Everything is changing.
AI is doing actual work for your customers. Buyers are demanding outcomes-based pricing. The bar for what counts as "value" keeps rising. And customers are using ChatGPT to learn your product before they ever talk to your CSM.
The Customer Success playbook you've been running?
It's becoming obsolete in real-time.
But this isn't a story about CS getting harder. It's about CS finally becoming what it was always supposed to be: strategic.
From polite relationship management to commercial leadership. From reactive support to value creation. From a cost to justify to a function you cannot scale without.
Personally, I am more excited than I have been in years.
Because what comes next is bold.
- A model where value compounds as you scale, instead of leaking momentum.
- A GTM engine that actually earns its place as the second engine of growth.
- A CS career path that leads to the C-suite, not burnout.
Here's a deep-dive into my predictions for what 2026 will bring:
1️⃣ Fewer CSMs. Higher retention.
There's an iron law in Customer Success: retention drops as you scale.
At 50 customers, your CSMs knew everyone personally. Retention was 95%+. At 500 customers, each CSM manages dozens of accounts. Early warnings get missed. Retention drops to 88%. You hire more CSMs, but it never fully recovers.
The 2026 breakthrough: AI meets customers at the right moment with the right message without humans in the loop.
Usage drops. An AI agent reaches out within hours with personalised suggestions. Problem solved, or it escalates to a human with full context: what the customer tried, what didn't work, and what similar customers did to succeed.
More customers get a fully digital experience without sacrificing value. Your best CSMs focus on high-value accounts. Retention at scale becomes possible.
The teams that orchestrate AI and human touchpoints will achieve what was previously impossible: higher retention with fewer CSMs.
2️⃣ Expansion will follow usage, not hype.
The "expansion based on vision" era is over. Customers now ask for consumption reports before discussing expansion. Finance wants utilisation rates. Your champion must defend why they need more seats or credits when half the team isn't using what they bought.
The 2026 opportunity: When customers actively use your product, expansion becomes natural. "You're at 95% license utilisation and power users are hitting feature limits" beats "Here's what else you could do."
The winning teams will have real-time usage dashboards their CSMs actually understand and can translate into expansion plays.
3️⃣ Business reviews split: usage vs value.
QBRs try to accomplish too much at once: reviewing adoption, discussing strategy, covering health metrics, and pitching expansion in 60 minutes.
Nobody leaves satisfied.
The customer wanted strategy, but spent 30 minutes on dashboards they could have read themselves. The CSM wants to discuss recommendations, but without the data foundation, they fall flat.
The 2026 shift: Two distinct engagement types emerge. Usage reviews become quick, data-driven conversations based on adoption and health that happen monthly or become AI-updates. Value reviews become strategic sessions with executives focused on business outcomes, future planning, and expansion.
The CSMs who master this split will drive more usage and consumption and in turn, better results, and will have tighter alignment to strategy. Plus, they will have customers who actually look forward to meetings because each one has a clear purpose.
4️⃣ Voice of the Customer decks disappear.
Every quarter, someone spends two weeks building a 40-slide deck summarising customer feedback. It gets presented once, filed away, and ignored. Meanwhile, product makes decisions based on the three customers who shouted loudest in Slack.
The 2026 evolution: Customer intelligence gets embedded directly into workflows. Product managers see customer feedback in their planning tools. Pricing teams access value perception data in real-time. Sales gets win/loss insights without quarterly presentations.
The leaders who make customer voice operational rather than presentational will finally have the influence they've been asking for.
5️⃣ Value articulation becomes table stakes.
Your champion loves you. Usage is strong. But when the CFO asks "What would we lose if we didn't renew?" your champion struggles to answer in terms that matter to finance. "The team really likes it" doesn't work anymore. Neither does "We use it every day."
The 2026 practice: Value articulation becomes continuous, not a renewal tactic. Every milestone gets documented with business impact. Every QBR includes a running value scorecard. Customers become so fluent in articulating your value that when budget season arrives, they're defending you before finance questions the spend.
