Compare / Rippling vs Pinterest
RIPPLING
Parker Conrad got fired as CEO of his first startup (Zenefits) in a compliance scandal, then built Rippling — …
Ben Silbermann built a virtual pinboard for collecting pretty pictures and accidentally created one of the mos…
AT A GLANCE
FUNDING HISTORY
Rippling
BUSINESS MODEL
Rippling
Rippling uses modular pricing — companies buy the modules they need and pay per employee per month. The core platform (employee directory) is the foundation, with add-on modules for payroll ($8/month per employee), benefits, time and attendance, learning management, IT device management, app management, corporate cards, and expense management.
This modular approach means Rippling can land with one module and expand to many. A company might start with just payroll, then add device management when they realize it's available, then corporate cards.
Average revenue per customer grows as companies add modules.
The compound effect is the strategy. Each individual module might not be the best standalone product, but the integration between modules creates value that no combination of point solutions can match.
When your payroll system, IT system, and expense system all share the same employee database, automation becomes trivial.
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
Rippling
Parker Conrad's origin story at Rippling is inseparable from his spectacular flameout at Zenefits. Conrad co-founded Zenefits in 2013 as an HR platform for small businesses and grew it to a $4.5 billion valuation in two years.
Then it imploded. Regulators discovered Zenefits employees had used software to cheat on insurance licensing exams.
Conrad was forced to resign as CEO in February 2016. The company he'd built was toxic, and his reputation was in ruins.
Most founders would have retreated. Conrad started Rippling in August 2016 — six months after being pushed out of Zenefits.
His co-founder Prasanna Sankar was a former Zenefits engineer. The insight behind Rippling came directly from the Zenefits experience: companies use dozens of disconnected systems for HR, IT, payroll, and finance.
When you hire someone, you set them up in the HR system, the payroll system, the benefits system, the laptop provisioning system, the software access system — all separately. When they leave, you have to remove them from each one individually.
It's a mess.
Rippling's premise was radical: build one unified platform with the employee record at the center. When you hire someone in Rippling, it automatically sets up their payroll, enrolls them in benefits, ships them a laptop, provisions their software accounts, issues a corporate card, and adds them to the right Slack channels.
One action triggers everything. When they leave, one click revokes it all.
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
Rippling
Rippling's growth strategy is "compound startup" — building many products simultaneously instead of one at a time. Most SaaS companies pick a niche and dominate it before expanding.
Rippling launches new product modules aggressively, banking on the thesis that integration is the killer feature.
The land-and-expand motion works because every module sells every other module. An HR team that uses Rippling for payroll sees that IT device management is available.
The IT team that uses device management discovers corporate cards. Each module is a door to the entire platform.
Mid-market focus (50-2,000 employees) hits the sweet spot — these companies are big enough to need multiple systems but small enough that a single platform is appealing. Enterprise companies have entrenched vendors.
Tiny startups don't need the full suite. The mid-market wants consolidation and Rippling delivers it.
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
Rippling
Building many products simultaneously means none of them is best-in-class individually. Gusto has better payroll for small businesses.
Jamf has better device management. Brex has better corporate cards.
Rippling's bet is that "good enough across ten categories" beats "best in one." That bet is unproven at scale.
The Parker Conrad factor cuts both ways. His Zenefits implosion is public knowledge, and some investors and customers remain wary.
Conrad has been open about the experience but the baggage is real. On the flip side, the "I failed and came back stronger" narrative resonates with many founders.
International expansion is complex. Rippling's Global product offers employer-of-record services in 100+ countries, but managing local labor laws, tax regulations, and benefits across dozens of jurisdictions is extraordinarily complicated.
Deel and Remote.com are dedicated international employment platforms that may execute better in global markets.
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
Rippling
Rippling Unity — the core employee data platform that connects all modules through a unified employee graph. Every system shares the same data, eliminating manual syncing.
Rippling Payroll — full-service payroll processing for US and international employees with automated tax filing. Rippling IT — device management (ship, configure, secure, and wipe laptops), software provisioning (manage employee access to hundreds of SaaS apps), and identity management.
Rippling Spend — corporate cards and expense management with policy enforcement built into the card itself. Rippling Global — international payroll and employer-of-record services covering 100+ countries.
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
Rippling
Founders Fund led the Series A — Peter Thiel betting on Conrad's comeback. Kleiner Perkins and Bedrock invested in growth rounds.
Greenoaks Capital, Coatue Management, and Y Combinator participated. The 2024 round valued Rippling at $13.5 billion, led by Coatue, and a 2025 round pushed it to $16.8 billion.
Notable for being founded by someone investors initially wouldn't touch after the Zenefits scandal.
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.