Senior Technical Customer Engineer Remote

Lead Simple helps property management companies make their operations simple, scalable, and consistent. We are a remote-first team that moves quickly, cares deeply about quality, and stays close to our customers.

We are redesigning how customer-reported problems move from first report to verified fix. AI will increasingly perform first-pass investigation, reproduce issues, and propose code changes. The hardest cases still require distinctly human judgment: asking the right follow-up questions, earning customer trust, determining whether a report is a defect, configuration issue, or product request, and ensuring the right resolution happens on time.

We are looking for a Senior Technical Customer Engineer to own that boundary. You will lead technical customer conversations, investigate issues across logs, data, APIs, and application code, review AI-generated fixes, coordinate Engineering response against tiered SLAs, and turn recurring escalations into systemic improvements.

What this role is

A senior individual-contributor role at the intersection of customers, Support, Product, and Engineering. It is not a traditional Tier 1 support position and it is not a conventional feature-development role.

What you will own

• Lead discovery and diagnostic calls for escalated customer issues, often alongside Customer Success or Support.

• Turn incomplete or ambiguous reports into clear reproduction steps, timelines, impact statements, and technical evidence.

• Investigate issues using application logs, SQL, APIs, browser tools, cloud and observability platforms, and source code.

• Classify each issue accurately: software defect, customer configuration, data or integration problem, education gap, feature request, or product decision.

• Review AI-generated analyses and pull requests for root-cause alignment, correctness, regression risk, tests, maintainability, and customer impact.

• Improve or ship bounded fixes when appropriate, while coordinating broader changes with the Engineering team.

• Own escalated issues from intake through validated resolution, including clear internal and customer-facing status updates.

• Maintain the operational SLA tracker across customer tier and issue severity, surface breach risk early, and ensure the responsible teams are keeping pace.

• Apply priority and commercial-promise rules defined with Engineering, Product, and Customer leadership; bring evidence when those policies need adjustment.

• Identify recurring failure patterns and improve runbooks, knowledge, diagnostic tooling, tests, support enablement, and AI investigation workflows.

• Use time between escalations to reduce repeat defects and increase the share of issues that can be resolved safely without Engineering intervention.

What success looks like

• Customers feel heard and leave technical calls with credible next steps.

• Engineers receive reproducible, evidence-rich issues rather than vague escalations.

• SLA risks are visible before they become breaches.

• AI-generated diagnoses and fixes become more accurate, testable, and safe to review.

• Repeat incidents decline as findings become durable product, tooling, and support improvements.

• Product questions reach leadership with the customer context and technical evidence needed for sound judgement.

Qualifications

• Five or more years in support engineering, production or application support, product engineering, solutions engineering, or a comparable customer-facing technical role.

• A track record of diagnosing complex production issues in a multi-tenant SaaS application.

• Comfort reading application code, reasoning about proposed changes, and participating in code review; you do not need to be a full-time feature engineer.

• Practical experience with SQL, REST APIs, logs, browser developer tools, cloud…