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.

About the Role

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.

What You’ll Do

• 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.

What You Bring

• 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.

What Sets the Ideal Candidate Apart

• 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

Why Join STACK?

• 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.

At STACK, our values shape how we work, collaborate, and serve our customers

• Radical Honesty: Communicate directly, respectfully, and transparently—even when conversations are difficult. Give and receive feedback with care.
• Customer Obsession: Put the customer at the center of every decision. Solve real problems, follow through, and measure success by customer outcomes.
• Move With Purpose: Take thoughtful action, remain accountable, and own both successes and mistakes. Anticipate what’s next and adapt as you learn.
• Grow Together: Share knowledge, collaborate across teams, and invest in one another’s development. Celebrate collective wins and treat setbacks as opportunities to learn.

We are an equal opportunity employer and value diversity at our company. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. We are committed to building a team that represents a variety of backgrounds, perspectives, and skills. The more inclusive we are, the better our work will be.

We are interested in every qualified candidate who is eligible to work in the United States. However, we are not able to sponsor visas.

We take into account an individual’s qualifications, skillset, and experience in determining final salary. This role is eligible for health insurance (medical, dental & vision), life insurance, 401(k) & paid time off. The expected compensation range for this position is about $85k-$128k USD. The actual offer will be at the company’s sole discretion and determined by relevant business considerations, including the final candidate’s qualifications, years of experience, skillset, and geographic location.