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#19 – From the Trenches - MSP Growth - Sales, Structure & ‘Who Not What’ (Jim Smith)
From the Trenches with Jim Smith digs into the messy middle of MSP growth—hiring, sales, and leadership. Join host Josh Peterson and Proper Sky founder Jim Smith for candid lessons you can apply immediately to build a stronger, more resilient MSP.
✅ Enjoyed this episode?
Like, subscribe, and share your biggest takeaway below.
https://beringmckinley.com/bering-mckinley-podcast-blog
Jim Smith, founder and CEO at Proper Sky, shares the real story behind scaling an MSP—from losing 90% of MRR and rebuilding, to shifting from “do it all” owner to vision-led leader. You’ll hear how he reframed growth around people, systems, and clear KPIs rather than heroics and hustle.
👉 The “who, not what” rule: why hiring people smarter than you accelerates scale and reduces owner dependency
👉 Owner-to-owner selling vs. “talking tech”: how to craft messaging that resonates with business outcomes
👉 Building a sales engine: effort vs. results, activity ladders (FTA → discovery → proposal → close), and realistic comp structure
👉 Avoiding concentration risk: lessons from losing a major client and the cash discipline that followed
👉 Onboarding sets the tone: protecting service capacity, managing chaos, and measuring NPS/ENPS alongside gross margin
This episode blends practical frameworks (KPIs, sales stages, onboarding capacity planning) with field-tested wisdom on leadership, empowerment, and process. If you’re stuck between 10–25 employees or rebuilding your sales function, this conversation gives you a concrete path to get unstuck—without burning out your team.
“Visit https://beringmckinley.com for more MSP resources.”
🔗 Resources & Links
• Jim Smith - Proper Sky: https://propersky.com
• Bering McKinley MSP Consulting: https://beringmckinley.com
⏱️ Chapters
00:00 – Why “From the Trenches”: unscripted lessons for MSPs
00:23 – Jim Smith’s path: entrepreneurship, Peace Corps, and Proper Sky
03:06 – From tech-doer to leader: empowerment vs. control
07:14 – Marketing missteps and the power of hiring experts
10:33 – Answers vs. questions: building decision-making muscle
15:42 – Setting 3 north-star KPIs (NPS, eNPS, 55% SDGP)
19:39 – Surviving a 90% MRR loss: cash discipline and diversification
27:20 – Sales realities: activity, ICP, and deal math that works
34:10 – Tooling up: moving to HubSpot and aligning process
44:28 – Effort vs. results: the activity ladder for reps
52:17 – Inside vs. outside roles and why first calls matter
1:04:01 – Final takeaway: “Who, not what.”
🔍 Primary Keywords
msp sales process, msp leadership, msp onboarding, connectwise psa, hubspot for msp, service gross margin
🔍 Secondary Keywords
msp marketing, customer nps, employee engagement, sales compensation, activity-based selling, concentration risk
#️⃣ Hashtags
#beringmckinley #bmkvisionpodcast #msp #managedservices #mspgrowth #mspsales #salesprocess #connectwise #hubspot #onboarding #customerexperience #nps #leadership #entrepreneurship #servicedelivery #grossmargin #owneroperator #fromthetrenches
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By Josh PetersonFrom the Trenches with Jim Smith digs into the messy middle of MSP growth—hiring, sales, and leadership. Join host Josh Peterson and Proper Sky founder Jim Smith for candid lessons you can apply immediately to build a stronger, more resilient MSP.
✅ Enjoyed this episode?
Like, subscribe, and share your biggest takeaway below.
https://beringmckinley.com/bering-mckinley-podcast-blog
Jim Smith, founder and CEO at Proper Sky, shares the real story behind scaling an MSP—from losing 90% of MRR and rebuilding, to shifting from “do it all” owner to vision-led leader. You’ll hear how he reframed growth around people, systems, and clear KPIs rather than heroics and hustle.
👉 The “who, not what” rule: why hiring people smarter than you accelerates scale and reduces owner dependency
👉 Owner-to-owner selling vs. “talking tech”: how to craft messaging that resonates with business outcomes
👉 Building a sales engine: effort vs. results, activity ladders (FTA → discovery → proposal → close), and realistic comp structure
👉 Avoiding concentration risk: lessons from losing a major client and the cash discipline that followed
👉 Onboarding sets the tone: protecting service capacity, managing chaos, and measuring NPS/ENPS alongside gross margin
This episode blends practical frameworks (KPIs, sales stages, onboarding capacity planning) with field-tested wisdom on leadership, empowerment, and process. If you’re stuck between 10–25 employees or rebuilding your sales function, this conversation gives you a concrete path to get unstuck—without burning out your team.
“Visit https://beringmckinley.com for more MSP resources.”
🔗 Resources & Links
• Jim Smith - Proper Sky: https://propersky.com
• Bering McKinley MSP Consulting: https://beringmckinley.com
⏱️ Chapters
00:00 – Why “From the Trenches”: unscripted lessons for MSPs
00:23 – Jim Smith’s path: entrepreneurship, Peace Corps, and Proper Sky
03:06 – From tech-doer to leader: empowerment vs. control
07:14 – Marketing missteps and the power of hiring experts
10:33 – Answers vs. questions: building decision-making muscle
15:42 – Setting 3 north-star KPIs (NPS, eNPS, 55% SDGP)
19:39 – Surviving a 90% MRR loss: cash discipline and diversification
27:20 – Sales realities: activity, ICP, and deal math that works
34:10 – Tooling up: moving to HubSpot and aligning process
44:28 – Effort vs. results: the activity ladder for reps
52:17 – Inside vs. outside roles and why first calls matter
1:04:01 – Final takeaway: “Who, not what.”
🔍 Primary Keywords
msp sales process, msp leadership, msp onboarding, connectwise psa, hubspot for msp, service gross margin
🔍 Secondary Keywords
msp marketing, customer nps, employee engagement, sales compensation, activity-based selling, concentration risk
#️⃣ Hashtags
#beringmckinley #bmkvisionpodcast #msp #managedservices #mspgrowth #mspsales #salesprocess #connectwise #hubspot #onboarding #customerexperience #nps #leadership #entrepreneurship #servicedelivery #grossmargin #owneroperator #fromthetrenches