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.
This role will fully own and manage benefits administration, payroll processing, onboarding and New Hire Orientation (NHO), and people culture initiatives, ensuring an outstanding employee experience at every stage. An ideal candidate will also have an interest in or experience with Learning & Development (L&D) to support our team's growth and professional development programs.
What you will do:- Benefits Administration
- Manage and administer employee benefits programs (health, dental, vision, 401(k), etc.).
- Partner with brokers and vendors to evaluate, recommend, and implement benefit offerings.
- Support annual benefits renewal and open enrollment processes.
- Act as a key resource for employees on benefits questions and issue resolution.
- Payroll Management
- Own the end-to-end payroll process ensuring timely, accurate pay runs for US and Canada.
- Manage and process documentation, data integrity and updates (new hires, terminations, promotions, etc.).
- Ensure reconciliation, reporting, and compliance with state and federal laws.
- Onboarding
- Own the onboarding process and continuously look to improve processes as needed to ensure a smooth, welcoming experience for all new hires.
- Coordinate and facilitate New Hire Orientation sessions, introducing company culture, processes, and key policies.
- People Culture & Employee Experience
- Champion company values and drive employee engagement initiatives.
- Maintain and improve People Ops systems, policies, and processes to ensure scalability and compliance.
- Support employee lifecycle processes including onboarding, New Hire Orientation, and offboarding.
- Serve as the primary point of contact (POC) for employees regarding workplace concerns, feedback, and team dynamics.
- Partner with people managers on a regular basis to understand team health, support resolution strategies and drive initiatives that foster a healthy, high-performing team culture.
- Learning & Development (Bonus Area)
- Assist in identifying training needs and L&D initiatives.
- Coordinate learning opportunities and manage L&D vendors or platforms.
- Help track and measure the impact of development programs.
- 5–8 years of People Operations, HR, or related experience.
- Minimum of 2 years of hands-on experience running payroll and administering benefits for the US and Canada
- PHR/SPHR/SHRM-CP certifications are preferred
- Strong understanding of employment laws, compliance, and best practices in the US and Canada.
- Comfortable working with HRIS, payroll, and benefits platforms (e.g., HiBob, Paylocity, Greenhouse).
- Exceptional organizational skills with keen attention to detail.
- Excellent interpersonal and communication skills.
- Ability to handle confidential information with discretion
- Adhoc projects as needed
What Cowbell brings to the table:
- Employee equity plan for all and wealth enablement plan for select customer facing roles
- Comprehensive wellness program, meditation app subscriptions, lunch and learn, book club, happy hours and much more
- Professional development and the opportunity to learn the ins and outs of cyber insurance, cyber security as well as continuing to build your professional skills in a team environment
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.
For more information, please visit https://cowbell.insure/.
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