Executive Assistant to the Founders

Location: Fully Remote (East Coast Preferred)

Travel: Occasional travel to Northport, NY preferred

Silhouette Group is a luxury event, travel, and experience design firm specializing in creating extraordinary moments for some of the world's most discerning clients. Our work spans global events, private celebrations, incentive travel, executive gatherings, brand experiences, and bespoke adventures around the world.

We are seeking an exceptional Executive Assistant to support our founders, Melissa Graham and Lori Hart.

This is not a traditional Executive Assistant role. The ideal candidate is highly organized, proactive, polished, and service-oriented, with a hospitality mindset and a genuine passion for creating seamless experiences behind the scenes.

Most importantly, this person will become deeply immersed in the Silhouette Group brand, voice, standards, and culture, serving as a trusted extension of the founders and leadership team.

The Executive Assistant will provide direct support to both founders while helping maintain continuity across the business.

This role will play an important part in helping the founders stay focused on client relationships, business development, leadership, and company growth by creating structure, organization, and follow-through across both professional and personal priorities.

The right person thrives in fast-paced environments, loves creating order from complexity, and naturally operates with a "consider it handled" mindset.

• Manage business and personal calendars for both founders
• Coordinate meetings, appointments, and travel
• Assist with email organization and follow-up
• Track action items and key deliverables
• Prepare meeting agendas and meeting notes when needed
• Conduct research and administrative support projects
• Manage special projects as assigned
• Assist with presentation preparation and client-facing materials
• Support day-to-day founder priorities and shifting needs

Working closely alongside the founders and Director of Events, this individual will:

• Attend weekly company meetings
• Participate in internal Slack channels and team communications
• Stay informed on active projects, clients, and company priorities
• Review client-facing materials to ensure consistency with Silhouette Group standards prior to final approval
• Assist with approval workflows when the Director of Events is traveling, on-site, on PTO, or managing a high volume of approvals
• Provide additional support during peak planning periods
• Help maintain consistency across client communications, presentations, budgets, proposals, and event materials
• Serve as an additional set of eyes to ensure quality, accuracy, tone, and attention to detail

While final approvals remain with company leadership, this role will become deeply familiar with Silhouette Group's standards, voice, client experience expectations, and overall approach to business.

• Household vendor coordination
• Personal appointments and scheduling
• Gift sourcing and special occasion planning
• Online purchases, returns, and exchanges
• Travel logistics
• Personal administrative support
• Family scheduling assistance
• General life management projects
• Assistance with special projects and personal priorities as needed

Melissa will begin maternity leave in July 2026. During this time, this individual will serve as an important communication bridge, helping keep her informed on key company updates, active projects, and company happenings as needed while maintaining continuity across the organization.

You are:

• Exceptionally organized
• Highly detail-oriented
• Resourceful and proactive
• Calm under pressure
• Professional and polished
• Trustworthy and discreet
• An excellent communicator
• Comfortable managing multiple priorities simultaneously
• Tech savvy and quick to learn new systems
• Naturally solutions-oriented
• Able to anticipate needs before they arise
• Service-minded and hospitality-driven

You enjoy helping others succeed and find satisfaction in creating structure, efficiency, and ease.

• Executive Assistant
• Senior Executive Assistant
• Personal Assistant
• Founder Support
• Household Management
• Luxury Hospitality
• Luxury Travel
• Concierge Services
• Client Services
• Event Planning
• Private Client Services
• Family Office Support

Experience supporting entrepreneurs, founders, executives, high-net-worth individuals, family offices, luxury brands, hospitality organizations, or private clients is strongly preferred.

• Full-time preferred
• Fully remote position
• East Coast candidates preferred
• Ability to travel periodically to Northport, NY preferred
• Competitive compensation based on experience
• Read more about Silhouette Group and the Founders here: https://silhouettegroup.com

This role is ideal for someone who loves creating order, solving problems, and helping busy leaders operate at their highest level.

You are dependable, thoughtful, proactive, and highly accountable.

You notice details others miss. You anticipate needs before they arise. You take pride in creating calm, consistency, and excellence behind the scenes.

Your mindset is simple: "I've got it handled."

Please submit the following to [email protected]

• Resume
• LinkedIn profile
• Location
• Availability
• A brief note explaining why you're interested in the role and why you'd be a strong fit for supporting founders in a blended executive and personal support capacity
• BONUS: include a short video introducing yourself and tell us why you're excited for this opportunity