Level 2 Platform Support Engineer II

Job Description

Job Description

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.

Responsibilities / What You'll Do

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.

Requirements / What will you bring to the roleEducation & 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.
• 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.

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.

Why This Role Matters

Level 2 Platform Support Engineers play a critical role in keeping the Cowbell Platform stable and reliable. This role bridges frontline support and advanced technical support and engineering teams by ensuring issues are properly understood, prioritized, validated, and escalated—helping users stay productive while enabling engineering teams to focus on long-term fixes.

Our US Benefits include (but are not limited to):

• 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
• Winner of Inc. Magazine's Annual List of Best Workplaces for 2022 & 2023

Work Location:

• This is a fully remote position, but we are currently only hiring candidates located in the following states: AL, AR, AZ, CA, CO, CT, DE, FL, GA, ID, IL, IA, KY, MD, MA, MI, MN, MO, MS, NC, NE, NJ, NV, NY, OH, OK, OR, PA, SC, TN, TX, UT, VA, VT, WA, DC, WI

Equal Employment Opportunity:

We are committed to equal opportunity in the terms and conditions of employment for all employees and job applicants without regard to race, color, religion, sex, sexual orientation, age, gender identity or gender expression, national origin, disability, or veteran status.

Cowbell is a leading innovator in cyber insurance, dedicated to empowering businesses to always deliver their intended outcomes as the cyber threat landscape evolves. Guided by our core values of TRUE—Transparency, Resiliency, Urgency, and Empowerment—we are on a mission to be the gold standard for businesses to understand, manage, and transfer cyber risk.

At Cowbell, we foster a collaborative and dynamic work environment where every employee is empowered to contribute and grow. We pride ourselves on our commitment to transparency and resilience, ensuring that we not only meet but exceed industry standards.

We are proud to be an equal opportunity employer, promoting a diverse and inclusive workplace where all voices are heard and valued. Our employees enjoy competitive compensation, comprehensive benefits, and continuous opportunities for professional development.

Cowbell is an E-Verify employer. E-Verify is a web-based system that allows an employer to determine an employee's eligibility to work in the US using information reported on an employee's Form I-9. The E-Verify system confirms eligibility with both the Social Security Administration (SSA) and Department of Homeland Security (DHS). For more information, please go to the USCIS E-Verify website.

For more information, please visit https://cowbell.insure/.

Cowbell Cyber does not permit the use of AI tools during any stage of our interview process. By submitting your application, you agree to complete all assessments and interviews without the use of generative AI assistance.