Leadership isn’t defined by a title; it’s demonstrated through influence, purpose, and the ability to inspire others to grow. For Jackie Kennedy, Founder and CEO of LeadMe Academy, leading at every level means creating meaningful impact, embracing continuous growth and empowering others to step into their own potential. As part of #WM2026, Jackie shares her insights on authentic leadership, navigating challenges, building confidence and creating opportunities for women to thrive in their careers and beyond.
1. What inspired you to start your business, and what opportunity did you see in the market?
I have always been fascinated by human behaviour and by what enables people to make meaningful changes in their lives. I discovered coaching in my early twenties and went on to train as a coach. After working for several years, I realised that coaching was where I wanted to focus my energy. I could see the difference it made in helping people understand themselves, take ownership of their lives and fulfil more of their potential.
After doing extensive one-to-one coaching and bespoke leadership development work, I began to notice a pattern in the process I was taking people through. I realised that we could turn this into a scalable offering that would make coaching and leadership development accessible to many people rather than only a few.
That was the idea behind LeadMe and our flagship programme. We wanted to help people develop greater personal mastery, lead themselves more effectively and develop leaders at every level of an organisation. We also saw an opportunity to create a shared language and way of leading across businesses.
2. What were the biggest hurdles you faced during your early growth journey?
One of the biggest hurdles was making the shift from being a coach and practitioner to becoming an entrepreneur building a scalable business. Being good at the work is very different from building the sales, systems, team, and operations required to grow it.
Gaining traction and earning the trust of established organisations was another early challenge. As a young business, you need clients who are willing to take a chance on you before you have an extensive track record. We were fortunate to have several early clients who believed in what we were building and grew with us.
COVID brought enormous uncertainty, but it also became a turning point. Because our programmes could be delivered online, we were able to continue supporting leaders and teams at a time when that support was deeply needed. Since then, the challenge has been scaling without compromising the quality and personal connection that underpin our work.
3. Which business decision has had the greatest impact on your company’s success?
If I had to choose one, it would be the decision to build a strong team rather than allowing the business to remain entirely dependent on me. I have intentionally surrounded myself with people who bring strengths, expertise, and perspectives that are different from my own. That has allowed LeadMe to grow beyond what I could have achieved alone.
Investing in long-term relationships has also been incredibly important. Our growth has been built on trust, both within our team and with our clients, coaches and partners. Many of our strongest opportunities have come from relationships that have developed over several years.
4. How have you navigated periods of uncertainty or economic pressure?
I have come to see uncertainty as a constant part of building a business, rather than something that appears only occasionally. My approach has been to remain focused on the problem we solve and the impact of our work. Leadership and human behaviour remain important regardless of the economic environment, although what organisations need and how they need it delivered may change.
We stay close to our clients, listen carefully and adapt where necessary, without losing sight of our core purpose. I also try to distinguish between noise that can distract us and important signals that require a response. That combination of focus and adaptability has helped us navigate change without making reactive decisions.
5. What role has innovation played in helping your business remain competitive?
Innovation has been central to LeadMe from the beginning. We challenged the idea that meaningful leadership development needed to be limited to one-to-one coaching or once-off training interventions that only reached a small number of people.
Our model combines coaching, science-backed micro-learning, small and consistent behavioural shifts, practical workplace application and measurement over time. We continually listen to our clients, learn from every programme and evolve our approach in response to what leaders and organisations need.
For us, innovation is not about chasing every new trend. It is about continually finding more effective and accessible ways to create meaningful, measurable and lasting behaviour change.
6. Looking back, what would you do differently if you were starting again?
I would build a more deliberate and repeatable sales strategy much earlier. For a long time, our growth came largely through relationships, referrals and my direct involvement. Those relationships remain one of our greatest strengths, but I would have introduced more structure, clearer processes and additional sales capacity sooner.
Doing that earlier would have made growth less dependent on me personally and given us a stronger platform from which to scale. Like many founders, I have learnt that being able to deliver excellent work and building the systems required to grow that work are two different disciplines.
7. What qualities do you believe every successful entrepreneur needs today?
Entrepreneurs need focus, resilience, adaptability and the courage to act before they have complete certainty. They also need the discernment to distinguish between noise that should be ignored and feedback that could make the business stronger.
Self-awareness and humility are equally important. You do not need to be the best at everything, but you do need to understand your strengths, recognise your gaps and build a team of people who are stronger than you in the areas where you need them. Ultimately, successful entrepreneurs remain anchored to their purpose while being willing to change the route they take to achieve it.
8. What advice would you offer women considering launching or growing their own businesses?
Do not wait for the perfect moment, complete confidence, or the promise of perfect balance. None of those things arrives before you begin. Entrepreneurship is not necessarily an easier path or a shortcut to greater flexibility. It will ask more of you than you expect, particularly when you are also raising a family and carrying responsibilities in other parts of your life.
There will be seasons when the business requires more and seasons when your family does. The answer is not to do everything perfectly, but to make conscious choices, build the right support around you, and accept that you do not have to carry everything alone.
Get close to the problem you want to solve, test your thinking, and learn as you go. Most importantly, do not diminish your ambition or wait for someone else to permit you. If you believe you can create something of value, back yourself and begin.
Short bio:
Jackie Kennedy is the Founder and CEO of LeadMe Academy. As a trained coach and entrepreneur, she specialises in human behaviour and organisational development. Jackie has transformed traditional one-to-one coaching into a scalable, science-backed digital learning model, empowering organisations to build high-performance leadership cultures at every level.
Contact information
Email: connect@leadme.academy
Website: https://www.leadme.academy/
Social media links
LinkedIn Profile: https://www.linkedin.com/in/jackie-kennedy-leadme/
LinkedIn Company Page: https://www.linkedin.com/company/leadme-academy/
