A Fax Machine, a Newborn and a Startup

The episode began with fitness. Bobbie and Gilad share a fitness-minded Twitter community, and she described the lockdown project that came out of it: a CrossFit-style gym in her basement, built up over family milestones as combined gifts. Gilad countered with weighted gloves for his runs.

The conversation turned to insurance, and to a story that explains why Bobbie is in it. When her daughter was born, she needed to file a disability claim, and the only way her carrier would accept the form was by fax. She doesn’t own a fax machine, or stamps, so she carried a days-old infant into a Kinkos to send it. That experience, she said, is how many policyholders feel, and it is the kind of problem she now builds software to remove.

About Bobbie Shrivastav

Bobbie Shrivastav is co-founder and Chief Product Officer of Benekiva, a B2B insurance platform for life, annuity and health carriers that is working to transform claims and move into servicing.

What Benekiva Does

Benekiva started in 2018 by looking at claims and chipping away at the back-office problems that hurt the customer, who is either a beneficiary or a policyholder. This is working “from the customer backwards,” as insurance consultant Pat Kelahan puts it. The company sells to carriers with life, annuity or health books, and the carrier then offers a portion of the platform, the portal side, to its own users: business owners, agents, funeral homes, beneficiaries and policyholders.

The product has grown from its customers’ requests. Benekiva has a digital intake solution it calls “FNOL on steroids,” and customers soon asked about address changes and beneficiary changes. Benekiva built a servicing offering, and a very large customer now uses it fully digitally and fully automatically, with no faxes or mail sent to the carrier. Another customer asked about new business, which Bobbie said is in the works and will be announced when there is a beta customer.

The Statistic That Brought Her Into Insurance

Benekiva’s CEO, Brent Williams, who came up with the concept, told Bobbie and her husband (Benekiva’s CTO and her business partner in a second startup together) that about 68 percent of life insurance claims go unclaimed, because policyholders often don’t tell their beneficiaries they have a policy. That money doesn’t stay with the carrier. Under laws passed around 2015, carriers can’t hold it and must turn it over to the state as unclaimed property, which she said grows by around a billion dollars a year.

Bobbie’s point is that insurers don’t want to hold onto this money: if they can’t pay a claim, the money goes to the state. The failure is in the process, across the whole life of a policy, in which at no point is the policyholder easily reached to update a beneficiary.

Founding Story

The founders’ first startup was Docsmore, a document management and facilitation product launched in 2015 when their daughter was six months old, driven by the paperwork that comes with a baby: employment, insurance and disability forms. The heart of the company was non-profits and small businesses, and they met Brent in 2016 when the product was in beta. He had a choice between bringing in co-founders who could build his idea or raising venture money to build a team, and the pair had just bought life insurance and were struck by his statistic.

Before that, Bobbie’s career ran through development and project management at Aon, PepsiCo (where she was among the first project managers on an individual-contributor track and led work such as OCR and an Oracle migration), AIG’s mortgage insurance business, and the Center for Creative Leadership, a leadership institute. She left corporate life to do something meaningful, and the path led her to startups.

Legacy Systems and Staff-First Thinking

Bobbie said that when Benekiva first reached the market, many carriers wanted to solve claims internally. She recalled a smaller company that was recognized with an award for building everything itself, including its own policy admin system, in a project that took years, and she thought about the technical debt it had already accrued. Carriers are getting better at partnering with the ecosystem, using mainframe data extraction and RPA to get at data from a “dinosaur” system while giving customers a modern experience.

She is also an advocate for being “staff first.” A new graduate won’t want to key into mainframe systems to process claims, so a modern work experience matters for retention, and at PepsiCo she remembers a scorecard in which the ability to get the job done was weighted as heavily as the customer-facing tools.

Be Honest With Startups: “Not Now” Is Fine

Gilad raised the vendor-startup relationship. Startups track budgets and sales cycles that can run a year or more, and they need an investor-ready story, so insurers running innovation programs should be clear about budget, timeline and the likelihood a pilot becomes real. Bobbie agreed that the industry is relationship-driven and polite, and that people don’t like saying no, so every conversation feels like progress. A clear “it’s not a no, it’s not now” lets startups put resources elsewhere. Gilad compared it to Hollywood, where nobody says no and they just disappear, and gave credit to an AF Group innovation leader who told him exactly how many pilots the company could handle in a year.

Where the Company Is

Benekiva works with about 12 customers, roughly half in production, and started three more implementations the quarter before. Headcount doubled in 2020, and Bobbie and the founders were spending that quarter training staff so they can focus on strategy. She hadn’t decided whether to raise capital, noting the company had been so focused on customers that the funding rounds’ labels (pre-seed or Series A) are still debated internally.

Women Founders: Hidden, Not Missing

Gilad asked about the small number of female founders in insurtech, and Bobbie gave a candid answer. They are there but hidden, in two ways. Some don’t get a platform to talk about what they’re building. Others are the engine of a family startup, doing the operations and heavy lifting, while a husband or male partner has the founder title and is the public face. When she tried to recruit participants for an all-women tech showcase in her local community of Winston-Salem, North Carolina, in 2019, she was told she was the only one, and found others by looking for the women behind the company. She argued that women need to claim the title when they’ve earned it.

On funding, Bobbie noted that startup weekends are diverse but the funding isn’t: she cited about 2 percent of investment going to women in 2019 and 2020, which leads to asking who sits at the investors’ table. Her advice to entrepreneurs is to be vocal and present, and her own pipeline answer is to hire diverse people, expose them to entrepreneurship at a startup, and encourage them to build things.

Advice: Crypto, With a Community

For her recommendation, Bobbie said she got into the gym and then into cryptocurrency during lockdown, drawn by the chance for ordinary people to invest at an early stage and by the global community around it. She looks for real use cases rather than meme coins, which she sees as pure gambling. She and Gilad both described setting aside a small “Vegas money” amount. This is not financial advice.

Key Takeaways

• About 68 percent of life insurance claims go unclaimed, partly because beneficiaries don’t know a policy exists, and the money ends up with the state as unclaimed property, growing by roughly a billion dollars a year.
• The failure is in the lifecycle process, not carriers’ intent: at no point is the policyholder easily prompted to update a beneficiary, and legacy systems make it hard to fix.
• Benekiva started in claims and expanded into servicing at customers’ request, with a fully digital servicing deployment at a very large carrier.
• About 12 customers, half live in production, with headcount doubled in 2020.
• Carriers should be explicit with startups about budget and timing; “not now” saves a startup resources better than a polite dance.
• “Staff first” matters: a modern work experience helps carriers keep talent.
• Women founders are often hidden behind a spouse’s title or without a platform, and visibility, hiring and funding all affect the pipeline.