Riding the Growth Curve, Shane O’Grady’s Leadership Journey with TR Group and Indicator
Shane O'Grady, National Sales & Marketing Manager at TR Group and Indicator Sales Syndicate Member since 2018.
In June 2025, the Indicator Sales Syndicate proudly celebrates 10 years of supporting sales leaders across Australasia. As part of our "Syndicate Spotlight" series, we’re thrilled to share the journeys of members like Shane O’Grady, who joined the Sales Syndicate in 2018. His story highlights not just an incredible career progression, but the power of community, connection, and continuous learning that comes from being part of the Indicator family.
When Shane joined TR Group nearly 11 years ago, the business was already a major player in New Zealand’s transport sector. But what followed was extraordinary growth, expanding from 4,000 to around 10,000 trucks and trailers in the fleet and stepping boldly into Australia in 2019. "It’s been an epic ride," Shane says. His role evolved alongside the business, from leading a small team focused on lease sales in New Zealand to a wide-ranging leadership role that today spans marketing, learning and development, recruitment, and supporting TR’s ambitious target of growing the fleet to 25,000 by 2035. Shane admits it’s a lofty goal, but one which we’re focused on achieving through deliberate, sustainable growth – and lots of hard work! Despite the rapid change, Shane’s job title has stayed the same, something he jokes about, but the scope and impact of his role have transformed significantly. As part of the Senior Leadership team, Shane juggles sales and being heavily involved with day to day operations, alongside his counterparts in operations, maintenance and rentals.
The Value of the Syndicate Connection
As Shane’s role expanded, the Indicator Sales Syndicate became a critical support system. “First and foremost, it’s the connections with a great group of people who understand and have empathy of the challenges which are part and parcel of being a sales leader," Shane reflects. Sales leadership can often be an isolating role, but finding a peer network through Indicator provided him not only with professional advice, but with genuine friendships. "A problem shared is a great truism," he says, and having a room full of like-minded leaders to download with, challenge each other, and celebrate wins (and losses) together has been invaluable. In our group, it’s been great to share others successes along the way. I know they’ve always supported and encouraged me, and I’d like to think they feel the same way about me.
Beyond connection, Shane values the consistent quality of expert speakers who bring fresh perspectives every month. Practical leadership strategies, personal development insights, and critical thinking tools have helped him not just as a sales leader but as a human being. All the experts deliver at least one insight, that I can take back to TR and use to help me lead, inspire, motivate and better support my team. Perhaps just as importantly, the regular discipline of stepping away from the day-to-day to work on himself and his leadership craft has paid dividends both personally and professionally.
Lessons in Leadership and Growth
Reflecting on his leadership journey, Shane admits he’s learned some big lessons, many of which have been reinforced through his involvement in Sales Syndicate. "You don’t have to do it all yourself, and your way isn’t the only way," he says. Trust, challenge, and support your team, and you’ll watch them flourish. He’s also come to appreciate that care, empathy, and vulnerability, are powerful leadership traits, not weaknesses.
One standout learning? Don't avoid confrontation. "Often the issues we blow up in our heads are way bigger than reality. Addressing things early, with care and directness, helps build stronger, healthier teams," Shane shares. Call out poor behaviour early. Most people will appreciate the feedback and make corrections before things go too far.
Through both the peer conversations and speaker insights at Sales Syndicate, he’s sharpened not just his leadership skills, but also his emotional intelligence, becoming a more deliberate and self-aware leader. “Syndicate has really helped with being able to check my thinking and triangulate my data with peers in similar positions. Quite often this has led me down different and far more effective paths had I just gone ahead without asking the view of the group”.
The Power of Shared Growth
The longevity and camaraderie of Shane’s Syndicate group have also left a lasting impact. Over the years, they’ve shared professional milestones, personal moments, and even losses, creating a deep sense of community. "We've seen each other through highs and lows, and that support is something I truly value," Shane reflects.
His advice to any sales leader thinking about joining the Sales Syndicate? "Do it, but know that the more you put in, the more you’ll get out. Build the connections, stay curious, and the payoff will be incredible."
Looking Ahead, Focused on the Long Game
As for what’s next? Shane is focused on staying the course during what he describes as "the most challenging period of my working life." Despite the hurdles, he remains confident that the deliberate groundwork being laid now will pay off. "We can only control what we do and how we do it, and when the market turns, I’m excited to see the fruits of the effort we’re putting in now."
Shane’s journey is a powerful example of how belonging to a strong community like Indicator Sales Syndicate can fuel growth, resilience, and leadership excellence, even through the toughest of times.
Indicator Sales Syndicate brings together sales leaders to develop skills, share knowledge and network via monthly membership, INDICATOR Sales Syndicate exists for those focused on advancing their sales leadership skills and performance.