Trunk Tools takes a market-based approach to pay, and pay may vary depending on your location. U.S. locations are categorized into one of four zones based on a cost of labor index for that geographic area. Your starting pay will be determined based on job-related skills, experience, qualifications, work location, and market conditions. For this role, the estimated base salary is $ - $ with a comprehensive benefits package and equity component.

At Trunk Tools, we’re the leading AI company revolutionizing construction—the second-largest industry on earth. We recently raised a $40M Series B led by Insight Partners, bringing our total funding to $70M from top-tier investors including Redpoint and Innovation Endeavors. This new round is fueling our next phase of growth as we scale AI agents across the jobsite.

Our mission is to build the future of construction through intelligent automation. Despite being a $13+ trillion industry, construction still runs largely on analog processes—we’re changing that by embedding AI directly into field operations.

Founded by builders and technologists (Stanford, MIT), our team has delivered software used by over 140,000 field professionals, impacting millions of users and contributing to $10B+ in built projects. Many of us come from the field ourselves, giving us a deep understanding of the industry’s unique challenges.

After years of building the “brain” of construction, we’re now launching production-ready AI agents—starting with intelligent document processing and Q&A, and rapidly expanding into core operational workflows. Our team has doubled in the past year, and with 65+ employees (25+ engineers), we’re scaling fast and entering a period of hypergrowth—this is a rare opportunity to join at an inflection point.

About the Role

We're looking for an experienced Senior Executive Assistant to provide dedicated support to our CEO, Dr. Sarah Buchner, and oversee operations for our NYC office. This position requires more than traditional executive assistance: you'll need strategic thinking, strong leadership in office management, and hands-on engagement with company operations. The right person will be a trusted partner to the CEO, bringing professionalism, discretion, and initiative to everything they do. We're looking for someone who sees this as a career, not a stepping stone, someone ready to grow with us long-term. This role requires being in the NYC office every day the CEO is in the office (up to 5 days a week.)

What You Will Do and Achieve:

Executive Leadership Support:

• Provide high-level administrative support to the CEO, including strategic calendar management, complex travel coordination, and thorough meeting preparation

• Anticipate the CEO's needs and address issues proactively, allowing her to concentrate on strategic initiatives and business growth

• Manage the CEO's email and inbox, flagging important communications and drafting responses

• Prepare and edit correspondence, communications, presentations, and other documents

• Handle confidential information with discretion and professionalism

• Provide select personal assistance to the CEO to support her focus on business priorities

• Plan travel arrangements for the executive team, including monthly executive onsites and conferences

• Serve as liaison between executive hires and People Operations to ensure smooth onboarding and engagement

Who You Are:

• 8+ years of experience as an Executive Assistant or in a similar role, with a proven track record supporting C-level executives in fast-paced, high-growth tech startups, and a demonstrated ability to grow in the role as an Executive Assistant

• Demonstrated ability to manage and prioritize a wide range of tasks while maintaining exceptional attention to detail and quality

• Occasional weekend or after-hours work may be needed as this is a customer-facing role, though this won't be a regular expectation.

• Strong written and verbal communication skills, with the ability to craft clear, compelling messages that reflect the voice of the CEO

• Advanced proficiency with Google Workspace (Gmail, Calendar, Drive) and other relevant office management and communication tools

• A strategic thinker with a proactive, problem-solving mindset and a can-do attitude

• Proven ability to handle sensitive information with integrity and confidentiality

• Experience working in dynamic environments, with the ability to stay resilient under pressure, adapt quickly to changing priorities, and drive projects to completion

• Skilled at managing challenging situations and working effectively with diverse personalities

• Committed to building a long-term Executive Assistant career—you're looking to grow in this role, not use it as a transition

What we offer

🎖️ A close-knit and collaborative early-stage startup environment where every voice is heard and every opinion matters

💰 Competitive salary and stock option equity packages

🏥 3 Medical Plans to choose from including 100% covered option. Plus Dental and Vision Insurance!

🤓 Learning & Growth stipend

🏠 Flexible long-term work options (remote and hybrid)

🥨 Free lunch provided in the office in NYC & Austin - you’ll never go hungry with us!

🛫 Unlimited PTO; We truly believe in work-life balance and that hard work should be balanced with time for rest and rejuvenation

🏝 IRL / In-Person retreats throughout the year

Please note: All official communication from Trunk Tools will come from an email address ending in @trunk.tools. If you receive outreach from any other domain, please disregard it or report it to us.

At Trunk Tools, we’re working hard to build a more productive and safer environment within the construction industry, and we strive to live by these same values here at Trunk Tools HQ. As an equal-opportunity employer, we are committed to building an inclusive environment where you can be you. We work hard to evaluate all employees and job applicants consistently, without regard to race, color, religion, gender, national origin, age, disability, pregnancy, gender expression or identity, sexual orientation, or any other legally protected class.

Compensation Range: $140K - $160K