Closing deals from the coast
Most SaaS sales directors are somewhere between an airport and a hotel lobby. Mike Wingfield is on the Sunshine Coast, Queensland, working remotely, leading a mid-market APAC team that covers five distinct regions - and the team actually hits quota.
He joined Deel, the global HR and payroll platform, after building his sales playbook at three of the defining SaaS companies of the last decade: Marketo, New Relic, and Twilio. At each stop, he ran APAC or ANZ sales. At Deel, he runs all of it - Greater China, ASEAN, ANZ, North Asia, and India - from a quiet stretch of Queensland coastline.
Fourteen years in SaaS is a long time. Long enough to understand that the difference between a team that hits quota and one that doesn't usually isn't the market or the product. It's the hiring, the coaching, and the culture. That's where Wingfield focuses. It's what earned him membership in the "100 x 100 Club" - a distinction handed to those who have led 100% of their sales team to 100% of quota. He's done it twice.
You must source top-down and be relentless in the hiring process - building a world-class team is the sales leader's responsibility. You cannot settle.
- Mike WingfieldDeel arrived at the right moment. After scaling enterprise and mid-market pipelines at Twilio's ANZ business, Wingfield moved to a company purpose-built for the world remote work was creating. Global payroll, employer-of-record services, HR compliance across borders - Deel's product suite maps exactly to the problems companies face when they stop being local.
The APAC mid-market is a particularly complex patch to own. It's not one market but five, each with different labor laws, payment rails, currencies, and hiring norms. Wingfield's team navigates all of it. His LinkedIn posts regularly reference the nuances: the SAP SuccessFactors integration for enterprise workflows, the specific pain points in Australian payroll compliance, the momentum building as Deel secures new regulatory licenses in the region.
The house near Noosa Heads
Locked down in Sydney, Mike and his colleague Jacquelyn Adama made the kind of decision that only happens when the regular world has stopped working. They drove north to Queensland and asked each other: "Would it be crazy if we bought a project house together?"
They bought it. Adama painted. Wingfield gardened. Somewhere in the middle of that renovation, he met the woman he would marry. When Sydney's offices reopened in 2021, they returned briefly - then turned back around. He and his wife relocated permanently to the Sunshine Coast, secured fully remote roles, and didn't look back.
That original renovation house is now being demolished - making way for something new. Wingfield has reflected on the image publicly. A life rebuilt from a spontaneous detour. "Remote work," he says, "unlocked a life we never thought possible."
This isn't background noise in his career story. It's why he works at Deel. Deel's mission - making it possible for anyone to work for any company, anywhere - is something he has lived, not just sold. That authenticity comes through in how he talks about the product and how he builds his team. He's not recruiting SDRs for a tech company; he's recruiting people into a new way of working.
The 100 x 100 playbook
The "100 x 100 Club" sounds like a marketing term until you realize how rarely it actually happens. Sales teams routinely have stars who overperform and stragglers who drag down the average. Getting every single person across the line requires a different kind of leadership - one focused less on the star performers and more on the conditions in which the whole team operates.
100% of the sales team at 100% of quota - not once, but twice. Mike Wingfield is among the very few sales leaders who have hit this mark at all, let alone repeatedly.
Wingfield's approach starts with hiring. He emphasizes what he calls "top-down sourcing" - actively recruiting from the best, rather than waiting for the best to apply. Once the right people are in place, the focus shifts to environment: creating conditions where the team can actually succeed, removing friction and barriers rather than piling on pressure.
Coaching runs through everything. Not the perfunctory check-in variety, but the kind that helps individual reps understand their own patterns, identify what's working, and adjust what isn't. The result is teams that don't need to be managed - they're equipped.
Once you have the right team, it's crucial to create an environment for them to be successful. Coaching is key to helping your team reach their full potential - a leader must remove any barriers in their way.
- Mike WingfieldDeel at scale
Deel has grown into one of the more significant HR infrastructure companies of the past decade. What began as a way to pay international contractors has expanded into a full HR platform: employer-of-record services, global payroll, compliance automation, benefits administration, HRIS, and now deeper integrations with enterprise systems like SAP SuccessFactors.
In the APAC region, Deel's momentum has been building steadily. The company secured an Australian Financial Services License (AFSL) - a significant regulatory milestone that expands what Deel can offer to Australian businesses. Wingfield celebrated this publicly, calling it "big news on the home turf."
On the payroll front, Wingfield commissioned the 2025 Deel Australia Payroll Report - a first-of-its-kind survey covering 500+ HR, finance, and operations leaders. The data was blunt: payroll in Australia is hard, superannuation errors top the pain list, and most teams lack the tooling to fix mistakes quickly. The report became a lead-generation and brand authority tool for Deel's Australian operations.