Executive Assistant to Founders

Executive Assistant to Founders

Obsidian Systems is a fully remote, global company with around 60 employees, and we’re scaling to 100+ over the next year. As we continue to grow rapidly, we are seeking a highly organized, proactive, and technically adept Executive Assistant to support our founders.

This is a high-impact, dynamic role for someone who excels in ambiguous situations, enjoys bringing order to fast-paced environments, and is adept at creating structure in complexity. You’ll act as a critical point of coordination for both high-priority internal and external relationships, requiring strong judgment, discretion, and the ability to balance competing priorities.

This opportunity is ideal for a seasoned Executive Assistant who thrives in growth-stage environments and is interested in emerging technologies such as blockchain.

Responsibilities

Executive Support

• Manage and prioritize communications with external stakeholders—including founders, investors, and board members—ensuring timely, professional, and context-aware engagement.

• Serve as a gatekeeper and facilitator for founders' time, using sound judgment to balance internal priorities with high-value external relationships.

• Oversee complex calendar and scheduling management across multiple time zones.

• Coordinate travel arrangements, expenses, and logistics.

• Support both business and select personal needs.

Founder & Project Support

• Drive execution of founder-led initiatives and serve as the primary contact for external stakeholders.

• Track project priorities, timelines, and deliverables.

• Coordinate efforts across internal and external teams.

• Prepare materials and conduct light research as needed to support projects.

Internal Meeting & Operations Support

• Organize and prepare leadership meetings, including creating agendas, documenting discussions, and following up on action items.

• Maintain leadership dashboards and scorecards, ensuring metrics are current, accurate, and visible to leadership.

• Track progress against company and team goals, providing regular updates aligned with leadership expectations.

• Ensure organization and consistency across shared drives, documentation, and reporting tools.

• Identify gaps in execution or visibility and proactively recommend improvements to workflows, tracking, and communication processes.

Qualifications

• 5+ years’ experience supporting C-level executives.

• Highly organized with excellent communication skills.

• Technically savvy and quick to learn new tools.

• Experience in a startup or high-growth environment preferred.

• Demonstrated judgment, discretion, and multitasking ability.

• Interest in blockchain or other emerging technologies is a plus.

• Bilingual in English and Spanish highly preferred.