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Battle Scars of a SaaS Leader
James Bergl
12 episodes
1 week ago
We unpack how Asian startups use Australia as a Western test bed, the cultural signals that make or break sales, and a repeatable path to validate markets fast. We also explore investor perspectives, AI reality versus hype, and why commitment on the ground beats fly-in fly-out. • why Australia appeals for first Western expansion • how to read Australian sales language and build trust • reverse‑engineering competitor playbooks for fast intel • when Australia’s TAM is too small and what to do ...
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We unpack how Asian startups use Australia as a Western test bed, the cultural signals that make or break sales, and a repeatable path to validate markets fast. We also explore investor perspectives, AI reality versus hype, and why commitment on the ground beats fly-in fly-out. • why Australia appeals for first Western expansion • how to read Australian sales language and build trust • reverse‑engineering competitor playbooks for fast intel • when Australia’s TAM is too small and what to do ...
Show more...
Careers
Business,
Entrepreneurship
Episodes (12/12)
Battle Scars of a SaaS Leader
Why Asia-Pacific Expansions Fail (and What Actually Works) with Duco Van Breemen - CEO Haymarket HQ
We unpack how Asian startups use Australia as a Western test bed, the cultural signals that make or break sales, and a repeatable path to validate markets fast. We also explore investor perspectives, AI reality versus hype, and why commitment on the ground beats fly-in fly-out. • why Australia appeals for first Western expansion • how to read Australian sales language and build trust • reverse‑engineering competitor playbooks for fast intel • when Australia’s TAM is too small and what to do ...
Show more...
1 week ago
44 minutes

Battle Scars of a SaaS Leader
Why Resilience Beats Paper Perfect CVs in Hiring With Adam Frank
Adam shares what relocating to the UK to launch Squiz taught about first‑principles GTM, why partnerships beat cold starts, and how revenue flipped once distribution clicked. He breaks down his whiteboard interview test, the red flags he screens for, and why resilience, values alignment, and coachability trump paper‑perfect CVs. Now at SugarCRM, he explains why he hires builders over big‑brand sellers, how GTM can shape product, and the role networks play in attracting top talent and sustai...
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3 weeks ago
48 minutes

Battle Scars of a SaaS Leader
Sales Success & Strategy: Insights from a 15-Year Industry Veteran
In this episode, we dive deep into the world of SaaS sales leadership in Australia with industry veteran Jamie Deveaux. With over 15 years of experience and multiple leadership roles, Jamie shares the principles that have allowed him to build a strong reputation and sustained success in a competitive market. "customer first, company second" and how this approach impacts sales success and employee happiness. Discover the critical need for a strong work ethic, the dangers of ...
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2 months ago
43 minutes

Battle Scars of a SaaS Leader
How to WIN the Aussie SaaS Market
In this insightful episode, we dive deep into the Australian SaaS market with Alex Wilson, author of a new paper for SaaS companies looking to expand into Australia. Alex shares his journey from London to Australia, highlighting the unique "barbell effect" of the Australian market, where 95% of companies are SMBs, while a small oligopoly of 5,000-6,000 enterprises drive 60% of SaaS revenue. Learn about different sales motions for market entry, the importance of localization (especially regar...
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3 months ago
33 minutes

Battle Scars of a SaaS Leader
The Revolution in Sales: Are You Ready for the AI Workforce?
James Bergl is join by Rosh Singh from Relevance AI, revealing how their "AI workforce" is empowring sales teams . Discover insights on building adaptable, resilient, and curious sales talent. A must-watch for leaders aiming to redefine growth through intelligent automation, scaling with the quality of ideas, not just headcount. Have a thought about this episode? Let's chat
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4 months ago
47 minutes

Battle Scars of a SaaS Leader
From Sales Rep to Leading APAC Sales at a Billion-Dollar Company
A masterclass in personal growth and sales leadership! Alex Haddon shares her extraordinary journey from equine sciences to leading APAC sales for a billion tech unicorn. In this captivating episode, she reveals how her entrepreneurial spirit and adaptability propelled her through diverse industries to become a top performer in SaaS sales. Learn how Alex leveraged her unique background to excel in the fast-paced world of tech startups. #TechSales #CareerTransition #salesleadership&n...
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10 months ago
42 minutes

