Chief of Staff, Office Founder

About the Role

Alert Venture Foundry is building the next generation of technology companies. Our founder and CEO leads multiple ventures spanning AI, advanced technology, and strategic investments, while also maintaining deep commitments to philanthropy, community engagement, and cultural leadership.

This role is his operational counterpart. You'll work directly with the CEO to drive execution across his full portfolio of work, from venture strategy to daily operations. The goal is straightforward: free up his highest-value time by owning everything that doesn't require him personally.

This is not an administrative support role. It's a thinking role. You'll need the judgment to act on incomplete information, the initiative to solve problems before they're assigned, and the technical fluency to use AI and digital tools as force multipliers across everything you touch.

• You’ll operate across multiple ventures and domains, not a single business unit. Every week looks different.
• AI fluency is a core requirement, not a nice-to-have. We expect you to use AI tools to research, draft, analyze, and automate. We’ll evaluate how you think with these tools, not just whether you use them.
• You’ll have real decision‑making authority. The CEO delegates to people he trusts, and this role is built to earn that trust fast.
• You’ll be exposed to venture building, philanthropy, and strategic operations at a level most roles don’t offer until much later in a career.

• Manage the CEO’s calendar across professional and personal commitments. Prioritize, protect, and prepare him for what’s ahead.
• Represent the CEO in written and verbal communications with investors, partners, vendors, and community stakeholders.
• Run daily check‑ins to review priorities, surface blockers, and align on what matters most.
• Conduct research and provide decision support so the CEO can move faster on high‑priority initiatives.
• Track commitments, follow‑ups, and open loops across all ventures and personal projects using shared task management tools.
• Proactively influence the CEO’s agenda by anticipating what’s coming, flagging what’s missing, and introducing ideas, people, or information that sharpen his thinking and expand what’s possible.

• Coordinate across Alert Venture Foundry’s portfolio companies, supporting the CEO’s involvement and tracking key milestones.
• Prepare briefing materials, presentations, and correspondence for partner engagements and meetings.

• Manage household logistics, vendor coordination, and property oversight for the CEO’s Cape Ann residence and a rental property near Boston.
• Handle bill pay, purchasing decisions, and day‑to‑day administrative needs across professional and personal domains.
• Plan and coordinate personal events, including large gatherings, out‑of‑town guests, and family engagements.

• Use AI tools daily to accelerate research, draft communications, organize information, and automate repetitive workflows.
• Evaluate and recommend new tools and applications. Learn them quickly and bring the CEO up to speed.
• Build and maintain shared systems (task management, document organization, communication protocols) that keep both of you operating efficiently.

• Prior experience supporting a CEO, founder, or senior executive directly. You understand the pace, the context‑switching, and the trust required. You’ve done this before and you were good at it.
• 2+ years in an operational, chief of staff, or senior EA role in a fast‑moving environment (startups, venture, consulting, or similar). Corporate‑only backgrounds are less likely to be a fit.
• Demonstrated AI proficiency. You’re already using AI tools regularly, not just for email drafts. You’ve built workflows, tested tools against each other, or used AI to solve problems others wouldn’t think to hand to a machine. We will ask you to show us.
• Strong digital fluency. You’re proficient across Microsoft Office, Mac/iOS, video and presentation tools, and you pick up new software quickly. Technology should feel like a natural extension of how you…