Executive Assistant to CEO — Strategic, AI-Driven Support

Red Oak Compliance; Austin (TX); Hybrid; USD 95,000 - 135,000; Full time

Benefits offered by this job

Equity Appreciation Rights

Health coverage (medical, dental, vis

401(k) with 3% employer match

20 days PTO annually, plus birthday, +

Enhanced family leave

Life insurance

Job summary

Red Oak in Austin is hiring an Executive Assistant to the CEO to act as a force multiplier across calendaring, travel, board materials, and data analysis. You will drive cross-functional coordination, maintain executives-ready reporting, and extend AI-powered workflows to accelerate insights while preserving discretion.

Based at Red Oak's Austin HQ, this hybrid role requires sharp judgment, autonomous execution, and a track record of supporting senior leaders in fast-paced environments.

Qualifications

• 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 (HubSpot, Salesforce, Monday, Gong) and the aptitude to learn financial systems quickly.
• AI fluency in daily workflow: hands-on use of generative AI (Claude preferred) for drafting, analysis, and workflow automation.
• 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.

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.
• 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.

Skills

Calendar management

Stakeholder coordination

Data analysis

Discretion

Written communication

Board materials

Organization

Tools

HubSpot

Salesforce

Monday

Gong

Claude AI

Job description

Red Oak in Austin is hiring an Executive Assistant to the CEO to act as a force multiplier across calendaring, travel, board materials, and data analysis. You will drive cross-functional coordination, maintain executives-ready reporting, and extend AI-powered workflows to accelerate insights while preserving discretion.

Based at Red Oak's Austin HQ, this hybrid role requires sharp judgment, autonomous execution, and a track record of supporting senior leaders in fast-paced environments.