Executive Assistant to Founders

Obsidian Systems

1d•Remote

About The Position

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.

Requirements

5+ years’ experience supporting C-level executives.
Highly organized with excellent communication skills.
Technically savvy and quick to learn new tools.
Demonstrated judgment, discretion, and multitasking ability.

Nice To Haves

Experience in a startup or high-growth environment preferred.
Interest in blockchain or other emerging technologies is a plus.
Bilingual in English and Spanish highly preferred.

Responsibilities

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.
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.
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.