Compare / Headway vs Pinterest
HEADWAY
Two guys who watched friends struggle to find therapists that took their insurance decided to fix the most bro…
Ben Silbermann built a virtual pinboard for collecting pretty pictures and accidentally created one of the mos…
AT A GLANCE
FUNDING HISTORY
Headway
BUSINESS MODEL
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.
Pinterest makes money through advertising — specifically through "Promoted Pins" that look nearly identical to organic content. This is the magic of Pinterest's business model: ads don't interrupt the experience because the experience IS discovering products and ideas.
A promoted pin for a kitchen knife set appears right alongside organic pins of kitchen designs. The user doesn't distinguish between "ad" and "content" because both serve the same purpose.
Shopping ads are the fastest-growing segment. Brands upload their product catalogs, Pinterest matches products to user searches and boards, and users can buy directly through the platform or click through to the retailer's site.
Pinterest gets paid per click or per thousand impressions.
Revenue reached $3.65 billion in 2024, up from $3.05 billion the year before, and 2024 was its first genuinely profitable year. Average revenue per user is growing but still well below Meta's — the upside is enormous if Pinterest can close that gap.
HOW THEY STARTED
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.
Ben Silbermann was a former Google ad operations employee who quit in 2008 to build apps. His first attempt was an iPhone app called Tote — essentially a mobile catalog that let women browse and bookmark products from fashion retailers.
Nobody downloaded it. But Silbermann noticed something in the data: users were saving products obsessively.
The collecting behavior was more interesting than the shopping behavior.
He teamed up with Paul Sciarra, a classmate from Yale, and Evan Sharp, a designer who was studying architecture at Columbia. Together they built Pinterest — a visual bookmarking tool that let people "pin" images from around the internet to organized boards.
Think of it as a digital mood board that anyone could make.
Pinterest launched as an invite-only beta in March 2010. Growth was painfully slow at first.
Silbermann personally wrote to the first 5,000 users, giving them his phone number and asking what they wanted. The early community was overwhelmingly women interested in home decor, fashion, recipes, and DIY projects.
By 2011, Time magazine named Pinterest one of the 50 best websites. By 2012, it was the fastest site in history to reach 10 million unique monthly visitors.
HOW THEY GREW
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.
Pinterest grew organically through women sharing boards with each other. The weddings use case was the killer app — brides-to-be would create boards for dresses, venues, flowers, and invitations, then share them with their wedding parties.
That viral loop drove millions of signups.
SEO is the secret weapon. Pinterest pages rank extremely well in Google Image Search.
Someone searching "modern living room ideas" often sees Pinterest results on page one. That drives a large stream of organic traffic from people who were not looking for Pinterest at all.
Unlike other social platforms, which compete with Google for attention, Pinterest quietly benefits from it.
The shopping pivot has been the growth unlock. Under CEO Bill Ready (former Google and PayPal executive who took over in 2022), Pinterest aggressively invested in shopping features — catalog integrations, buyable pins, merchant verification, and visual search for products.
The thesis: Pinterest users are already in a shopping mindset, so removing friction between "I like this" and "I bought this" is the straightforward path to revenue growth.
THE HARD PART
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.
Pinterest's demographics are both an advantage and a limitation. The platform skews heavily female (over 60% women) and is strongest in home, fashion, food, and weddings.
Expanding beyond these categories to attract male users, younger demographics, and different use cases has been slow.
Competition for ad dollars is fierce. Pinterest competes with Meta, Google, TikTok, and Amazon for advertising budgets.
Most advertisers allocate the bulk of their spend to Meta and Google first, then consider others. Pinterest needs to prove its return on ad spend is competitive to win larger budget allocations.
Creator economy is underdeveloped. While Instagram, TikTok, and YouTube have massive creator ecosystems with monetization tools, Pinterest has historically been about content discovery, not content creation.
Users pin other people's content — the original creators often don't even know their work is on Pinterest. Building a creator program and driving original content creation on the platform has been a recent focus but lags far behind competitors.
THE PRODUCTS
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.
Pinterest Home Feed — the core discovery surface showing personalized pins based on user interests, boards, and search history. Pinterest Lens — visual search technology that lets users take a photo of any object and find similar items to buy on Pinterest.
Pinterest Shopping — integrated e-commerce allowing users to browse and purchase products directly from pins linked to retailer catalogs. Pinterest Boards — the organizing system where users save and categorize pins into collections, used for wedding planning, home renovation, recipes, fashion, and more.
Pinterest Shuffles — a collage-making app for Gen Z users to create aesthetic mood boards, driving younger user adoption.
WHO BACKED THEM
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.
Bessemer Venture Partners, FirstMark Capital, and Andreessen Horowitz were early investors. Fidelity and Valiant Capital participated in later rounds.
Rakuten invested strategically. The April 2019 IPO raised $1.4 billion at a $12.7 billion valuation.
Elliott Management, the activist investor, took a large stake in 2022 and pushed for operational improvements that contributed to the company's path to profitability.