Jason Howard and Greg Ryan on the Financial Planner Life Podcast – one of Apple’s top 10 career podcasts
Inside Insight’s approach to culture, careers and adviser development
Why mentoring, freedom and long-term thinking matter
Our ambition to grow to 100 advisers by January 2028
What makes Insight a great place to build a career in financial planning?
That’s one of the big questions explored when Insight CEO Jason Howard and Performance Director Greg Ryan joined Sam Oakes from Financial Planner Life on 22 October 2026.
The Financial Planner Life podcast brings together people from across the financial planning profession for open conversations about careers, culture and what it’s really like to work in the industry.
Hosted by Sam Oakes, the podcast explores the experiences behind successful careers and businesses, from training and personal development to wellbeing, leadership and the future of financial planning.
In this episode, the focus turned to Insight. Jason and Greg took listeners behind the scenes of our business, discussing how we develop the next generation of financial planners, support experienced advisers and create an environment where people have the freedom to build rewarding, long-term careers.
And, of course, they shared a little about where Insight came from, and where we’re heading next.
Why is Insight a great place to work?
Growth is important to us, but how we grow matters just as much.
People come into financial planning at different stages of their lives. Some are starting out and learning the profession. Others have years of experience behind them and want to develop further, take on new challenges or work differently. We want Insight to be a place where people can do all those things.
Jason and Greg discussed how training, coaching and mentoring help financial advisers develop their knowledge, confidence and ability. They also explored the importance of financial security while people are building their careers, alongside the personal qualities that make a difference over the long term.
And development isn’t only about technical knowledge. Mindset, communication, self-discipline and wellbeing all play an important part in building a successful, long-term career. Jason and Greg explained how these ideas have helped shape the way we support our people.
Creating opportunities for the next generation
The podcast also looked at a bigger question facing the financial planning profession: how do we create opportunities for the next generation?
Jason and Greg discussed Insight’s approach to developing homegrown talent and why age shouldn’t be a barrier to becoming a great financial planner.
At Insight, mentoring is a big part of this. Newer advisers benefit from the experience of colleagues who have faced similar challenges. Experienced financial advisers can develop their own leadership and communication skills by helping others grow.
Knowledge gets passed on. People learn from each other, and the whole business benefits.
For us, investing in the next generation is also part of taking responsibility for the future of financial planning. We want to build a business where advisers can develop fulfilling careers and where clients and their families continue to receive support as their own lives change.
Our advisers should be able to live the life they want to live. And we should support that by having the right infrastructure so that it happens.
Building a business that lasts
At Insight, we think about the long term. We want to build a business that will still be here in 100 years.
That ambition influences the decisions we make today. We invest in people, develop future leaders and create opportunities for progression. We also think about continuity for our clients, so they can build lasting relationships with financial advisers who understand them and their families.
Longevity matters to our people, too. We want them to see a future at Insight and have the opportunity to shape what that future looks like.
That includes having the freedom to organise their working lives around what matters to them. As Jason puts it:
“Do not make the job fit the hours. Make the hours fit your life.”
That freedom comes with responsibility. Advisers need to understand what helps them perform at their best, develop the discipline to achieve their goals and take ownership of how they work. Our role is to provide the support and infrastructure that help them do that.
We have an ambitious goal: to grow Insight to 100 advisers by January 2028
But growth in numbers is only one measure of progress. How we grow matters just as much.
As the business expands, we want to preserve the things that make Insight a good place to work – personal relationships, shared knowledge, opportunities to develop and the freedom to take responsibility for your own success.
That means continuing to invest in our people and the support around them, so our advisers can focus on doing their best work for clients.
Our ambition is to build a business that creates opportunities for the next generation while continuing to look after the people who already make Insight what it is. If Jason and Greg’s conversation has given you a feel for the culture and opportunities at Insight, visit our careers page to find out more about joining our growing team.
Focused on you applies to our people just as much as it does to our clients.
Watch or listen to the full conversation here. We won’t give everything away.
