Introduction

Thoughtful AI is a trailblazing Series A startup on a mission to redefine the B2B landscape through AI solutions. With a culture that fosters innovation and excellence, we're making waves in the massive healthcare industry, continuously pushing the envelope of what's possible. We're seeking a world-class Executive Assistant, a tenacious individual who mirrors our CEO’s pursuit of elite standards and relentless drive.

His ecosystem thrives on resilience, ambition, and the ceaseless pursuit of improvement. If you are passionate about making an impact and excel in high-intensity, high-reward environments, Thoughtful AI could be your next arena.

Your Role

We're looking for an operationally excellent Executive Assistant / Personal Assistant to support the CEO with day-to-day administrative, personal, and operational needs while also contributing to projects that help drive the company’s strategic priorities. The ideal candidate for this position is highly organized, a self-starter, an excellent writer, exercise good judgment in complex situations, and is committed to advancing the organization's mission through the CEO's support. So, if you like hard problems, are extremely detail-oriented, and are an amazing teammate, we want to hear from you!

Executive Assistant Responsibilities

Provide proactive calendar support and make recommendations with regard to prioritization, delegation, and organization.
Contribute to team meetings and offsites by assisting with the production of materials and pre-reads, taking notes, and tracking action items.
Partner with the CEO to track key project milestones as well as progress against team and company goals/targets.
Establish new—and improve existing—administrative systems and processes.
Assist with ad hoc projects, events, and travel arrangements as needed.

Personal Assistant Responsibilities

Provide personal assistance to the CEO, including booking appointments, personal travel, and performing other miscellaneous projects and tasks.
Experience with complex international travel schedules, including research and recommendations for local activities and dining options.
Stays up-to-date with industry trends, including restaurant openings, art exhibits, and concerts, and has the ability to manage hard-to-get reservations.
Vendor procurement for services such as handymen, cleaners, etc.
Research and execution of research-heavy projects (e.g., investment properties, dual passport, etc.).
Organized processes and systems in place to present research and findings.
Responsive on nights and weekends and joins CEO and wife on trips when assistance is needed.

We’re looking for someone who has

You are incredibly organized, with superb attention to detail and a strong ability to execute.
You are excellent with time management and can quickly shift tasks and priorities.
You have a knack for working across various roles and teams in a fast-paced, changing environment while remaining flexible, proactive, resourceful, and efficient.
You communicate, perform, and react well under pressure or ambiguity.
You enjoy optimizing processes to make them more efficient.
You are adept at handling sensitive information and situations with care and confidence.
You are able to anticipate and respond to the needs of others before they arise.
You have experience in a high-growth technology startup.
An interest in RCM or AI and a technical mindset to keep up-to-speed in topics surrounding automation, RPA, OCR, NLP, and LLMs is helpful.

Your Qualifications

A proven record of 5-7 years supporting C-suite executives in a high-growth, fast-paced environment.
Exceptional verbal and written communication skills, exhibiting both professionalism and approachability.
A growth-oriented mentality and adaptability to rapidly change tasks and priorities as situations demand (a common occurrence in our fast-paced startup environment).
Familiarity with a variety of computer software applications, including word processing, spreadsheets, databases, and presentation/visual software (e.g., Notion, Slack, G-Suite, etc.)
Ability to manage time well, organize, and prioritize workload. Flexible, adapting to change quickly and easily.
Ability to juggle multiple projects, identify primary and secondary objectives, prioritize time, and communicate a timeline to team members.
Communicates directly and on behalf of the CEO and executive team, with Board members, investors, partners, and others, on matters related to executive programmatic initiatives.
Ability and desire to take product/project ownership.
Ability to work a flexible schedule based on company needs.

Thoughtful AI Benefits

Employee Stock Options
Medical, dental, and vision insurance for you and your dependents
A comprehensive time-off policy
Paid company holidays

Executive Assistant to the CEO