Assurant vs Twilio: Founders, CEOs and History
Assurant was founded in 1892 by Founders of La Crosse Mutual Aid Association and is led by Keith Demmings. Twilio was founded in 2008 by Jeff Lawson, John Wolthuis, Evan Cooke and is led by Khozema Shipchandler.
Company facts
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.
Twilio
Jeff Lawson
Jeff Lawson co-founded Twilio in 2008 and was CEO until January 2024, leading it through its 2016 IPO and the SendGrid and Segment acquisitions. He wrote Ask Your Developer (2021) about developer-led software.
John Wolthuis
John Wolthuis co-founded Twilio in 2008. He architected the initial telephony backend that allowed developers to send text messages and make phone calls using a simple web API.
Evan Cooke
Evan Cooke co-founded Twilio and served as its first CTO. He was instrumental in designing the company's highly reliable cloud architecture, ensuring the API could scale to handle massive, instantaneous spikes in SMS traffic (such as during Uber surges or Airb…
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
Twilio
- Jeff Lawson2008–2024
Co-founder and CEO
As the long-time CEO, he aggressively scaled the company into a $60 billion behemoth before intense pressure from activist investors forced him to resign in 2024 following growth stagnation.
Source - Aidan Viggiano2023–present
Chief Financial Officer
As CFO, she strictly enforces the new profitability mandates, cutting massive amounts of real estate and software expenses across the enterprise.
Source - Khozema Shipchandler2024–present
Chief Executive Officer
Taking over as CEO in 2024, he shifted the company's focus away from unprofitable hyper-growth toward heavily optimizing the highly lucrative core communications platform.
Source
Timeline: Assurant and Twilio 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.
2008Twilio
Company Founded
Jeff Lawson, Evan Cooke, and John Wolthuis founded Twilio and launched its first voice API for developers.
2010Twilio
SMS API Launched
Twilio added programmable SMS, which became its largest product line.
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…
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.
2015Twilio
Authy Acquired
Twilio acquired the two-factor authentication company Authy in 2015.
2016Twilio
NYSE IPO
Twilio listed on the NYSE under the ticker TWLO in June 2016, pricing shares at $15.
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.
2019Twilio
SendGrid Acquisition
Twilio completed its all-stock acquisition of email platform SendGrid, announced at about $2 billion.
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.
2020Twilio
Segment Acquisition
Twilio acquired customer data platform Segment for about $3.2 billion, its largest deal.
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…
2021Twilio
Revenue Passes $2.8 Billion
Twilio reported FY2021 revenue of $2.842 billion, up 61% year over year, with a net loss of $949.9 million.
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.
2023Twilio
Restructuring
Twilio cut about 17% of its workforce in February 2023 and made further reductions later in the year as it shifted toward profitability.
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.
2024Twilio
CEO Transition
Co-founder Jeff Lawson stepped down as CEO in January 2024 and Khozema Shipchandler succeeded him.
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…
2025Twilio
First Full-Year GAAP Profit and Stytch Deal
Twilio reported FY2025 revenue of $5.067 billion and net income of $33.8 million, and completed its acquisition of identity platform Stytch on November 14, 2025.
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.
2026Twilio
Growth Re-accelerates
Twilio reported Q2 2026 revenue of $1.50 billion, up 22%, and raised its 2026 revenue growth outlook to 18%-18.5%.
Acquisitions
Assurant
- RL Circular Operations2026Undisclosed
- OptoFidelity mobile device test automation portfolio2025Undisclosed
- iSmash2024Undisclosed
- HYLA Mobile2020$325M
- The Warranty Group2018$2.5B
- Lifestyle Services Group2013$172M
Questions about Assurant vs Twilio
Who is the CEO of Assurant, Inc. and Twilio Inc.?
Assurant, Inc. is led by Keith Demmings and Twilio Inc. is led by Khozema Shipchandler. Both serve as the top executive responsible for the company's strategy, operations, and financial performance.
When was Assurant, Inc. founded vs Twilio Inc.?
Assurant, Inc. was founded in 1892 — 116 years before Twilio Inc., which was founded in 2008. Assurant, Inc.'s longer operating history gives it a deeper track record but also potentially more institutional inertia compared to the younger Twilio Inc..
How many employees does Assurant, Inc. have compared to Twilio Inc.?
Assurant, Inc. employs approximately 14,800 people, while Twilio Inc. employs approximately 5,492. Assurant, Inc. has the larger workforce at 14,800 employees, compared to Twilio Inc.'s 5,492. 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 Twilio Inc. headquartered?
Both Assurant, Inc. and Twilio Inc. are headquartered in United States, meaning they operate under the same primary regulatory and tax environment.
Who founded Assurant, Inc. and Twilio Inc.?
Assurant, Inc. was founded by Founders of La Crosse Mutual Aid Association. Twilio Inc. was founded by Jeff Lawson, John Wolthuis, Evan Cooke.
Which company has a longer operating history — Assurant, Inc. or Twilio Inc.?
Assurant, Inc. has been operating for approximately 134 years, making it the more established of the two companies. Twilio Inc. has been in operation for around 18 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 Twilio overview