Executive Assistant to the CPO, Thoughtful AI
$140-190k
+ Equity. Salary representative of California based roles
AI operating system for healthcare RCM teams
Open for applications
AI operating system for healthcare RCM teams
21-100 employees
Open for applications
$140-190k
+ Equity. Salary representative of California based roles
21-100 employees
Company mission
Tto fix the U.S. healthcare system.
Role
Who you are
- We’re looking for a detail-oriented and highly organized Executive Assistant to support our Chief Product Officer (CPO)
- This is a role for someone who is highly responsive, has a strong sense of judgment, and takes pride in enabling leaders to operate at peak efficiency
- You have 5+ years of experience supporting senior executives in fast-paced, high-growth environments
- You’re a highly organized and responsive calendar and logistics pro
- You take ownership of your work, anticipate needs, and solve problems before they arise
- You communicate with clarity, calmness, and professionalism—both written and verbal
- You bring a high degree of judgment and discretion to sensitive workstreams
- You’re energized by helping leaders stay focused and effective
- You work well independently, but collaborate with empathy and curiosity
- Experience supporting multiple stakeholders simultaneously is a plus
- Experience in healthcare or tech/startups is a plus
What the job involves
- This is a critical support role for an EA who thrives in dynamic environments and can seamlessly manage the complexity of a senior executive’s calendar, email, meetings, task management, team logistics, and travel
- In addition to supporting the CPO directly, this role will also provide light calendaring and logistics support to the CPO’s direct reports as needed
- This role will also require taking on special projects to support the CPO and his team
- Own and manage all aspects of the CPO’s calendar—ensuring meetings are strategically scheduled and time is aligned with top priorities
- Proactively manage and coordinate meetings, events, and internal touchpoints with CPO’s direct reports and other key stakeholders
- Provide scheduling and logistical support (meetings, travel, briefings) to CPO’s department leads as needed—high-leverage assistance that helps the whole org run more smoothly
- Coordinate complex travel planning and itineraries across time zones
- Prepare and organize materials for key meetings (e.g., agendas, briefing docs, notes)
- Monitor the CPO's inbox, identifying areas that need action and supporting the CPO by proactively using discretion to handle action items, clearly communicating what's been completed and what still needs attention, then blocking his time to ensure nothing gets missed
- Maintain discretion and handle confidential information with care and professionalism
- Serve as a dependable liaison between the CPO’s office and internal teams
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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