People Operations Specialist, Thoughtful AI
$130-170k
+ Employee stock grants & bonus
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
$130-170k
+ Employee stock grants & bonus
21-100 employees
Company mission
Tto fix the U.S. healthcare system.
Role
Who you are
- 2+ years of experience in HR, People Operations, or a related field
- Familiarity with tools like Gusto, Greenhouse, Notion, and Clerky preferred
- Detail-oriented and process-driven, with a strong sense of ownership
- Ability to navigate sensitive and confidential information with discretion
- A systems thinker who loves to improve and document processes
- Strong communication and project management skills
What the job involves
- We’re seeking a detail-oriented, systems-savvy People Operations Specialist to help us deliver a seamless and high-impact employee experience across the full lifecycle—from onboarding to offboarding and everything in between
- In this role, you’ll be the backbone of our People Operations function, supporting HR systems, benefits, payroll, compliance, and internal programs that keep our organization running smoothly
- Own and optimize the onboarding experience in Greenhouse, including automated communications and coordination with L&D and Workplace Experience
- Process and track I-9s, background checks, and laptop provisioning
- Manage offer letter and employment agreement workflows in Clerky, including equity and CIIA documentation
- Create and maintain legal employee folders and contractor documentation
- Serve as administrator for Gusto (payroll, benefits, time off), identifying and implementing process improvements
- Maintain accurate records in partnership with leadership
- Conduct regular audits and data cleanups across HR systems
- Administer payroll for employees and contractors in Gusto
- Support PTO and leave management, including FMLA, parental leave, and other types of absence
- Assist with benefits administration
- Support new hire orientation as needed
- Partner on Employee Handbook redesign and relaunch; build and maintain a Notion-based Employee Wiki
- Field and resolve ad hoc employee inquiries
- Support performance management cycles in partnership with leadership
- Support and/or manage employee relations cases, including performance issues, investigations, and terminations
- Support execution of company-wide events such as TKOs and team gatherings that drive engagement and alignment
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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