Client Onboarding Success Stories To Learn From

I improved retention and onboarding success by making a change to the first step in the onboarding process. A few years (and a few companies) ago, I made a small tweak to the way we onboarded new customers—a tweak that ended up making all the difference. We stopped diving headfirst into the technical implementation. Instead, we started with what I called a Partnership Kickoff. This one shift transformed the customer experience, boosting retention and improving onboarding success rates. Here’s why: The Partnership Kickoff brought intention to the relationship right from day one. Instead of rushing to “get things done,” we: 1️⃣ Engaged all the key stakeholders in the partnership 2️⃣ Discussed goals and confirmed success criteria upfront 3️⃣ Set proper expectations on BOTH sides 4️⃣ Clarified roles and responsibilities for onboarding and beyond 5️⃣ Created space to ask questions and address concerns This wasn’t just a feel-good meeting. It was about getting ahead of risks, ensuring alignment, and setting the stage for success. Here’s the secret sauce: ⚫️ Set expectations early Sales aligned on the importance of this meeting, and CSMs communicated the who, what, and why in their first email. ⚫️ Use a New Customer Intake Form We asked customers to provide key information upfront—no assumptions or overreliance on Sales handoffs. ⚫️ Prep the right way Sending the kickoff deck in advance meant our meeting focused on conversation, not presentations. ⚫️ Lead with goals and expectations Capturing customer goals was the priority, setting the tone for how we’d measure success. ⚫️ Clarify next steps We left every kickoff aligned on what happens next and who’s doing what. The result? Customers felt heard, understood, and set up for success. It wasn’t magic, but it sure felt like it. That small change? It delivered BIG impact—the kind every CS leader dreams about. Are you being intentional about how you’re starting your partnerships? If not, maybe it’s time to rethink step one. ________ 📣 If you liked my post, you’ll love my newsletter. Every week I share my learning, advice and strategies from my experience going from a CSM to CCO. Join 12k+ subscribers of The Journey and turn insights into action. Sign up on my profile.

I almost killed the feature that drove the biggest MRR jump of my career. We were scaling fast — but churn was creeping in, onboarding was dragging, and our best features were buried. So I built something bold. And honestly, I hesitated to ship it. A gamified onboarding flow. Modeled after tradesmen. Not software users. It mirrored how contractors actually grow: Apprentice → Journeyman → Master Here’s how it worked — and why it worked: Step 1: Apprentice We taught users how to price a job using our price book. Because estimating is the first real win for a contractor. Behind the scenes, our data science team delivered hyperlocal pricing — based on real invoices that converted in similar markets. Step 2: Journeyman Once they created an estimate, we introduced our built-in payments feature. They could accept credit cards right inside the app — with lower fees than Square. It solved a core friction: getting paid faster. And it increased ARPU almost instantly. Step 3: Master After the first invoice, we unlocked a 30-day trial of Engage — our premium customer comms tool. Built on Twilio, it let contractors pull up estimates, invoices, and message customers in real time. It turned silent contractors into trusted pros. And silent trials into high-converting accounts. It felt risky. • Would tradesmen engage with gamification? • Would the “Apprentice” metaphor click? • Would this slow down onboarding? I almost pulled the plug. But we shipped it. And it helped drive: • 1,300% MRR growth • +30 point NPS jump • One of the biggest ARPU lifts we’d ever seen All because we stopped treating onboarding like a checklist — and started treating it like a journey users wanted to succeed in. Moral of the story? The feature you’re afraid to ship might be the one that breaks everything open. Comment “Journeyman” and I’ll send you the onboarding model.

Last month, I had a call with a CEO who was about to make a $50,000 mistake. He wanted to hire a new employee to handle their growing client onboarding process. "We're drowning, each new client takes 40+ hours to get set up properly." I asked him one simple question: "Can you walk me through your current process?" What followed was painful to hear: → Manual contract creation (2 hours per client) → Back-and-forth email chains for signatures (5+ days) → Manually setting up 12 different software accounts (3 hours) → Creating folder structures in 4 different platforms (1 hour) → Scheduling multiple onboarding calls (30+ minutes of coordination) The most insane part: his team was re-entering the same client information into 7 different systems. The same exact information seven times. Instead of hiring a new person at $50K, we built a simple automation system in 2 weeks: ✅ Smart intake form that captures everything once ✅ Auto-generates contracts with client data ✅ Triggers signature requests automatically ✅ Creates all software accounts simultaneously ✅ Sets up folder structures across all platforms ✅ Schedules onboarding calls based on client preferences Onboarding time dropped from 40+ hours to 2 hours. Client satisfaction increased (they loved the smooth process). His team could focus on actual value-add work instead of data entry. Total cost: $8,000 Annual savings: $50,000+ Before you hire more people, ask yourself: "Are we solving the right problem?" Sometimes the answer isn't more hands. It's smarter systems. Follow me Luke Pierce for more content on automations, AI, and scaling systems that actually work.