Battle Scars of a SaaS Leader
From Engineer to CEO: How Brian Swift CRACKED the Code to Success!
Brian Swift is a dynamic tech leader who transitioned from hardware engineering at Samsung to influential product and go-to-market roles at major tech companies including Twitter, Atlassian, Safetyculture and Dovetail. He is now the CEO and co-founder of Twine, a SaaS business that connects the dots across customer calls, CRM, and roadmap to deliver crucial information to the right people when they need it most. In this insightful conversation, Brian shares his evolution from engineer...
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11 months ago
47 minutes

Battle Scars of a SaaS Leader
From Startup to Global VP: Mastering Modern Sales Leadership
James sits down with Andrew Morton to learn about his journey from a Nova Scotia farm to a cybersecurity sales leader, showing that success often comes from unexpected places. Starting with technical roles, he quickly discovered his talent for sales in the early 2000s. Now as VP of Global Sales at DefenseX, Andrew has consistently turned difficult situations into opportunities for growth. What makes Andrew's story special is his ability to adapt and grow in the fast-changing tech world. ...
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11 months ago
44 minutes

Battle Scars of a SaaS Leader
How to Build a Loyal Community of Brand Advocates with Rob Rae
Rob Ray, a 25-year MSP veteran who transformed from accountant to industry titan by breaking every conventional sales rule. In this value-packed episode, James discusses Rob's exact strategies to build one of the largest MSP communities and why traditional business growth methods are failing in today's market. He shared his unexpected strategies that turned regular clients into fierce advocates. A must-listen for MSP owners, sales leaders, and tech entrepreneurs who want to build las...
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1 year ago
45 minutes

Battle Scars of a SaaS Leader
Cybersecurity Startup Growth: 0 to 300 Customers in 3 Years
What if the key to success in entrepreneurship lies in mastering every aspect of a business? In this episode of Battle Scars of a Sales Leader, James sits down with Dane Meah, CEO and co-founder of MyCISO, a cutting-edge security SaaS platform. Dane shares his incredible journey from selling plastic bags to building a successful cybersecurity company. In this episode you'll learn: Dane's early career experiences and his passion for sales and business improvementThe serendipitous path that l...
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1 year ago
51 minutes

Battle Scars of a SaaS Leader
Disrupting Markets and Scaling Up with Matt Loop
Building a robust team culture and scaling tech companies internationally is no easy task. Learn from Matt's inspiring journey from his early days at Salesforce to impactful roles at LinkedIn, Slack, and now Rippling. We promise you'll gain invaluable insights into the importance of passion, perseverance, and smart risk-taking in the fast-paced world of technology and cloud computing. Matt shares practical advice on navigating career opportunities in tech, offering a behind-the-scenes look ...
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1 year ago
44 minutes

Battle Scars of a SaaS Leader
From Imposter Syndrome to Leading a 65-Person Sales Team | Samantha Borg
James sits down with Samantha Borg, Senior Director of Sales for Kaseya in Australia and New Zealand, to uncover the secrets of successful sales leadership. Samantha reveals the lessons she's learned during her seven-year tenure at Datto and Kaseya, including the importance of hard work, passion, and building a team that thrives on trust and accountability. Navigating the challenges of imposter syndrome, managing a large go-to-market team post-Datto acquisition, and dealing with...
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1 year ago
31 minutes

Battle Scars of a SaaS Leader
We unpack how Asian startups use Australia as a Western test bed, the cultural signals that make or break sales, and a repeatable path to validate markets fast. We also explore investor perspectives, AI reality versus hype, and why commitment on the ground beats fly-in fly-out. • why Australia appeals for first Western expansion • how to read Australian sales language and build trust • reverse‑engineering competitor playbooks for fast intel • when Australia’s TAM is too small and what to do ...