Monitoring & Observability Engineer @ Herald

About Us

Herald builds digital infrastructure for commercial insurance. Today we provide developers a single API to get quotes for insurance products from multiple carriers. Tomorrow we want to build anything that helps developers connect their applications to the insurance ecosystem. We think buying insurance should be as easy as buying anything else online and we want your help!

We’re a team of insurtech veterans with experience at At-Bay, Kin, and Insurify. We’ve raised our Series A funding from top-tier VCs (Lightspeed, Brewer Lane, Afore, Underscore) along with a panel of insurtech founders (At-Bay, Marble), insurance executives (CRC), and early employees of other successful API infrastructure companies (Plaid, Alloy, Stytch).

The Role

We are building a platform that integrates with dozens of insurance carriers, processing high volumes of transactions through carrier APIs and data feeds. Ensuring reliability, transparency, and traceability across these integrations is mission-critical.

As a Monitoring & Observability Engineer, you will design, implement, and scale observability systems that give us complete visibility into carrier integrations, APIs, and backend services. You will empower our engineering, product, and operations teams to detect issues early, troubleshoot effectively, and ensure our customers always have accurate and timely data.

Why This Role Matters

By making our carrier integrations observable and reliable, you will:

Ensure policies, claims, and updates flow seamlessly across systems.
Give business and operations teams full transparency into integration health.
Reduce downtime, speed up troubleshooting, and protect customer trust.
Build the observability foundation that lets us scale integrations with dozens of carriers without losing visibility.

What you'll do

Build Observability into Integrations

Instrument TypeScript/Node.js services with logs, metrics, and traces using OpenTelemetry and related tooling.
Ensure end-to-end visibility across API calls, message queues, and data pipelines with insurance carriers.
Develop dashboards that highlight transaction flow health, error rates, anomalies, and latency trends.

Ensure Reliability of Carrier Data Flows

Detect failures such as API outages, data mismatches, and delayed feeds.
Build proactive alerting systems to minimize downtime and impact.
Automate observability for new carrier integrations to accelerate onboarding.

Incident Response & Troubleshooting

Partner with integration engineers to rapidly diagnose and resolve carrier-related issues.
Conduct root cause analysis on failed transactions and provide data-driven recommendations.
Improve incident response processes by refining alerting, runbooks, and playbooks.

Scale Monitoring & Automation

Build reusable templates for dashboards and alerts, so observability scales with new integrations.
Automate checks for data integrity, anomaly detection, and validation pipelines across large carrier data volumes.
Enhance developer productivity with self-service observability tools.

What we're looking for

5-7+ years of experience owning monitoring & observability projects while shaping best practices and driving adoption across the tech org.
Strong proficiency in TypeScript/Node.js (experience instrumenting backend services).
Hands-on experience with observability tooling (OpenTelemetry, Datadog, Grafana, ELK/Loki, or similar). ç
Proven experience with data anomaly detection and validation pipelines.
Familiarity with APIs (REST, SOAP, GraphQL) and async messaging systems (Kafka, SQS, RabbitMQ).
Experience with cloud environments (AWS/GCP/Azure) and containerized apps (Kubernetes, Docker).
Solid knowledge of SQL for querying and investigating data anomalies.
Comfort with automation scripting (Python, Bash, or Terraform) for monitoring infrastructure.

Nice to Have

Background in insurance, fintech, or other integration-heavy industries.
Knowledge of carrier-specific standards (ACORD formats, EDI transactions).
Familiarity with compliance/regulatory requirements (HIPAA, SOC2).

What we bring

💰 Competitive compensation packages based on experience
📈 Company equity
✈️ Relocation stipend (if you want to join us in the Northeast)
🌛 Quarterly in-person meetups (on the company)
🏝 20 days of PTO (that roll over) + 12 company holidays + 5 sick days
💊 Quality health, vision, and dental insurance
🚆 Pre-tax commuter benefits to be used towards parking & transit costs for those working hybrid in our offices
👵 401K plan
🏠 $500 additional home office stipend (beyond the standard equipment)
👨‍👩‍👧‍👦 Parental leave for all kinds of parents (including adoption and foster care)
🏃‍♀️ An agile and motivated team

Full compensation packages are determined based on candidate experience. Please note that some roles may include variable compensation (such as commission, bonuses, and/or equity) that are not outlined here. This range is depicting base pay only. Any variable compensation will be discussed throughout the hiring process.

New York Pay Range

$170,000—$200,000 USD

Additional information

Diversity, equity, and inclusion are featured prominently in our company's values which you can read about below. Please reach out if you would benefit from any assistance throughout the application or have suggestions about how we can make our process more accessible and inclusive to all people.

One more note: We want to build an incredible team. As a result, we make a point of being open to surprising candidates who are the right person even though their experience doesn't exactly match up to our job description. Our job descriptions are gestures, not strict criteria. If you think you would be a great addition to our team, but might not fit the criteria perfectly, we still encourage you to apply! We recognize there are many transferable skills and traits that we may not have captured in this description and welcome all interested candidates to apply.

Life at Herald

We're just getting started and building our culture with purpose every day. One of the joys of joining a small company early is that you get to build that culture too. Come join us and help us make Herald an (even more) amazing place to work!

Actions we value

There are many actions that we hope for and even demand from members of our team: communicating honestly, working hard, behaving with integrity. These are expectations. But we value these five actions above and beyond the level of "baseline expectation." We believe that if we excel at these, our business will thrive. We’re betting the company on it.

Build trust

We always lead with empathy. We publicly own and learn from our mistakes just as we are confident and transparent in explaining our decisions. And we help get the work done because we recognize that no job is too small.

Create a shared reality

We each articulate the facts, assumptions, questions, and fears we hold about our business. We listen to and learn from others. We create a shared set of information before making decisions.

Get better every day.

We constantly seek ways to improve ourselves. We provide each other candid feedback coupled with support to elevate those around us. We refine how we work together to become more effective as a team.

Build a diverse, equitable, and inclusive community.

We thrive when our team has a variety of lived experiences, values each other for their unique perspectives, and shares equitably in our mutual success. We invest in building an inclusive community for people who are oppressed because of their race, ethnicity, age, religion, gender expression, sexual orientation, physical ability, or socio-economic class.

(Remember that) we make the rules.

We once created the ways we work and therefore can change them. We do not default to momentum. We challenge ourselves to deconstruct the status quo and create a better future.

Monitoring & Observability Engineer

Multiple Teams

Herald

Compensation Overview

The Role

Why This Role Matters

What you'll do

What we're looking for

What we bring

Actions we value

Build trust

Create a shared reality

Get better every day.

Build a diverse, equitable, and inclusive community.

(Remember that) we make the rules.

Simplify's Take

What believers are saying

What critics are saying

What makes Herald unique

Benefits

Growth & Insights and Company News

6 month growth

1 year growth

2 year growth