Executive Assistant

About Red Oak Red Oak is the purpose-built compliance and distribution platform trusted by the biggest names in financial services. More than half of the top 20 global asset managers are Red Oak clients — including BlackRock, Vanguard, PIMCO, and Morgan Stanley. Over 15 years we've grown into the sole-source integrated compliance platform in our space, scaling to roughly $45M in ARR at about 60% year-over-year growth. We've earned a spot on the Inc. 5000 seven years running and the RegTech100 six years in a row. Why This Role Matters Red Oak's CEO operates in a demanding, high-velocity environment — extensive travel, multi-time-zone coordination, client engagement, and cross-functional leadership across a roughly 200-person organization. This role exists to protect and multiply that time: ensuring commitments are tracked and executed, board-ready materials land on schedule, and the metrics and action items that surface in meetings get the follow-through they need. The Executive Assistant is an extension of the CEO's presence and voice, driving continuity and accountability across the business. It's a highly autonomous seat that rewards judgment, initiative, and discretion — and it's a proven launchpad: the person previously in this role was promoted into a Business Operations position. High autonomy. High trust. A real path forward. What Success Looks Like The CEO's time is demonstrably maximized — less spent on logistics, calendar conflicts, and follow-up tracking, more on strategy, clients, and decisions. 95%+ of tracked action items and commitments closed by their due date, with zero commitments dropped. Data and metrics requested in meetings are investigated, validated at the source system, and delivered within 24–48 business hours. Board and executive materials arrive on schedule and review-ready, with minimal rework required from the CEO or Finance. Travel, events, and scheduling run seamlessly; last-minute changes are absorbed proactively and the calendar reflects protected, strategic time. The Role You'll be the force multiplier behind the CEO — operating across Red Oak's full technology stack, moving fluidly between calendar, logistics, board materials, and data investigation, and exercising independent judgment across competing priorities. This is execution at a high bar, with the trust and autonomy to match. Responsibilities Manage the CEO's complex calendar across multiple time zones — scheduling, conflict resolution, meeting prep, and proactive coordination with internal and external stakeholders Coordinate all travel logistics from Austin — flights, accommodations, ground transportation, itineraries, and real-time adjustments as business needs shift Plan and execute team events, client dinners, and other business events with seamless logistics aligned to Red Oak's brand and client experience Track, follow up on, and close meeting action items and commitments made by the CEO, driving accountability across departments Prepare and maintain board-level and executive materials — including board deck assembly, data gathering, and iteration with the CEO and Finance — and coordinate board meeting logistics and correspondence with the executive team Investigate metrics, statistics, and data that surface in meetings using Red Oak's core systems — Monday, HubSpot, Salesforce, Gong, and Rillet — and provide supporting analysis and drill-downs Conduct financial analysis and compile data reports to support the CEO's strategic initiatives and leadership discussions Operate and extend AI tools daily — Claude is Red Oak's primary AI platform — to automate recurring reporting, surface insights, flag calendar and action-item trends, and accelerate access to data. You'll build and maintain lightweight AI-assisted workflows, not duplicate them by hand Represent the CEO's voice and authority in meetings when the CEO is unavailable, conveying decisions and follow-ups with discretion and clarity Provide personal administrative support to the CEO as needed — including personal scheduling, travel, and errands — handled with the same discretion and reliability as business tasks What You'll Bring 3+ years supporting C-level executives, ideally in high-growth SaaS or private-equity-backed environments Financial and data literacy — able to produce accurate analyses and board-ready materials with minimal supervision Working fluency with CRM and operations systems (e.g., HubSpot, Salesforce, Monday, Gong) and the aptitude to learn financial systems quickly AI fluency in your daily workflow: hands-on use of generative AI (Claude preferred) for drafting, analysis, and workflow automation. This is table stakes here, and you'll be screened on practical proficiency Impeccable discretion and a track record of handling confidential, market-sensitive information Exceptional organization and written communication; comfortable representing the CEO to internal and external stakeholders Preferred: experience assembling board materials or supporting a founder/CEO through a high-growth phase Benefits Equity Appreciation Rights — share in what we're building Comprehensive health coverage: medical, dental, and vision 401(k) with 3% employer match 20 days PTO annually, plus your birthday off and paid sick leave Enhanced family leave Life insurance How We Work We move fast, we own our outcomes, and we don't hide behind process. You'll have real autonomy and the trust that comes with it — and you'll be expected to use both. Direct communication, high standards, and discretion are the baseline. Work Structure Based at Red Oak's Austin HQ, hybrid with Tuesday–Thursday in-office. Reports directly to the CEO.