Senior Product Designer

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Our mission is to enable all people to do the best work of their lives. In order 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)—this frees up humans to do their most creative and engaging work. At Thoughtful Automation, we're building a new way to help customers automate their most mundane and robust processes. Unlike typical RPA, we develop software robots in the cloud and enable customers to manage and collaborate with their new software colleagues. While all of our bots are designed for specific use cases, the platform that you will be designing will empower customers to engage, interact with, train, and report on their digital workforce in a nuanced and collaborative experience.



  • Will be a leading voice in defining our product — addressing difficult challenges with bold, holistic design solutions that will make our customers love working with their evergrowing digital workforce.
  • You'll lead your own design projects from brief, research, and concept exploration through prototyping, visual design details, motion design, and stewardship through development.
  • You will organize and conduct user research and test prototypes to understand people's needs and emotions and the resonance of our product—synthesizing the results to inspire comfort and trust with our digital workers.
  • Work with engineers and product managers to define both the long-term strategy and the short-term tactics for our products.
  • Sometimes work on very broadly defined, loose concepts, and sometimes on narrowly defined, tactical deliverables.
  • Work in a highly collaborative fashion with product and project teams.
  • Participate in design reviews and share your work regularly with company leadership.


You may be fit for this role if you:

  • Can reduce complex problems down to the right balance of flexibility, power, and ease of use
  • Have experience designing for business and developer-focused products
  • Keep pushing your work until all details are attended to
  • Are skilled in explaining your work, process, and decisions to cross-functional stakeholders and crave feedback to help you produce your best work
  • Are an expert in either UI, UX, or visual design, but skilled in more disciplines across product design
  • You care about details and are excited to keep pushing your work until is pixel-perfect
  • Think in systems and are able to extrapolate and extend shared patterns and behaviors
  • Are uncompromisingly service-minded towards our users and your colleagues, but able to set and achieve priorities that find the perfect balance between benefiting the project, the Design team, and all of Thoughtful Automation
  • Have 5+ years relevant design experience at a tech, product-driven company


If you have some or all of the following please apply:

  • Passionate about our mission to "enable all people do the best work of their lives".
  • Naturally curious and want to push boundaries of what's possible
  • Methodical with a strong attention to detail
  • Self-directed and biased towards action
  • Constantly improving and open to feedback through collaboration
  • Expert verbal and written communicator with remote teams
  • Previous experience contributing as the primary senior level Product Designer
  • Strong design portfolio that demonstrates depth of skill in both UX and UI
  • Deep knowledge of UX/UI patterns
  • Experience leading the end to end design process


You should include these in your application:

  • A link to your online portfolio
  • Your CV or LinkedIn profile
  • A few words about why Thoughtful Automation is interesting to you

Up for the challenge? Send portfolio to [email protected]

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171 N Aberdeen St, Chicago, IL 60607

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