Principal Software Engineer

Wagmo

11d•$200,000 - $250,000•Hybrid

About The Position

As Principal Engineer at Wagmo, you will be the named owner of our application architecture. Wagmo sells pet wellness and insurance directly to consumers and through employers, brokers, and benefits administrators. Over the past two years we moved our insurance program to a new carrier partner and built a provider-agnostic interface to make that possible. It works, and it is not finished: two generations of models still coexist behind feature flags, and the legacy path is to be supported for years. On the partner side, each new benefits administrator we onboard currently arrives as its own build, with its own file format, renewal cadence, and eligibility rules. Our growth depends on that stopping. Architecture has been owned by the CTO to date. This role takes it over. You will set technical direction across insurance, claims, partner integration, and our AI systems, decide what we will not build, and leave designs that two squads can execute without escalating. You will do this with no direct reports, real influence, and your hands in the codebase. The scope here is wide for our team, which is the appeal and also the challenge. There is no platform organization beneath you and no architecture review process to inherit beyond the one we started this year.

Requirements

Experience holding a cross-cutting architectural decision that touched several domains at once, and driving it from ambiguity to a shipped, documented outcome that other engineers built on. You should be able to name the option you rejected and the cost you knowingly accepted.
A track record of retiring and scaling systems, not just building them. You have lived inside a half-migrated codebase running two paths in parallel and know what it takes, organizationally as well as technically, to finish.
Depth in Python and Django, relational data modeling, and third-party integration at scale. Familiarity with Kubernetes and GCP is useful; you will not own the cluster.
Experience putting non-deterministic systems into production, with real opinions about evaluation, versioning, and who is allowed to change a model's behavior.
The judgment to say what not to build, and the written and verbal clarity to carry that argument with people who outrank you.
Comfort that "principal" here means unblocking two squads rather than presiding over ten.

Nice To Haves

Experience in insurance, benefits, payments, healthcare, or another regulated, integration-heavy domain is a strong plus.

Responsibilities

Own the end state of Wagmo's insurance provider interface, including a documented retirement path for legacy provider models and the decision about when dual-write paths come out.
Design partner and carrier onboarding so that adding a new benefits administrator is a configuration exercise rather than an application build. File format, renewal cadence, group structure, and product eligibility should be configured, not coded.
Own architecture review: run it, hold decision rights in it, and maintain a decision log that the team can rely on. Success is squads unblocked without escalation.
Define a single identity architecture spanning enterprise SSO tenants, our partner portal, and consumer authentication, with per-tenant onboarding reduced to a documented, repeatable process that stands up to enterprise security diligence.
Own the architecture of our AI systems across claims adjudication, customer support, and internal engineering tooling: versioned prompts and strategies with a promotion path, controls that match their documentation, and a measured cost per automated decision.
Mentor squad tech leads and raise the standard of technical design across the team, without taking on people management.