Join The Team

Thoughtful is revolutionizing digital automation. Our mission is to accelerate the world's adoption of Automation and AI so humans can solve our most complex, existential problems. With $20M in venture capital raised, join our rocket ship and participate in something massive!

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Who We Are Looking For

We’re looking for people who are ready to stretch beyond their comfort zones, who take educated risks, have high emotional intelligence, and embody our brand — Thoughtful AI. Do you align with our values below?

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.

Be in the arena

We step into the arena, ready to face challenges head-on, knowing that true growth comes from being actively engaged, not from the sidelines. We embrace the effort and resilience required to drive meaningful progress, believing that greatness is achieved by being fully present in our mission.

Do the work

We believe in the power of hard work and dedication, showing up every day with the commitment to achieve our goals. Success is earned through persistence and a relentless focus on excellence, valuing action over words and results over excuses.

Disagree and commit

We foster an environment where diverse opinions are encouraged, believing the best ideas often come from healthy debate. Once a decision is made, we commit fully to its execution, aligning as a team to maintain unity and focus.

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.

Lead with integrity

We hold ourselves to the highest standards of honesty and ethical behavior, leading by example with transparency, fairness, and accountability. Our integrity is the foundation of our relationships, and we believe long-term success is built on doing the right thing, even when it’s difficult.

Perks Include

Modern offices in Austin, Miami, & Chicago

Monthly cultural events
(Past events include Justin Bieber and Rufus du Sol concerts)

Creating something EPIC in the world

Early employee equity

Getting your hands dirty at the ground level

Thoughtful AI Accelerate 2023

Our bi-annual 2-day all-hands event where team members get together to discuss goals, strategy, and have a little fun!


Warrior Culture at Thoughtful AI

We’re a warrior culture that promotes a competitive spirit, a relentless pursuit of success, and a willingness to face challenges head-on. Encouraging individuals and teams to adopt a proactive and passionate approach to achieving goals.