Job Details

Job Title: Executive Assistant & Office Manager

Location: San Francisco, CA (In-Person)

Job Type: Full Time

Manager: Human Resources

About Us

Cinnamon is a healthcare technology company focused on improving patient access to care by automating and streamlining patient assistance and affordability workflows. We partner with healthcare organizations and life sciences companies to reduce friction in financial assistance processes, improve data integrity, and enable secure, compliant exchange of healthcare data.

Role Summary

Cinnamon is seeking a highly capable, detail-obsessed Executive Assistant to serve as a strategic partner to our CEO while also owning day-to-day operations of our San Francisco office.

This is primarily a CEO-facing role. Approximately 80 percent of your time will be dedicated to executive support. The remaining 20 percent will focus on office operations and ensuring our San Francisco workspace runs seamlessly.

You will operate as an extension of the CEO. This role requires exceptional judgment, discretion, prioritization skills, and the ability to anticipate needs before they surface. You will help create focus, remove friction, and increase executive leverage across the company. This is a fully in-person role based in our San Francisco office.

Key Responsibilities

Executive Partnership and CEO Leverage

• Own and strategically manage the CEOs calendar, ensuring time is allocated to the highest impact priorities
• Proactively evaluate meeting requests and recommend tradeoffs aligned with company goals
• Prepare structured daily and weekly briefings so the CEO is fully prepared for every engagement
• Manage and triage the CEOs inbox, drafting responses and ensuring timely follow-up on key threads
• Serve as liaison across leadership, board members, investors, customers, and external partners
• Prepare executive-level materials including agendas, slide decks, summaries, and briefing documents
• Track action items from leadership meetings and drive accountability across stakeholders
• Coordinate complex domestic travel, offsites, customer visits, and investor meetings
• Manage expense reporting and administrative documentation with precision
• Anticipate operational gaps and resolve issues before they impact the CEOs focus
• Maintain strict confidentiality across sensitive company matters

Office Operations and Cross-Office Alignment

• Own the daily operations and presentation of the San Francisco office
• Manage incoming and outgoing company mail and packages, including sensitive or time-critical documents
• Ensure timely distribution of mail, scanning, forwarding, and handling of official correspondence
• Maintain organized physical and digital filing systems as needed
• Manage vendor relationships including facilities, maintenance, internet, cleaning services, and building management
• Oversee supplies, equipment, and workspace readiness
• Support onboarding for San Francisco team members including workspace setup and orientation
• Plan and execute in-office team events, leadership gatherings, and client visits
• Partner closely with the Seattle Office Manager to standardize processes, share best practices, and create consistency across offices
• Identify operational inefficiencies and implement improvements that elevate employee experience and productivity
• Support special projects and company initiatives that require executive-level coordination

Required Qualifications

• 3+ years of experience as an Office Manager, Workplace Manager, or similar role
• Experience supporting an in-person office in a fast-paced or growing environment
• Strong organizational and time-management skills with excellent attention to detail
• Comfortable managing vendors, facilities, and operational logistics independently
• Excellent written and verbal communication skills
• Proficiency with Google Workspace (Gmail, Calendar, Docs) and common office tools
• Proactive, resourceful, and comfortable wearing multiple hats

What We Offer

• Competitive salary and benefits package.
• High-impact role reporting directly to revenue leadership.
• Opportunity to shape marketing strategy at a growing healthcare technology company.
• Mission-driven culture focused on improving patient access to care.

How to Apply

Send your resume and a cover letter detailing your leadership experience and interest in the position to ...@cinnamon.health. We look forward to reviewing your application and exploring how you can help us advance healthcare through innovation and technology!