Ep 44: First in Region: Hard Won Lessons from Scaling Revenue in APAC

Timestamps:

03:21  Go Where Others Don’t—and Win Where Others Can’t

05:12 Be the Rep Who Asks What Everyone Else Is Afraid To

08:48 Don’t Scale Fast—Scale Right

09:59 Sell First. Then Build the Team.

15:53 Product Knowledge Isn’t Optional—It’s a Weapon

18:56  Discovery Is Where the Deal Is Won (or Lost)

20:40 Great Sellers Are Comfortable Being Uncomfortable

25:59 The Challenger Mindset Isn’t a Style—It’s a Standard

30:04 Influence > Rapport (Every Time)

About Gerard D’Onofrio:

Gerard D’Onofrio is a true scale-up operator with sales in his DNA. His father was a Senior Vice President of Sales in tech, his twin brother is an enterprise rep in the US, and Gerard himself has carved an exceptional career in tech sales—earning accolades like 5x Century Club Winner, President’s Club, and #1 global rep at AdRoll.

But what sets Gerard apart is what he’s built, not just what he’s sold.

After a powerhouse five-year stint at AdRoll—including launching their APAC HQ in Sydney—Gerard moved permanently to Australia. Soon after, he was tapped by Dialpad to do it all over again: open the region, land early wins, and scale from scratch. As the first sales hire on the ground, he sold solo for the first 10 months before building a high-performance go-to-market team from the ground up.

Today, Gerard leads Dialpad’s APAC operation, overseeing SMB, mid-market, BDR, SDR, Channel, Sales Engineering, and Customer Success functions across Australia, New Zealand, Japan, and the broader Asia region. In just five years, he’s helped turn a zero-footprint market into a thriving growth engine.

Introduction: From the Ground Up, Not Top-Down

Gerard D’Onofrio didn’t enter sales by accident—he was born into it.

His father was a Senior Vice President of Sales in tech. His twin brother is an enterprise rep in the US. Growing up, sales wasn’t just a career—it was a language spoken at the dinner table.

But what makes Gerard's story different isn’t pedigree. It’s what he did with it.

He earned his stripes at AdRoll in San Francisco during the chaotic, CRM-less startup days. He didn’t chase Silicon Valley logos—he sold into Iowa and Australia. He became the #1 global rep. And when AdRoll needed boots on the ground in APAC, Gerard was it. Six months in Sydney turned into five years.

Then he did it again. Dialpad tapped him as the first hire in-region. No team. No playbook. Just him. Ten months as an individual contributor. Then he built the machine. Today, Gerard leads teams across Australia, New Zealand, Japan, and the rest of Asia, with functions spanning Sales, BDR, SDR, Channel, Sales Engineering, and Customer Success.

This post isn’t fluff. It’s the real playbook of how to land, expand, and lead in APAC—straight from someone who built it all, from scratch.

Go Where Others Don’t—and Win Where Others Can’t

The best salespeople don’t follow heat maps. They find their own fire.

“I was calling into companies in the middle of the country and getting some good traction.”
“I actually called into Australia a lot… I think that’s part of the reason I’m over here today.”
“My best year at AdRoll? It was with a couple of customers in Iowa.”

Rather than joining the pack in San Francisco and New York, Gerard targeted overlooked regions with less noise and more attention. This wasn’t just tactical—it was foundational to how he thinks.

• Find whitespace others ignore
• Build early traction where buyers aren’t overwhelmed
• Create long-term opportunity in unexpected places 

Be the Rep Who Asks What Everyone Else Is Afraid To

If you’ve ever left a meeting thinking, “I should’ve just asked…”—you already know the power of this next point.

“I just straight up asked the CEO: what’s going to prevent you from signing this contract?”
“My manager nearly fell out of his chair.”
“The CEO said, ‘Really, if you guys go out of business.’ So basically, not.”

That one question landed the largest deal in company history. Not because Gerard was smoother or smarter—but because he was braver.

• Ask questions that move the deal forward, not just fill airtime
• Don’t wait for the perfect moment—it rarely arrives
• Clarity is better than comfort

Don’t Scale Fast—Scale Right

One of the biggest mistakes Gerard sees is when US companies try to force their domestic model into APAC. It rarely ends well.

“They think: ‘Australia’s similar enough, let’s do exactly the same thing.’”
“They’ll hire 20 people from day one, call it a day... but that’s not the case.”
“Start small. Build relationships. Then scale.”

