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're Series B, well-funded ($51M total raised from Y Combinator, General Catalyst, a16z, and Bain), and growing pipeline 15% MoM.

We want someone who can scale with us from 10M ARR to 100M ARR and beyond. Someone who wants to build the financial infrastructure from the ground up who's lived it before.

What You'll Do

Be the expert in the room. We need someone who can challenge our decisions and add rigor to how we plan for the company. Proactively identify the unknown unknowns. We don't know about finance, you do.
Work closely with GTM as a RevOps-leaning Head of Finance. How do we maintain the sustainable growth we've had up to this point? How do we accelerate it?
Take the numbers and weave it into a story. Our data is relatively clean, but we can't deeply analyze it. Extract those hidden insights to transition us from vibes-based to evidence-based decisions.
Build the entire finance function from scratch - owning our accounting firm, implementing FP&A, and establishing real-time visibility into burn and spending.
Be a strategic partner to leadership, challenging headcount decisions, evaluating sales targets, negotiating major contracts, and providing 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)
System builder mindset, not team builder - 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
Ideally early career experience in investment banking or private equity, showing you're willing to grind, plus experience at a high-growth startup
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

This Role Might NOT Be For You If

You're excited about building and leading a large finance team from day one - this role is about rolling up your sleeves and using modern tools to scale efficiently before hiring
You come from a pure accounting background and prefer focusing on compliance and reporting - we need someone who leans strategic and forward-looking
You thrive with established processes and systems already in place - we're building finance infrastructure from scratch, which is exciting but messy
You're looking for a more predictable environment at a later-stage company. We're Series B and still moving very fast
You're not able to be in San Francisco - we value our in-person culture and this role works best when you're here with the team