How to Improve Customer Onboarding

Your first 90 days with a customer can make or break the entire relationship. I've seen it happen too many times: - Great sales process - Solid product demo - Strong contract value - Excited stakeholders Then onboarding happens. And everything falls apart. Why? Most companies treat onboarding like a checklist: - Setup call ✓ - Product training ✓ - Technical integration ✓ - Documentation shared ✓ But here's the truth about onboarding: It's not about your process. It's about their success. After managing hundreds of onboarding sessions, here's what I've learned: The best onboarding isn't standard. It's personalized. Think about it: - Every customer has different goals - Every team has different challenges - Every organization has different paces - Every stakeholder has different priorities Your onboarding needs to reflect this. Here's what works: 1. Start with clear expectations - Define success metrics upfront - Set realistic timelines - Map out key milestones - Align on responsibilities 2. Build a dedicated team - Assign specialists who understand their industry - Create cross-functional support - Have clear escalation paths - Enable quick problem-solving 3. Monitor health signals - Track early usage patterns - Watch engagement levels - Note stakeholder participation - Measure progress velocity 4. Automate the right things - Regular check-in reminders - Progress updates - Resource sharing - Usage alerts But here's where most companies fail: They don't plan for challenges: - Low customer engagement - Complex technical integrations - Unclear success metrics - Resource constraints - Scalability issues The solution? Build feedback loops: - Collect input at every stage - Adjust plans based on signals - Iterate on materials - Improve processes continuously Remember: Onboarding isn't about getting customers to use your product. It's about helping them achieve their goals through your product. The first 90 days set the tone for everything that follows. Make them count. What's your approach to customer onboarding? What challenges have you faced? ------------------ ▶️ Want to see more content like this and also connect with other CS & SaaS enthusiasts? You should join Tidbits. We do short round-ups a few times a week to help you learn what it takes to be a top-notch customer success professional. Join 1993+ community members! 💥 [link in the comments section]

If your onboarding feels clunky, confusing, or last-minute… your client can feel it too. The work doesn’t begin after the payment. It begins the moment someone says “yes.” And this is where most people drop the ball. I’ve been there too. Until I started using AI to simplify, personalize, and hold space for my onboarding flow, without losing the human in the process. Here’s what that looks like: Step 1: Welcome, with intention: As soon as a client signs up, I feed their context to ChatGPT: “Write a warm welcome email to a new client who just signed up for [X service]. Acknowledge their goals, set the tone for our work together, and share what to expect this week.” It helps me start the relationship right, with presence, not a template. . . . Step 2: Kickoff kit, custom to them Instead of sending a generic Notion board or onboarding doc… I use AI to create a personalized one-pager: - Their name, goals, timeline - Pre-work checklist - Tools we’ll use - Access links - FAQs based on their niche It makes them feel seen. . . . Step 3: Pre-call prep that’s actually useful If I’ve collected form answers or voice notes, I prompt: “Summarize this client’s challenges and suggest 3 angles I should explore in our kickoff call.” I walk into the call aligned and calm. They feel it. . . . Step 4: Clarity recap - fast After the call, I feed my notes to ChatGPT: “Turn this into a call recap email with clear next steps and aligned expectations. Keep it real, not robotic.” It saves 30 minutes of staring at the screen and helps me build trust in the tiny details. . . . Step 5: Ongoing onboarding, quietly handled Need reminders? Nudges? Status updates? I’ll set up small AI workflows that keep things moving without nagging or micro-managing. Because onboarding isn’t a task. It’s the first chapter of your client experience. You don’t need AI to replace the way you work. But you can use it to hold the edges, so you show up more fully in the middle. That’s what onboarding should feel like. Intentional. Warm. Clear. And deeply human. If you want the actual AI stack I use to support this flow (without feeling cold or corporate), comment "ONBOARD" or DM me and I’ll send it over. Follow Vartika Mishra !

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.

