In this episode, Andrew Romeo speaks with Halen Youles, Founder & CEO of ScaleMate and a seasoned sales strategist helping startups from Australia, India, and Singapore break into the U.S. market. Based in Florida, Halen shares his journey from the Central Coast of NSW to leading sales teams in the U.S., and offers practical, tech-driven insights on how early-stage companies can crack global expansion. From cold calls to automation tools and founder-led sales, this episode is packed with tactical advice for anyone looking to scale their startup, optimise their outreach, or successfully enter the U.S. market.
Halen kicks things off by reflecting on his path from cold calling in Sydney to landing a role with Travis Kalanick’s CloudKitchens. What started as a curiosity in the startup world turned into a full-blown career pivot, shaped by a passion for scale and sales. He shares how his early embrace of Zoom and remote selling helped him build momentum in a changing world and adapt quickly to the evolving sales environment—especially in the vast and competitive U.S. market.
Throughout the conversation, Halen highlights the strategic shift from relying solely on referrals to building scalable outbound systems. His multi-touch approach—leveraging email, LinkedIn, content, and cold calls—helps warm up leads before making contact. For startups looking to break into the U.S., he advises a structured testing approach to validate messaging, backed by metrics like conversion and engagement rates. He also introduces the concept of message–market fit, the idea that your messaging needs to resonate long before product–market fit can be proven.
Drawing from years of B2B SaaSThe term SaaS stands for Software as a Service. SaaS is an evolution of an application that runs on the... experience, Halen outlines how funnel metrics like reply rates, meeting conversion, and stakeholder involvement act as key signals of traction. With LinkedIn reply rates as high as 25% and call booking rates around 70%, he demonstrates the importance of refining every stage of the outreach funnel. He also explains how founders can track and optimise performance using tools like Clay, Airtable, and HubSpot to bring data into one central view—critical for making informed decisions as you scale.
A strong advocate for founder-led sales, Halen explains why founders should stay hands-on in the early stages—especially when entering new markets. Their intimate product knowledge, agility in conversations, and ability to adapt strategy in real-time make them the best fit for initial sales. While parts of the funnel can be outsourced or automated, the founder should always be the one leading calls, understanding objections, and spotting new opportunities. Only after this process is defined should companies consider hiring sales reps or expanding teams.
To close out the episode, Halen and Andrew discuss what it really takes to expand into the U.S.—from understanding time zones to making the right hires. Halen cautions against hiring too early without a clear sales process, recommending fractional leadership or agency support for lean teams. Whether it’s an SDR, AE, or VP of Sales, every hire should serve the larger strategy, not burden a broken process. Their final takeaway? In the U.S., successful founders sell first and build later—a mindset shift that could redefine how early-stage startups grow and scale.
Topics Covered
- Halen’s journey from Australia to the U.S.
- Transition from cold calling to remote and digital sales
- Understanding and applying message–market fit
- The role of cold calling in modern sales outreach
- Multi-channel outbound strategies (email, LinkedIn, content, calls)
- Tracking and optimising funnel metrics
- Importance of founder-led sales in early-stage startups
- When to move your business to the U.S. market
- Hiring the right sales roles for U.S. expansion
- Adopting the “sell first, build later” mindset
Important Time Stamps
- Cracking the US Market: Aussie Founder Shares His Game Plan (0:07 – 3:56)
- Sales Ain’t Easy: Turning Cold Leads into Warm Wins (3:57 – 6:10)
- From LinkedIn Message to LA: Halen’s Wild Ride with Travis Kalanick (6:11 – 11:10)
- 30–40% from Cold Outreach? Here’s How Halen Does It (11:11 – 17:28)
- Breaking into the U.S. Market? Start Here. (17:29 – 22:39)
- Message–Market Fit: The Metric You’re Probably Ignoring (22:40 – 26:38)
- You Can’t Optimise What You Don’t Measure – Track the Funnel! (26:37 – 31:58)
- Sell First. Build Later. The U.S. Startup Mentality (31:59 – 39:07)
