Founding Head Of Finance (AI-Native)

About Searchable

We're building the future of AI search visibility. As ChatGPT, Claude, and Perplexity reshape how people find information, we help brands understand and optimize their presence in this new landscape. Backed by top angels and VCs, we're creating the essential platform for the AI search era.

Our core values:

1. Customer First

Every decision starts with the user in mind.

Whether it's product features, support, or strategy, if it doesn’t make their lives better, it’s not worth doing.

2. Progress, Not Perfection

Done is better than perfect.

Real growth comes from iterating, testing, and improving fast. Perfection slows us down, and customers don't benefit from things that never ship.

3. Radical Ownership

Act like an owner. Because you are one.

If something’s broken, we fix it. If there’s an opportunity, we chase it. We don’t wait for someone else to step up, we lead from wherever we are.

4. Feedback Is a Gift

Direct. Constructive. Always with care.

Feedback - when given with intention and received with openness - is how we sharpen our thinking, improve our work, and build trust.

5. Leave the Ego at the Door

No drama. No politics. No heroes.

We’re here to win as a team. That means listening more than talking, crediting others, and being willing to change our minds.

The Mission

We’re building an AI-native company and we want finance to be AI-native too. This is not a traditional VP of Finance role.

This is a finance + systems + commercial strategy role where you’ll build the finance function as a real-time operating system: automated, deeply integrated into the product stack, and designed to drive decision-making at speed.

You will reinvent how financial planning, reporting, forecasting, and commercial decision-making is done and build a function that stays lean, automated, and powerful, even as the company scales.

You’ll be responsible for designing and developing the financial model that becomes the company’s “single source of truth” and then building the pipelines, tooling, and AI workflows that keep it always-on.

If you are not fully AI native but have the skills, we can train you in a 2-4 week period to be cutting edge.

We want to see the work, the imagination, the skills and the interest in what is possible before.

What You’ll Own

1) Build the AI-Native Finance Function From Zero

• Build our finance function end-to-end: tooling, systems, models, dashboards, reporting cadence, and controls

• Design a finance architecture that is real-time, automated, and scalable

• Build processes that are fast and flexible, without losing financial discipline

• Create the foundation for a world-class finance org without bloated headcount

You are not inheriting a finance department.
You are building one.

2) Design and Build the Financial Model That Runs the Company

You will design and maintain the core models that leadership uses to make decisions:

• ARR model

• unit economics model

• retention / churn / expansion model

• cohort-based revenue model

• CAC payback and contribution margin model

• pricing model

• product usage → revenue model

• scenario planning engine (base case / upside / downside)

• runway + cash flow model

• hiring plan + burn model

• Monthly management accounts for Investor meetings

3) Become a Financial Commercial Driver (Not a Reporting Function)

You will sit at the center of the commercial engine and drive decisions like:

• Which customers are profitable?

• What pricing is optimal?

• What usage patterns predict churn?

• What segments expand fastest?

• Where are we leaking margin?

• What is the best GTM motion?

• What should we automate vs hire for?

• What are the best growth loops?

This is a role for someone who wants to be a business builder, not just financial reporting.

4) Build Automated Data Pipelines Into a Finance Control Center

You will create automated pipelines that ingest, transform, and reconcile data from systems like:

• Stripe (billing + subscriptions)

• product usage + event data

• CRM data (Attio / HubSpot / Salesforce)

• marketing attribution

• data warehouse tooling (DBT, Snowflake/BigQuery)

• bank feeds

• expense systems

• payroll

Then convert it into:

• live dashboards

• finance-grade data layers

• “agent-ready” datasets

• automated alerts and anomaly detection

5) Build AI Workflows That Replace Traditional Finance Work

Instead of building a big finance team, you’ll build an AI-driven system that automates work such as:

• anomaly detection on revenue / churn / usage

• forecasting updates weekly or daily (not quarterly)

• auto-generated board reporting

• automatic metric commentary (“why did revenue dip?”)

