#19 – From the Trenches - MSP Growth - Sales, Structure & ‘Who Not What’ (Jim Smith)

In this From the Trenches episode, Jim Smith, founder of Proper Sky, joins Josh Peterson to share how resilience, structure, and hiring the right people transformed his MSP after losing 90% of recurring revenue in 2015. Jim discusses rebuilding Proper Sky through leadership evolution, diversification, and creating a scalable sales and management framework.

He offers practical lessons on empowering teams, avoiding client dependency, and building sales compensation plans that reward effort as well as results. Jim’s story captures what it means to shift from technician to visionary CEO—focusing on “who” to hire rather than “what” to do.

For MSPs navigating leadership and sales growth, explore our resources on leadership lessons on ego and partnerships, building a scalable MSP sales process that actually closes, and hiring for culture fit and long-term growth in your MSP.

For more episodes and insights, visit the BMK Vision Podcast main page →

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Episode Highlights

• 00:00:00 – Losing 90% of MRR and rebuilding through resilience and structure.
• 00:04:50 – Moving from control to empowerment—hiring smarter people.
• 00:24:21 – Diversifying clients and avoiding overdependence on one source.
• 00:28:12 – Why MSP owners must lead sales and invest in marketing.
• 00:45:16 – Creating structured compensation that rewards sales effort.
• 01:04:20 – “Who not what”: hiring for capability and culture, not tasks.

About the Guest

Jim Smith is the founder and CEO of Proper Sky, a managed IT services firm helping organizations improve operational efficiency and security. Jim brings over two decades of experience in IT and entrepreneurship, focusing on leadership, sales, and building strong teams.

🌐 Connect with Jim on LinkedIn →

About the Host

Josh Peterson is the CEO of Bering McKinley and host of the BMK Vision Podcast. Through the From the Trenches series, Josh showcases MSP leaders who have built resilient, people-first organizations through smart strategy and authentic leadership.

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