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Building a successful Customer Success (CS) career and securing a seat at the executive table is no small feat. Once you’re there, keeping that seat requires constant evolution, strategic thinking, and strong cross-functional relationships. During a recent webinar with Rod Cherkas, CEO of HelloCCO, and Gemma Cipriani-Espineira, Founder of CS Angel, they shared key strategies for post-sale leaders to solidify their position. Here's a recap of how Rod and Gemma’s collaboration began, and three actionable insights to help you stay at the executive table.
The Backstory: How Rod and Gemma First Collaborated
Rod, a highly regarded consultant and author of REACH: A Framework for Driving Revenue Growth from Your Existing Customers, has led post-sales at major companies like Gainsight, Marketo, RingCentral, and Intuit. He first connected with Gemma in 2021 when she hosted CCO Secrets, a YouTube series dedicated to helping more CS leaders become Chief Customer Officers. They quickly found common ground in their mission to elevate post-sale leaders.
Their collaboration continued with Rod’s The CCO Playbook, which provides a step-by-step guide for CS leaders to secure executive roles. Gemma’s insights, particularly in the challenges CS leaders face when advocating for their seat at the executive table contributed to the book’s preface. Fast forward to today, and their combined expertise is a powerful resource for anyone aspiring to excel in post-sale leadership. Here are 3 tips from their pay it forward webinar, sponsored by Grey Space Consulting.
1. Master the Art of Strategic Communication and Prioritization
Rod emphasized that communicating your strategic vision effectively is critical to maintaining your seat at the executive table. This includes being able to align your work with company-wide objectives and clearly demonstrating how your initiatives drive financial impact. Here are some practical steps:
Create a Strategic Roadmap: Just like product teams, CS leaders should develop a roadmap that highlights key initiatives, expected outcomes, and alignment with the company’s financial goals.
Build Strong Relationships with Finance: Rod advised that CS leaders must understand the financial decision-making process. Develop a close partnership with finance leaders to make sure your efforts translate into tangible, financial results. Learn from your sales counterparts on forecasting and inspection processes to bring more precision to your reporting.
Having a solid communication plan that connects your strategic initiatives to company metrics ensures that your voice is not only heard but trusted.
2. Leverage AI to Elevate Your Team's Efficiency
AI is transforming the way businesses operate, and CS is no exception. Both Rod and Gemma emphasized that AI isn’t about replacing jobs—it’s about enhancing them. Here’s how you can leverage AI to your advantage:
Integrate AI into Your Workflow: Experiment with AI tools that can handle repetitive tasks, like note-taking (e.g. UpdateAI) or converting customer feedback into actionable insights (e.g Bagel AI). This will allow your team to focus more on building customer relationships and driving growth.
Prioritize Data Hygiene: Clean and well-organized data is the foundation for successful AI implementation. Ensure your team is committed to maintaining data accuracy so that AI tools can deliver valuable insights.
By adopting AI, you demonstrate forward-thinking leadership, which is critical to remaining indispensable at the executive table in today’s rapidly evolving market.
3. Build Cross-Functional Relationships That Drive Results
The ability to collaborate across departments is essential for CS leaders. With so many departments that CS intersects with, Gemma polled the audience to determine where they currently focus their attention.
Rod highlighted three key relationships that CS leaders must focus on: sales, product, and finance. Here are actionable ways to strengthen these relationships:
Collaborate with Sales for Consistent Customer Experiences: Work closely with sales to ensure a smooth handoff and consistent messaging throughout the customer journey. This alignment can significantly improve customer retention.
Engage with Product for Market Feedback: Your customers are a valuable source of insights for the product team. Regularly share feedback to ensure customer needs are reflected in the product roadmap.
Partner with Finance to Understand the Numbers: Finance is crucial for making data-driven decisions. Rod recommended that CS leaders work with finance to ensure their work translates into the metrics that matter most—such as customer lifetime value and retention.
Evolving Role of the CS Leader
As customer acquisition becomes increasingly difficult, the role of a CS Leader is more important than ever. Rod pointed out that there’s growing pressure to expand revenue from existing customers by delivering exceptional customer experiences. According to a poll conducted during the webinar, 90% of attendees said their company already has a post-sales leader at the executive level—a clear indicator of the importance of this role.
However, Rod also highlighted the challenges that come with staying at the table. With shifting expectations for CS leaders, pressure to grow both revenue and profitability, and the unknown impacts of AI, navigating this landscape requires constant adaptation.
Ready to Learn More?
If you’re eager to dive deeper into Rod and Gemma’s discussion, register here to watch the webinar on-demand and check out Rod’s Strategic Roadmap and Goal Setting templates at rodcherkas.com/resources. Thank you to Rod Cherkas and our sponsors at Grey Space Consulting for paying it forward!
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