• churn prediction and risk flags

• pricing recommendations based on behavior

• cost leak detection and margin alerts

• contract / invoice workflow automation

• intelligent cashflow forecasting

You’ll partner with engineering and ops to build “agentic workflows” that continuously monitor the business and surface insights.

6) Define the Metric System (Single Source of Truth)

You will own metric definitions across the company and enforce consistency, including:

• ARR / MRR definitions

• net revenue retention (NRR)

• gross revenue retention (GRR)

• churn and logo churn

• expansion and contraction

• activation and conversion rates

• usage-based revenue metrics

• customer profitability

• payback period

• pipeline coverage and sales efficiency

• contribution margin and gross margin

7) Build the Lean Team (Only After Automation)

We want a finance function that stays small and effective.

You’ll:

• automate first

• hire second

• design workflows where one person can do what a traditional team of five would do

• build tooling that compounds

You will be expected to personally build early systems, then scale the function with minimal headcount.

What You’ll Do (Day to Day)

• Build and maintain our ARR, retention, unit economics, and runway models

• Build automated pipelines from Stripe + CRM + product usage into dashboards

• Build a “finance operating system” for leadership (always-on, always accurate)

• Design finance workflows that run continuously rather than in monthly cycles

• Partner with GTM and product to drive pricing, packaging, and monetization decisions

• Work directly with engineering to ship automation and agent workflows

• Create a scalable monthly close process (lean, fast, auditable)

• Own forecasting cadence and financial planning

• Drive board/investor reporting and strategic finance insights

• Identify the highest leverage automation opportunities across the company

You Might Be a Fit If…

You are AI-native and systems-driven

You see finance as an engineering problem.

You’re excited by:

• automation-first operations

• agent workflows

• data pipelines

• replacing repetitive reporting with systems that run themselves

You're commercially hungry

You want to win.
You want to drive growth and profitability.
You want to shape pricing, GTM, and product decisions.

You’re humble, curious, and adaptable

You don’t care about ego or job titles.
You care about building what works.
You’re excited to learn and implement new tools constantly.

You’re comfortable in chaos

You thrive in fast-moving environments where:

• requirements evolve weekly

• there’s no existing process

• you build structure while running at speed

Requirements (What We Actually Care About)

• Strong experience building ARR / retention / SaaS models

• Ability to work directly with raw data and systems

• Strong strategic thinking and commercial instincts

• Comfortable operating as both strategist and builder

• Clear communicator (you can explain complex truths simply)

• Extreme ownership and execution speed

Strong Signals

• SQL fluency

• DBT experience

• Claude Code or similar

• Stripe billing familiarity

• building forecasting systems in modern SaaS businesses

• experience building finance stack from scratch

• experience in product-led growth (PLG)

• experience with usage-based pricing

• ability to build lightweight internal tools

• strong sense of “finance as product”

Tech Stack You’ll Likely Touch

• Claude Code

• Stripe

• CRM (Attio / HubSpot / Salesforce)

• Data warehouse (BigQuery / Snowflake)

• DBT

• Segment / product event tracking

• Metabase / Looker / Mode

• Finance systems (NetSuite / Xero / QuickBooks — depending on stage)

• AI tooling + agent frameworks (internal or external)

The Person We’re Looking For

We’re looking for someone who is:

• AI-native: defaults to automation and tooling

• hungry: wants to win and build something huge

• humble: learns fast, adapts fast, no ego

• a builder: wants to create systems, not inherit them

• fast: executes at startup speed

• commercial: sees finance as a growth driver

Compensation

Competitive salary + meaningful equity.

$150,000 + founding team equity

How to Apply

Send us:

• your CV / LinkedIn

• 2–3 examples of models, dashboards, or systems you’ve built (if you have them)

• 2-3 examples of how you have affected commercial improvements in cost or revenue for previous roles

• a short note on how you would build an AI-native finance function from scratch