From Imposter Syndrome to Leading a 65-Person Sales Team | Samantha Borg

Battle Scars of a SaaS Leader

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 underperformers—Samantha opens up about the emotional and operational aspects of sales leadership. Her candid reflections on balancing empathy with assertiveness and the demanding nature of VC-backed software companies are eye-opening. Learn how she leverages fundamental sales processes and mentorship to overcome these obstacles and lead her team to success.
Lastly, discover the strategies Samantha employs to hit sales targets, understand the path to deal closures, and maintain a cohesive team culture amidst significant acquisitions. Drawing inspiration from experts like Simon Sinek and James Kerr, she discusses eliminating organizational toxicity and aligning team goals. Tune in for invaluable insights that aspiring sales leaders won't want to miss, and connect with Samantha for more guidance on LinkedIn, where she actively engages with the professional community.

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Chapters

1. Battle Scars of Sales Leadership (00:00:00)

2. Navigating Sales Leadership and Success (00:02:58)

3. Nurturing Growth Through Leadership Challenges (00:11:32)

4. Sales Leadership Operations and Trust Building (00:16:25)

5. Typical Day in Sales Leadership (00:21:24)