Josh Peterson sits down with Jim Smith, founder and CEO of Proper Sky, to unpack the messy, real work of scaling an MSP. From losing 90% of MRR and rebuilding, to building a sales engine (HubSpot + PSA), hiring leaders, and living the mantra “Who, not what,” Jim shares what actually moves the needle.n this From the Trenches episode, Josh Peterson talks with Jim Smith of Proper Sky (https://propersky.com) about growing an MSP the hard—but right—way.
Jim traces his path from one-big-client risk (and the painful collapse that followed) to rebuilding with discipline: owner-led sales, a clear message (“IT the proper way”), and purpose-built systems in HubSpot (https://www.hubspot.com) tied to ConnectWise PSA (https://www.connectwise.com). If you’re wrestling with churn, pipeline, or leadership layers, this conversation is a blueprint for maturing your MSP without losing your soul. Mentioned: IT Nation (https://www.connectwise.com/it-nation) and Entrepreneurs’ Organization (https://www.eonetwork.org). For proven MSP playbooks—pricing, sales comp, service KPIs, and the Vision system—tap the resources at https://beringmckinley.com
[MSP growth] [MSP sales process] [HubSpot CRM for MSP] [ConnectWise PSA] [MSP onboarding] [MRR diversification] [service gross margin] [SDR/BDR for MSPs] [MSP marketing] [EOS for MSPs] [who not what hiring] [owner-led MSP selling] [top-down vs bottom-up sales] [building MSP sales infrastructure] [effort vs results in sales] [IT Nation networking] [HubSpot–ConnectWise integration] [MSP pipeline metrics] [client NPS and eNPS targets] [avoiding single big client risk]
#msp , #FromTheTrenches, #ProperSky,#mspgrowth ,#mspsales ,#hubspotcrm ,#connectwise ,#SDR,#bdr ,#mrr ,#onboarding , #WhoNotWhat, #eos , #ITNation,#entrepreneurship #Entrepreneurship, #BeringMcKinley
Popular Podcasts
Dateline NBC
Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com
Stuff You Should Know
If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.
My Favorite Murder with Karen Kilgariff and Georgia Hardstark
My Favorite Murder is a true crime comedy podcast hosted by Karen Kilgariff and Georgia Hardstark. Each week, Karen and Georgia share compelling true crimes and hometown stories from friends and listeners. Since MFM launched in January of 2016, Karen and Georgia have shared their lifelong interest in true crime and have covered stories of infamous serial killers like the Night Stalker, mysterious cold cases, captivating cults, incredible survivor stories and important events from history like the Tulsa race massacre of 1921. My Favorite Murder is part of the Exactly Right podcast network that provides a platform for bold, creative voices to bring to life provocative, entertaining and relatable stories for audiences everywhere. The Exactly Right roster of podcasts covers a variety of topics including historic true crime, comedic interviews and news, science, pop culture and more. Podcasts on the network include Buried Bones with Kate Winkler Dawson and Paul Holes, That's Messed Up: An SVU Podcast, This Podcast Will Kill You, Bananas and more.