Executive Assistant to the Founders

About Silhouette Group

Silhouette Group is a premier luxury event, travel, and experience design firm dedicated to crafting exceptional moments for a sophisticated global clientele. Our expertise encompasses international events, private celebrations, incentive travel programs, executive gatherings, brand experiences, and unique adventures worldwide.

The Opportunity

We are seeking an outstanding Executive Assistant to provide comprehensive support to our founders, Melissa Graham and Lori Hart. This is a unique role that extends beyond traditional executive assistance, requiring a highly organized, proactive, polished, and service-oriented individual with a strong hospitality mindset and a passion for creating seamless behind-the-scenes experiences. The ideal candidate will become an integral part of the Silhouette Group brand, embodying its voice, standards, and culture, acting as a trusted extension of the founders and leadership team. This position is crucial in enabling the founders to concentrate on client relationships, business development, leadership, and company expansion by establishing structure, organization, and diligent follow-through across both professional and personal spheres. The successful candidate will excel in dynamic environments, thrive on bringing order to complexity, and possess a natural 'consider it handled' approach.

Key Responsibilities

• Manage and maintain complex business and personal calendars for both founders.
• Orchestrate and confirm meetings, appointments, and all travel arrangements.
• Assist with the organization and prioritization of founder inboxes and email correspondence.
• Monitor and track action items, key deliverables, and project milestones.
• Prepare meeting agendas and accurately document meeting minutes as required.
• Conduct thorough research and undertake various administrative support projects.
• Oversee and manage special projects as assigned by the founders.
• Support the preparation of presentations and client-facing materials.
• Provide responsive support for day-to-day founder priorities and evolving needs.

Leadership Team Support

• Collaborate closely with the founders and the Director of Events.
• Attend and contribute to weekly company-wide meetings.
• Actively participate in internal Slack channels and team communications.
• Maintain a comprehensive understanding of active projects, clients, and company objectives.
• Review client-facing documents to ensure adherence to Silhouette Group standards before final approval.
• Provide interim approval workflow support when the Director of Events is unavailable due to travel, on-site duties, or PTO.
• Offer additional assistance during periods of high operational demand.
• Help ensure consistency across all client communications, proposals, budgets, and event collateral.
• Serve as an additional quality assurance check for accuracy, tone, and meticulous attention to detail.

While ultimate decision-making authority rests with company leadership, this role will develop a deep familiarity with Silhouette Group's established standards, brand voice, client experience expectations, and overall business philosophy.

Personal & Lifestyle Support

• Coordinate household vendors and services.
• Manage personal appointments and scheduling.
• Source gifts and plan for special occasions.
• Handle online purchases, returns, and exchanges.
• Organize personal travel logistics.
• Provide general personal administrative support.
• Assist with family scheduling.
• Undertake general life management projects.
• Support special projects and personal priorities as needed.

Maternity Leave Support

During Melissa's maternity leave commencing July 2026, this role will be vital in maintaining communication flow, ensuring she is updated on critical company developments and ongoing projects, and supporting organizational continuity.

Additional Information

This is a fully remote position, with a preference for candidates located on the East Coast. Occasional travel to Northport, NY, may be required. Compensation will be competitive and commensurate with experience. Further details about Silhouette Group and the Founders can be found at https://silhouettegroup.com.