Season 3 Episode 1 - Navigating Cyber Insurance with Tim Stephenson from SherpaTech

Season 3 Episode 5 – The Expert Season Halfway Recap with Kayla and Pete

Kayla and Pete pause halfway through Season 3 to reflect on everything covered so far in the Expert Series.   From navigating insolvency and restructuring with Bryn Hardwood, to ISO certifications and AI governance with Jason Maricchiolo, cyber insurance with Tim Stephenson from SherpaTech, and the people and culture conversation with Carla Canning, this episode brings it all together.   They share the key takeaways from each guest, what surprised them, and what they are personally applying to their own businesses, before providing a preview of the four expert guests still to come in the back half of the season.

Season 3 Episode 4 – Leadership, Culture and Performance in MSPs with Carla Canning

Carla Canning, founder of Connect Lead Achieve, joins Kayla and Pete to unpack the people challenges that come with growing a business. With a background in HR, Carla shares a practical perspective on building high-performing teams, exploring why employees leave, the gap between intention and action, and the challenges of managing performance and leadership.

Season 3 Episode 3 - How ISO & AI Governance Are Changing MSPs with Jason Maricchiolo

Jason Maricchiolo, founder of ISO 365, joins Kayla and Pete to unpack what ISO compliance really means for MSPs and IT providers. From ISO 27001 and quality standards to AI governance and cyber insurance, this episode explores how businesses can use compliance to build trust, improve processes, and stand out in a crowded market.

Season 3 Episode 2 – Cash Flow, Insolvency and Restructuring in Tech with Bryn Hardwood

Bryn Hardwood, a restructuring specialist at Carbon Corporate Restructuring with a background in accounting and advisory, joins Kayla and Pete to discuss what really happens when cash flow pressure escalates inside a tech business. From navigating ATO debt to understanding director responsibilities, this episode unpacks the practical options available to business owners and why acting early can make all the difference.

Season 3 Episode 1 - Navigating Cyber Insurance with Tim Stephenson from SherpaTech

Season 3 of Two Sides of the Table kicks off with Tim Stephenson, CEO of SherpaTech. In this episode, we unpack the realities of cyber insurance—what it covers, what it does not, and how MSPs and IT businesses can better manage risk in a changing landscape.