Headway

Zoom

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.

Zoom

Zoom uses a freemium model. Free accounts get unlimited one-on-one meetings and 40-minute group meetings.

Paid plans start at $13.33/month per user for Pro (meetings up to 30 hours), $18.33/month for Business, and custom pricing for Enterprise. Zoom also charges for add-ons — Zoom Phone (cloud phone system), Zoom Rooms (conference room hardware), and Zoom Contact Center.

The free tier is the hook. The 40-minute limit on group calls creates just enough friction to push power users to pay.

And once one person in a company pays, the whole team follows because nobody wants to be the one whose meetings keep getting cut off.

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.

Zoom

Eric Yuan grew up in Tai'an, a mining city in Shandong province, China. In the mid-1990s he was in his twenties and inspired by the internet boom happening in America.

He applied for a US visa. He was rejected.

He applied again. Rejected again.

Eight times in total over about two years before he was finally approved in 1997. He moved to Silicon Valley with barely any English and joined WebEx as one of its first engineers.

Yuan spent 14 years at WebEx, eventually becoming VP of Engineering. Cisco acquired WebEx in 2007 for $3.2 billion.

Yuan watched Cisco slowly bloat the product with enterprise features while the core video quality deteriorated. He kept telling Cisco leadership they needed to rebuild the product from scratch.

They kept saying no.

In 2011, Yuan quit and took 40 WebEx engineers with him. He founded Zoom Video Communications with a simple thesis: video meetings should just work.

No downloads. No lag.

No "can you hear me?" No IT department required. He built the product that Cisco refused to build.

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.

Zoom

Zoom grew on one thing: it worked. In a world where every video call started with five minutes of technical issues, Zoom calls just connected.

That reliability was the entire marketing strategy for the first five years.

The freemium model did the rest. Teachers, coaches, therapists, book clubs, and small teams all started on the free tier.

When they hit the 40-minute limit, enough of them converted to paid. And every free meeting was essentially a demo — everyone in the meeting saw how good Zoom was.

Yuan obsessed over simplicity. While competitors like WebEx and GoToMeeting required downloads, plugins, and IT involvement, Zoom worked in the browser with one click.

The learning curve was essentially zero. Your grandmother could figure it out.

That turned out to be extremely important when a pandemic suddenly required your grandmother to figure it out.

Then COVID happened. In March 2020, the world shut down.

Every meeting — work, school, family, doctor, church, happy hour — moved to video. Zoom was already the easiest option.

Daily participants exploded from 10 million to 300 million in four months. The stock went from $70 to $588.

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.

Zoom

The post-pandemic hangover has been severe. Zoom's stock peaked at $588 in October 2020 and crashed to under $70 by 2022 — an 88% drop.

The company went from the most exciting tech stock on the planet to a cautionary tale about pandemic valuations. Revenue growth slowed from 300%+ to single digits as people returned to offices and competitors caught up.

Security and "Zoombombing" were early crises. In early 2020, as millions of new users flooded in, trolls discovered they could join open Zoom meetings and share offensive content.

Schools, churches, and AA meetings were disrupted. It turned out Zoom's encryption wasn't truly end-to-end as advertised.

Yuan had to halt all feature development for 90 days and focus exclusively on security fixes. It was a near-death reputational crisis.

Competition from Microsoft Teams and Google Meet intensified. Both companies bundled video calling for free into products that hundreds of millions of people already used.

Microsoft Teams integrated directly into Office 365. Google Meet was built into Gmail.

Zoom had to compete against free products from two of the richest companies on Earth.

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.

Zoom

Zoom Meetings is the core — video calls that actually work. Zoom Webinars handles large-scale events with up to 50,000 attendees.

Zoom Phone is a full cloud-based phone system replacing traditional office phones. Zoom Rooms turns physical conference rooms into one-click video meeting spaces.

Zoom Contact Center competes with established call center software. Zoom Team Chat is their Slack/Teams competitor.

Zoom Whiteboard is a collaborative digital canvas. Zoom Revenue Accelerator uses AI to analyze sales calls.

And Zoom AI Companion summarizes meetings and drafts messages.

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.

Zoom

Sequoia Capital, Emergence Capital, Horizons Ventures (Li Ka-shing), Qualcomm Ventures