𝗔𝗜 𝗱𝗶𝗱𝗻'𝘁 𝗳𝗶𝘅 𝗠𝗶𝗰𝗿𝗼𝘀𝗼𝗳𝘁'𝘀 𝗺𝗲𝘀𝘀 𝗶𝗻 𝗰𝘂𝘀𝘁𝗼𝗺𝗲𝗿 𝗼𝗻𝗯𝗼𝗮𝗿𝗱𝗶𝗻𝗴 𝗖𝗼𝗻𝘁𝗶𝗻𝘂𝗼𝘂𝘀 𝗶𝗺𝗽𝗿𝗼𝘃𝗲𝗺𝗲𝗻𝘁 𝗱𝗶𝗱 When Carolina Dybeck Happe became Microsoft's COO, the complaints started rolling in almost immediately. Not angry emails. Quiet frustration from customers who genuinely wanted to work with Microsoft but found themselves trapped in what felt like administrative quicksand in onboarding of new customers. Here's what happened next. Carolina and her team did something many executives avoid: they went to the Gemba. They actually mapped the entire onboarding journey - every form, every handoff, every "please wait 3-5 business days." Here's what the team found out: 𝟮𝟯𝟬 steps to onboard a customer. What they discovered wasn't laziness or incompetence: • It was layer upon layer of good intentions that had grown into complexity. • Many functions were involved: Sales, Marketing, Product, Finance. • Nobody owned the whole process. Everyone owned a piece. So they did the work. They challenged every single step: 𝐼𝑠 𝑡ℎ𝑖𝑠 𝑎𝑑𝑑𝑖𝑛𝑔 𝑣𝑎𝑙𝑢𝑒 𝑓𝑜𝑟 𝑡ℎ𝑒 𝑐𝑢𝑠𝑡𝑜𝑚𝑒𝑟? 𝑊𝑜𝑢𝑙𝑑 𝑡ℎ𝑒 𝑐𝑢𝑠𝑡𝑜𝑚𝑒𝑟 𝑝𝑎𝑦 𝑓𝑜𝑟 𝑡ℎ𝑖𝑠? 𝗙𝗿𝗼𝗺 𝟮𝟯𝟬 𝘀𝘁𝗲𝗽𝘀 𝘁𝗼 𝗳𝗲𝘄𝗲𝗿 𝘁𝗵𝗮𝗻 𝟯𝟳. Only 37 steps added value for the customer, i.e. 16%. So the team revised the process to focus on these 37 value-adding steps. This is where AI comes in: Once they'd simplified the process, 75% of those remaining steps were automated using AI agents. Not the bloated original process. The streamlined one. This is why I bang on about process improvement before technology. You can't automate your way out of a poorly designed system. You'll just create expensive chaos faster. The sequence matters: 1. 𝗠𝗮𝗽 𝗿𝗲𝗮𝗹𝗶𝘁𝘆 – What's actually happening? 2. 𝗖𝗵𝗮𝗹𝗹𝗲𝗻𝗴𝗲 𝗮𝘀𝘀𝘂𝗺𝗽𝘁𝗶𝗼𝗻𝘀 – Why does each step exist? 3. 𝗘𝗹𝗶𝗺𝗶𝗻𝗮𝘁𝗲 𝘄𝗮𝘀𝘁𝗲 – What adds no value? 4. 𝗦𝗶𝗺𝗽𝗹𝗶𝗳𝘆 𝗳𝗹𝗼𝘄 – How do we connect what remains? 5. 𝗧𝗵𝗲𝗻 𝗮𝘂𝘁𝗼𝗺𝗮𝘁𝗲 – Where can technology multiply the improvement? Speaking at the Wall Street Journal's Technology Council Summit, Carolina summed it up perfectly: 𝐼𝑛 𝑡ℎ𝑒 𝑒𝑛𝑑, 𝑤ℎ𝑎𝑡 𝑐𝑎𝑚𝑒 𝑜𝑢𝑡 𝑤𝑎𝑠 𝑎 𝑝ℎ𝑒𝑛𝑜𝑚𝑒𝑛𝑎𝑙𝑙𝑦 𝑏𝑒𝑡𝑡𝑒𝑟 𝑒𝑥𝑝𝑒𝑟𝑖𝑒𝑛𝑐𝑒 𝑓𝑜𝑟 𝑡ℎ𝑒 𝑐𝑢𝑠𝑡𝑜𝑚𝑒𝑟𝑠 𝑎𝑠 𝑤𝑒𝑙𝑙 𝑎𝑠 𝑓𝑜𝑟 𝑜𝑢𝑟 𝑡𝑒𝑎𝑚𝑠. (Video link in the comments below). That's the point of continuous improvement. It's not about hitting arbitrary reduction targets or creating pretty charts. It's about making work actually work - for customers and for your people. 𝗧𝗵𝗲 𝗿𝗲𝗮𝗹 𝗰𝗼𝗺𝗽𝗲𝘁𝗶𝘁𝗶𝘃𝗲 𝗮𝗱𝘃𝗮𝗻𝘁𝗮𝗴𝗲 𝗶𝘀𝗻’𝘁 𝗔𝗜. 𝗜𝘁’𝘀 𝗸𝗻𝗼𝘄𝗶𝗻𝗴 𝘄𝗵𝗮𝘁 𝗮𝗱𝗱𝘀 𝘃𝗮𝗹𝘂𝗲 𝗯𝗲𝗳𝗼𝗿𝗲 𝘆𝗼𝘂 𝗮𝘂𝘁𝗼𝗺𝗮𝘁𝗲 𝗶𝘁. If you want to simplify workflows before you automate them, follow me continuous improvement insights.

