Executive Assistant

Cadence Group Software Inc

2d • Hybrid

About The Position

Cadence Group Software is a privately funded startup applying AI and deep industry expertise to Workers’ Compensation claims management — a $100B+ market where an estimated $40B annually is lost to administrative inefficiency. We are a lean, remote-first team of eight, moving quickly and building something that genuinely matters. We offer competitive compensation, meaningful benefits, and equity.

We are looking for an exceptional Executive Assistant to serve as a trusted partner to our CEO. This is a high-trust, high-visibility role at the center of the organization. Our CEO engages daily with customers, investors, board members, vendors, and a growing team — and the right person will ensure all of that operates smoothly, professionally, and with the care it deserves.

We are looking for someone with genuine polish, sound judgment, and the kind of discretion that doesn’t require reminding. You anticipate needs, take ownership without being asked, and find real satisfaction in making the people around you more effective.

This role is primarily remote, but it requires reliable local presence. We need someone within approximately 20 miles of Aptos, CA who can be on-site at least one day per week to manage physical correspondence, executed documents, and in-person logistics. Flexibility to come in more frequently as business needs arise is expected.

Requirements

• 5+ years supporting a CEO, founder, or senior executive. We value judgment, professionalism, and a strong track record above tenure alone.
• Exceptional written and verbal communication. You can hold the right register with anyone — a board chair, a first-time customer, a vendor’s accounts department.
• Impeccable organization and follow-through. You build reliable systems; nothing slips.
• Discretion that is instinctive, not practiced.
• Composure when priorities shift. You recalibrate quickly and move forward without friction.
• Fluency with modern productivity tools: Google Workspace or Microsoft 365, Slack, video conferencing, expense management platforms, and AI-assisted workflows.
• Located within approximately 20 miles of Aptos, CA, with availability for regular in-person engagement.
• Professional fluency in written and spoken English.
• Bachelor’s degree preferred; equivalent professional experience considered.

Nice To Haves

• Prior experience supporting leadership at a high-growth or venture-backed company.
• Exposure to operations, project management, or a chief-of-staff function.
• Notary commission or experience managing formal document execution workflows.
• Experience supporting board meeting preparation or investor communications.
• Familiarity with healthcare, legal, or insurance industries.

Responsibilities

• Manage the CEO’s calendar with rigor — protecting focused work time, coordinating across time zones, and resolving conflicts before they surface.
• Serve as the first point of contact for a wide range of stakeholders: investors, board members, customers, partners, and vendors. Your communication will reflect the standards of the office.
• Draft and send correspondence on the CEO’s behalf — emails, introductions, follow-ups, and acknowledgments — with precision and the right tone for every audience.
• Own travel coordination end-to-end: flights, accommodations, ground transportation, dining reservations, and itinerary management.
• Prepare and run logistics for internal and external meetings — agendas, briefing materials, attendee coordination, follow-ups, and action item tracking.
• Support board meetings, investor communications, leadership offsites, and customer engagements with thorough preparation and end-to-end execution.
• Manage expense reporting, reimbursements, and recurring administrative workflows.
• Handle weekly in-person responsibilities: mail, packages, signed documents, and any logistics requiring a physical presence.
• Exercise absolute discretion in handling sensitive and confidential matters.
• Anticipate what’s coming, get ahead of it, and handle it — before anyone has to ask.

Benefits

• The base salary range for this role is $72,000–$95,000, commensurate with experience.
• Remote-first with flexible working hours and one required in-person day per week near Aptos, CA.
• Startup equity — you are joining at an early stage, and that carries real upside.
• Health, dental, and vision coverage.
• 401(k).
• Generous paid time off and standard holidays.
• A direct working relationship with the CEO and meaningful visibility into how the business operates.

What This Job Offers

• Job Type: Full-time
• Career Level: Executive