Ways to Make Customer Onboarding Smooth in Retail

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.

After 5 years helping 800+ companies streamline onboarding, here's the most underestimated way I’ve found to eliminate delays: Prescriptive playbooks. Most onboarding failures happen before customers even start using your product. We dump endless configuration options on them and ask them to figure out what they want. I know a software vendor in our space who gives a spreadsheet with 800 rows for their customers to fill, before they can “start” implementing. The result? Analysis paralysis, delayed launches, and frustrated users wondering if they're doing it "right”. Customers do sometimes blame themselves for these delays, but they’ll steer away from your software and software in your space if they have this experience Ever notice how many tools give you templates instead of a blank page? There's a reason for that. Smart companies use more prescriptive and preset configurations: For ex, Slack: Suggested channels and workflows This leverages two psychological principles: → People are more likely to use tools when they feel they've already started → Once started, momentum keeps them going Instead of asking "What do you want to set up?" start with, "Based on companies like yours, here's what we recommend." Map your customer types to proven configurations. Present these as the starting point. This approach eliminates decision fatigue, ensures customers benefit from your best practices, and de-risks launches with proven setups Your customers don't want infinite choices. They just want confidence that they're set up for success.

Think your onboarding process is smooth and simple? Here’s what it actually feels like from the customer’s side. This is a real-life example I'm currently in the middle of: ✅ Sign up for new service we're really excited about and are eager to get started with quickly. ✅ Receive email with 9 "simple" steps to get started. Looks easy enough at a glance! ✅ Carve out time in the afternoon to work through them. 🚧 Immediately hit a wall: I can't proceed until Daniel Zarick signs the contract. Stuck until that gets done. ✅ Contract finally signed! Okay, I'll work through the next steps later this afternoon after my calls. 🚧 Next step is granting access to some tools. But which email address should I grant access to? Ping the team to ask and wait for a reply. 🚧 Need to provide "a few voice of customer examples." We've got thousands. Unclear what they're looking for. Ping them again to ask for clarity. 🚧 Need to schedule a kickoff call. No meeting link provided. Should I be reaching out to find time? Will they let me know when they're ready for me to schedule? I set aside an hour to tackle this list. The result? I completed ONE out of NINE tasks. 😲 And just like that, we're delayed by a day. At least. What looks like a "simple list of things to do" on paper quickly becomes a complex web of dependencies, permissions, and unclear expectations. To truly enable your customers from the get-go: ✅ Provide all necessary context upfront—don’t make them ask for clarity ✅ Clearly define each step: what's needed, who’s responsible, and by when ✅ Give them the tools and instructions to actually complete the steps in one go Remember: Every moment of customer confusion is a loss of momentum and a potential delay in your onboarding timeline. And that's why we built Arrows: https://lnkd.in/guZwtrNS