Gerard brings perspective because he’s lived and sold on both sides. What looks like a mirror market on paper is actually a maze in practice.

• Localise your hiring plan, not just your messaging
• Build relationships before you build headcount
• Play the long game—it’s the only game that wins here 

Sell First. Then Build the Team.

When Gerard joined Dialpad, there was no team. No structure. Just him and a target.

“I was the first salesperson on the ground in June 2020.”
“For the first 10 months, I carried my own target, hit my number.”
“Now we have 20+ employees across ANZ and I’ve taken over Japan.”

That hands-on start wasn’t just tactical—it was critical. Selling before scaling meant he could build the right team, with the right message, for the right market.

• Prove the model before you hire
• Build empathy for your future team’s blockers
• Use real experience to inform process and feedback loops 

Product Knowledge Isn’t Optional—It’s a Weapon

Time zones kill momentum. If your reps can’t answer questions in the room, you lose deals.

“You need to be an end-to-end product expert.”
“You’ve got to be able to answer questions without waiting overnight.”
“After month six, you should really know the product inside and out.”

Gerard built a culture of technical fluency. Sellers at Dialpad are trained to own product knowledge—not defer it.

• Great sellers don’t outsource confidence
• Knowing your product builds trust and shortens cycles
• Product fluency = independence = speed

Great Sellers Are Comfortable Being Uncomfortable

Gerard compares sales to long-distance running. On the outside, you look calm. On the inside, you’re grinding.

“Great sellers are comfortable being uncomfortable.”
“You build this muscle of discomfort.”
“Do things before you’re ready—improve 1% each day.”

Whether it’s asking hard questions, running tough discovery, or taking on new roles—his approach is about leaning into resistance, not avoiding it.

• Don’t wait until you feel ready—do it anyway
• Get used to discomfort—it’s where the wins live
• Coach improvement over perfection

Discovery Is Where the Deal Is Won (or Lost)

Every seller says discovery matters. Gerard proves it with how he sells and how he coaches.

“Deals are truly won by understanding and amplifying pain.”
“If we can quantify the impact early… that’s where momentum builds.”
“The best sellers introduce friction when it matters.”

Forget fluffy rapport. Gerard uses frameworks like SPICED not to check boxes, but to drill deep.

• Don’t assume the buyer knows their own problem
• Introduce friction to slow the deal down if needed
• Move past features—sell outcomes

Influence > Rapport (Every Time)

Being liked is nice. Being trusted is better. But being influential? That’s where deals happen.

“Being liked opens the door. Being trusted keeps it open. Influence moves the deal.”
“You’re not here to make friends with buyers.”
“Strong relationships get you in. Influence gets you over the line.”

Gerard’s team knows that coffee meetings don’t close deals unless they lead to movement. Charm is not a strategy.

• Stop relying on being “well-liked” to move deals
• Build influence by shaping decision criteria
• Push for next steps, not just pleasant chats

The Challenger Mindset Isn’t a Style—It’s a Standard

Gerard doesn’t just use Challenger principles—he lives them. Especially in a market like APAC, where prospects often know what they want... but not always what they need.

“Sometimes, what they think they need isn’t the priority.”
“That’s where we build credibility—by reframing.”
“We’re not just vendors—we’re consultants.”

This approach makes you harder to replace, even when the competition undercuts you.

• Challenge respectfully, but don’t default to consensus
• Educate and reframe to create urgency
• Consultative equals defensible

Your First Hires Will Make or Break You

When you’re building in-region, your first 2–3 people set the tone for everything. Gerard hires differently—and deliberately.

“Your early hires won’t be well supported—they need grit.”
“They’ll need to create their own processes, wear many hats.”
“I often overstretch into roles… to see who steps up.”

He doesn’t optimise for polish—he looks for potential and adaptability.

• Hire builders, not passengers
• Test for self-starting, not CV shine
• Stretch early hires—they’ll either rise or reveal

Summary: Sales Leadership Is Built in the Trenches

Gerard D’Onofrio didn’t scale Dialpad in APAC by following a slide deck. He built it in real time—through calls, deals, mistakes, wins, and team building.

His story is proof that success in new markets doesn’t come from copying what worked elsewhere. It comes from:

• Showing up early
  
  
• Selling before scaling
  
  
• Hiring people with grit
  
  
• And asking the questions that matter
  
  

If you want to drive and grow in a region like APAC, don’t just hire a country manager. Hire a builder. A seller. Someone who’s lived the pain—and knows how to turn it into growth.

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