Executive Assistant; Onsite, Georgetown

About Us:

STACK is a leading provider of cloud-based construction estimating and takeoff software solutions, committed to helping businesses transform through innovative solutions. We pride ourselves on fostering a collaborative, dynamic environment where team members have the opportunity to grow and make a real impact.

Location:

Onsite in
Georgetown, Washington D.C.

We're looking for an experienced Executive Assistant to provide high-level support to our CEO and executive leaders at a fast-growing Construction AI and B2B SaaS company. This role is ideal for someone who thrives in a dynamic, fast-paced environment, is highly organized and proactive, and enjoys partnering closely with senior leaders to keep priorities, schedules, and day-to-day operations running smoothly.

This position requires someone who thrives in complexity, can easily switch gears without missing a beat, and brings both strategic thinking and flawless execution to everything they touch. The position will require serving as the right hand to the Executive, supporting all admin functions, event management, and personal responsibilities.

• Calendar management and coordination across multiple time zones
• Own end-to-end travel logistics including international and domestic flights, accommodations, ground transportation, visa/entry requirements, and detailed itineraries
• Prepare briefing materials, agendas, presentations, and/or follow-up communications for board meetings, investor calls, leadership offsites, and media engagements
• Serve as trusted gatekeeper and first point of contact- triaging communications across email, phone, and messaging platforms with sound judgement and discretion
• Draft and manage correspondence on behalf of the executive
• Track action items and follow through on delegated tasks to ensure nothing falls through the cracks
• Serve as the liaison between executive and employees fulfilling executives "servant leadership style" of making himself available as employees need guidance/support.
• Support coordination of leadership meetings, stakeholder communications, team offsites, and company-wide communications across North American and emerging global offices
• Own project management across key initiatives led by the Executive across the leadership team
• Help manage relationships with board members, investors, and strategic partners - handling scheduling, material prep, and follow-up.
• Assist with coordination of Executives' presence as needed.
• Serve as the primary point of contact to the Executive for VIP relationships and partnerships.

• 7+ years of executive assistant experience, ideally supporting multiple c-level executives principal with multiple professional priorities
• Proven ability to manage competing, high stakes demand across distinct organizations with grace under pressure
• Exceptional organizational skills and extreme attention to detail - you don't let things fall through the cracks
• Outstanding written and verbal communication skills; ability to represent the executive's voice authentically across correspondence
• Demonstrated discretion and integrity in handling sensitive personal and professional information
• Strong proficiency with productivity and communication tools (ChatGPT/Claude, Google Workspace, Microsoft 365, Slack, Monday/Asana)
• Comfortable working across consumer, B2B, and personal contexts - no task is beneath you, and no challenge is too large
• Flexibility to accommodate non-traditional hours, last-minute changes, and occasional travel when needed
• Valid driver's license required; familiarity with the DC/Northern Virginia area is a plus
• Willingness to learn and test new AI tools to help streamline communication and operational processes.

• Experience working with a high-profile executive and ecosystem of high-profile business and personal contacts.
• Experience supporting an executive with multiple simultaneous ventures
• Experience managing events with meticulous attention to detail
• Familiarity with the tech startup or AI ecosystem
• A genuine passion for discretion, loyalty, and long-term partnership with a principal

• Opportunity to work in a fast-paced, growth-oriented environment.
• Async-friendly environment with a focus on ownership and deep work.
• Be part of a dynamic, supportive team where your contributions are valued.

• Radical Honesty:
  Communicate directly, respectfully, and…