Assurant vs Cloudflare: Founders, CEOs and History
Assurant was founded in 1892 by Founders of La Crosse Mutual Aid Association and is led by Keith Demmings. Cloudflare was founded in 2009 by Matthew Prince, Michelle Zatlyn, Lee Holloway and is led by Matthew Prince.
Company facts
Assurant
- Founded
- 1892
- Headquarters
- Atlanta, Georgia
- Current CEO
- Keith Demmings
- Employees
- 14,800
Cloudflare
- Founded
- 2009
- Headquarters
- San Francisco, California
- Current CEO
- Matthew Prince
- Employees
- 5,156
Founders
Assurant
Founders of La Crosse Mutual Aid Association
The La Crosse Mutual Aid Association was established to provide disability insurance to consumers. It was later licensed as the Time Insurance Company in 1910 and evolved into a Wisconsin health and disability underwriter.
Cloudflare
Matthew Prince
Matthew Prince is Cloudflare's co-founder, CEO, and board chair. In 2004 he and Lee Holloway built Project Honey Pot, which let website owners track spammers harvesting email addresses but could not stop them.
Michelle Zatlyn
Michelle Zatlyn is Cloudflare's co-founder, President, and Chief Operating Officer, and a member of its board. She met Matthew Prince at Harvard Business School, where the two developed the business plan that became Cloudflare in 2009.
Lee Holloway
Lee Holloway co-founded Cloudflare in 2009 and was its first lead engineer and systems architect. He had earlier built Project Honey Pot with Matthew Prince starting in 2004, and he designed much of Cloudflare's early software infrastructure.
CEOs and their tenures
Assurant
- J. Kerry Clayton2004–2006
Former Chief Executive Officer
Led Fortis, Inc. through its February 2004 initial public offering and rebranding as Assurant, Inc. and ran the company for its first two years as an independent listed insurer.
Source - Robert B. Pollock2006–2014
Former President and Chief Executive Officer
Ran Assurant through its first decade as an independent specialty insurer, holding together a portfolio that spanned health, employee benefits, prearranged funeral insurance and lender-placed property.
Source - Alan B. Colberg2015–2021
Former President and Chief Executive Officer
Took Assurant out of health insurance and employee benefits and rebuilt it around lifestyle and housing protection, then bought the scale to make that work.
Source - Keith W. Demmings2022–present
President and Chief Executive Officer
Has run Assurant as a two-segment protection company, pushing it further into device repair, trade-in and resale while growing the lender-placed housing book.
Source
Cloudflare
- Matthew Prince2009–present
Co-Founder, Chief Executive Officer, and Chair
Co-founded Cloudflare in 2009, led it through its September 2019 NYSE IPO, and has grown annual revenue past $2 billion (2025) while expanding from web security into Zero Trust, developer, and AI services.
Source - Michelle Zatlyn2009–present
Co-Founder, President, and Chief Operating Officer
Co-founded Cloudflare in 2009 with Matthew Prince and Lee Holloway and, as President and COO, has led operations and company-building as Cloudflare scaled to more than 5,000 employees.
Source - Thomas Seifert2017–present
Chief Financial Officer
As CFO, he consistently delivered high revenue growth while carefully controlling capital expenditures, allowing Cloudflare to heavily invest in its serverless Edge computing network.
Source
Timeline: Assurant and Cloudflare side by side
1892Assurant
La Crosse Mutual Aid Association formed
Assurant traces its history to the La Crosse Mutual Aid Association, established in La Crosse, Wisconsin in 1892 to provide consumers with disability insurance. No founder of the association is named in the company own histories.
1910Assurant
Licensed as Time Insurance Company
The Wisconsin Office of the Commissioner of Insurance records Time Insurance Company, the successor to the La Crosse Mutual Aid Association, as originally licensed as an insurer in 1910.
1978Assurant
N.V. AMEV of the Netherlands buys Time Insurance
Dutch insurer N.V. AMEV acquired Time Insurance Company through its US holding company, AMEV Holdings, Inc., then expanded it by buying American Security Insurance, United Family, Western Insurance Company and Superior Insurance over the next 12 years.
