Executive Assistant the Founders

About the Role

Silhouette Group Inc. is looking for a proactive, high-caliber Executive Assistant to serve as the primary point of contact and strategic partner to our Founders. In this pivotal role, you will act as a force multiplier, managing complex operations and ensuring the leadership team remains focused on high-level growth and innovation. This is a fully remote position that requires a unique blend of sophisticated administrative expertise, impeccable discretion, and the ability to navigate a fast-paced environment with grace and precision. While the role is remote, candidates located on the East Coast are preferred to ensure optimal synchronous collaboration.

• Manage and optimize complex, ever-changing calendars, ensuring the Founders' time is allocated to the highest priority initiatives while preventing scheduling conflicts.
• Act as a professional gatekeeper and liaison, managing internal and external communications, including high-level correspondence with investors, clients, and partners.
• Coordinate seamless domestic and international travel arrangements, including detailed itineraries, transportation, and accommodation, while remaining available for real-time troubleshooting.
• Lead the preparation and organization of board meetings, executive retreats, and speaking engagements, including the creation of briefings, presentations, and agendas.
• Execute specialized projects and research initiatives that support the Founders’ strategic goals, demonstrating a high degree of autonomy and resourcefulness.
• Monitor and manage personal and professional administrative tasks, ensuring all deadlines are met and sensitive information is handled with absolute confidentiality.
• Facilitate effective communication across the organization, ensuring the Founders' vision and directives are clearly articulated to the broader team.

• A minimum of 5-7 years of experience supporting C-suite executives or founders, ideally within a fast-scaling startup or a high-growth corporate environment.
• Exceptional organizational skills and an obsessive attention to detail, with the ability to anticipate needs before they arise.
• Advanced proficiency in modern productivity tools including Google Workspace, Slack, Zoom, and project management software like Asana or Trello.
• Superb written and verbal communication skills, with the ability to draft professional correspondence that reflects the Founders’ voice and brand standards.
• Proven ability to handle high-pressure situations and sensitive information with diplomatic tact and unwavering confidentiality.
• A self-starter mindset with the flexibility to adapt to changing priorities and occasional travel requirements for offsites or key events.
• Strong problem-solving abilities and a "no task is too small" attitude combined with a "big picture" strategic perspective.

• Competitive salary package reflective of high-level executive support experience.
• Comprehensive health, dental, and vision insurance plans.
• Fully remote work environment offering flexibility and a focus on work-life integration.
• Professional development opportunities and the chance to work closely with visionary leadership.
• Generous paid time off and holiday schedule.
• A dynamic, inclusive company culture that values innovation, transparency, and personal growth.

Required Skills