Ep 39: The Secrets to Customer Success in 2026 with Guest, Craig Bloom

This Week's Episode:In this episode of Software Sales Simplified: Move to Success, Kevin and Matt sit down with Craig Bloom, an expert in SaaS onboarding and customer success. They explore the importance of customer engagement and alignment between sales and service delivery teams. Craig shares his journey from film and advertising to customer success, highlighting how storytelling strengthens customer interactions. He explains how effective onboarding, proactive engagement, and early alignment on customer objectives improve satisfaction and retention. The conversation also emphasizes how curiosity about a customer’s business leads to better outcomes, with practical advice on fostering a culture of curiosity to drive long-term success.About our Guest - Craig Bloom:Craig Bloom is a post-sale leader operating at the intersection of software sales, onboarding, and customer value. He leads Americas Onboarding at Contentsquare, overseeing enterprise implementations and building the operating rhythms, handoffs, and cross-functional accountability that drive adoption, retention, and expansion. Throughout his career, Craig has led Enterprise Customer Success teams, improved net retention, and partnered closely with Sales and Solutions to align expectations and de-risk delivery. He also brings a background in behavioral analytics from Clicktale and consulting, helping teams identify journey friction and turn insights into measurable improvements.Where to Learn More About Craig:You can find Craig’s profile on LinkedIn: Craig Bloom on LinkedInChapters00:00 Introduction01:13 The Importance of Engagement03:27 Meet Craig: A Journey from Storytelling to SaaS06:04 The Role of Onboarding08:19 Using Storytelling to Enhance Customer Communication10:31 Engagement vs. Enablement12:30 Building Trust Through Curiosity17:43 The Risk of Poor Engagement20:50 Creating Effective Engagement24:26 Bringing in Experts for Effective Execution25:31 Understanding Customer Objectives27:43 Building a Maturity Assessment29:29 The Importance of Communication30:46 Identifying Implementation Challenges32:28 Creative Solutions for Resource Constraints33:51 The Risk of Poor Engagement Plans36:55 The Role of Communication in Customer Success39:23 Positioning Professional Services Effectively42:40 Fostering a Culture of Curiosity49:51 See you next episode! About Software Sales Simplified:Visit us at:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.strategicsalesoptimization.com/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Follow us on Linkedin:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://tinyurl.com/2tcx7mjx⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Send us your questions at ⁠- ⁠⁠⁠⁠⁠⁠⁠⁠[email protected]⁠⁠⁠⁠⁠⁠⁠⁠⁠"What is a Sales Engineer?" - Education Series on YouTube:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.youtube.com/playlist?list=PLxuHbkRfIWtVj_Hg1GYBIg-o5M-icJLn0⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Get Your Copy of "Winning Faster"!Available Here:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.strategicsalesoptimization.com/move-book⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Why Listen to Software Sales Simplified?Make Software Sales Simplified: MOVE to Success, your go-to podcast for mastering enterprise software sales through authentic customer engagement and actionable consulting insights. Join us for each episode as we break down proven strategies and real-world experiences to help you build trust, close deals, and drive long-term success along your Enterprise Software Sales or Consulting journey.Copyrighted Broadcast:Thank you for tuning in to Software Sales Simplified: MOVE to Success. This podcast is produced by and is the sole property of Strategic Sales Optimization LLC, copyright 2025 and 2026. Reproduction or use of this broadcast in whole or in part without express written permission from Strategic Sales Optimization LLC is strictly prohibited. All rights reserved.