In the second episode of Vitally's video series One Vital Question, five Customer Success leaders share the innovative strategies that transformed how their teams operate. From revamping data storytelling to bridging sales and CS, each initiative offers insights into how strategic change drives customer retention and business growth.
Key Takeaways:
- Data storytelling can replace static dashboards to create more engaging and actionable QBRs.
- Customer health scores help CS teams proactively manage risk and align departments.
- Customer advocacy content amplifies both user success and internal CSM value.
- Career pathing boosts CS team morale, retention, and performance.
- Cross-functional branding like "Growth Squads" enhances collaboration and revenue.
Featured Participants:
- Michi Pezeshki / Chief Customer Officer and CoFounder at RecastSuccess
- Sarah Steingraber / Former Customer Success at Vitally
- Marija Skobe-Pilley / Founder & Host, 'Women in Customer Success' Podcast
- Maranda Dzienkonski / Former Customer Success Executive at Datasembly
- Katie Bugas / Former Chief Customer Officer at Triptease
“We stopped showing data. We started telling stories.”
Michi Pezeshki, the Chief Customer Officer at RecastSuccess, led a transformation in how QBRs were conducted. Customers had been tuning out data-heavy sessions filled with charts and tables. The solution? Storytelling with data. By contextualizing spikes in engagement—like a surge during back-to-school season—teams empowered customers to retell those stories in internal budgeting meetings. This innovative Customer Success strategy required retraining but led to more meaningful conversations and deeper engagement.
“Customer health scores changed how we think about risk.”
Sarah Steingraber introduced comprehensive customer health scores in her B2B SaaS organization. Combining qualitative and quantitative inputs—from platform usage to CSM sentiment—these scores enabled teams to preemptively act before renewal crunch time. This Customer Success innovation created a shared understanding of account health across departments and changed the rhythm of proactive engagement.
“Our customers became the stars — and our CSMs, their champions.”
During her time at ClickUp, Marija Skobe-Pilley partnered with the marketing team to launch ClickUp Chronicles, a digital series showcasing how customers use ClickUp to transform their operations. From onboarding acceleration to company-wide transparency, the stories spotlighted not just outcomes, but the CSMs behind them. What started as a European initiative quickly scaled globally, generating pipeline and elevating advocacy to a strategic function—demonstrating Customer Success as a growth engine.
“Career pathing gave our team purpose — and boosted retention.”
While at Datasembly, Maranda Dzienkonski introduced clear career pathing to her CS organization, addressing a common gap: the uncertainty of ‘what’s next.’ By outlining expectations and behaviors required to advance, she fostered a happier, more stable team. Her guiding belief: happy teams lead to happy customers—and happy customers drive business growth. This reflects a strategic Customer Success best practice.
“The Growth Squad broke silos and boosted upsell revenue by 130%.”
During her time at Triptease as Chief Customer Officer, Katie Bugas initiated a cultural shift by rebranding Sales and CS as the Growth Squad. Though no structural changes were made, aligning incentives, goals, and regional collaboration led to a 130% upsell increase. The real win? A shared mentality. Sales and CS began celebrating wins and learning from losses together, fostering a unified growth engine and showcasing one of the most effective Customer Success strategies for cross-functional alignment.
Conclusion: The Future of Customer Success Is Cross-Functional, Strategic, and Human
These stories illustrate a larger trend in Customer Success transformation: evolving from reactive support to proactive growth engine. Whether it's through storytelling, data alignment, career development, or cross-departmental unity, these leaders prove that innovative Customer Success strategies create lasting impact on customer retention and business performance.
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