25 Weeks Left. What Will You Fix First?

Mid-Year Business Reflection

We’ve officially turned the summer corner. We have only 25 weeks left to make material impacts before the year’s end. That number feels both energizing and clarifying.

The first half of 2026 has reinforced a few truths across B2B SaaS. Growth is still possible, but it is no longer being rewarded when it is disconnected from efficiency, retention, and measurable customer value. AI is no longer a side conversation. It is reshaping how teams sell, serve, forecast, renew, and expand. And customer success is continuing to move from a relationship-led function to a value-led growth engine.

So what have we learned so far? First, retention is still the revenue strategy. Boards, investors, and operators are watching GRR, NRR, churn risk, expansion potential, and customer health with more scrutiny than ever. Second, AI works best when it is connected to clean processes, aligned teams, and clear business outcomes. Buying another tool will not fix a broken journey. Third, the companies pulling ahead are not just adding automation. They are redesigning how marketing, sales, customer success, professional services, and revenue operations work together across the full customer lifecycle.

That is the final-half opportunity. Before the year closes, now is the time to ask: Where are customers still experiencing friction? Where are renewals being managed too reactively? Where are handoffs between teams slowing down time to value? Where could AI remove manual work, improve visibility, or help teams act faster? Where do we need a clearer playbook for expansion? The next 25 weeks do not require a complete reinvention. They require focus. Pick the customer moments that matter most. Tighten the systems that support them. Align your teams around the same revenue outcomes. Then execute with the kind of discipline that turns customer value into durable growth.

Upcoming Industry Events

• CS100 AI Summit (September 8-9, 2026): The Immersive AI Experience for Customer Success Leaders. An intimate, hands-on bootcamp on the mountain at Sundance to build real AI agents side-by-side with your peers and world-class faculty.
• GTM 2026 (September 28 - October 1, 2026 in New York City): 1,000 GTM operators. 4 days. One room. Come for the strategies. Stay for the conversations. For executive (VP+) GTM operators.
• At The Top Ops Accelerator (November 4, 2026 in San Francisco): A private executive forum for 120 women leading Post-Sales Organizations. A half-day event for Senior Directors, VPs, and C-suite leaders across Customer Success, Support, and Revenue Operations. By application only.

Roles on the Radar

• Renewals Manager at GitLab
• Director of Customer Success, APAC - Industrial at Seeq
• Head of Customer Success at Hermetic AI - Mia

Molecule Maker: Featured Leader

Meet Josh Livesay, Director, Client Success at Rithum.

Josh's fun fact: I spent nearly a decade in New York City before moving back to North Carolina, and that mix of big-city energy and Southern perspective has heavily influenced my leadership style. I’m also a proud dad of two boys, and when I’m not thinking about customer success or AI, I’m usually spending time with them, my favorite and most important role by far.

Josh's current curiosity: I'm incredibly curious about how AI will reshape leadership and Customer Success over the next five years. Specifically, I'm fascinated by how we can use AI to improve forecasting, identify customer risk earlier, and give teams more time to focus on strategy, creativity, and human connection.

Systems Josh has in progress: I'm currently building systems around scalable, revenue-focused Customer Success. That includes creating frameworks for customer health, forecasting, and expansion identification that help teams move from reactive account management to proactively driving business outcomes. I'm also experimenting with AI workflows to automate operational tasks and accelerate decision-making.

A recent challenge Josh has solved: One of the most rewarding challenges I've tackled recently was leading the integration of global Renewals and Customer Success teams into a single operating model. We redesigned processes, clarified accountability, and implemented forecasting discipline that gave leadership much better visibility into retention risk and revenue opportunities. Watching the teams embrace a more commercially focused approach and seeing predictability improve has been incredibly fulfilling.