Cowbell · 3 hours ago
Level 2 Platform Support Engineer II
United States
Full-time
Remote
Entry, Mid LevelCowbell is a leading innovator in cyber insurance, providing advanced warning of cyber risk exposures to SMEs. The Level 2 Platform Support Engineer II will bridge frontline support and advanced technical support, ensuring efficient resolution of user-reported issues and maintaining platform stability.
Artificial Intelligence (AI)FinTechInsuranceInsurTechRisk Management
No H1B
Responsibilities
Triage and troubleshoot user-reported issues to identify root causes and determine the most effective path to resolution
Investigate platform, workflow, and API-related issues beyond Level 1 support scope
Maintain clear, timely communication with stakeholders throughout the issue lifecycle
Own support tickets end-to-end, from intake through closure, using Jira Service Management and related tools
Drive timely resolution in alignment with established SLAs
Document findings, troubleshooting steps, and outcomes to support future issue resolution
Exercise judgment in determining when issues require escalation
Prepare high-quality escalation context, including reproduction steps, impact assessment, findings, and working hypotheses
Participate in incident response activities by supporting investigation, coordination, and stakeholder communication
Based on experience and assignment, drive daily production syncs by setting agendas, coordinating discussions, and tracking follow-ups
Facilitate alignment between business users, engineers, and other stakeholders during production issue review and resolution
Provide operational continuity to ensure production issues progress toward resolution efficiently
Validate fixes and configuration changes by reproducing issues, verifying expected behavior, and confirming resolution prior to closure
Partner with engineering and QA teams to ensure fixes address root causes and avoid regression
Build and maintain strong knowledge of the Cowbell Platform, including workflows, APIs, and system behavior
Contribute to Level 0–3 knowledge bases, incident documentation, and internal runbooks
Ensure documentation remains accurate and reflects current platform behavior and support practices
Collaborate closely with engineering, QA, product, and support teams to resolve issues and improve platform reliability
Participate in root cause analysis discussions and share operational insights to help prevent recurring issues
Qualification
Required
Bachelor's degree in a relevant field, or equivalent practical experience
Prior experience in a technical support, platform support, or software-adjacent role
Experience troubleshooting and debugging software applications or platforms
Familiarity with incident management and escalation workflows
Ability to manage multiple issues in a fast-paced, evolving environment
Ability to clearly explain technical concepts to non-technical audiences, both verbally and in writing
A proactive, empathetic, and customer-focused mindset
Willingness to continuously learn new tools, systems, and workflows
Comfortable using developer assistance tools (such as GitHub Copilot, Cursor, and other LLM-based tools) to support troubleshooting, investigation, and understanding of code behavior
Preferred
Exposure to support and observability tools such as Jira, Jira Service Management, FireHydrant, Datadog, Sentry, Logrocket, Postman, or similar tools is a plus, but not required
Benefits
Flexible PTO policy, 13 paid holidays in the US
Company subsidized medical, dental, and vision insurance (90% for employee and eligible dependents)
Flexible Spending Accounts or Health Savings Accounts, depending on your selected health insurance
Stock options in a rapidly scaling startup
401(k) program with employer matching
Company paid basic Life, AD&D, STD & LTD and Voluntary benefits
16 weeks paid Parental Leave for all new parents
Company
Cowbell
Cowbell provides cyber insurance for small and medium-sized businesses, as well as upmarket businesses using AI-driven risk assessment.
Founded in 2019
51-200 employees
Funding
Current Stage
Growth StageTotal Funding
$208.3MKey Investors
Zurich Insurance GroupProsperity7 VenturesAnthemis
2024-07-26Series C· $60M
2023-11-01Series B· $25M
2022-03-15Series B· $100M
Leadership Team
Jack Kudale
Founder and CEO
Rajeev Gupta
Co-Founder and Chief Product Officer
Recent News
2026-01-15
2026-01-15
Insurance Thought Leadership
2026-01-15
Company data provided by crunchbase