Headway

Stripe

Headway

Headway makes money by taking a percentage of the insurance reimbursement for each session facilitated through the platform. When a patient sees a Headway-credentialed therapist and pays their copay, Headway processes the insurance claim and takes a service fee from the reimbursement before paying the therapist.

The model aligns incentives well. Headway only makes money when therapy sessions actually happen, which means they're incentivized to help therapists see more patients and reduce no-shows.

Therapists make more than they would on their own (because Headway's negotiated rates are often better than individual therapists can get), and patients pay only their insurance copay ($0-$50 typically) instead of full out-of-pocket rates.

Scale creates a data and negotiation advantage. With 40,000+ therapists on the platform, Headway can negotiate better reimbursement rates with insurers.

More therapists attract more patients. More patients justify better rates.

The flywheel spins.

Stripe

Stripe charges a flat 2.9% + $0.30 per transaction. That's it.

No setup fees, no monthly fees, no hidden charges. The simplicity is the product.

When a customer pays on a website using Stripe, Stripe handles everything — fraud detection, currency conversion, bank transfers, tax calculation, compliance. The merchant just sees money arrive in their account.

On top of the core payments, Stripe has built an entire financial infrastructure stack. Billing for subscriptions, Connect for marketplace payments, Atlas for incorporating a company, Issuing for creating virtual cards, Treasury for banking-as-a-service, and Radar for fraud prevention.

They're basically building the financial plumbing for the entire internet.

Headway

Andrew Adams and Jake Sussman founded Headway in 2019 after watching people in their lives struggle to access affordable mental healthcare. The problem was specific and structural: most therapists operate as solo practitioners who don't accept insurance.

Not because they don't want to — because the process of getting credentialed with insurance companies, submitting claims, and chasing reimbursements is so bureaucratically painful that most therapists give up and go cash-only.

The result is a two-tier mental healthcare system. People with money pay $150-$300 per session out of pocket.

People without money either can't afford therapy or wait months for the few in-network providers available. Meanwhile, therapists who only accept cash are leaving money on the table — insurance pays reliably once the system works, and the patient pool is vastly larger.

Headway's solution was to build the infrastructure layer that makes insurance billing painless for therapists. They handle credentialing (getting the therapist accepted into insurance networks), claims submission, payment processing, and compliance — all the administrative work that therapists hate.

The therapist shows up, does therapy, and Headway handles everything else.

Stripe

Patrick Collison was 19. His brother John was 17.

They had already built and sold a company — Auctomatic, an eBay auction tool — for $5 million while still teenagers in Limerick, Ireland. Patrick went to MIT, John went to Harvard, and they both dropped out because they had a better idea.

The idea was embarrassingly obvious in hindsight. In 2010, accepting payments on the internet was a nightmare.

You had to get a merchant account, negotiate with a payment processor, deal with a gateway provider, handle PCI compliance, and write thousands of lines of code. It took weeks or months.

The Collisons thought it should take five minutes.

They built a simple API — seven lines of code — that let any developer start accepting credit card payments immediately. No merchant account.

No paperwork. No phone calls with banks.

Just paste seven lines of code and you're in business. They originally called it /dev/payments, then changed it to Stripe in 2011.

Peter Thiel and Elon Musk — the PayPal mafia — were among the first investors. Sequoia and Andreessen Horowitz piled in soon after.

The Collisons had built exactly what every developer on Earth had been wishing for.

Headway

Headway grew by solving the supply-side problem first. If you can get enough therapists on the platform and credentialed with insurance, patients will come because affordable therapy is in massive demand.

They recruited therapists with a compelling pitch: "keep doing therapy, we'll handle the business side."

Insurance partnerships were the growth unlock. Headway partnered with major insurance companies (Aetna, Cigna, United Healthcare, Anthem) to become an authorized credentialing partner.

This meant Headway could get therapists in-network faster and with less friction than the traditional process.

The mental health destigmatization wave amplified demand. Post-COVID, demand for therapy skyrocketed.

The conversation around mental health became mainstream. Headway was positioned perfectly to absorb that demand by connecting patients with affordable, insurance-covered therapists.

Stripe

Stripe grew almost entirely through developer love. They didn't hire a sales team for years.

