Inside Ollie: How We Built the World’s First Operations Co-Pilot

For years, we’ve seen the same story play out across hundreds of startups: brilliant founders with powerful ideas slowly losing momentum, not because their product didn’t work, or their customers didn’t care, but because their operations were holding them back. The data backs this up: 10%+ of work is around operations (not including context switching).

Payroll deadlines. Compliance filings. State registrations. Bookkeeping errors. Vendor payments. These aren’t just tasks; they’re distractions that quietly chip away at focus, speed, and creativity.

We built Chore to solve that problem for hundreds of companies, taking on their back-office work so founders can build, grow, and focus. But as our clients grew, we saw a new challenge emerge: speed of insight.

In the age of AI, knowledge is a differentiator. Speed of access to knowledge and then ability to execute with intelligence is the new secret to success.

Founders wanted answers—right now.

“How’s my burn trending this quarter?”

“When is my D&O insurance up for renewal?”

“What’s the status of that contractor’s onboarding?” 

They wanted a single place to get clarity on everything happening behind the scenes.

So we decided to build it.

And that’s how Ollie was born.

The Vision: A COO in Every Founder’s Pocket

The idea behind Ollie was simple, but ambitious:

To build an AI-powered operations co-pilot that gives founders the same level of visibility, control, and confidence as having a world-class COO—without the overhead.

Ollie isn’t another chatbot. It’s the first intelligent layer sitting atop a startup’s operational stack—designed to understand how your business actually runs.

It integrates with your existing tools — QuickBooks, Rippling, Ramp, Carta, Gusto (and more) — to fuse all of that data into a unified database of company operations. Then you can converse with your operations.

You don’t have to dig through spreadsheets or dashboards anymore. You can just ask:

“What’s my cash runway?”

“How many offer letters have we sent this quarter?”

“Which contractors are due for renewal next month?”

Ollie responds instantly—pulling live data across systems, interpreting it, and presenting it in plain English.

How We Built Ollie

Over five years of running operations for hundreds of startups, we built an enormous dataset—real, structured operational knowledge across HR, finance, equity, and compliance.

That knowledge became Ollie’s foundation.

1. The Data Bedrock

At the base of Ollie is what we call the Data Bedrock—a system that turns static, unstructured files into living, queryable data.

Every offer letter, W-9, tax registration, or compliance document is parsed by Chore’s Document AI and File Classification system, transforming messy PDFs into structured data.

This means Ollie doesn’t just read your operations—it understands them.

For example, when you ask, “What’s our next Delaware filing due date?”, Ollie can instantly reference the parsed certificate and tell you the exact timeline—no human searching required.

2. The Ops Dashboard

Next is the Ops Dashboard, a real-time command center.

It connects the Data Bedrock to live integrations from your operations stack: Rippling, Gusto, Deel, QuickBooks, Ramp, Carta, Mercury, and more.

This layer synthesizes all your operational inputs: financial metrics, HR data, and compliance milestones into one cohesive source of truth.

No more toggling between five dashboards. Ollie sees your entire operational universe, understands the context, and can answer complex, cross-functional questions.

3. Ollie + Chief Chore Officer

Finally, at the top of this architecture sits Ollie + Chief Chore Officer.

This is where AI meets human execution.

Ollie delivers instant answers and insights. But when something needs action, like sending an offer letter, filing a tax form, or updating payroll, Chore’s expert team steps in to execute.

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This is a complete system for command and control.

• Ask Ollie: "Which customer MSAs still have a 30-day termination clause?"
• Command the Crew: "Proactively renegotiate those MSAs to net-60 terms."

It’s not just automation. It’s augmentation—AI for context and clarity, humans for judgment and precision.

We call this workflow Query → Insight → Execution.

Ask Ollie a question, get an answer, and instantly trigger the right next step—all in one place.

Is this the back-office operations singularity?

How Ollie Helps Founders

Every founder knows the pain of context switching. You’re building a product, pitching investors, hiring your next engineer—and then a compliance deadline hits, or payroll needs fixing, or your accountant asks for a reconciliation.

Ollie eliminates that distracting friction.

Instant Insight

With Ollie, information is no longer buried in spreadsheets or siloed across tools. Founders can access financial, HR, and compliance data instantly, without having to dig or delegate.

Operational Clarity

Ollie doesn’t just report numbers—it interprets them. It can explain trends in burn, flag anomalies, and surface insights proactively, helping founders make smarter, faster decisions.

Execution at Speed

Need to act on something? Ollie seamlessly connects to Chore’s human team—so if you ask about a late payment, the Crew can issue it; if a compliance filing is due, it can be scheduled immediately.

Time Reclaimed

The most valuable outcome isn’t just efficiency—it’s focus. Ollie gives founders back their most limited resource: time. The time to build, think, and lead. The time to focus on what matters.

How Ollie Is Different

Most AI tools today stop at information retrieval. They answer questions—but they don’t take responsibility. Ollie is different because it’s not a chatbot sitting outside your business—it’s embedded in it.

Here’s Ollie stands apart:

• Built from Real Startup Operations
  • Ollie is trained on Chore’s proprietary dataset, insights gathered from managing operations for hundreds of startups. This means its intelligence is grounded in how real companies actually run.
• Deep Integrations Across the Stack
  • It’s not scraping data; it’s pulling directly from the source. Every integration—from QuickBooks to Rippling—feeds Ollie a live stream of operational data.
• Insight + Action
  • Most systems stop at “here’s what’s wrong.” Ollie continues to “Here’s how we’ll fix it.” Every insight connects directly to Chore’s team for execution.
• Human-in-the-Loop Design
  • Ollie was never meant to replace people: it was built to empower them. Chore’s operations experts ensure every AI-powered decision translates into flawless execution.
• End-to-End Visibility
  • Ollie doesn’t just handle a slice of your operations; it unifies them. Finance, HR, equity, compliance, every back-office function lives in one intelligent system.

Why It Matters

Startups today move at breakneck speed. The ones that win are the ones that can execute faster than their competitors, without sacrificing focus. But every hour spent buried in operations is an hour not spent building or selling.

We believe operational excellence is a great differentiator.

Ollie isn’t just about saving time; it’s about changing the trajectory of companies. It’s about enabling founders to operate with the same clarity, control, and sophistication as companies 10x their size.

Just like AWS made infrastructure scalable and accessible to everyone, Ollie makes operations scalable and intelligent.

This isn’t the future - it’s happening now.

Hundreds of founders are already using Ollie to run smoother, smarter, and faster.

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The End of the Back-Office

For too long, founders have been forced to choose between growth and control.

With Ollie, that trade-off disappears.

You don’t have to build an operations team to have world-class operations.

You don’t have to drown in admin to stay compliant.

You don’t have to lose focus to stay organized.

Ollie gives you back the clarity, speed, and bandwidth to build your vision—and build it faster.

The age of bloated operations teams is over.

The age of the Operations Co-Pilot has begun.

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