Customer Success Playbook PS3 E50 - Joe Di Grande - Your CS Tech Stack

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Gear up for an energizing discussion on tech stacks and smart scaling! In this midweek episode of the Customer Success Playbook, Kevin Metzger and Roman Trebon welcome Joe Di Grande back to tackle a pressing issue: bloated CS tech stacks. Joe shares why so many organizations fall into this trap and delivers actionable advice on how to avoid or fix it. From building cross-functional committees to starting tech ops planning early, Joe's wisdom is essential for anyone striving to build a lean, mean customer success machine.

Detailed Analysis: Joe Di Grande's return to the Customer Success Playbook is like having your favorite professor hand you the cheat sheet to a passing grade. In this session, he unpacks why bloated tech stacks happen: a lack of operational foresight, siloed decision-making, and the absence of data-first strategies. Acquisition fever might keep the lights on, but without systems thinking, organizations find themselves in a tangled mess of redundant tools.

Joe highlights a proactive cure: form a cross-functional committee that includes sales, marketing, CS, and product voices. Bonus points if you find your "ops-minded" champions by tapping the power users of existing tools! His approach is practical, tactical, and refreshingly unpretentious.

For those starting from scratch (aka "dream budget approved!" scenarios), Joe delivers a fantasy list of tech essentials: a reliable CRM, a centralized data warehouse, sales engagement tools, data enrichment platforms, marketing automation solutions, and customer success platforms—all strategically selected to foster scalability and transparency.

Joe’s core advice? Think operations early, communicate often, and let your data be the thread tying it all together. It's a masterclass in balancing ambition with operational excellence for any customer success playbook.

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You can also find the CS Playbook Podcast:
YouTube - @CustomerSuccessPlaybookPodcast
Twitter - @CS_Playbook

You can find Kevin at:
Metzgerbusiness.com - Kevin's person web site
Kevin Metzger on Linked In.

You can find Roman at:
Roman Trebon on Linked In.