large team. Own planning and forecasting for 2026+, building scenarios across revenue, hiring, and burn to help leadership see around blind corners.

What You've Done

• 5-10 years of experience with at least one stint scaling a company from $10M to $100M ARR (as the finance leader or #2).
• A system builder mindset, comfortable leveraging modern finance tools to do the work yourself rather than immediately hiring a large team.
• RevOps-oriented finance experience. You naturally think about CAC, payback periods, and unit economics; bonus if you have SQL/data skills.
• Equally comfortable building three-year financial models and diving into why burn spiked 50% last month.
• Deep understanding of how the business works, not just the numbers - you can read a P&L and know exactly what each line means and why it matters.

Why Join Pylon

• Build finance from zero - this is your chance to establish the entire function the right way from day one.
• Work directly with founders on GTM strategy and all major business decisions.
• Join a strong in-person culture in San Francisco.
• Comp package includes competitive salary, equity, and benefits.

Our Perks

• Fully covered medical, dental, and vision insurance for employees.
• 401(k) retirement plan.
• Commuter benefits.
• Parental leave.
• 14 company holidays + unlimited PTO.
• Annual offsite.
• Lunch, dinner, and snacks at the office.
• Fitness stipend.

More About Pylon

Traction: 1000+ paying customers and growing 15% MoM.
Funding: Series B led by a16z and BCV ($51M total raised)
Founders: Advith Chelikani, Robert Eng, and Marty Kausas
Team: Currently 90 and growing!