🧠 The Psychology Behind Successful Customer Onboarding A hard truth I've learned as a CS leader is that perfect features mean nothing if your onboarding fails. Another hard truth: Psychology matters more than process. You must focus on human behavior rather than just feature adoption. Here are my three principles to live by in onboarding: The Momentum Principle: We discovered that customers who achieve value in the first 48 hours are 3x more likely to become long-term advocates. So we redesigned our onboarding to focus on quick wins before complex features. By breaking down the journey into smaller, achievable milestones, we create a pattern of success that builds confidence and momentum. The Ownership Effect: When customers invest time in customizing their setup, they're significantly more likely to stick around. We now encourage early personalization through guided setup sessions. Rather than doing it for them, we coach customers through the process. This has increased product stickiness by 47% and reduced early-stage churn by 34%. The Contextual Learning Framework: We stopped treating onboarding as a linear checklist. Instead, we now adapt the journey based on user behavior and role. Our data shows that contextual learning – delivering guidance at the moment of need – increases feature adoption by 68% compared to traditional training methods. The results speak volumes: Time-to-value was reduced from 45 days to 15 and adoption rates increased by 56%. Successful onboarding is about building confidence and creating habits. Every friction point isn't just a technical issue; it's a psychological barrier waiting to be understood and removed. Are you designing your onboarding for features or humans? #CustomerSuccess #SaaS #Onboarding #CustomerExperience

Your customers don't care about your tasks. They care about outcomes. But most onboarding processes are just glorified to-do lists. → "Complete your profile." → "Upload your data." → "Schedule training sessions." → "Review documentation." That's not onboarding. That's busy work. When I was leading CS at Troops, I used to think a successful onboarding meant customers completed all our tasks on time. Check the boxes, move to the next phase. Then I started actually talking to customers who churned early. They'd say things like: "We did everything you asked, but we still don't see how this helps our business." That's when it hit me: customers have to see the entire plan to achieve success. Not a list of disjointed to-dos. They want to understand the journey from where they are today to where they want to be. And they want to see progress toward that outcome at every step. Here's how to flip your onboarding from task-focused to outcome-focused: 1. Start with their desired end state. What does success look like for them specifically? It’s not your generic definition of success — it’s theirs. 2. Map backwards from that outcome. What are the actual milestones they need to hit to get there? 3. Show them the connection. At every step, explain how this task moves them closer to their goal. 4. Celebrate progress toward outcomes, not task completion. "You're now 40% closer to reducing manual reporting" hits different than "You completed step 3 of 8." Customers aren't buying your product to complete your tasks. They're buying transformation. They're buying results. They’re buying completion of a job Your onboarding should be framed around that from day one.

