From HR Leader to AI Innovator: Hannah’s Journey from Well-being Tech to Contented AI

Introduction
Hannah’s entrepreneurial path was shaped by personal experiences, a deep commitment to well-being, and a keen understanding of technology’s potential. After over a decade in HR, a pivotal life event led her to create The Kite Program, a microlearning app aimed at supporting new mothers. Through this journey, she gained invaluable insights into the startup world, the challenges of well-being tech, and the importance of user research. Now, as the founder of Contented AI, Hannah is pioneering a tool that transforms voice conversations into actionable insights, helping industries worldwide leverage the power of AI.

In this interview, Hannah shares her transition from corporate stability to entrepreneurship, the lessons she learned while building The Kite Program, and how she refined her vision for Contented AI. She also offers guidance for non-technical founders, tips for validating business ideas, and the crucial mindset shifts needed to succeed in the startup world.

Part 1: Personal Journey and Foundational Insights

Question: After working for almost 12 years as an HR professional and leader, how did you know you were ready to leap into entrepreneurship? How did you get the clarity that you wanted to start something of your own?

Hannah: My journey started with a mental health diagnosis following the birth of my first baby- and while it took a few years for me to recover and return back to work, I knew that returning to my HR career was to be temporary and that my purpose and drive was to help support new parents (particularly mothers). After my second child and my return to my career that second time I knew that I was ready to focus on the idea I had and dedicate my time into that. The pull of making a difference in the world outweighed my love for my career! I had the support I needed at home and with childcare and felt ready to jump into entrepreneurship. 

Question: For those considering leaving a stable career, what are the most critical factors working professionals should evaluate to determine if entrepreneurship is the right path?

Hannah: User research is key. I surveyed 150 mothers as part of my initial research (prior to leaving my career). This gave me enough insight into the problem and that it was big enough to solve. The other factor is- “are people willing to part with their hard earned money for your product or solution??” Everyone will tell you it’s a good idea but will they actually buy it and for how much. I wouldn’t make any decisions to leave a career before answering those questions. 

Question: What key questions should professionals ask themselves to gauge if they’re prepared for the challenges of running their own business?

Hannah: 

Is the problem big enough to solve? And if it is, will this keep me going through the bad days?

Do I need capital to start and do I have those options accessible (raising money is hard!)

Do I need a co-founder? What skills am I missing and can they be filled with a co-founder? 

Is the market big enough to sustain my business in the early days?

What support do I have around me and how deep is this support system?

Are there some small steps I can take without quitting my role/career?

Question: What was “The Kite Program” was about? When you started with “The Kite Program,” did you have any reservations or uncertainties, and how did you work through them?

Hannah:  Kite was a microlearning app designed to give small steps each day (only one). It was built within a beautiful app designed to be like a coffee table book. Small steps lead to great change. The concept for new mums was more of an HR/development resource rather than parenting. Helping mums through the personal challenges of motherhood. 

I was nervous about how to build the tech and who to use. I got a few quotes but to be honest I should have spent a lot longer investigating developers! I would have moments of overwhelm and imposter syndrome but my “why” kept me going. 

Question: After operating  “The Kite Program”  for over 5 years, what learnings would you like to share with someone looking to start something in the well-being space? 

Hannah: There is a huge lack of funding or focus on wellbeing- from corporates right through to individuals. It is a very crowded market and now with AI it is much easier to build a tech solution. So your point of difference needs to be big or very niche. So a lot of energy needs to go on solving a big problem for a small group of people and then scaling from there. Do your user research and know the problem deeply. 

Question: Contented AI is your new venture. What is your mission and vision for Contented AI? And how did you come up with the idea?

Hannah: At Contented, we believe all human conversation should be able to be turned into extraordinary outcomes.

Our tool turns voice audio into incredible outputs- accurate rich insights, thoughtful summaries and user research findings and information modelling. Capturing every word and transforming it in ways that drive action, reflection and human connection. Our goal is to be part of the world’s most important conversations and help facilitate change from those interactions. 

We came up with the idea after building many niche AI tools. Time and time again we saw voice input as being the most powerful way to use AI. So we went in this exciting direction and now work with many industries around the world including wealth management, charities, constructions, primary health, consultants and SME’s. 

Question:  What are common signs that someone might be motivated by the wrong reasons to start a business, and how can they refocus their intentions?

Hannah: Money is often the driver- they see startups raising millions or companies exiting and want to do the same. While money has to be part of it in terms of revenue and growth the underlying “why” needs to be more than that. Having a strong personal why and vision is key. Ego also plays a part and a business started on ego is often a huge issue. 

Part 2: Refining and Validating the Business Idea

Question: For experienced professionals with industry knowledge, how can they best leverage their expertise to find a niche within the space?

Hannah: User research and surveying- its the only way to understand a problem. Keep asking questions and go deeper to understand. No matter how much knowledge you think you have it is never enough! You need customer feedback an insights. 

Question: What advice would you give for identifying and refining a business idea, especially for someone unsure where to start?

Hannah: As above- come up with some hypothesis and test them out. Everything should be customer led not tech or product led. That comes next. 

Question: How did you refine your own business idea before launching Contented AI ? What mistakes did you make in the early stages that helped shape your vision?

Hannah: We started off building custom niche AI tools for customers before landing on a product idea. Once we knew voice was powerful, we iterated and built around some key customers until we had a solid grasp of a product that would meet many pain points so we could scale. We made many mistakes especially around onboarding and pricing but this was trial and error and a quick way to learn! We also rushed to wanting to capital raise and we pulled the pin on this after realizing it was too early and we needed more freedom. 

Question: If someone feels stuck with too many ideas or needs clarification on a single direction, what would you recommend to help them focus and gain clarity?

Hannah: Again go back to the people that would buy your product or buy into your idea. Start with one idea and go deep on that. Read and listen to podcasts for other ideas and also find a mentor or advisor!

Part 3: Technical Considerations for founders from non-technical background

Question: What are the essential skills or knowledge areas a non-tech founder should develop to succeed in a tech business?

Hannah: Leave the tech to the team with those skills but always has a layman’s understanding of all parts of the product (can you describe the product and tech to a 10-year-old?). Focus on the people, leadership, and influencing skills you need in your role. The non-tech founder will mostly be the salesperson, so hone in on that. 

Question: When you started your business, how did you prioritize learning about technology versus relying on experts? What balance do you recommend for non-tech founders?

Hannah: Keep a high-level understanding of the tech (use ChatGPT to grow knowledge and understand it from a non-tech perspective). As a non-tech founder, you should not focus at all on the tech, as this is not your domain, unless it impacts strategy and revenue growth. 

Question: What advice would you give on finding and working with a technical co-founder, especially for those needing help knowing where to start?

Hannah: It has to be organic and natural- I am not sure it is easy to “recruit” for a co-founder. Go to networking functions and meet ups and find connections that way. Often early customers will link you up with people too! The relationship is like a marriage so don’t rush into anything or give too much equity away. 

Closing: Reflective Advice

Question: If you could give one piece of advice to your younger self before starting out on the entrepreneurial journey, what would it be, and why?

Hannah: Listen to advice and be open to feedback- don’t think you have all the questions or know best just because you are close to the problem!!

About Clarity Club:

The Clarity Club initiative aims to empower working professionals with a decade of experience to get clarity on their 

  • business idea, 
  • the market in which they will operate,
  • the demand for their product/service, and 
  • the business model & tech product that will give it flywheels.  

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