Executive Assistant to the CEO, Thoughtful AI
$140-190k
+ Equity. California salary range shown, other locations may vary
AI operating system for healthcare RCM teams
Be an early applicant
AI operating system for healthcare RCM teams
21-100 employees
Be an early applicant
$140-190k
+ Equity. California salary range shown, other locations may vary
21-100 employees
Company mission
Tto fix the U.S. healthcare system.
Role
Who you are
- You have 5+ years of experience supporting C-level executives in high-growth or fast-paced environments
- You are an exceptional communicator - clear, concise, and thoughtful in every format
- You are a radical owner of all your work taking pride and accountability to ensure all work is top tier
- You’re a scheduling and logistics wizard. Nothing falls through the cracks on your watch
- You operate with a high degree of professionalism, discretion, and integrity
- You are obsessively organized and systems-oriented, always thinking about how to improve processes and anticipate needs
- You are a proactive problem solver. You don’t wait to be told what to do—you see what needs to be done and go do it
- You’re energized by being behind the scenes, enabling others to be their best and most effective
- Willingness to travel occasionally to support CEO during high profile trips
- You’re comfortable working remotely, but thrive in high-collaboration environments
- Experience in healthcare or tech/startups a plus
- Experience managing a personal assistant a plus
What the job involves
- We’re looking for a high-caliber, trusted Executive Assistant to support our CEO
- This is a critical, dynamic role for a proactive, organized, and resourceful professional who thrives in fast-paced environments and takes ownership end-to-end
- You’ll be the right hand to two of our most senior leaders—responsible for optimizing their schedules, keeping them focused on their most important priorities, and helping Thoughtful run smoothly at the highest levels
- This is not your average EA role. It’s for someone who sees three steps ahead, thrives on solving for ambiguity, and brings precision, poise, and discretion to every interaction
- Own all aspects of calendaring and scheduling for the CEO - anticipating conflicts, managing shifting priorities, and ensuring they are always where they need to be. Being context aware is key!
- Serve as a gatekeeper and force multiplier—protecting executive time and helping prioritize what matters most
- Coordinate internal and external meetings, including board meetings, investor calls, and key cross-functional syncs
- Provide light personal support for the CEO (e.g., travel logistics, occasional errands, gifting, etc.)
- Partner with our Office Manager in Austin on occasional in-office coordination (though this is not an office management role)
- Ensure smooth travel planning and itinerary management across multiple time zones
- Prepare briefing materials, notes, and follow-ups for key meetings
- Handle confidential information with discretion and judgment
- Support hiring and managing personal assistant who will support CEO with personal and family related work
Our take
Staffing is one of the most expensive contributors to business operation expenses, leading OpEx teams to minimize workforce sizes to cut costs. However, this often results in unfilled roles leading to larger workloads for employees, a sacrifice that can lead to lower-quality work and expensive errors.
Thoughtful develops bespoke back office automation bots, allowing businesses to hire bots that are specifically designed to automate their tasks and workflows. After onboarding, the company monitors and provides reports on the performance of each bot, allowing clients to see the value of each bot and whether adjustments are needed.
Whilst back office automation tools are nothing new, these generally work as integrations within other platforms, whereas Thoughtul’s bots are uniquely designed to emulate a position that would otherwise be staffed by a human. The company claims that its bots can help OpEx teams minimize staffing costs and optimize workflows whilst preventing any risk associated with cost cutting.
Freddie
Company Specialist at Welcome to the Jungle
Insights
12% employee growth in 12 months
Company
Funding (last 2 of 4 rounds)
Jul 2024
$20m
SERIES A
Mar 2022
$10m
SEED
Total funding: $35.9m
Company benefits
- Robust Medical/Dental/Vision plans with Employer supported premiums
- Quarterly Company get-togethers
- Gym/Health Perks
- Early employee equity
- Getting your hands dirty at the ground level
- PTO (Sabbatical after 4 years)
Company values
- Experiment always - Don’t let the fear of failure hold you back from doing incredible, original work. We don’t expect perfection on the first swing, just the willingness to keep going until we get it right. It takes grit, a lot of experimentation, and failing fast to optimize learnings
- Do less, deliver more - We focus on doing the right things, not all things. Focus on work that creates an outsized impact for our customers and team. We practice ruthless prioritization and intentionally make trade-offs that best serve our customers and mission
- We are givers - We put our customers and our team ahead of our personal ambitions. We intentionally give without condition in the spirit of advancing our mission. We won’t succeed with a “gimme” culture, but we will win as a team of endless baton-passers who support each other until the race is won
- Be ALL in - We make outsized bets to earn outsized returns for our customers, fellow colleagues, investors and stakeholders. If something critical is broken, we work relentlessly to not only fix it but solve the core issue using first-principles thinking. We obsess everyday to advance the mission and plan on building a durable, resilient 100+ year old company
- Expect to WIN - Winning is the outcome of compounding wins every moment, day, month and year. We are disciplined executors that strive to achieve mastery in everything we do. We win with grace and help elevate everyone around us. We are market makers and leaders
Company HQ
Congress Avenue Historic District, Austin, TX
Articles
Leadership
Alex Zekoff
(CEO)Co-founder and CEO of Like Wallet from 2017 to 2018. Experience as Lead Process Automation Engineer for Deloitte Consulting.
Dan Parsons
(CPO)Experience as CEO of ORA Interactive. Co-founder and CEO of DRYV from 2014 to 2018.
Salary benchmarks
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