AT A GLANCE

Rippling
Dandy
2016
Founded
2020
San Francisco, California
HQ
New York, NY
$1.4 billion
Total Raised
$250M+
Parker Conrad, Prasanna Sankar
Founder
Henry Stott
HR Tech
Type
Health Tech
Private ($13.5B valuation)
Status
Private (Series C)

FUNDING HISTORY

Rippling

Series A2017
$10M raised
Series B2019
$145M raised$1.4B val.
Series C2021
$250M raised$6.5B val.
Series D2022
$500M raised$11.3B val.
Series E2024
$200M raised$13.5B val.

Dandy

Seed2020
$6M raised
Series A2021
$20M raised
Series B2022
$90M raised
Series C2023
$130M raised$1.8B val.

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.

Dandy

Vertical SaaS plus manufacturing. Dandy provides dental practices with intraoral scanners (often subsidized or free to eliminate the switching cost), cloud-based software for managing cases, and its own network of digital dental labs that manufacture the final restorations.

Dentists pay per case — each crown, bridge, veneer, or implant restoration is priced individually. The margin comes from manufacturing efficiency: digital workflows are faster, more precise, and require less manual labor than traditional hand-sculpted methods.

As volume grows, Dandy's labs get more efficient and per-unit costs drop. It's the classic razor-and-blades model — give away the scanner, make money on every restoration.

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.

Dandy

Henry Stott was a repeat entrepreneur who had previously co-founded a tech company in the UK. When he looked at the dental industry, he saw a $15 billion lab market that was shockingly analog.

Here's how it worked: a dentist jams a tray of gooey putty into your mouth, waits for it to harden, mails the physical mold to a dental lab, where a technician hand-sculpts your crown out of ceramic. Turnaround: 2 to 3 weeks.

Error rate: high. Patient experience: miserable.

The technology to do this digitally had existed for years — 3D intraoral scanners, CAD/CAM software, CNC milling machines — but nobody had stitched it into a seamless end-to-end platform for the average dental practice. Stott started Dandy in 2020 to be that platform.

Provide the scanner, build the software, run the lab — and make it so easy that any dentist can switch from analog to digital without changing how they practice.

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.

Dandy

Land-and-expand with dental practices. Dandy gives practices the scanner for free or at heavy discount, which eliminates the biggest barrier to switching from analog.

Once a practice starts submitting digital scans, they become recurring revenue — every patient who needs a crown is a Dandy order. Sales team targets mid-size practices (3 to 10 dentists) that are high-volume but haven't invested in digital yet.

Referral programs where existing dentists recommend Dandy to colleagues. Geographic density strategy — build lab capacity in a region, then saturate practices nearby to optimize logistics and turnaround times.

Content marketing educating dentists on why digital is better, faster, and more profitable than analog workflows.

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.

Dandy

Dental practices are notoriously resistant to change — many dentists have used the same lab for 20 years and switching feels risky. The scanner hardware is expensive to subsidize at scale, creating a capital-intensive land grab.

Quality control across distributed manufacturing is hard — a crown that doesn't fit means a remake, an unhappy patient, and a dentist who might switch back to their old lab. Competition from established digital players like Align Technology and legacy lab companies investing in their own digital capabilities.

The dental industry is fragmented — 200,000+ practices in the US, mostly small businesses, which means enterprise-style sales don't work. Each practice is its own decision maker with its own habits.

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.

Dandy

Dandy Scanner — provided to dental practices, captures a full 3D digital impression of the patient's mouth in minutes. No more putty molds.

Cloud-based case management platform where dentists submit scans, approve designs, and track orders. AI-powered restoration design that generates crown and veneer designs automatically from 3D scans, reducing turnaround from weeks to days.

Digital dental lab network with automated CNC milling and 3D printing for manufacturing restorations. Shade matching technology using AI to color-match restorations to surrounding teeth.

Integration with practice management software so cases flow seamlessly from scan to delivery.

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.

Notable for being founded by someone investors initially wouldn't touch after the Zenefits scandal.

Dandy

Investors include Bessemer Venture Partners, IVP, DST Global, and IA Ventures. Series C in 2023 valued the company at approximately $1.8 billion.

MORE COMPARISONS

Rippling vs Dandy — Head-to-Head Comparison | Netfigo