Fresh Perspectives: New Voices at Gilligan Sheppard

Two of our newest team members share their first impressions of the market, the work, and what makes this place different.

There’s something uniquely valuable about fresh eyes. When you’re new to a company, or new to the workforce entirely, you notice things that others might overlook. You ask the questions that long-timers stopped asking years ago. And you feel the culture in a way that only newcomers can.

We sat down with two of our newest team members to hear what they’re seeing, learning, and experiencing. Sahil joined us almost two months ago, bringing experience from a family office in New Zealand and Equity Research-led IR firm in London. Toby returned after completing an internship last year, just nine days into his first full-time corporate role. Their perspectives offer a window into both the current market and the Gilligan Sheppard way of doing things.

Reading the room: What’s happening in the market

When asked about the mood among clients and investors, both Sahil and Toby painted a picture of cautious optimism, with the emphasis shifting from caution to action.

“There’s a certain level of urgency in the market because of what’s happening with AI,” Sahil observed. Coming from London’s research sector, he’s seen firsthand how companies are scrambling to incorporate artificial intelligence into their operations. It was one of the first questions he asked during his interview process: What are we doing on this front? Because, as he put it, “If we don’t focus on that, we’ll get left in the dust.”

But alongside that urgency sits something else: a growing readiness to move forward. Six months ago, Sahil notes, people were still waiting, hands in pockets, watching to see what would happen. Now? “People are tired of waiting. They’re starting to peek at the other side.”

The central bank’s moves to lower interest rates are helping. Investors are cautious (they’ve either tied up capital or are being particularly careful about where they put their money), but there’s a sense that conditions are improving. “We’re also in a period of slower growth, and with the global focus on AI accelerating so quickly, we’re heading into a major paradigm shift. And with transformations of that scale inevitably comes uncertainty.”

Toby’s work reflects the seasonal rhythm of business. “This time of year, people aren’t really pushing for big projects,” he explained. “It’s more about tightening down loose ends before the new year, getting everything tied up with a bow so they can start fresh.”

The work: Diverse, challenging, real

Both newcomers have found themselves immersed in varied, meaningful work from day one.

Toby’s been getting well-versed in the range of services our Special Advisory team offers, and more recently, a tax opinion for a client dealing with significant losses, as well as NZFT work. In his downtime, he studies recent valuations to understand how the methodology has evolved since his internship. “I want to be ready when the bigger projects come through in the new year,” he said.

Sahil’s plate is equally full. He’s working on a valuation for an up-and-coming recruitment service , and he’s deep in a commercial property development capital raise, currently in the second tranche. The capital raise work has given him direct insight into investor sentiment: Sahil is seeing investors become more hesitant about traditional asset classes and more drawn to opportunities that leverage technology; the kind of innovation that, in their eyes, feels more scalable, future-proof, and exciting.

The culture: Family, freedom, and the art of bouncing ideas

When the conversation turned to what surprised them about Gilligan Sheppard, both spoke immediately about the people and the culture.

For Toby, this is his first corporate job, so Gilligan Sheppard has set the standard rather than deviated from one. But even without a point of comparison, he recognises something special. “The sense of team and family, everyone’s keen to lend a hand,” he said. “Everyone’s open to sharing their wisdom, whatever the topic. And their life stories too. It’s really interesting to hear where each person started and how they ended up here.”

He feels grateful to be starting where others have built their careers. “I feel very lucky to be joining at this point.”

Sahil, with a few more years of experience under his belt, has context to draw on, and it makes Gilligan Sheppard stand out even more sharply. “In my previous jobs, you’d have to follow a structured process when working through problems,” he explained. “Here, you have the structure and the freedom to bounce ideas around.”

That freedom isn’t just nice to have; it produces better outcomes. “When you’re bouncing ideas off such a diverse group of people with different career backgrounds and life experiences,” Toby observed, “the end product is so refined. It’s had input from all these different angles.”

The accessibility of senior leadership surprised them both. Sahil sits opposite Bruce, and near Humphrey, Nicola, Richard, and Arran, people with decades of experience in valuations, tax, capital raises and investing. “These guys have dealt with so much of what I’m working on,” he said. “And they won’t just give you the answer. They’ll allow you to think in a way that gets you to where you need to go.”

Teach a man to fish, as the saying goes.

“I don’t know how common it would be at a larger firm to just talk to Joshna the CEO,” Toby mused. “Here, it’s normal.”

No shocks, only pleasant surprises

Asked whether anything had shocked or surprised them, good or bad, both paused. “No shocks,” Sahil confirmed. “The surprises have been good. Really good. Pleasant surprises.”

That environment of support, Sahil believes, creates a virtuous cycle. “You feel welcomed. You feel like you want to do the best you can because that’s what you’ve been given. It really helps you wanting to do your best, because you’ve got this amazing support of people around you.”

The inclusiveness, both agreed, is rare. “Very hard to come by,” Sahil said. “And you can feel it when you’re working on a project. You can just put your hand up and say, ‘Hang on, I’m stuck. Give me a hand.’”

For two newcomers finding their feet in a challenging market, that makes all the difference.

Welcome to the team, Sahil and Toby. We’re glad you’re here.