They didn't run ads. They just built the best developer documentation anyone had ever seen and let word of mouth do the rest.

The developer-first strategy was deliberate. The Collisons realized that in a startup, the developer usually decides which payment provider to use.

If you make the developer happy, you win the company. Stripe's API documentation became legendary — clear, beautiful, with working code examples in every language.

They also grew by growing with their customers. Early Stripe customers included tiny startups that later became giants — Lyft, DoorDash, Instacart, Shopify.

As those companies scaled to billions in revenue, Stripe's processing volume scaled with them. Stripe didn't need to acquire new customers because its existing ones kept getting bigger.

The international expansion was methodical. Instead of launching everywhere at once like Uber, Stripe carefully added country after country, making sure each one worked perfectly with local payment methods, currencies, and regulations.

By 2024 they were processing payments in 195 countries.

Headway

Therapist retention is a challenge. Solo practitioners are independent by nature, and some leave the platform once they've built a full patient roster through Headway.

The platform needs to continuously demonstrate value beyond initial credentialing to keep therapists from going direct.

Insurance reimbursement rates are notoriously low. Therapists who accept insurance often earn 30-50% less per session than cash-pay rates.

While Headway negotiates better rates than individual therapists typically get, the fundamental economics of insurance-based mental healthcare remain challenging.

Regulatory complexity varies by state. Each state has different licensing requirements, insurance regulations, and telehealth rules.

Expanding to all 50 states means navigating 50 different regulatory frameworks, each with their own credentialing requirements and compliance standards.

Stripe

Valuation whiplash. In 2021, Stripe hit a peak valuation of $95 billion during the fintech boom.

By 2023, they had to mark it down to $50 billion during the tech correction — a 47% drop that made headlines everywhere. Employees who had been paper millionaires suddenly weren't.

The valuation has since recovered to $91 billion after a secondary share sale in 2025, but those two years were rough for morale.

Competition is relentless. Adyen, the Dutch payments company, has been eating into Stripe's enterprise market.

Square (now Block) competes on the small business side. PayPal is everywhere.

New fintech players pop up constantly. The payments business has razor-thin margins and everyone is fighting for the same 2.9%.

Going public is the elephant in the room. Stripe has been expected to IPO for years.

Investors, employees, and the media keep asking when. The Collisons have consistently said they're in no rush, but with $8.7 billion raised and thousands of employees holding stock options, the pressure to provide liquidity is enormous.

As of 2025, they've opted for secondary sales instead of a public offering.

Headway

Headway Provider Platform — the core system where therapists manage their practice: scheduling, credentialing, claims submission, payment tracking, and patient communications. Headway Patient Matching — a directory and matching service that connects patients with in-network therapists based on insurance, location, specialty, and availability.

Insurance Credentialing Service — Headway handles the months-long process of getting therapists accepted into insurance networks, reducing what typically takes 6-12 months to weeks. Claims and Billing Engine — automated insurance claims submission and tracking that eliminates the paperwork therapists dread.

Practice Management Tools — scheduling, intake forms, session notes, and telehealth capabilities integrated into one platform.

Stripe

Stripe Payments is the core — accept credit cards, debit cards, Apple Pay, Google Pay, and 135+ payment methods in 195 countries. Stripe Connect lets marketplaces and platforms pay out to sellers (Shopify, Lyft, DoorDash all use it).

Stripe Billing handles subscription and recurring billing. Stripe Atlas lets you incorporate a US company from anywhere in the world — fill out a form, get a Delaware C-corp, bank account, and tax ID in days.

Stripe Radar uses machine learning to block fraud in real time. Stripe Treasury lets platforms offer banking services to their customers.

Stripe Tax automatically calculates and collects sales tax in every jurisdiction.

Headway

Andreessen Horowitz led the Series C at a $2.3 billion valuation. Accel and Thrive Capital invested in earlier rounds.

GV (Google Ventures) and Spark Capital also participated. The company has raised approximately $226 million total.

Stripe

Peter Thiel, Elon Musk, Sequoia Capital, Andreessen Horowitz, General Catalyst, Founders Fund, Tiger Global, GV (Google Ventures), Goldman Sachs, Baillie Gifford