1991Assurant
AMEV Holdings renamed Fortis, Inc.
After AMEV combined with VSB Groep NV in 1990 to create Fortis, the US holding company AMEV Holdings, Inc. was rebranded Fortis, Inc. in 1991. It acquired John Alden in 1998.
1999Assurant
Fortis acquires American Bankers Insurance
Fortis, Inc. bought American Bankers Insurance Group of Miami, adding credit insurance and specialty warranty underwriting that became the core of the modern specialty lines. Fortis sold its life insurance business to The Hartford in 2001.
2004Assurant
NYSE listing as Assurant, Inc.
Fortis took the US business public on February 5, 2004 in a $1.76 billion initial public offering, the fourth largest of that year, and renamed it Assurant, Inc. The company was incorporated as a Delaware corporation in 2004 and trades as AIZ.
2006Assurant
Robert B. Pollock succeeds J. Kerry Clayton as CEO
Founding chief executive J. Kerry Clayton retired on March 17, 2006 and was succeeded by Robert B. Pollock, then president and chief operating officer, who also joined the board that day.
2009Cloudflare
Cloudflare Founded
Matthew Prince, Michelle Zatlyn, and Lee Holloway founded Cloudflare, building on the Project Honey Pot spam-tracking project.
2010Cloudflare
TechCrunch Disrupt Launch
Cloudflare launched publicly at TechCrunch Disrupt in San Francisco in September 2010, offering free website protection and acceleration.
2013Assurant
New York consent order on force-placed insurance
Assurant, American Security Insurance Company and American Bankers Insurance Company of Florida settled a New York Department of Financial Services investigation into force-placed homeowners insurance on March 21, 2013, paying a $14 million penalty plus homeow…
2014Cloudflare
Universal SSL and Project Galileo
Cloudflare gave free SSL certificates to all customers with Universal SSL and launched Project Galileo to protect at-risk nonprofits and journalists for free.
2015Assurant
Exit from health insurance and employee benefits
On June 10, 2015 Assurant announced it would leave the health insurance marketplace and wind down Assurant Health, and on September 9, 2015 it agreed to sell its employee benefits business to Sun Life for $940 million.
2017Cloudflare
Cloudflare Workers Announced
Cloudflare introduced Workers, a serverless platform built on V8 isolates that lets developers run code across its network.
2018Assurant
The Warranty Group acquisition closes
Assurant completed its purchase of The Warranty Group from TPG Capital on May 31, 2018 for a total enterprise value of about $2.5 billion, expanding vehicle service contracts and international retail protection. Assurant also sold Time Insurance in 2018.
2019Cloudflare
NYSE IPO
Cloudflare completed its IPO on the New York Stock Exchange under the ticker NET in September 2019 at $15 per share, raising about $525 million.
2020Assurant
HYLA Mobile acquisition closes
Assurant closed its acquisition of smartphone trade-in and upgrade provider HYLA Mobile on December 1, 2020, in a transaction the company valued at about $325 million, roughly doubling its device processing volumes.
2020Cloudflare
Cloudflare One Launched
Cloudflare bundled its Zero Trust access, secure web gateway, and network services into Cloudflare One, its SASE platform.
2021Assurant
Global Preneed sold to CUNA Mutual Group
Assurant closed the sale of its prearranged funeral and final expense business to CUNA Mutual Group on August 2, 2021 for about $1.35 billion, generating roughly $1.2 billion of net proceeds, and said it intended to return about $900 million of that through sh…
2022Assurant
Keith Demmings becomes CEO and headquarters moves to Atlanta
Keith W. Demmings became president and chief executive officer in January 2022, succeeding Alan B. Colberg, who retired at the end of 2021 after seven years in the role.
2022Cloudflare
Area 1 Security and R2 General Availability
Cloudflare acquired email security company Area 1 Security for about $162 million and made R2 zero-egress object storage generally available.
