Executive Assistant to the COO and CoS Product

About Us

We are a fast-growing startup in the legal AI space, building cutting-edge solutions that are reshaping the litigation workflow. Our platform is being used by a range of customers in the legal industry, including some of the world’s largest law firms.

We are looking for an experienced and proactive Executive Assistant to support our Chief Legal Officer (CLO) and Chief of Staff of Engineering . This role is crucial to keeping our operations running smoothly and strategically as we scale.

About the Role

As the Executive Assistant to the CLO and Chief of Staff of Engineering, you’ll act as a trusted partner and right hand to both executives. You will manage daily workflows, communications, and priorities — often with limited input — and must be comfortable operating in ambiguity while driving clarity.

You’ll be expected to understand different aspects of Syllo’s business, work autonomously, and communicate confidently on behalf of both executives with internal and external partners.

We're looking for someone who is resourceful, hands-on, and highly self-motivated , who exercises excellent judgment, and who has the ambition to grow into a broader operational or leadership role in the future.

What You'll Do

• Provide high-level administrative and strategic support to the CLO and Chief of Staff of Engineering, including:

• Calendar and inbox management, including helping each executive prioritize and protect their time

• Meeting coordination, preparation, and follow-ups

• Internal and external communication handling

• Keep both executives organized by building and maintaining their task tracking in Monday.com or a similar task management system

• Maintain alignment across multiple internal projects and ensure key action items stay on track

• Operate with limited instruction — anticipate needs and take initiative

• Exercise sound judgment in prioritizing competing requests and deciding what needs executive attention

• Draft, review, and manage written communications, presentations, and reports

• Handle sensitive information with the highest level of discretion and professionalism

• Identify opportunities to optimize workflows and implement simple operational systems

What We're Looking For

• 5+ years of experience as an Executive Assistant supporting executives at the VP level or higher (startup or fast-paced tech environment preferred)
• Proven ability to operate autonomously and with minimal supervision
• Exceptional written and verbal communication skills
• Strong organizational, multitasking, and prioritization abilities
• Expert-level calendar management and a track record of helping executives manage their time
• Expertise keeping executives organized through a task management system (Monday.com preferred)
• Proactive, resourceful, and calm under pressure, with excellent judgment
• Tech-savvy and quickly adapt to new tools and platforms

Why Join Us?

• Join a growing AI company with a bold vision and strong impact
• Gain unique insight into strategic operations
• Have the freedom and autonomy to shape how the role evolves
• Clear potential to grow into higher-level roles in operations or leadership
• Fully remote culture, flexible work environment, and a collaborative team
• Competitive salary.
• Paid time off and holidays.

United States - Remote Pay Range

$90,000 — $120,000 USD