Our Story
At Endear, we’re building a modern CRM for retail teams—starting with the frontline. Our software helps sales associates have more personal, effective customer conversations through AI-powered tools that drive measurable revenue.
Despite retail being significantly larger than eCommerce, most software overlooks the in-store experience. Endear helps brands turn real customer relationships into growth through intuitive software and thoughtful design.
As Endear grows, we are investing in the reliability and platform systems that keep our product fast, resilient, and easy for engineering teams to operate.
Position Overview
We’re hiring a Senior Site Reliability Engineer to become Endear’s first dedicated reliability hire. This is a hands-on builder role for someone who wants to solve the underlying systems problems that create on-call burden—not simply respond to pages.
You will own the work of making Endear’s systems more observable, reliable, and scalable. You’ll investigate recurring incidents, drive root-cause fixes, improve alerting and incident playbooks, and partner with engineers on database, queue, and event-processing reliability.
You will also help establish a nearshore triage layer for routine, well-understood issues, so product engineers can spend more time building product and less time on operational interruptions.
What You’ll Accomplish
In your first 6 months, you’ll…
Build a clear view of Endear’s highest-impact reliability risks, recurring incidents, and on-call pain points.
Establish a prioritized reliability backlog and drive root-cause fixes for the most important issues.
Improve alert quality, severity definitions, escalation paths, and runbooks for common incidents.
Strengthen observability, queue health, database capacity planning, and operational readiness ahead of peak retail periods.
Create the foundation for a nearshore triage process for low-priority, repeatable issues.
In your first year, you’ll…
Make on-call materially quieter and less disruptive for product engineers.
Build scalable systems for observability, alerting, incident response, database reliability, and queue/event-processing health.
Own and improve the nearshore triage relationship, playbooks, and escalation process.
Help establish the technical roadmap and future resourcing plan for Endear’s broader platform and reliability function.
You’ll Thrive in This Role If You…
Have deep hands-on experience with Kubernetes, production databases, and event-driven systems.
Have operated and improved high-volume production systems with meaningful reliability, performance, and data-scale requirements.
Enjoy finding root causes, fixing repeat incidents, and building tooling that makes engineers’ lives easier.
Have experience with observability, alerting, incident response, capacity planning, and operational runbooks.
Can work effectively as a senior IC: owning complex technical work directly while coordinating across teams.
Are comfortable in a lean environment where priorities move quickly and you will need to make practical trade-offs.
Bring experience from a scaling, mid-size company rather than only an early-stage startup or hyperscaler environment.
Have GCP or ClickHouse experience, which are strong pluses.
About the Team
You’ll partner with:
JP Grace, CTO: Align on reliability priorities, technical risks, and the roadmap for improving on-call health.
Engineering team: Partner on root-cause fixes, platform improvements, and architecture decisions that improve reliability.
Nearshore triage partner: Build and maintain playbooks, escalation paths, and expectations for routine incident handling.
Product and Support: Help ensure issues are surfaced, prioritized, and resolved with the right level of urgency.
Endear is a lean, remote team where individuals have broad ownership. This role will directly shape how the company handles production reliability as it grows.
Our Hiring Process
Recruiter screen — 30 minutes
Behavioral interview with CTO — 60 minutes
Technical panel with Engineering — 60 minutes
Final conversation with Co-Founders
Offer 🎉
Compensation & Benefits
Base salary: $140,000-180,000
Fully remote, U.S.-based role
Comprehensive healthcare, including medical, dental, and vision, plus a 401(k) plan
Monthly stipend for co-working and home-office setup
Flexible PTO and unlimited vacation
Opportunity to build Endear’s first dedicated reliability function from the ground up
Apply Even If You Don’t Check Every Box
If this role excites you but you’re unsure if you meet every requirement, reach out anyway. We care about skills, motivation, and how you think more than perfect resumes.
Endear is building a modern CRM platform designed specifically for retail teams, with a focus on empowering frontline sales associates. Their AI-powered software enables sales associates to have more personal and effective customer conversations while driving measurable revenue growth. Unlike most software that overlooks the in-store experience, Endear helps retail brands turn real customer relationships into growth through intuitive software and thoughtful design. The company recognizes that retail is significantly larger than eCommerce and is addressing this underserved market by providing tools tailored to the retail environment.
