Executive Assistant

Dapple; Connecticut; Hybrid; USD 100,000 - 170,000; Full time

Benefits offered by this job

Medical, dental, vision, disability

401(k)

Maternity/Parental leave

6 weeks PTO

Flexible work schedules

Job summary

Dapple is seeking an experienced Executive Assistant to the CEO to keep the CEO’s world running and free her to focus on high-leverage work. You will own the calendar, inbox and travel, act as a discreet gatekeeper, and coordinate meetings, materials and follow-ups across a fast-moving organization.

Beyond daily support, you’ll help sustain rhythm and culture, organizing offsites, team events and company swag for a distributed, remote-first team across time zones.

Qualifications

• 5+ years as an executive assistant to a CEO, founder or senior executive, ideally in startup or fast-moving environment.
• Exceptional gatekeeper with mastery of complex calendars and independent time management.
• Exceptional organization, discretion and reliability with confidential, high-stakes information.
• Proactive, low ego; anticipates needs and owns details.

Responsibilities

• Own the CEO's calendar, inbox and travel with the judgment to prioritize, decline and reschedule.
• Be an exceptional gatekeeper: protect time and surface what needs attention.
• Prepare the CEO for meetings with agendas, materials, briefing notes and follow-ups.
• Handle scheduling, expenses, documents and day-to-day tasks to prevent slips.
• Plan and coordinate company programs and team events, including offsite and swag.
• Maintain the small but important things that hold the company together.

Skills

Executive support to CEO

Calendar management

Gatekeeper

Discretion

Reliability

Written communication

Microsoft 365

DocuSign

Tools

Microsoft 365

DocuSign

Job description

Department: Office of the CEO Reports to: CEO Location: Remote (US, CT or ET preferred) Employment type: Full-time

About Dapple

Dapple is the Enterprise OS Cloud, a new category of AI infrastructure between the public cloud and the private data center. We give regulated enterprises and high-growth digital natives dedicated, in-country, single-tenant capacity to run production AI, extending the cloud ecosystems they already use rather than asking them to leave. We are an early-stage, venture-backed company moving quickly.

About the role

The Executive Assistant keeps the CEO's world running. Reporting to the CEO, this role owns her calendar, inbox, travel and day-to-day, freeing her to focus on the highest-leverage work at a company moving very fast.

This is a senior, experienced EA role. The right person is an exceptional gatekeeper who knows which meetings matter and which do not, manages a complex calendar with judgment, and protects the CEO's time without being asked. They are organized, discreet and proactive, and the people around them are more effective because of them.

Beyond supporting the CEO directly, this role helps keep the company's rhythm and culture intact, owning the things that matter but have no natural home, such as the offsite, team events and swag.

Key responsibilities

Executive support to the CEO:

• Own the CEO's calendar, inbox and travel, with the judgment to prioritize, decline and reschedule on her behalf.
• Be an exceptional gatekeeper: protect her time, surface what needs attention and keep her a step ahead of what is coming.
• Prepare her for meetings with agendas, materials, briefing notes and follow-ups.
• Handle scheduling, expenses, documents and the day-to-day so nothing slips.
• Plan and coordinate company programs and team moments, including the annual offsite, team events and swag.
• Keep the small but important things that hold the company together from falling through the cracks.
• Support broader executive and team coordination as needed

Qualifications

• 5 or more years as an executive assistant to a CEO, founder or senior executive, ideally at a startup or in a fast-moving environment.
• An exceptional gatekeeper with mastery of complex calendars and the judgment to manage an executive's time independently.
• Exceptional organization, discretion and reliability, trusted with confidential and high-stakes information.
• Proactive and low ego: anticipates needs and owns the details, with no task too big or too small.
• Calm and steady under pressure in a high-change environment.
• Clear, concise written communication, comfortable acting in the CEO's voice.

Preferred experience

Long-tenured support of one or two executives, the kind of EA who becomes indispensable, is strongly preferred. Additional nice-to-haves: familiarity with the Microsoft 365 stack, DocuSign and common travel tools; experience supporting a distributed, remote-first team across time zones; experience coordinating events, offsites or team culture programs.

Compensation and benefits

Competitive base salary plus bonus and equity, calibrated to experience.

• Medical, dental, vision and disability insurance
• 401(k)
• Maternity and parental leave
• 6 weeks of PTO per year
• Flexible work schedules

Three rounds: an initial screen; a take-home exercise on a real scheduling or prioritization scenario; and a final round with the CEO. We move quickly, with a typical end-to-end timeline under two weeks.

Equal opportunity

Dapple is an equal opportunity employer. We consider all qualified applicants without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, veteran status, or any other protected characteristic.