Level 2 Platform Support Engineer II

Cowbell Cyber • Pleasanton, CA

10d • Remote

About The Position

Cowbell is signaling a new era in cyber insurance by harnessing technology and data to provide small and medium-sized enterprises (SMEs) with advanced warning of cyber risk exposures bundled with cyber insurance coverage adaptable to the threats of today and tomorrow. Championing adaptive insurance, Cowbell follows policyholders’ cyber risk exposures as they evolve through continuous risk assessment and continuous underwriting. In its unique AI-based approach to risk selection and pricing, Cowbell’s underwriting platform, powered by Cowbell Factors, compresses the insurance process from submission to issue to less than 5 minutes. Founded in 2019 and based in the San Francisco Bay Area, Cowbell has rapidly grown, now operating across the U.S., Canada, U.K., and India. This growth was recently bolstered by a successful Series C fundraising round of $60 million from Zurich Insurance. This investment not only underscores the confidence in Cowbell’s mission but also accelerates our capacity to revolutionize cyber insurance on a global scale. With the backing of over 25 prominent reinsurance partners, Cowbell is poised to redefine how SMEs navigate the evolving landscape of cyber threats. About The Role The Platform Support team at Cowbell provides technical expertise and product knowledge to support internal users and API partners. Our primary goal is to keep platform users productive, unblocked, and confident in their day-to-day operations. This Level 2 role refers to the type and complexity of issues handled , not job seniority. Level 2 Platform Support Engineers bridge frontline support (Level 1) and advanced technical support and engineering teams , coordinating investigation, validation, and escalation to ensure issues are resolved efficiently.

Requirements

• Education & Experience Bachelor’s degree in a relevant field, or equivalent practical experience.
• Prior experience in a technical support, platform support, or software-adjacent role.
• Experience level may vary depending on demonstrated skills, judgment, and overall team needs.
• Technical & Operational Experience 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.
• Communication & Mindset 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.
• On-Call & Coverage Expectations This role may require on-call availability based on business needs.
• Flexible working hours may be required, including coverage aligned with West Coast business hours, depending on assignment and operational needs.

Nice To Haves

• 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. Team members are expected to learn and adapt to the tools used to support and operate the Cowbell Platform.

Responsibilities

• Issue Triage & Troubleshooting 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.
• Ticket Ownership & Resolution 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.
• Escalation & Incident Support 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.
• Production Sync Coordination (Based on Experience & Assignment) 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.
• Testing & Validation 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.
• Platform Knowledge & Documentation 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.
• Cross-Team Collaboration 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.

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

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Number of Employees: 101-250 employees