Executive Assistant to CEO

Executive Assistant to the CEO

Full-time Hybrid - Boston + remote.

Reports to:

Dave Balter, CEO.

for enterprise AI deployments, the semantic layer enterprise AI has been missing.

We're in an active, fast-moving moment: acquisition conversations, new product architecture, a lean leadership team moving fast. This role keeps the center of that operation running.

Dave moves fast. This role exists to make sure nothing slows him down.

That means work and life, together - not as separate tracks to be managed, but as one continuous thing that needs to run smoothly. A board meeting lands the same week as a family trip. A vendor needs a decision on the same morning as a deal call. The person in this role doesn't ask which matters more, they handle both and Dave never has to think about it.

You're not a scheduler. You're a blocker-remover. The job is to stay one step ahead, anticipate what's coming, and clear the path before it's needed.

• A daily morning briefing that is more than a punchlist- warm, specific, actionable, and maybe occasionally funny.
• A calendar that runs clean: nothing double-booked, nothing without a Zoom link, travel time built in, confirmations sent.
• Travel research & logistics that just work: flight options, car is confirmed, the vendor knows what time, the boarding pass is ready, the Friday routine runs without a reminder.
• Deal, BOD and recruiting coordination: external partners scheduled correctly, candidate materials in every invite, nothing falling through the cracks during a busy stretch.
• Expense management across multiple entities - organized, timely, no surprises.
• Weekend awareness: if something needs Dave's attention before Monday, he hears about it.

Dave is CEO of Flipside/edisyl and a Venture Partner at True Ventures. There are active acquisition conversations, an enterprise sales buildout, and a board across two entities. The leadership team is small and moves fast.

This is a high-trust, high-access role. You'll be in the room - or close to it - on real deal activity, board prep, and company leadership. You'll also know the garage door code. Both are part of the job, and neither is more important than the other.

You're inheriting a well-documented setup and expected to make it your own.

• Responsive - an acknowledgment within minutes is the standard
• Obsessive about details
• Absolute discretion, always
• Owns mistakes fast and moves on
• Flags problems when they surface, not after they land

• Warm, natural communication style - can match the tone of a fast-moving, informal CEO
• Experience supporting someone whose work and life are genuinely intertwined
• Good judgment about when to act vs. when to ask
• Comfortable with ambiguity and rapid context-switching
• Proficient in Google Workspace, Slack

This role rewards people who find genuine satisfaction in making someone else's life run well - not as a stepping stone, but as the thing itself. The working relationship is warm, the expectations are high, and the pace is real. If that sounds like the right kind of challenge, we'd like to hear from you.

This is a remote first role with in-office time for key meetings and leadership offsites (mainly Boston-centric). East Coast preferred.