Executive Assistant

Field sales powers the economy — but most teams are struggling. Reps are buried in admin work, managers are stretched thin, and leaders can’t see what’s really happening in the field.

Siro is redefining how field sales teams learn, perform, and win.

We started as an AI-powered coaching platform that helped reps improve their outcomes in the field.

Today, we’re something much bigger — an intelligent companion that automates sales reps’ tedious admin work, gives managers real-time visibility, and helps executives see around corners.

Our platform integrates with systems like Salesforce, analyzing thousands of in-person sales conversations to surface insights, automate workflows, and drive better outcomes across the org. Think Iron Man’s Jarvis for sales — proactive, personalized, and built directly into the tools teams already use.

Siro has raised $75M and is backed by world-class investors like Index, Fika, CRV, and SignalFire. We are trusted by leading home-improvement, retail, hospitality, and automotive brands, and powered by a lean team from Meta, McKinsey, Doordash, and Uber.

We’re building the future of human-AI collaboration in sales — and we’re just getting started.

Most executive assistant roles are about protecting a calendar. This one is about deciding what belongs on it.

Siro 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.

We are seeking an Executive Assistant to

• 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.

Requirements

• 5+ years supporting senior executives, ideally in a startup environment, where things are exceptionally fast-moving and travel-heavy

• Exceptional EQ paired with obsessive attention to detail. That pairing is the job

• Strong taste and judgment. You can 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 be

• NYC-based and in office. You'll sit next to the CRO

• Real pride in the craft. The best people in this role don't treat it as a stepping stone, they treat it as ownership

Why join Siro as an Executive Assistant?

• 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.

• Room to grow. As the company scales, so can this role, toward Chief of Staff or executive business partner scope.

• 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.

At Siro, we are committed to creating a diverse and inclusive environment where all people feel that they are equally respected and valued, whether they are applying for an open position or working at the company. We provide equal employment opportunities to all applicants without regard to race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.