AT A GLANCE

UiPath
Pinterest
2005
Founded
2010
New York, New York
HQ
San Francisco, California
$2 billion
Total Raised
$1.5 billion
Daniel Dines, Marius Tîrcă
Founder
Ben Silbermann, Paul Sciarra, Evan Sharp
Automation
Type
Social Media
Public (NYSE: PATH)
Status
Public (NYSE: PINS)

FUNDING HISTORY

UiPath

Series A2017
$30M raised$110M val.
Series B2018
$153M raised$1.1B val.
Series C2019
$225M raised$3.0B val.
Series D2019
$568M raised$7.1B val.
Series F2021
$750M raised$35.0B val.
IPO2021
$1.3B raised$36.0B val.

Pinterest

Series A2011
$10M raised$40M val.
Series B2012
$100M raised$1.5B val.
Series D2013
$225M raised$3.8B val.
Series G2015
$367M raised$11.0B val.
IPO2019
$1.4B raised$12.7B val.

BUSINESS MODEL

UiPath

UiPath sells software licenses and cloud subscriptions for its automation platform. Pricing is based on the number of software robots (called "attended" and "unattended" robots) deployed plus platform fees for orchestration and management tools.

The land-and-expand model works well. A company might start with 5 robots automating invoice processing, then expand to 50 robots handling HR onboarding, then 500 robots across the entire organization.

Revenue per customer grows as automation spreads through departments.

Annual recurring revenue exceeded $1.5 billion in fiscal year 2025. The shift from on-premise licenses to cloud subscriptions has been a major focus, with cloud ARR growing faster than overall revenue.

Professional services and training (UiPath Academy) generate additional revenue.

Pinterest

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

UiPath

Daniel Dines grew up in communist Romania and taught himself to code as a teenager. After working at Microsoft in Seattle for several years, he returned to Bucharest in 2005 and started a small software company called DeskOver with Marius Tîrcă.

Their initial product was an SDK — a software library that let developers build automation scripts for Windows applications.

For nearly a decade, DeskOver (later renamed UiPath) survived as a tiny bootstrapped company selling development tools. Dines ran the operation from a small apartment in Bucharest with a handful of employees.

Revenue was modest — enough to keep the lights on but not enough to grow. The company was unknown outside a niche developer community.

The pivot came around 2013-2015 when Dines noticed that large enterprises were spending billions on outsourcing repetitive digital tasks — copying data from one system to another, processing invoices, updating spreadsheets. He repositioned UiPath from a developer tool into an enterprise RPA platform: software "robots" that could mimic human actions on a computer screen.

Click this button. Copy that field.

Paste it here. Send that email.

The timing was perfect — every large company had thousands of employees doing exactly this kind of work.

Pinterest

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

UiPath

UiPath grew through a community-first strategy. UiPath Academy offered free training and certification, creating hundreds of thousands of developers who knew the platform before their employers bought it.

When those developers advocated for UiPath internally, the sales team had warm leads.

The free Community Edition let individual developers and small teams use UiPath at no cost. This bottoms-up adoption mirrored the playbook of Slack and Atlassian — get individual users hooked, then sell enterprise licenses to the organization.

Partners and system integrators drove enterprise deals. Deloitte, Accenture, EY, and PwC all built RPA practices around UiPath, recommending it to their enterprise clients.

These consulting firms had existing relationships with every Fortune 500 CIO, and they directed automation budgets toward UiPath.

Pinterest

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

UiPath

AI threatens to leapfrog RPA entirely. Traditional RPA automates repetitive, rule-based tasks by mimicking human clicks.

But generative AI and large language models can understand context, handle exceptions, and process unstructured data — potentially replacing the need for screen-scraping robots. If AI agents can directly interact with APIs and databases, the "robot that clicks buttons" approach may become obsolete.

Competition from Microsoft is the most dangerous threat. Microsoft Power Automate is bundled into Microsoft 365, which virtually every enterprise already pays for.

Offering "good enough" automation for free inside a suite companies already use is devastating for a standalone RPA vendor charging premium prices.

Growth has decelerated. After explosive growth during COVID (when every company rushed to automate), UiPath's revenue growth slowed significantly.

The stock dropped over 80% from its all-time high. CEO Daniel Dines stepped back as CEO in 2023 (Rob Enslin took over, then left, and Dines returned in 2024), creating leadership instability at a critical moment.

Pinterest

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

UiPath

UiPath Studio — the development environment where automation workflows are designed using a visual drag-and-drop interface. No coding required for basic automations.

UiPath Robots — the software agents that execute automated workflows, either alongside human workers (attended) or independently (unattended) on virtual machines. UiPath Orchestrator — the centralized management platform for deploying, monitoring, scheduling, and scaling thousands of robots across an organization.

UiPath Autopilot — an AI-powered assistant that uses generative AI to help users build automations through natural language descriptions. UiPath Document Understanding — AI models that extract data from unstructured documents like invoices, contracts, and forms.

Pinterest

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

UiPath

Accel led the Series A in 2017 — the first major venture investment after a decade of bootstrapping. CapitalG (Alphabet's growth fund), Sequoia Capital, and IVP participated in later rounds.

Dragoneer, Tiger Global, Alkeon Capital, and Coatue Management invested in the 2019-2021 growth rounds. The April 2021 IPO raised $1.3 billion at a $36 billion valuation.

Pinterest

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.

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