Executive Operations Lead, Paystand

• 5+ years of experience in executive support, executive operations, or high-trust coordination roles
• Experience supporting senior leadership in a fast-paced or founder-led environment
• Strong written communication skills and experience preparing executive-level materials
• High discretion and emotional intelligence
• Ability to manage multiple evolving work streams simultaneously
• Comfort using AI-enabled tools to improve productivity and execution efficiency

Desirable

• This position is intended to be based onsite at our Santa Cruz, CA headquarters. However, we may consider highly qualified remote candidates who can commit to 25–35% travel out of the year, both domestically and internationally
• The Executive Operations Lead within the Office of the CEO supports the CEO’s ability to operate effectively across evolving company priorities. This role combines executive support, communication preparation, and coordination across key work streams to help ensure board deliverables, leadership rhythms, and priority initiatives are organized and well-prepared
• This position requires strong organizational skills, sound judgment, and the ability to manage sensitive materials with discretion — while operating comfortably in a fast-moving, founder-led environment
• Executive & Board Support
• Support preparation and coordination of board materials, including organizing metrics, assisting with narrative drafts, and preparing presentation materials
• Coordinate logistics and ensure board-related communications and materials are organized and prepared in advance
• Assist in preparing executive-level updates and presentation flow to reflect professionalism and clarity
• Executive Scheduling & Relationship Coordination
• Manage executive scheduling and prioritization in alignment with evolving priorities
• Coordinate travel, engagements, and key meetings with attention to timing and context
• Support follow-up and communication flow with internal and external stakeholders as appropriate
• Maintain organized systems for contacts, documentation, and high-value relationship materials
• Leadership Rhythm & Communication Support
• Support the preparation and organization of recurring leadership meetings and Friday town halls
• Assist in structuring materials and presentation flow for internal company-wide communications
• Help ensure materials for leadership forums are prepared clearly and on time
• Contribute to improving clarity and consistency in executive messaging where appropriate
• Priority & Initiative Coordination
• Support the CEO in organizing and prioritizing a portfolio of active initiatives that may shift weekly
• Help coordinate planning and next-step clarity across select CEO-driven projects
• When applicable, provide coordination support for 1–2 contributors aligned to specific executive priorities
• Assist in maintaining visibility into timelines and deliverables across these efforts
• Efficiency & AI-Enabled Workflow Support
• Use AI-enabled tools and modern productivity systems to streamline preparation of communications, presentations, and executive materials
• Introduce lightweight templates or repeatable formats where helpful to improve efficiency
• Stay current on practical applications of AI to increase speed and quality of output in a fast-moving environment