The teams who build value definition and measurement into standard procedures will see renewal rates that defy market trends.
6️⃣ Small, private circles replace "community".
Customer communities promised connection and peer learning. They delivered spam and crickets. Meanwhile, your best customers are already in small Signal groups sharing real talk about what actually works.
The 2026 model: Curated, invitation-only circles of 6-12 similar customers who actually want to know each other. Facilitated conversations with real agendas. Closed spaces where people can be honest about challenges.
These intimate networks create relationships customers don't want to lose.
7️⃣ The CSM role splits: strategist or orchestrator.
The jack-of-all-trades CSM model is breaking. You hired people to be strategic advisors, project managers, product experts, data analysts, and relationship builders simultaneously. It's an impossible job description.
The role was never only one job. It was three jobs masquerading as one.
Two distinct tracks emerge in 2026: Strategic CSMs focus on high-value accounts, business outcomes, and executive relationships. They're in fewer accounts but driving long-term value and expansion. Orchestrator CSMs manage operations, coordinate cross-functional teams, and ensure adoption and value delivery at scale.
The leaders who create clear career paths for both will finally hire for specific skills instead of searching for unicorns.
8️⃣ Strategic influence becomes the top CSM skill.
Product knowledge is commoditised. Customers ask ChatGPT how to use features. Best practices are documented. Implementation playbooks are automated.
What customers can't get from AI is someone who understands their business well enough to challenge their thinking, connect dots they're missing, and influence their strategy.
The 2026 investment: The CSMs who develop true strategic influence skills become exponentially more valuable. They're not just retaining accounts, they're becoming trusted advisors customers won't leave because they can't replace the strategic value (I am dropping a new guide on this in just a few weeks!)
This is the only defensible competitive advantage left.
9️⃣ LLM access will be basic. Purpose-built agents win.
Every CS platform is announcing "AI features." Most are just ChatGPT with limited access to your data. Generic CSM AI assistants that "answer questions about customers" are table stakes and not particularly valuable.
The 2026 differentiator: Purpose-built AI agents, plugged to the entirety of your data (calls, slacks, emails, support tickets, usage data etc), that do specific jobs with a high degree of expertise.
For example: An agent that analyses usage patterns and automatically flags expansion opportunities with reasoning. An agent that drafts strategic recommendations for struggling accounts based on playbook patterns learned from your best CSMs.
The leaders who figure out which specific workflows to build agents for will see actual productivity gains while competitors figure out what their generic AI should do.
🔟 Humans show up less. When they do, it matters more.
Customers don't want more meetings. They want problems solved and goals achieved. The weekly check-in that accomplishes neither is worse than no meeting.
AI and automation can handle updates, answer questions, and monitor health without calendars. The customer experience can actually improve with fewer meetings.
The 2026 balance: Every human interaction becomes intentional and high-impact. CSMs show up for strategic planning sessions, critical adoption inflection points, nurturing expansion, and crisis management. Everything else runs through automated workflows, self-service tools, and AI agents.
The teams who master this balance will deliver better customer experiences with fewer resources, proving that quality of interaction matters infinitely more than quantity.
The Future Is Already Being Built
Customer Success is finally becoming what it was always meant to be.
The teams who embrace these changes will reach retention rates that seemed impossible a few years ago, expansion that looks effortless, and influence that spans the entire company. And they'll do it with leaner teams doing work that actually matters.
This is the future I'm excited about building.
That's why I will be launching two new tools for CS professionals:
- A "CSM Skills in the age of AI" Guide, with a super robust set of skills, tools and AI prompts to help you win as a strategic CSM in 2026.
- A cohort-based workshop to help CS leaders navigate these shifts with the models, tools and conversations that will unlock a new era of CS.
If this newsletter resonated with you, you're exactly who I built this for. More details coming soon.
2026 will define the future of Customer Success.
Let's build it together.
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