Staff Application Support Engineer

Location: Global Remote-first (hybrid optional) | Employment Type: Full-time

About CINC Systems CINC Systems is a leading provider of accounting and management software purpose-built for homeowners associations and community management companies. Our platform supports mission-critical financial operations including general ledger accounting, payments, reporting, compliance, and day-to-day association management. Reliability, accuracy, and trust are foundational to what we build. As our platform grows in scale and complexity, application support is no longer a reactive function. It is a core engineering capability. We are investing in senior support engineers who think in systems, automate relentlessly, and help ensure that operational excellence is built directly into the product.

About The Role The Staff Application Support Engineer is a senior, hands-on technical leader responsible for Level 2 application support and for building the systems that automate, streamline, and improve how CINC operates in production. This role goes well beyond ticket resolution. You will design and evolve observability pipelines, alerting, knowledge systems, and AI-enabled support capabilities so that common issues are resolved automatically, signals are surfaced early, and product teams receive clear, actionable feedback. You approach repetitive work as a temporary state and treat support as a product capability to be engineered, not a queue to be worked. You will write scripts, build internal tools, and own automation workflows that meaningfully reduce manual effort. You will work closely with customers, application support peers, engineering, product, and platform teams to ensure fast recovery from incidents, high-quality communication, and continuous reduction of failure modes in the software.

Key Responsibilities Application Support and Incident Management

• Diagnose and resolve complex production issues across CINC's applications, services, integrations, and data layers
• Act as a senior escalation point for Level 2 support, providing deep technical investigation and clear resolution paths
• Participate in and lead incident response activities, including triage, mitigation, recovery, and post-incident analysis
• Provide calm, structured, and timely communication during incidents to internal stakeholders and customer-facing teams
• Ensure incidents are thoroughly documented with root cause, impact, and preventative actions

Automation, Scripting, and Tool Development

• Identify repetitive or high-volume support activities and eliminate them through automation — scripting is your first instinct, not an afterthought
• Build and maintain internal tools that accelerate investigation, streamline case handling, and surface operational intelligence
• Write scripts in Python, Bash, or similar to automate data lookups, diagnostics, remediation steps, and reporting workflows
• Design and maintain Datadog monitors, dashboards, alert routing rules, and synthetic checks that provide early warning and reduce noise
• Implement and evolve AI-enabled support platforms, such as Intercom Fin, to deflect issues and improve response quality
• Treat support automation and tooling as first-class engineering work with appropriate documentation, versioning, and maintainability
• Build and maintain knowledge bases that enable faster resolution and customer self-service

Observability and Operational Excellence

• Work within and help evolve CINC's Datadog environment, including monitors, dashboards, alert routing, log pipelines, and observability workflows
• Design alerting and escalation mechanisms that surface issues early and reduce customer impact
• Establish and maintain high-quality operational documentation, runbooks, and incident playbooks
• Partner with platform and engineering teams to improve observability, diagnostics, and operational readiness

Feedback Loops and Continuous Improvement

• Maintain tight feedback loops between customers, application support, and Level 3 product engineering teams
• Surface recurring issues, failure patterns, and systemic risks with clear recommendations for remediation
• Help ensure that lessons from incidents lead to durable product and process improvements
• Advocate for operational excellence and reliability as shared responsibilities across engineering

Required Skills And Experience

• 10+ years of experience in application support, production support, or support engineering roles
• Deep experience with incident management, operational workflows, and production environments
• Strong hands-on experience with Datadog, including monitors, dashboards, log management, and alerting
• Demonstrated scripting ability (Python, Bash, or similar) to build tools, automate workflows, and streamline support operations
• Proven ability to troubleshoot complex SaaS systems across application, integration, and data layers
• Experience designing or working with alerting and monitoring systems
• Excellent written and verbal communication skills, especially in high-pressure situations
• Ability to work independently, manage priorities, and operate effectively in a fast-paced, distributed environment

Preferred Experience

• Experience supporting financial, accounting, ERP, or other business-critical SaaS platforms
• Familiarity with SQL or other data investigation techniques
• Experience implementing or operating knowledge bases and AI-assisted support tools
• Background working closely with software engineering teams in production environments
• Exposure to APM, distributed tracing, or log analytics within Datadog or similar platforms
• Experience building lightweight internal tooling or CLIs used by support or engineering teams

Mindset and Values

• "Automate everything" mindset, with a bias toward eliminating repetitive work through code and tooling
• Treats support as an engineering discipline and a product capability
• Calm, structured, and reliable under pressure
• Customer-focused, with strong empathy for real-world impact
• Learning-first attitude and openness to new tools and techniques
• Collaborative and respectful, with a strong sense of ownership

What Success Looks Like

• Production issues are detected early and resolved quickly with minimal customer impact
• Incidents are handled with clarity, professionalism, and strong communication
• Repetitive support work steadily decreases through automation, scripting, and better tooling
• Internal tools and scripts built by this role are actively used across the support and engineering teams
• Knowledge bases and AI support tools meaningfully reduce ticket volume and resolution time
• Product teams receive clear, actionable feedback that leads to fewer failure modes
• The Staff Application Support Engineer is trusted as a senior technical partner across the organization

Why CINC Systems

• Opportunity to build a state-of-the-art application support function from the ground up
• High-impact role with real ownership over systems, tooling, and outcomes
• Remote-first culture with flexibility and autonomy
• Competitive compensation aligned to senior-level impact
• Collaborative, respectful, and high-bar engineering culture
• Clear growth paths into Principal Support Engineering, Platform, or Reliability leadership roles

Benefits

• Great working environment
• Opportunity for growth
• Learning & development resources
• Work/life balance
• Medical
• Dental
• Vision
• Life Insurance
• Short-term & Long-term disability insurance
• Flexible Spending Plan (childcare & healthcare)
• 401K (matching available)
• 136 hours of paid time off per year
• 10 paid holidays per year
• 2 self-care/mental health days per year
• Your birthday is a paid holiday!
• Free Coca-Cola beverages and snacks (when in office)