--- title: 'Executive Assistant at Siro' canonical: 'https://feeny.ai/job/executive-assistant-siro-new-york-skv4jh60qdb6' type: 'job' last_seen: '2026-09-18' --- # Executive Assistant at Siro - **Company:** Siro - **Location:** New York, NY - **Compensation:** $135k–$145k - **Employment:** full-time - **Work type:** hybrid - **Posted:** 2026-09-15 - **Last confirmed live:** 2026-09-18 - **Apply:** https://jobs.ashbyhq.com/siro/d667ed4e-d37c-4e77-9903-43a1ef7ceacf ## Job description 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 own - 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. - 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. ## About Siro ## Company Overview - **One-liner**: Siro builds an AI-powered platform that records, transcribes, and analyzes in-person sales conversations to provide coaching, automate admin work, and surface strategic insights for field sales teams. - **Entity Type**: Private (Series B) - **Headquarters**: New York, New York, United States - **Founded**: 2020 - **Founders**: Jake Cronin ## Core Business - **Industry**: Sales Intelligence / AI-powered Conversation Intelligence - **Target Customers**: B2B – field sales teams in home improvement, retail, distribution, hospitality, and automotive sectors - **Mission**: “To make in-person sales the most empowered, data-driven, and coachable aspect of any business” and “rewire the trillion-dollar world of in-person sales by turning every customer conversation into winning insights.” ## Products & Services - **Siro Platform**: An intelligent sales companion (often described as “Iron Man’s Jarvis for sales”) that captures and analyzes in-person conversations via mobile/audio, integrates deeply with Salesforce, automates CRM workflows, and provides real-time coaching, performance dashboards, and trend analysis. Type: AI SaaS with mobile and web applications. ## Market Standing - **Total Funding**: $75M (according to the company’s about page) or $68M (per LinkedIn funding history – conflicting reports) - **Key Metric**: $50M Series B led by SignalFire (June 2025) - **Notable Investors**: Index Ventures, CRV, SignalFire, Fika Ventures, 01A, Stepstone - **Growth Signals**: - Headcount grew 107.5% YoY (86 employees as of mid-2026) - Trusted by ServiceTitan’s Field Pro and leading home-improvement, retail, and automotive brands - Expanding into new verticals (automotive, hospitality) with dedicated GMs (e.g., Grant Shisler – GM Automotive) ## Competitive Advantages - **In-Person Focus**: Unlike most conversation intelligence tools that only capture virtual meetings, Siro solves for the large, untapped market of in-person field sales conversations. - **AI Infrastructure for Unstructured Data**: Builds proprietary pipelines to decode industry-specific conversation data that is not recorded anywhere else. - **Deep Integrations**: Seamless connection with Salesforce and other enterprise tools to automate workflows and provide actionable insights in real time. - **Lean, Experienced Team**: Core team includes alumni from Meta, McKinsey, Doordash, and Uber, enabling fast execution. ## Strategic Focus - **Product Vision**: Evolve from a coaching platform into an “intelligent companion” that automates reps’ admin work, gives managers real-time visibility, and helps executives anticipate trends. - **Vertical Expansion**: Targeting new industries beyond home improvement, such as automotive and hospitality, with dedicated product and go-to-market teams. - **Engineering Investment**: Hiring heavily in backend, full-stack, mobile, and AI/ML roles to scale the platform. ## Why Work Here - **Hybrid Policy**: Employees work from the NYC Flatiron office three days a week (Tuesday–Thursday), with WFH on Mondays and Fridays. - **Benefits**: 100% medical coverage, 75% dental and vision, 401k, unlimited PTO (genuinely encouraged), paid parental leave, gym/wellness stipend, paid lunch on in-office days, and memberships covered. - **Culture**: Described as fast-paced, impact-driven, collaborative (“We before Me”), with a focus on ownership and raising the bar. Egos are discouraged; the best ideas come from anywhere. - **Compensation**: Real equity (meaningful stake) and competitive pay. - **Rating**: 4.6/5 on Built In (27 reviews) – Culture 4.8, Compensation 4.5, Career 4.5. - **Tech Stack**: TypeScript, Node.js, React, React Native, Swift, Redux, BigQuery, Google Cloud, Natural Language Processing. ## Sources 1. [siro.ai](https://www.siro.ai/careers) 2. [siro.ai](https://www.siro.ai/about) 3. [linkedin.com](https://www.linkedin.com/company/siro-ai) 4. [builtin.com](https://builtin.com/company/siro) 5. [pitchbook.com](https://pitchbook.com/profiles/company/467099-38) ## Other roles at Siro - [Customer Success Manager](https://feeny.ai/job/customer-success-manager-siro-new-york-353mhzvkykg2) — New York, NY - [Senior Manager, Demand Generation Marketing](https://feeny.ai/job/senior-manager-demand-generation-marketing-siro-new-york-4164906bbyqs) — New York, NY - [Staff Product Designer](https://feeny.ai/job/staff-product-designer-siro-new-york-f90x26611r2q) — New York, NY - [Director, Product Design](https://feeny.ai/job/director-product-design-siro-new-york-n29p5dyv25b7) — New York, NY - [Staff Product Manager](https://feeny.ai/job/staff-product-manager-siro-new-york-n3pereqfhj22) — New York, NY - [VP of Marketing](https://feeny.ai/job/vp-of-marketing-siro-new-york-3q2t4z6xfx3a) — New York, NY - [Senior Manager/Director Product Marketing](https://feeny.ai/job/senior-manager-director-product-marketing-siro-new-york-83jmv15a015x) — New York, NY - [Senior Product Manager](https://feeny.ai/job/senior-product-manager-siro-new-york-5mc6zp6p3mdp) — New York, NY - [Commercial Counsel (in-house)](https://feeny.ai/job/commercial-counsel-in-house-siro-new-york-fkxg9hkcsqm6) — New York, NY - [Senior Mobile Engineer](https://feeny.ai/job/senior-mobile-engineer-siro-new-york-v81yeaytwm3w) — New York, NY