Announcing our $42M Series B, led by Sequoia & Khosla

engineering / withcoverage

Build the services brain

We encode the judgment behind corporate risk decisions into models that run in the critical path. Insurance is just where we start.

// tl;dr
role
member of technical staff
stack
aws, vercel, eks, argocd, postgres, iceberg
ai
custom-built harnesses, autonomous coding, self-improving loops
where
nyc, in office, five days

// changelog

Recent production changes.

live
PRs merged / wk
232
median time to merge
22m
AI calls / wk
398k
AI tokens / wk
5.3B

Today

Sandboxed automation runners isolated on Spot-only ARC capacity

infra

Durable reconciliation and bounded polling for 100+ row bulk certificate runs

platform

Workflow observability canvas links live activity stats to trace history

platform

Mobile video playback pauses offscreen work to reduce device load

product

Yesterday

Warm replica pool sized for bursty bulk certificate workloads

infra

Deterministic inbox drain semantics for dependent conversation metadata

platform

Warm replica pool sized for bulk certificate workloads with bounded DB pressure

infra

Fri · Aug 21

Serialized billing orchestration with idempotent provider-write boundaries

platform

Resumable communications archive import handles split batches and parent worklists

infra

Communication mirror retry policy classifies terminal writes and stable alerts

infra

Communication read APIs typed end to end with generated contract coverage

platform

Email sign-in codes backed by bounded attempts and additive token state

infra

Archive loader tracks resumable repair worklists across split export batches

infra

Communication mirror uses row-level classification for edge-denied writes

infra

Thu · Aug 20

Encrypted communication archive codified with scoped loader identity and retention

infra

Resumable communication archive loader validates batches before insert-only import

platform

Current policy billing projection split into workflow, storage, and batch API

platform

Collaborative draft writes flow through synchronized editor transactions

platform

Dedicated export archive codified with KMS, access logs, and ephemeral loader identity

infra

Large workflow inputs moved to immutable activity references below orchestration limits

infra

Collaborative draft writes use transactional editor state with stale-write guards

platform

Wed · Aug 19

Type-aware linting runs 7-11x faster across app and backend

platform

Service-backed conversation reads shipped with fallback and comparison telemetry

platform

Communication mirror stores account identities, inbox memberships, and delivery state

infra

Communication mirror expanded for internal comments, accounts, handles, and bounces

platform

Entity-access assignments updated atomically with bulk scope replacement

platform

Tue · Aug 18

Communication servicing workers launched with scoped credentials and schema grants

infra

Account-entity APIs wired with service-only permissions and idempotent writes

platform

Communication mirror replay keyed by dependency digests for convergent retries

infra

Marketing media pipeline optimized with responsive video and deferred loading

infra

// why_this_job_exists

Engineering is suddenly very different

Companies used to hire people to fuel growth and pay SaaS vendors for software they could use. That's all changed — now companies want to buy outcomes.

Our team builds the platform and tools to enable our risk management experts to scale themselves 2x, 10x, or 100x more than was possible in the past.

We are working to break the scaling laws of services businesses with AI agents. We are a deeply collaborative, in office, hard working and curious team in NYC.

Diagram: AI agents pull insurance documents from a task queue, work them concurrently, and ship finished artifacts without supervision. Interactive: choose a file in the queue to dispatch it to an idle agent, select an agent to see its live log, or select a shipped artifact to preview it.

Diagram: an engineer and a risk expert deploy as a pair into client verticals — defense, hospitality, logistics, energy — build on site, and ship measurable outcomes. Interactive: choose a site to deploy the pair there, or select a deployed site for details.

Diagram: an AI harness loops through run, eval, learn, and update stations. Each lap appends an improvement to the harness changelog, evals flip from fail to pass, and the pass rate climbs from 62 to 94 percent. Interactive: select the next station to drive an iteration by hand, or any station for details.

Diagram: a fleet of AI agents serves a growing wall of client accounts, routing only rare judgment calls to a single risk expert. Accounts per expert climbs from 10 to 100. Interactive: choose an unlit account tile to onboard it, or select the expert or an agent for details.

Real, interesting problemsYou'll build AI infrastructure that can read and understand complex documents, ask questions, make decisions, and take actions that have real consequences for our clients' businesses. You'll learn what it takes to build and deploy autonomous agents that manage risk at scale in the real world.

// inside_the_team

The actual work

Sasha R.Cole S.Mitch R.

engineering

Sasha R.
What are you building?
An AI-driven claims platform that gives clients full visibility into their claims, losses, and legal processes — turning messy insurance data into something clear.
Where does your time go?
Deep dives into a problem, designing the system, shipping it, then iterating fast with the people who use it. One day I'm evaluating the latest AI, the next I'm shipping what the team uses tomorrow.
What was hard to get right?
Nuance. Insurance is a language-based industry — every policy is specific to the client and their business, and one small detail flips the answer. Building repeatable systems on that takes real domain depth.
Why did you join?
The team, and how embedded we are with our users. I get to shape the product next to the people using it and watch the impact land in real time.

// who_you_build_with

Who you'll build with.

  • JD Ross

    JD Ross

    Co-founder

    An entrepreneur and product leader with a track record of building category-defining companies. He co-founded Opendoor, taking it from inception through IPO, and brings a product-first instinct to everything we build.

  • Naveen Kasthuri

    Naveen Kasthuri

    CTO

    A pioneer in AI-native engineering with a background that blends finance and technology. Previously a senior principal engineer and chief architect in charge of transforming a 700-person R&D org to be AI-native.

// how_we_hire

A process built to respect your time.

  1. 01

    Technical Deep Dive

    precision and depth

    We go deep on the decisions, the tradeoffs, and what you'd do differently. No trivia, no whiteboard puzzles.

  2. 02

    Coding Round with AI

    how you steer the model

    Bring your own AI tooling and pair on a real problem. We don't ban the model or treat it as cheating — using it well is the job. We watch how you prompt, review, debug, and steer it, because that's exactly how you'll ship here.

  3. 03

    Onsite — 2–3 Interviews

    systems and product judgment

    A few focused sessions on systems design and product thinking. Architect something real, then reason about what to build, for whom, and why.

// join_us

Work where the model has to be right.

Interested? We’re always looking for talented problem-solvers to join our team.

View open roles