Executive Assistant

Siro; United States; On-site; USD 65,000 - 90,000; Full time

Job summary

Iro is seeking an Executive Assistant to reclaim the CRO and CEO’s time and to extend their reach with judgment and taste. You will own calendars, triage communications, and manage travel, ensuring decisions and critical tasks are executed with precision.

Ideal candidates have 5+ years supporting senior executives in fast-moving, travel-heavy environments, with exceptional EQ and strong judgment. You will work in NYC and be trusted with high-level access and responsibilities.

Qualifications

• 5+ years supporting senior executives in fast-moving environments.
• Startup/travel-heavy experience preferred.
• Exceptional EQ and attention to detail.
• Fluent with AI tools and room-reading ability.

Responsibilities

• Own calendars end-to-end for the CEO & CRO; resolve conflicts proactively.
• Triage emails and Slack to 24-hour response; inbound management.
• Plan and optimize travel including flights, hotels, itineraries, and prep notes.
• Attend CRO-hosted meetings and drive accountability.
• Monitor and report on time allocation and ROI for executive time.

Skills

Executive support

Calendar management

Travel planning

Stakeholder mgmt

AI tools

Inbox triage

Tools

Ashby

Job description

• Iro is scaling fast, and the two people with the most leverage over that — our CEO and CRO — are losing hours every week to work that doesn’t need them. We’re hiring an Executive Assistant to take that work back, and then go further: to run the office of the CEO & CRO with enough taste and judgment to close decisions, not just execute them
• Calendar ownership: Own calendars end to end for the CRO (primary) and CEO. Resolve conflicts proactively, protect thinking time, and make sure the week that happens is the week we agreed on Monday
• Inbound triage: Own email and Slack so nothing sits past 24 hours and nothing gets dropped
• Travel and the road: Maximize the value of every trip. Flights, hotels, itineraries, dinners, and prep notes, including canvassing the sales team for who has deals in a given city so each trip earns its cost
• Executive follow-through: Ensure the small but important things get done. Gifts, notes, key dates, and commitments made in passing
• Time ROI: Run a monthly read on where the hours actually went versus where we said they’d go, and make the case for where they should go next. We run the CRO’s time the way we run pipeline
• Meeting accountability: Sit in the meetings the CRO hosts, including GTM Leadership and Big Deal Review, and drive accountability into and out of them
• Decision ownership, over time: Close decisions independently. Which inbound request actually warrants executive attention, what the right venue is depending on audience and context, and which thoughtful gesture should simply be executed because you know our execs would approve
• What Success Looks Like:
• Month 1 — Execution is clean. Zero dropped commitments, nothing inbound past 24 hours
• Month 3+ — You’re making calls without checking first. Success is measured by how many decisions you close, not how many hours you saved. You’re an extension of the office of the CEO & CRO, carrying and amplifying the culture rather than just the calendar
• You’ll be an extension of two operators, not a scheduling layer. Full transparency across systems, a standing Monday planning session, and a constant working relationship in between. You’ll know what’s happening before most of the company does
• The scope grows as fast as your judgment does. This role is deliberately designed to expand from execution into decision-making. We’re hiring for the ceiling, not the floor
• A front-row seat to how a Series B scales. GTM leadership, big deal reviews, board prep, customer dinners on the road. You’ll see the whole machine
• Human judgment is the point. AI can book a flight. It can’t tell you which dinner matters, which rep just closed their first deal and deserves a note, or which meeting the CRO should have walked out of
• A mission worth the hours. Most field sellers in the U.S. get almost no on-the-job coaching. We’re changing that, for an industry the tech world has spent decades ignoring

5+ years supporting senior executives, ideally in a startup environment, where things are exceptionally fast-moving and travel-heavyComfortable operating with full access and the trust that comes with it: calendar, email, credit cards, Ashby, LinkedInExceptional EQ paired with obsessive attention to detail. That pairing is the jobFluent with AI tools, or genuinely hungry to beStrong taste and judgment. You can read a room, an inbox, and a guest listNYC-based and in office. You’ll sit next to the CROReal pride in the craft. The best people in this role don’t treat it as a stepping stone, they treat it as ownership