From Detective to Defender: How Kylee Dennis Turned Pain Into Purpose

There are some leaders who command attention because of their title. And then there are leaders who leave a mark because of their courage, authenticity, and deep commitment to helping others.
Kylee Dennis is one of those leaders.

When I sat down with Kylee Dennis for the Courage to Lead interview series, I knew I’d be speaking to someone with a remarkable background. What I didn’t fully appreciate until we began talking was just how powerful her story really is.

Kylee Dennis is the Director of Two Face Investigations, an author, a forensic romance scam investigator, and the winner of Micro Business of the Year 2025 at the Women Changing the World Awards in London. But behind those achievements is a story of service, heartbreak, resilience, and purpose.

Her journey is one that reminds us leadership is not always about rank or position. Sometimes leadership is forged in pain. Sometimes it emerges when life forces us to rebuild. And sometimes it shows up in the decision to use our hardest moments to protect others.

Kylee Dennis – A life shaped by service

Kylee Dennis was born into a policing family. Her father, a respected police officer, had a profound influence on the way she saw the world. Growing up in a small country town, she experienced firsthand the mateship, responsibility, and sense of purpose that came with police life.

One defining moment came when she was just 12 years old. A violent domestic incident unfolded on her family’s doorstep. Her father, unarmed, rushed out to confront the offender and protect the victim. For Kylee, that moment became a turning point.

It cemented what she already felt deep down — that her path would be one of service.

From that point on, her focus was clear. She would join the police force, and she would do everything she could to make a difference.

Learning leadership the hard way

Kylee Dennis entered policing with determination, grit, and a strong sense of purpose. Her early years in the job taught her a great deal — not just about policing, but about leadership itself.

She spoke with deep respect about one of her earliest leaders, Barry, who made a lasting impression on her. He created a culture where people felt safe, supported, and able to learn. He allowed people to make mistakes without fear, helped them find their feet, and led with kindness.

That kind of leadership mattered.

It mattered even more because Kylee also experienced the opposite. In some workplaces, she encountered leaders who were dismissive, unsupportive, and damaging. She learned what poor leadership feels like — and how isolating it can be.

But instead of letting those experiences define her, she used them to sharpen her understanding of the kind of leader she valued most: someone authentic, calm, generous, and committed to helping others grow.

That contrast shaped her.

Kylee Dennis – A career built on courage, skill, and compassion

Kylee Dennis’ policing career was extraordinary in both breadth and depth.

She worked in some of the toughest environments in New South Wales policing, including Marrickville, Flemington, Auburn and Bankstown. She became a detective, served in demanding investigative roles, worked in child protection, and joined the negotiation unit — a role she still speaks about with enormous passion.

Listening to Kylee Dennis reflect on negotiation work was powerful. For her, it was never just about tactics. It was about listening without judgment, understanding human behaviour, remaining calm under pressure, and helping people find a way back from crisis.

Those skills would later become central to the work she now does.

Her story is also a reminder that leadership is often developed in teams. Again and again, she spoke about the importance of belonging, trust, and working alongside good people in difficult circumstances. Whether it was Goulburn training, frontline policing, detective work, or negotiation roles, one theme remained consistent: the best teams are built on mutual respect and shared purpose.

Kylee Dennis – When identity is taken away

Then came one of the most difficult chapters of her life.

After having children, Kylee Dennis reached a point where she needed just a little flexibility from the organisation she had given so much to. She asked for six more months of leave without pay, or a temporary part-time arrangement.

Both requests were denied.

As a result, she made the painful decision to resign from the police force.

It was a devastating moment.

For Kylee Dennis, policing was never just a job. It was part of her identity, her purpose, and her pride. Leaving the organisation she loved cut deeply. She described it as though part of her had been taken away.

What followed was not a quick recovery. It was years of feeling lost, disconnected, and unsure where her purpose now lived.

That part of the conversation was incredibly honest. And it matters because so many people experience something similar. Sometimes we lose roles, careers, identities or dreams that once defined us. When that happens, finding a way forward is not easy.

Kylee Dennis didn’t pretend otherwise.

Kylee Dennis – Rebuilding, one step at a time

In the years that followed, Kylee Dennis kept moving.

She raised her daughters. She supported the family business. She joined boards. She completed the Company Directors course. She studied business law. She worked on her health and challenged herself physically, even completing half marathons in New York, London and Australia.

But even while doing all of that, something was still missing.

She described it beautifully as though she had a 1,000-piece puzzle — and one key piece was gone.

That missing piece didn’t reappear until 2023, when her mother became the victim of a romance scam.

Kylee Dennis – Turning personal pain into public purpose

When Kylee’s mother shared that she had met someone online, there were initially no obvious alarm bells. But when Kylee began looking more closely at the photos and story, she discovered the profile was fake. The images had been stolen. The relationship was not real. Her mother had been targeted by an offender using deception, manipulation and emotional grooming.

That moment changed everything.

Rather than simply helping her mother and moving on, Kylee began digging deeper. She created online dating profiles to better understand the scale of the problem. She researched fake identities, reverse image searching, scam tactics, language patterns, and the psychological grip these offenders have over victims.

What she found shocked her.

And once again, she saw people in danger.

So she did what great leaders do. She acted.

Kylee Dennis founded Two Face Investigations, bringing together her background in policing, investigations, negotiation, and human behaviour to help individuals and families navigate the devastating world of romance scams and online deception.

Fighting a hidden epidemic

What makes Kylee Dennis’ work so powerful is that she understands this issue from every angle.

She knows the investigative side.
She knows the emotional side.
And she knows the human side.

She understands that victims are not foolish. They are targeted, groomed, manipulated, and isolated. Shame becomes one of the biggest weapons used against them. Many never report what has happened. Many suffer silently. Many lose not just money, but confidence, trust, dignity, and hope.

Kylee Dennis now spends her time investigating suspicious profiles, speaking to families, educating older Australians, working with media, and advocating for broader awareness and stronger responses to online scamming.

She is tackling a modern crime problem with old-fashioned courage, persistence, and heart.

And she is doing it with the same instincts that drew her into policing in the first place: protect people, tell the truth, and don’t look away from hard problems.

Leadership lessons from Kylee Dennis

There were so many lessons in this conversation, but a few stood out strongly.

The first is that leadership begins with authenticity. Kylee’s advice was simple and powerful: don’t change you — be you.

The second is that leadership requires courage to step forward, even when the path is uncertain. Her willingness to give things a go, take risks, and back herself has shaped every chapter of her life.

The third is that great leaders stay curious. They ask questions. They don’t accept things at face value. They keep learning.

And perhaps the biggest lesson of all is this: our greatest pain can sometimes point us toward our greatest purpose.

Kylee Dennis’ journey has not been neat or easy. It has included challenge, grief, disappointment, reinvention and remarkable resilience. But through it all, she has stayed true to who she is — someone who wants to help, protect and serve.

That is leadership.

Final reflection

Kylee Dennis is living proof that courage does not always arrive in loud moments. Sometimes it looks like quietly rebuilding your life after loss. Sometimes it looks like learning a new battle after an old one ends. Sometimes it looks like answering the phone when someone is scared, ashamed, and doesn’t know where else to turn.

Her work is making a difference. Her voice matters. And her story deserves to be heard.

For anyone navigating change, searching for purpose, or wondering whether their past experiences still matter, Kylee’s example offers real hope.

Your past is not wasted.
Your pain does not have to define you.
And the qualities that made you strong before may be exactly what the world needs from you now.

That is the courage to lead.