2024Assurant
iSmash acquired in the United Kingdom
Assurant acquired UK tech repair retailer iSmash on April 4, 2024, giving it 68 drop-in repair locations in the UK under the iSmash and Pocket Geek Tech Repair banners. Assurant also sold its mainland China operations during 2024.
2024Cloudflare
Revenue Reaches $1.67 Billion
Cloudflare reported 2024 revenue of $1.67 billion and free cash flow of $166.9 million.
2025Assurant
FY2025 revenue of $12.81B and the OptoFidelity purchase
Assurant reported FY2025 revenue of $12.81 billion and GAAP net income of $872.7 million, its ninth consecutive year of profitable growth, launched Assurant Home Warranty, and in October 2025 acquired OptoFidelity mobile device test automation portfolio to add…
2025Cloudflare
Revenue Passes $2 Billion
Cloudflare reported 2025 revenue of $2.17 billion (+29.8%) and closed its largest contract ever, averaging $42.5 million per year in ACV.
2026Assurant
RL Circular Operations acquired in Australia and New Zealand
In January 2026 Assurant acquired RL Circular Operations, formerly TIC Reverse Logistics, the reverse logistics division of Australia and New Zealand based TIC Group, extending its post-purchase and circular economy capabilities across Asia Pacific.
2026Cloudflare
VoidZero Acquisition and Growth Acceleration
Cloudflare acquired VoidZero, the company behind the Vite JavaScript tooling ecosystem, in June 2026 and reported Q2 2026 revenue growth of 36%.
Acquisitions
Assurant
- RL Circular Operations2026Undisclosed
- OptoFidelity mobile device test automation portfolio2025Undisclosed
- iSmash2024Undisclosed
- HYLA Mobile2020$325M
- The Warranty Group2018$2.5B
- Lifestyle Services Group2013$172M
Cloudflare
- Human Native2026Undisclosed
- Astro Technology Company2026Undisclosed
- VoidZero2026Undisclosed
- Replicate2025Undisclosed
- Nefeli Networks2024Undisclosed
- Baselime2024Undisclosed
Questions about Assurant vs Cloudflare
Who is the CEO of Assurant, Inc. and Cloudflare, Inc.?
Assurant, Inc. is led by Keith Demmings and Cloudflare, Inc. is led by Matthew Prince. Both serve as the top executive responsible for the company's strategy, operations, and financial performance.
When was Assurant, Inc. founded vs Cloudflare, Inc.?
Assurant, Inc. was founded in 1892 — 117 years before Cloudflare, Inc., which was founded in 2009. Assurant, Inc.'s longer operating history gives it a deeper track record but also potentially more institutional inertia compared to the younger Cloudflare, Inc..
How many employees does Assurant, Inc. have compared to Cloudflare, Inc.?
Assurant, Inc. employs approximately 14,800 people, while Cloudflare, Inc. employs approximately 5,156. Assurant, Inc. has the larger workforce at 14,800 employees, compared to Cloudflare, Inc.'s 5,156. A higher headcount does not necessarily imply greater efficiency — it often reflects differences in business model (e.g., manufacturing vs. software).
Where are Assurant, Inc. and Cloudflare, Inc. headquartered?
Both Assurant, Inc. and Cloudflare, Inc. are headquartered in United States, meaning they operate under the same primary regulatory and tax environment.
Who founded Assurant, Inc. and Cloudflare, Inc.?
Assurant, Inc. was founded by Founders of La Crosse Mutual Aid Association. Cloudflare, Inc. was founded by Matthew Prince, Michelle Zatlyn, Lee Holloway.
Which company has a longer operating history — Assurant, Inc. or Cloudflare, Inc.?
Assurant, Inc. has been operating for approximately 134 years, making it the more established of the two companies. Cloudflare, Inc. has been in operation for around 17 years. A longer operating history often signals greater institutional resilience and brand recognition, though it can also mean slower adaptation to new market conditions.
Figures come from each company's filings and the sources linked beside them. Amounts reported in another currency are shown in US dollars at an approximate rate and marked with ~. Back to the Assurant vs Cloudflare overview