Pros
Under its original VP of engineering, Bestow was clearly a technology company first and an insurance company second. It attracted a number of high-caliber engineers, established a strong technical foundation, and conceived a rare engineering culture focused on building platforms and teams for the long term. The company will likely eventually exit in the green. A number of capable, wonderful people still work at Bestow in several different departments and disciplines.
Cons
A recent change in engineering leadership seems to have left Bestow without a strong technical advocate among an otherwise non-technical C-suite, and support for the engineering culture has slowly waned at the top. It's unclear whether Bestow's new Engineering chief is unwilling to push back on the CEO and President or whether they are simply less willing to listen to him, but top leadership seems to not understand what an engineering culture is, understand its value, or see it as compatible with the company's financial goals. Bestow's product roadmap feels optimized for telegraphing progress on short-term investor milestones at the expense of building healthy technology with long-term capabilities. Despite consistent line-level feedback, Bestow is adding complexity too quickly before its platform is ready to manage it. Its engineers feel unheard and are beginning to burn out, its most senior thought leaders are running out of patience, and the engineering culture is beginning to atrophy as key individuals who established and modeled it are choosing to leave. To add insult to injury, Bestow seems intent on maintaining the same reckless pace despite the recent (and ongoing) departure of much of its senior engineering talent. The company is introducing dozens of relatively unvetted contractors with no prior knowledge of Bestow's platforms or problem domain - essentially doubling its remaining engineering headcount overnight - either in a misguided pursuit of a Mythical Man Month, or perhaps simply to maintain an increasing headcount on paper. Completely separately and of perhaps greater importance, Bestow's leadership recently failed to adequately respond to an ethically-troubling situation brought to their attention by several of their employees. It seems like an early whistleblower may even have faced negative consequences related to their decision to speak out. It took a high-profile resignation to spur any apparent response from the executive team, but their actions read to me as reactionary rather than substantive in nature: too little, too late. It feels like trust between company leadership and employees has worn thin.
