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Siro is an AI-powered field sales platform that automates admin work, provides real-time visibility to managers, and helps executives make better decisions. The company has raised $75M from top-tier investors and serves leading brands in home improvement, retail, hospitality, and automotive. The team includes veterans from Meta, McKinsey, Doordash, and Uber.
This Executive Assistant role is not a traditional calendar-management position. Instead, you will be a strategic operator for the CEO and CRO (primary focus), handling high-leverage work that directly impacts company scaling. You will own end-to-end calendar management for both executives, proactively resolving conflicts and protecting thinking time. You will manage inbound email and Slack triage, ensuring nothing sits past 24 hours. You will coordinate all travel logistics—flights, hotels, itineraries, dinners, and prep notes—while maximizing the value of each trip by identifying relevant customer and deal opportunities in each city.
Beyond execution, you will drive executive follow-through on commitments, gifts, notes, and key dates. You will run monthly analyses of time allocation versus planned priorities, treating the CRO's calendar like a pipeline. You will sit in key meetings (GTM Leadership, Big Deal Review) and drive accountability. Over time, you will evolve into a decision-maker, independently determining which inbound requests warrant executive attention, selecting the right venue for different audiences, and executing thoughtful gestures without approval.
Success in Month 1 means clean execution with zero dropped commitments. By Month 3+, you will be making independent calls and closing decisions, measured by decisions closed rather than hours saved. You will become an extension of the office of the CEO & CRO, amplifying culture and strategy.
Requirements:
- 5+ years supporting senior executives, ideally in a fast-moving startup environment with heavy travel
- Exceptional emotional intelligence paired with obsessive attention to detail
- Strong taste and judgment; ability to read rooms, inboxes, and guest lists
- Comfortable with full access and trust (calendar, email, credit cards, systems, LinkedIn)
- Fluent with AI tools or genuinely eager to learn them
- NYC-based and in-office; you will sit next to the CRO
- Real pride in the craft; view this as ownership, not a stepping stone
