Aaron Shapiro
Mallika Khandelwal
Hudson Structured, Munich Re Ventures, Tusk Ventures

Dayforward is a technology-driven life insurance company founded in 2019 by CEO Aaron Shapiro and Juxtapose. The company developed a proprietary underwriting process allowing it to better serve families of deceased policyholders by guaranteeing they'll continue to receive income, alleviating financial security concerns in the face of tragedy. Dayforward is able to deliver this innovation by integrating through the carrier level via an acquisition of Commercial Travelers Life Insurance Company (a storied insurance carrier founded in 1883). The acquisition coincides with launching Dayforward's innovative life insurance solution in most of the country. Dayforward modernizes the traditionally archaic life insurance industry by delivering a best-in-class consumer experience that allows people to complete a simple online application and get an instant decision at a great price. The company is also pursuing new financial products to enable the offering of a comprehensive financial security suite outside of life insurance. By leveraging technology, Dayforward will continue to innovate with personalized new products that respond to modern families' needs.

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founding CEO

Aaron Shapiro

Aaron partnered with Juxtapose to found Dayforward with a unified vision of ensuring families' financial security after the loss of a loved one. Aaron is a serial entrepreneur who founded the marketing business Silverpop, which he sold to IBM, and co-founded the digital marketing agency Huge, which he led as CEO through major growth. The challenge of the life insurance industry, with its myriad of regulations and cross-functional complexity, is what motivates Aaron and the Dayforward team.


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Article Title
Aaron Shapiro

"Life insurance is a $150B industry that has not changed in decades. Literally. It is also critically important for a family’s financial security - 1 of 17 children in America will experience the loss of a parent. We need to do better."

Year Founded
Personalizing financial security for modern families

We partnered with Aaron to found a new kind of life insurance company, one built from scratch to simplify the process of providing families financial security. Dayforward offers a first in kind innovative life insurance solution that guarantees a policyholder's family the continuation of salary income in the event that the policyholder passes away. Today, Dayforward has launched the first new life insurance product that the industry has seen in over ten years, and has become a full-fledged national insurance carrier. Aaron is a serial entrepreneur, previously having founded and led Huge - a 1,500-person global digital agency (that sold to IPG) - as well as Silverpop, a marketing technology company (that sold to IBM).

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Aaron before Dayforward

I’ve spent my entire career at the intersection of technology and marketing… and I’ve always been an entrepreneur. The first company I founded and served as CEO, Silverpop, was a marketing automation SaaS. That company was sold to IBM at a several hundred million dollar valuation and became the anchor of IBM’s marketing automation site. I was then on the founding team and served as CEO of Huge, a digital marketing agency. We built up the business from a small startup to 1,500 professionals across 12 offices, and the company was sold to Interpublic. At Huge, a lot of our work was large scale digital transformation for many of the world’s largest companies. This kind of work is what got me interested in starting Dayforward—the same kind of disruptive work we did at Huge, but now as a startup.

Career Highlights


Left Huge after the acquisition by IPG, and in partnership with Juxtapose, started the journey of learning about the opportunity and challenges of life insurance (something I had real experience with given my time at Huge).


Published Users Not Customers, which advises entrepreneurs and SMBs on how to focus on their user experiences.


Started my co-founding and partner stint at Huge, where I eventually became CEO and led a 1,500+ team across several continents.


Graduated from Harvard and founded Activegrams, which eventually became Silverpop Systems (later acquired by IBM).