Staff Quality Engineer - Exploratory Test Lead

ABOUT BESTOW

life insurance is one of the world's most important products. It's also one of the hardest to build, distribute, and modernize. Bestow exists to change that.

Bestow is a leading vertical technology platform serving some of the largest and most innovative life insurers. Our platform unifies the fragmented, legacy value chain, enabling carriers to launch products in weeks instead of years. Carriers choose us to scale and operate at unprecedented speed, powered by AI and automation.

Bestow isn't selling policies. We're building the infrastructure that helps an entire industry move faster, reach more people, and deliver on its promise.

Backed by leading investors (Goldman Sachs, Hedosophia, NEA, Valar, 8VC) and trusted by major carriers, Bestow is powered by a team that moves with precision, purpose, and heart. If you want to help reimagine a centuries-old industry with lasting impact, join us.

Bestow offers flexible remote/hybrid work, meaningful benefits, equity, and substantial growth opportunities.

Bestow uses E-Verify to confirm the employment eligibility of all newly hired employees. To learn more about E-Verify, including your rights and responsibilities, please visit E-Verify.gov.

Bestow's Quality Engineering organization is building the verification backbone for an AI-enabled software development lifecycle: specification-driven development, Definition-of-Ready enforcement, requirements-to-test traceability, and a growing non-functional verification stack. We are not a downstream test team. We shape how software is defined, not only how it is checked.

This Staff Quality Engineer role is embedded first within Bestow Innovation Lab, the R&D group that invents the next generation of our platform and then scales the practice across Engineering. You will work alongside domain experts and researchers, product engineering teams, Platform Engineers, Technical Program Management, Compliance, and the rest of the Quality Engineering team. This role reports to the Director of Quality and is open to Remote (US).

We are stating this explicitly so you can tell whether this is your kind of job.

Test automation and automated checks confirm what we already knew to ask, but they cannot tell us whether we asked the right questions.

Testing is the process of evaluating a product by learning about it through exploration and experimentation; questioning, modeling, observation, inference, and yes, output checking.

We distinguish testing from checking. A check applies a decision rule to an observation and reports the outcome. Checks are enormously valuable and we invest heavily in them. They are also incapable of noticing anything they were not told to notice, which is why they cannot substitute for a person who is trying to find out what is true.

Tools extend the tester. We expect you to build and use tools, including but not limited to AI technologies, aggressively for a wide variety of things including data generation, state manipulation, differential comparison, log and trace analysis, oracle construction. "Automated" and "manual" is not a distinction we find useful.

Testers inform decisions; they do not own quality. Our Quality Engineering team’s north star is to give the people accountable for a release the clearest possible account of the product and its risks, including an honest account of what was not examined. The decision is theirs. Making it well-informed is ours.

Risk analysis is an argument, not arithmetic. We want risk stated as a specific failure story that our colleagues can inspect and dispute, not as a number that ends the conversation.

We are careful about what we claim. "So far I haven't found a problem here" and "this area is fine" are very different statements. In a regulated business the difference eventually matters to someone outside the company.

Testing, Embedded in Labs / R&D (~40%)Embed with Labs / R&D through invention and specification, developing a model of the product as it is being conceived, capturing risks and questions as they form before they become code.

Design and execute chartered, time-boxed testing sessions. Through structured debriefs, teams capture vital learnings, refine session charters, and validate the return on testing efforts.

Investigate critical failure modes that structural checks cannot catch: multi-tenant isolation, configuration interaction, concurrency and lifecycle state transitions, integration timing, operability and observability gaps, and long-horizon temporal behavior such as renewals, lapses, and mid-term endorsements.

Model risk using the Heuristic Test Strategy Model and related approaches; product elements (structure, function, data, interfaces, platform, operations, time), quality criteria, and risk heuristics and maintain a living risk catalogue across policy lifecycle, claims, partner integrations, and regulatory workflows. Each significant risk is written as a failure story: what could go…