Head of Finance at Pylon

San Francisco, California, United States

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Not SpecifiedCompensation

Expert & Leadership (9+ years), Senior (5 to 8 years)Experience Level

Full TimeJob Type

UnknownVisa

Technology, SaaSIndustries

Requirements

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, comfortable leveraging modern finance tools to do the work yourself rather than immediately hiring a large team
RevOps-oriented finance experience - naturally think about CAC, payback periods, and unit economics; bonus if 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
Deep understanding of how the business works, not just the numbers - can read a P&L and know exactly what each line means and why it matters
Able to work onsite in San Francisco (in-person culture required)

Responsibilities

Be the expert in the room, challenge decisions, and add rigor to company planning; proactively identify unknown unknowns
Work closely with GTM as a RevOps-leaning Head of Finance to maintain and accelerate sustainable growth
Take the numbers and weave them into a story; extract hidden insights to transition from vibes-based to evidence-based decisions
Build the entire finance function from scratch - own accounting firm, implement FP&A, and establish real-time visibility into burn and spending
Be a strategic partner to leadership, challenging headcount decisions, evaluating sales targets, negotiating major contracts, and providing financial rigor for big decisions
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

Skills

Key technologies and capabilities for this role

FP&ARevOpsFinancial PlanningForecastingAccountingFinancial ModelingScenario PlanningBurn Rate AnalysisContract NegotiationModern Finance Tools

Questions & Answers

Common questions about this position

What is the compensation package for the Head of Finance role?

The comp package includes competitive salary, equity, and benefits.

Is this Head of Finance position remote or onsite?

The position is onsite in San Francisco.

What experience is required for the Head of Finance role?

Candidates need 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 leveraging modern tools, and RevOps-oriented experience with metrics like CAC and unit economics.

What is the company culture like at Pylon?

Pylon has a strong in-person culture in San Francisco.

What makes a strong candidate for this Head of Finance position?

A strong candidate has scaled a company from $10M to $100M ARR in finance, prefers building systems over large teams, has RevOps experience with unit economics, and wants to build finance from scratch without leading a big team immediately.

Pylon

Digital mortgage integration platform for businesses

About Pylon

Pylon Lending provides a digital mortgage infrastructure that allows businesses to integrate mortgage services into their products efficiently. Their platform offers APIs and pre-built UI components, enabling clients, mainly in the financial and real estate sectors, to embed a complete digital mortgage experience with minimal coding. Unlike traditional mortgage services that require extensive infrastructure, Pylon offers a customizable Software Development Kit (SDK) that covers the entire mortgage origination process, from application to closing. This approach helps clients save time and reduce costs. Pylon's goal is to simplify the mortgage process for businesses, allowing them to launch new mortgage products quickly while enhancing customer satisfaction.

New York City, New YorkHeadquarters

2022Year Founded

$8.3MTotal Funding

SEEDCompany Stage

Fintech, Financial ServicesIndustries

11-50Employees

Benefits

Medical, vision & dental

Unlimited PTO

Hardware allowance

Annual off-sites

Risks

Increased competition from fintech companies could erode Pylon's market share.

Potential regulatory changes may require costly adjustments to Pylon's platform.

Reliance on Citi's trading desk for liquidity poses partnership risk.

Differentiation

Pylon offers a fully digital mortgage experience via APIs and pre-built UI components.

Freddie Mac approval enhances Pylon's credibility in the mortgage industry.

Pylon's platform allows quick integration of mortgage services, reducing time and cost.

Upsides

Citi's investment provides Pylon access to institutional-grade products and rates.

Pylon raised $8.5M in seed funding, boosting its growth potential.

Increased AI adoption in mortgage underwriting can enhance Pylon's platform efficiency.

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