Rippling

Zoom

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

Zoom

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