We are looking for a Head of Engineering.

The Mission

Cass.ai builds AI powered mental health chatbots, which are proven in many research studies to lower symptoms of anxiety and depression. We believe that combining these AI chatbots with traditional therapy, is the best way to get everyone the care they need to help them with any mental health events they might be dealing with. With positive engagement of the AI chatbots studies have shown that individuals can maintain a stable mental health state and reduce the incidents where active therapy is required

The Team

At Cass.ai you get to work with a small but diverse team that includes senior engineers, researchers, and psychologists.

The engineering team at Cass.ai comes from strong technical backgrounds, and share a passion to make a positive impact in the lives of the 29,000,000 people who have paid access to our service. In your role, you will have the opportunity to lead, mentor, and grow this team and set the Technical direction of the company.

The Tech

Joey Trevino who built the foundation of online bank Chime ($5.8B valuation) retired and is our previous VP Eng. He led a complete rewrite of our codebase, so it has very little technical debt, which allows for adding new features rapidly. We use Python on the back-end and React on the front-end. Our UI mainly consists of text chats on different communication channels and a content creation/training platform for psychologists.

Research is at the core of what we do. We have published 7 research papers, and have 13 more studies in the works. The engineering team’s work directly influences how much symptoms of our users are reduced, of which the results will get published.

The Opportunity

We’re growing, and already millions of messages are exchanged by Tess with people in need, making your impact even bigger.

The engineering team is expected to double before the end of the year. We are looking for a hands-on Engineering Leader who can take over the existing platform and team, and lead and grow this team through an exciting acceleration of the Company. In this role, you will oversee all Technology related decisions, including full architectural responsibility for the platform, collaborate on and oversee the execution of a product roadmap that is aligned to the strategic vision of the company, grow and mentor the team, with full responsibility to define the team composition and how the team operates. 

The role does require an Engineering Leader that is hands on, you must be willing to roll up your sleeves and dive into the code, leading the way for the other engineers and setting a high bar of excellence for the Engineering team.

In this role you will:

  • Work with other stakeholders to set the short and long term roadmap for NLP / NLU and AI at the company
  • Provide hands on coding leadership to the team and tackle some of the hardest engineering challenges
  • Lead your team to impacting high level company goals by facilitating the integration of AI/Automation solutions into the product.
  • Coach and mentor team members from different backgrounds to grow in both their technical and leadership skills
  • Collaborate with engineers to review designs and advise on high-level and modeling decisions and approaches
  • Grow the team and help shape processes and culture as the company grows

An ideal candidate has:

  • A Bachelor Degree in Computer Science or other related field
  • At least 2 years of management experience, leading small to mid size engineering organizations
  • Passion for making a positive impact on the lives of millions of people
  • Experience in web-scale/consumer-facing organizations
  • Broad knowledge of machine learning approaches in general (expertise in NLP, Deep Learning will be valued, not strictly necessary)
  • Ability to work and thrive in a fast-paced, diverse and cross-disciplinary work environment that includes engineers with different backgrounds, psychologists, and UX researchers
  • Bonus: 2+ years of machine learning (NLP) and/or other AI related activities


  • Unlimited paid time off: as a mental health startup we help keep each other in check to use this policy, and prevent burn-out
  • Choose an annual donation by our Foundation to help a population of your choice, see past examples at: https://www.cass.ai/foundation
  • Health, dental, and vision insurance
  • Parental leave
  • Remote work
  • 401(k) benefits

Interested? Email rebecca.frezza@cass.ai

Watch a video about our impact:

"We serve the most vulnerable, mental health is very important."

We help thousands of people for free: 

Learn more

We really value our culture:

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Meet your future team:

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"We serve the most vulnerable, mental health is very important."