Leaving behind a stable career to venture into entrepreneurship is never an easy decision, especially for professionals deeply rooted in corporate life. Philippa Youngman, a former HR executive with over two decades of experience, took the leap when she saw a problem that technology could solve—not just for her own organization, but for businesses everywhere.

In this interview, she shares how she transitioned from the structured world of HR to the unpredictable world of startups, the challenges she faced as a non-technical founder, and the hard-earned lessons that shaped her journey. Whether you’re an experienced professional wondering if entrepreneurship is the right path or someone struggling to refine a business idea, Pip’s insights will provide clarity on what it takes to build something truly impactful.

Part 1: Personal Journey and Foundational Insights

Question: After working for almost 22 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 independently?

Pip: I got hooked on the value that internet technology was creating. I could see how it could solve a major problem I had in my corporate role. However, this problem was not limited to the business I worked in but all large businesses.

I have always had the mindset of “this could be done better”, never settling for the status quo.

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?

Pip: I think it is more about the idea than whether entrepreneurship is the right path—this was not a label I ever gave myself until relatively recently.

Nothing about entrepreneurship is stable so it is the complete opposite of the status quo.

The most rewarding part about it for me, is that I could be authentically myself, my own values were reflected in what I created.

But you need to be able to handle ambiguity, uncertainty, and disappointment.

In the early days, unless you have good funding, you have to be everything:  design, deliver,  marketing, sales, customer service, financial whizz or you have to be able to afford to hire for your gaps.

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

Pip: Can you afford not to earn a stable living for a while? – it will take some time to generate revenue, recoup investment costs and then take a dividend of some sort.  I really didn’t earn anywhere near what my corporate job was paying – the only major return was the sale of the business 17 years after starting. 

You also need to be a life-long learner, be able to be your own cheerleader (it can be very lonely), be able to “bounce” when things go bad, have a close confidante/mentor who you trust implicitly to tell you how it is.

Question: When you first started with Pivot, did you have any reservations or uncertainties, and how did you work through them?

Pip: I was very fortunate in that I was never risking my family’s wellbeing as my husband was working full-time and we could afford to live on his income only.

As I was not a technology developer, I had to outsource the initial development – this was expensive and very time-consuming as there was no concept of “iterative design” – full design specifications were needed before anyone started.  Not always did I get what I wanted – even though I got what I asked for 🙂.

I had no doubt about the problem I was solving and knew there was a market for it.  I was not in the habit of looking forward to foresee challenges – just dealing with each one as they came up.

If I knew about all of the “curve-balls” that were thrown along the way, I probably never would have started, but once you start, you just put one foot in front of the other and keep your eye on the goal (my “Why”).

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?

Pip: Why? Is always the best question.  Knowing the problem and then the passion for solving the problem has to be the major motivation.

If financial gain is the first reason when this question is asked, then it is very definitely the wrong reason – the financial goalposts can change in an instant – competitors, commercial environment, legislation etc.I always refer to the Japanese concept of Ikigai

Part 2: Leveraging Expertise and Finding a Niche

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

Pip: For me, it is about what you are passionate about.  I was an HR Professional, however I also loved numbers – that is not exactly “normal” for HR professionals – that is when Remuneration/Compensation became my niche and that is where I discovered the major (financially based HR) problem that needed solving – leading to the creation of Pivot.

A person I greatly admire is Dr Catherine Mohr – she combined her passion for engineering, aerospace, healthcare – she has an MS in engineering and an MD from Stanford (she is a NZer) – and was the pioneer of surgical robotics.  She used her passion and knowledge across many disciplines to solve a problem.

Part 3: Refining and Validating the Business Idea

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

Pip: To me, it is best if you are immersed or very close to the problem that needs solving and then it needs validated – (is this just a problem that I have or could my solution help others), so then can it be quantified – how big is it, can the solution be monetised, is the solution scalable (and therefore more profitable as it gets bigger). What are the current solutions to this problem? What would my investment be (both time and $) and is this the best use of both of those resources.

Question: What steps can aspiring entrepreneurs take to validate whether there’s a real demand for their product or service in the market?

Pip: This is about finding “who has the problem” and what are the current solutions – there are many statistics available from the Statistics Bureau, that can help (company size, industry, people demographics etc). 

Question: How did you refine your own business idea before launching, and what mistakes did you make in the early stages that helped shape your vision?

Pip: I thought that the perfect solution had to be delivered before anyone would buy it – no pain points.  In reality your best feedback is when your customers get their hands on your product so you need to really invest time in keeping close to your customers, listening to them and delivering to their suggestions for enhancements.  A solution is never “perfect” for everyone, so we were never going to get there unless we launched.  The concept of MVP (Minimum Viable product) is now firmly set in my mind for anything I do now

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?

Pip: To me that is where Ikigai comes in. 

Part 4: 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?

Pip: You need to find a strong, strategically focused technology person as a mentor or for part of your business that you trust implicitly because it is impossible to be all things Tech. A consultant, an employee, etc., will have different motivations to provide you with advice, so where possible, you need to get advice from someone who has no ulterior motive other than ensuring you succeed. Your tech problem will either be your biggest foundation or your biggest problem.

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?

Pip: I was very lucky to have a family friend who was the technology expert and he patiently answered all of my silly questions.  I continue to learn to this day as technology platforms, languages, toolsets are changing rapidly and so I always ask the silly questions to make sure I understand.  The most important decisions that you can make relate to security of your customer data – this can be your downfall if not done correctly.

When learning about technology, as a non-tech person you have to be sure that you stay up at the strategic level and not the detail to be sure that you can give your technology team the space to be creative.  So for me it was about understanding security, reliability (uptime and performance), future-proofing (or at least understanding the lifetime of decisions).

Question: What advice would you give on finding and working with a technical co-founder or CTO, especially for those who may not know where to start?

Pip: Finding them is hard – after my early mentor died, I had a significant gap in my close circle and made several bad choices as a replacement.  Don’t rush your decision as this one is perhaps the most crucial.  Be careful about offering equity too early (a hard lesson I learned) – only do it when you are 110% sure they are the right person to be with you “till the end”.

As per 12. Above – provide high level strategic requirements (from a customer perspective) – you are the expert at the problem – they need to be the expert at the technical solution.

It is your job to mentor them on the non-tech part of the business and their job to mentor you on the tech side.

You will be spending a lot of time together, so you have to “like” each other, share the same vision for the business and trust in each other’s expertise and decision-making.

Closing: Reflective Advice

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

Pip: Don’t wait for perfection, always listen to your customers (they are not always right but their opinion should be valued), hire slowly, and “if you can’t change the people, change the people” Gilbert Enoka. Your company culture is your biggest asset – build it, believe it, live it – no compromises.

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.