If your Customer Success (CS) team feels stretched thin, you’re not alone. Many CS leaders are being asked to do more with less, often buried in admin work that leaves little time for the relationships that matter most.
That’s the challenge we discussed recently on [Un]Churned, the number one podcast for customer retention, hosted by Josh Schachter, SVP of Strategy and Market Development at Gainsight. In the episode, “How a 5-Person Team Built 150 AI Workflows That Changed an Entire Company”, Josh spoke with Colin Slade, SVP of AI Strategy and Customer Success at Cloudbeds, who faced that exact reality.
When Cloudbeds’ post-sales organization hit 120% capacity with no budget and declining efficiency, Colin made a bold move: he rebuilt the operation around AI. The result? A team with greater capacity, higher morale, and a renewed focus on strategic relationships.
Colin didn’t just adopt AI—he reimagined how Customer Success could work alongside it. Here’s how you can do the same.
Before You Automate, Redefine the Work
You’ve probably heard the advice: “Let AI handle the repetitive stuff.” This way of thinking is the foundation for everything that comes next. The difference between teams that talk about AI and teams that transform with it starts with one question: What should humans stop doing?
Spend time shadowing your CSMs or asking where their hours actually go (not where the org chart says they should). You’ll likely find that much of their day is spent on tasks that don’t need creativity, judgment, or empathy. They need consistency, speed, and pattern recognition—the things AI does best.
Hand these to AI: sentiment analysis, ticket triage, meeting transcription, follow-up emails, health-signal monitoring, knowledge-base searching, and escalation alerts.
Keep these human: complex problem-solving, relationship building, strategic conversations, and proactive outreach guided by AI-driven insights.
When you get that balance right, your team shifts from executing playbooks to shaping outcomes. Once you’ve clarified that balance, the next step is focus. It may sound unconventional, but Cloudbeds’ experience shows that dedicating even part of your CS Ops team to AI initiatives can create outsized results. You don’t need to hire new specialists, just realign the ones you have.
Cloudbeds defined the following key roles to keep momentum going:
- AI Visionary: An executive champion who stays curious about what’s possible, removes roadblocks, and keeps leadership aligned.
- AI Operators: Operational experts who can learn to build and iterate workflows—no engineering degree required.
- Knowledge Masters: Subject-matter experts who validate AI outputs and ensure workflows match real-world processes.
- Project Lead: A connector who coordinates progress and keeps initiatives moving.
Your team doesn’t need to drop everything, just focus on quick, high-impact AI wins. At Cloudbeds, short sprints delivered early results that built confidence fast and turned curiosity into company-wide adoption.
Build, Learn, and Scale What Works
Your first AI workflow won’t be perfect but that’s part of the process. At Cloudbeds, the team’s early projects were ambitious but overengineered. Real progress began when they focused on quick, outcome-driven wins that solved specific problems.
Colin recommends that your team starts with simple tasks. Experiment with workflows that tackle one clear use case, like flagging frustrated customers or summarizing support conversations. Small, fast wins build credibility and spark new ideas for what’s next.
However, experimentation doesn’t always mean starting from scratch. Solutions like Gainsight’s Atlas AI Agents and Staircase AI provide a head start with pre-built intelligence, context, and workflows that can be customized to your business. They let you test, learn, and scale faster, without the heavy lift of building everything in-house.
Whether you’re building your own workflows or applying pre-built solutions, small experiments are the foundation of lasting change. Each one helps your team learn faster, refine what works, and build confidence in the process.
Redesign the Team (And the Mindset)
As automation scales, your org chart will evolve. However, the biggest shift can often be more emotional than structural.
Cloudbed saw that as AI introduces new capacity, roles naturally start to change. Strategic CSMs spend more time on relationships and planning, supported by AI-driven insights. CS Ops became an AI Solutions Team, focused on building and maintaining workflows. Support transitioned from volume processing to specialist consulting. Training and Enablement turned its attention to helping both customers and internal teams make the most of these new tools.
Change like this can be exciting, but also unsettling. It’s normal for your team to wonder what it means for their careers. The truth is, AI doesn’t replace people; it redefines how their talent is used.
To make that shift successful:
- Lead with clarity. Frame AI as a support system, not a threat.
- Show, don’t tell. Demonstrate small wins before rolling out big changes.
- Celebrate early adopters. Share their results publicly and build momentum through proof.
- Repeat the “why.” The goal is better work, not fewer people.
At Cloudbeds, these principles led to higher morale, less burnout, and a renewed sense of purpose. AI doesn’t just scale your business, it re-energizes your people.
Lead the Change That’s Already Underway
When Cloudbeds hit 120% capacity with no budget, the traditional model simply couldn’t keep up. That constraint became their catalyst. By reimagining how work gets done, they built a more energized, efficient, and human-centered organization. In this new org, AI handles the repetitive tasks and people focus on what truly drives success: relationships, strategy, and empathy.
This is the future of Customer Success. Not replacing humans with AI, but redesigning work so humans can finally do what they do best.
To hear the full story—including specific workflow examples, lessons learned, and practical advice for CS leaders starting their AI journey—listen to the full [Un]Churned episode with Colin Slade. Subscribe wherever you get your podcasts to stay ahead in the era of AI-powered Customer Success.
