Executive Assistant & Office Manager
About the job
- At least 5 years of experience supporting a CEO, founder, or senior executive in a demanding, fast-moving environment.
- A track record of anticipating needs, making sound decisions independently, and following through without repeated reminders.
- Experience managing complex calendars and travel, including competing priorities and last-minute changes.
- Comfort supporting both business and personal matters, with resourcefulness and a willingness to handle practical details.
- Experience with office operations, vendors, events, or comparable responsibilities.
- A highly polished, professional manner, with clear, courteous correspondence and confidence interacting with senior stakeholders.
- Exceptional attention to detail, discretion, and reliability across sensitive business and personal information.
- Strong proficiency with scheduling and productivity tools, and an interest in improving how work gets done.
- Based in the NYC area, or willing to relocate before starting, and able to work in the office at least three days per week with overlap with the CEO; flexibility for additional on-site coverage and occasional time-sensitive support around travel and events.
- Own the CEO's calendar across business and personal commitments, manage scheduling across time zones, resolve conflicts, and protect time for priorities; confirm meeting details and ensure materials are ready.
- Arrange business and personal travel, build complete itineraries, anticipate complications, resolve last-minute changes, and keep expenses and supporting records accurate and organized.
- Handle appointments, reservations, purchases, errands, and other personal administrative matters; coordinate with service providers, resolve issues that would otherwise require the CEO's time, and exercise discretion and good judgment.
- Handle correspondence related to scheduling, travel, reservations, vendors, and other logistical matters; represent the CEO and Kalepa professionally in interactions with customers, investors, candidates, colleagues, and service providers.
- Own vendors, building coordination, supplies, meeting spaces, visitors, and office spending within an agreed budget; anticipate needs, resolve problems, and maintain a welcoming, well-organized workplace.
- Partner with Operations and Marketing to plan and execute logistics for offsites, team gatherings, board meetings, and other events; coordinate venues, travel, catering, and schedules, including the CEO's participation in commercial events.
- Coordinate onboarding equipment, access, and first-day logistics with relevant teams; help visiting colleagues work effectively from NYC and support team milestones.
- Maintain useful checklists, track outstanding requests, and see tasks through to resolution; use approved AI and productivity tools to reduce repetitive coordination while handling confidential information carefully.
- Startup experience is helpful; candidates from other demanding environments are also welcome if they demonstrate strong judgment, ownership, and adaptability.
About the company
Kalepa provides an AI-powered decision support platform called Copilot for commercial insurance underwriters. It combines artificial and human intelligence to identify true hazards and exposures in businesses, helping underwriters make more accurate risk assessments and pricing. The platform is offered as a software-as-a-service (SaaS) to specialty carriers and other commercial insurers, enabling them to write new and renewal business more efficiently. Copilot works by blending data-driven insights with expert review to guide underwriting decisions, reducing time to quote and improving binding rates. Kalepa differentiates itself by integrating AI with human judgment to focus on real-world hazards and exposures, delivering measurable improvements in underwriting speed and accuracy. The company’s goal is to help insurance carriers reduce anticipated losses and operate more efficiently, ultimately increasing profitability through better risk selection and pricing.
Company Size
51-200
Company Stage
Series A
Total Funding
$14M
Headquarters
New York City, New York
Founded
2018
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Simplify's Take
What believers are saying
- Kalepa signed Church Mutual in September 2026, expanding its carrier footprint.
- James River partnered in February 2026 to improve efficiency and portfolio management.
- Bishop Street expanded Kalepa in February 2026 across London MGAs Avid and Landmark.
What critics are saying
- Munich Re specialty, Bowhead, and others can internalize similar underwriting workflows.
- Church Mutual and James River depend on continued product performance, not brand loyalty.
- If underwriting losses hit Kalepa Insurance Services, the software story gets overshadowed quickly.
What makes Kalepa unique
- Copilot combines underwriting AI with human judgment for commercial risk selection.
- Kalepa’s platform is embedded across carriers and MGAs, including James River and Merchants.
- Kalepa now couples software with its own MGA, Kalepa Insurance Services.
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Benefits
- Competitive salary
- Significant equity options package
- 100% covered medical, 100% covered vision and dental
- 20 days of PTO a year.
- Global team offsites
- Healthy living/gym stipend.
- Mobile phone bill stipend
- Continuing education credits
- Home office stipend