Join The Team

Thoughtful is a fast-moving, fast-growing tech company creating a new category in the digital automation space. Our mission is to enable all people to do the best work of their lives. To deliver on this mission, we've set out to enable companies of all sizes to build, trust, manage, and grow a thriving digital workforce (bots).

With a 21M (as in millions) seed raise, let’s just say our investors know we are up to something massive. We think that’s an understatement. Ready to join the rocket ship and prove us right?

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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. 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.

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.

Perks Include

Modern office in Chicago’s trendy Fulton Market

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