We once spent weeks building a really sophisticated onboarding process (which I was really proud of). But I later find out that our clients HATED it. They felt like there was too much forms for them to fill and they would much rather speak to us on the phone. Sure, the onboarding process I had built out made things more organized. But I had to ask myself: Is this onboarding process actually serving my customer? I realized it did not, so I just scrapped it. I've learned with time that every question you ask in your onboarding form pushes your customer further from the result they signed up for. So only keep a question if it truly helps you deliver better results. For example, we run a cold email service at ListKit. If we don't collect information from our clients about their ideal customer profile, their offer, their goals, we can't build their leads list or write their scripts. That onboarding form saves us hours of back-and-forth later. But if you're asking questions just for the sake of having an onboarding process, you're only creating friction. Here's how to fix your onboarding right now: Step 1 - Open your current onboarding form Step 2 - Go through every single question and ask yourself: "Do I actually use this information to deliver the service?" If the answer is no, delete it immediately. Step 3 - For questions you keep, write down exactly how you use that information Example from our cold email service: - Question: "Who is your ideal customer?" → We use this to build their leads list - Question: "What problem does your offer solve?" → We use this to write their scripts - Question: "What's your revenue goal?" → We use this to set campaign targets Step 4 - Test your new form on the next three customers Ask them: "Was this onboarding process helpful or annoying?" If they say annoying, cut more questions. Your onboarding process should establish trust and set your customer up for success. Not make them regret buying. Start this audit today. It takes 15 minutes max and will save you from losing customers who feel overwhelmed before they even start.

In the last year, Demandbase has cut our TTV (time to value) by 55%. How? Our onboarding leader Graham Grome redesigned our onboarding process around 6 core principles: 1. Start Onboarding During the Sales Process Onboarding doesn’t start with the onboarding kick-off meeting, it starts with the first conversation with the customer. The very first interaction begins the process of understanding needs, roles and responsibilities, and timelines. Through the sales process the scope plan is in development and it is essential that this is handed off to CX and the onboarding team (and that pre-Sales resources stay involved) after the deal is closed. 2. Ground in Strategy to Generate a Value Roadmap Even with the scope in place, it’s critical to begin with strategy in onboarding (not dive into tactics and tasks). You need to know what the business outcomes the customer wants to achieve and the path to get there. That is why we begin with GTM Strategy Discovery sessions and deliver a Value Roadmap with clear now, next, and later actions that align to the customer’s GTM goals. 3. Tailor Configuration to Outcomes Every onboarding should be tailored to customer priorities. No two GTM’s are the same, being flexible in configuration is really important. Out-of-the box will not grow with your goals. We keep projects moving on target, surface risks early, and ensure that platform configuration supports business outcomes, not just your setup. The goal is to help you drive measurable value as quickly as possible. 4. Bring Customer Success into Onboarding As you grow, Onboarding and Customer Success become specialized functions. To maintain a “zero hand-off” approach make sure to include the Customer Success team members who will work with the customer moving forward through the onboarding process. 5. Make sure you leave Onboarding with a Value Measurement Plan You cannot show value without it. Every customer leaves onboarding with a Value Measurement Plan aligned to their objectives, so progress and impact are clear from day one. 6. Measure CSAT Post Onboarding It all sounds good, but how do you know it’s actually happening and where the process can improve? Customer Satisfaction (CSAT) surveys. Feedback on onboarding has to be operationalized, it’s too important to have any blind spots or to stagnate as customer needs evolve. ——— Customers have more options than ever, they are under pressure to justify their spending, they want results now (as they should!), and they know new AI-driven solutions are coming out every day. If you don’t adapt your onboarding to meet these demands, you will be in a world of hurt on churn.

Imagine your first day at a new job: a mountain of papers, endless weird words, and enough confusing terms to make your brain hurt. That's onboarding overload! Here's how to make it a smooth ride : 1. Go Slow: Give newbies small info bits, like a welcome email on day one. ↪ Welcome to the team, Alex! Today, you’ll learn about our coffee machine and meet your buddy, Sam. 2. Clear Goals: Tell them what they’ll do and check if it’s what they expected. ↪ Your first week’s goal is to learn our 5 main products, just like the ones listed in your job post. 3. Step by Step: Build their knowledge bit by bit, like teaching a kid to ride a bike. ↪ After you’re comfy with emails, we’ll show you how to use our client database. 4. Talk Vision: Share the big dream of the company and how they help. ↪Our dream is to make games that families love. You’re helping by making sure our code is bug-free. 5. Keep It Real: Set tasks they can actually do, so they don’t feel lost. ↪This week, try answering three customer emails with help from your team leader. 6. Easy Words: Skip the hard jargon, make them feel at home. ↪Instead of saying ‘leverage synergies,’ we say ‘work together.’ 7. Ask Questions: Encourage them to ask about anything, anytime. ↪ Not sure what ‘ROI’ means? Just ask! We’ve all been there. Do you prefer a slow and steady onboarding process, or do you learn best by jumping right in?

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