Executive Assistant

About the role

Siro is an AI‑powered companion for field sales teams that automates admin work, surfaces insights from in‑person conversations, and gives leaders real‑time visibility. The Executive Assistant will own the calendars of the CRO (primary) and CEO, manage inbound communication, optimize travel, ensure follow‑through on commitments, track time ROI, drive meeting accountability, and close decisions independently — acting as an extension of the office of the CEO & CRO rather than just a scheduling layer.

Responsibilities

• Own calendars end to end for the CRO and CEO: resolve conflicts proactively, protect thinking time, and ensure the week reflects Monday’s plan.
• Own email and Slack inbound triage: nothing sits past 24 hours and nothing gets dropped.
• Maximize the value of every trip: flights, hotels, itineraries, dinners, prep notes, and canvassing the sales team for local deals so each trip earns its cost.
• Executive follow‑through: ensure gifts, notes, key dates, and passing commitments are completed.
• Time ROI: run a monthly read on where hours actually went versus planned, and make the case for where they should go next.
• Meeting accountability: sit in the CRO’s hosted meetings (GTM Leadership, Big Deal Review) and drive accountability into and out of them.
• Decision ownership over time: independently decide which inbound requests warrant executive attention, the right venue, and which thoughtful gestures to execute because you know the execs would approve.
• Success metrics: Month 1 – execution is clean with zero dropped commitments and no inbound older than 24 hours. Month 3+ – success measured by how many decisions you close, not hours saved; you become an extension of the office of the CEO & CRO, carrying and amplifying the culture.

Requirements

• 5+ years supporting senior executives, ideally in a startup environment that is fast‑moving and travel‑heavy.
• Exceptional EQ paired with obsessive attention to detail.
• Strong taste and judgment: ability to read a room, an inbox, and a guest list.
• Comfortable operating with full access and the trust that comes with it (calendar, email, credit cards, Ashby, LinkedIn).
• Fluent with AI tools, or genuinely hungry to become fluent.
• NYC‑based and able to work in the office.
• Real pride in the craft — viewing the role as ownership, not a stepping stone.

Benefits

• Be an extension of two operators, not just a scheduling layer.
• Full transparency across systems and a standing Monday planning session.
• Constant working relationship with the CEO and CRO; you’ll know what’s happening before most of the company.
• The scope grows as fast as your judgment does — role deliberately designed to expand from execution into decision‑making.
• Hiring for the ceiling, not the floor.
• Front‑row seat to how a Series B scales: GTM leadership, big deal reviews, board prep, customer dinners on the road.
• Human judgment is the point: AI can book a flight, but it can’t tell which dinner matters, which rep just closed their first deal and deserves a note, or which meeting the CRO should have walked out of.
• Mission worth the hours: changing the lack of on‑the‑job coaching for field sellers in an industry the tech world has ignored.