The Customer Onboarding Problems We Keep Hearing About

We’ve had hundreds of conversations with the people running customer onboarding operations at B2B SaaS companies.

After a while, the patterns get hard to ignore.

We recently ran an analysis across hundreds of discovery conversations with onboarding teams from companies ranging in size, segment, and complexity. The same core issues showed up in nearly every conversation. 

We think there’s value in naming these things clearly and in showing what’s actually being created to address them in the market. This is our attempt to document them honestly. We hope you find it valuable, too. 

Problem 1: Lack of macro-level visibility

This was the most universal finding in our analysis. 100% of the teams we spoke with cited some version of a visibility problem. Either leadership can’t see portfolio health, customers can’t see their own progress, or both. One team described it as “a black hole.” Another said they lacked “one location or source of truth” across their entire implementation org.

Even teams with reasonably well-run individual projects often struggle with portfolio-level visibility. A VP of Implementation shouldn’t have to ask someone to compile a spreadsheet to know which projects are on track, which are at risk, and what’s behind the delays. But that’s the reality for a lot of the teams we talk to.

A gap in macro-level visibility matters because it delays intervention when projects move off course. By the time leadership gets visibility into a problem, it’s too late to meaningfully intervene. Teams in this boat are forced into a constant reactive position and can’t proactively improve their onboarding motion for their customers. 

To fill this gap, implementation teams need to be able to see the health and status of their onboarding projects at the portfolio level, meaning across every active project. For example, in GUIDEcx, users have several ways of getting this visibility:

1. Users can now see automated alerts across their portfolio that surface when a project meets certain risk criteria, such as overdue tasks, unassigned roles, or lack of recent activity. 
2. An AI Agent we call RAG Agentic Coach proactively reviews all projects in your portfolio, detecting risk factors that could cause delays, and then coaches users through a contextual mitigation plan. 

For larger teams with a high velocity of projects, capacity and workload views add another layer. These features help you see not just which projects are at risk but also whether the people managing them have the bandwidth to actually fix them. 

Problem 2: Chasing customers for information

This challenge comes up almost as often as a lack of macro-level visibility, and it’s easy to understand why. Implementation is fundamentally dependent on inputs from customers. When inputs like signed documents and configuration details come in through email threads or phone calls, your process can be dependent on a single point of failure. 

96% of the teams we spoke with described manual chasing as a primary time-drain, with emails, phone calls, and Slack messages all going toward getting information that the project can’t move without. One team put it plainly: “It’s all of us chasing them via text, phone call, and email. And it’s really time-consuming.”

The overhead of managing this follow-up ends up costing teams more than time. Teams end up spending a disproportionate amount of their capacity on coordination rather than delivery.

What tends to help is shifting the dynamic from push to pull. In GUIDEcx, we’ve built a dedicated portal where all of a customer’s outstanding tasks, requests, and documents live in one place, and they’re no longer waiting for an email to know what’s needed. It’s just there. 

GUIDEcx and other solutions in the market have introduced structured intake forms, too, to replace the back-and-forth of email threads. With these, the customer answers everything in one sitting rather than responding to questions piecemeal over days. And when automated reminders handle the nudging on a set schedule, your team stops being the ones who have to decide when to follow up and how many times before it gets awkward.

Problem 3: Manual data collection and inefficient workflows

Related to the above but still a distinct challenge: even when teams are getting what they need from customers, the way they’re capturing and organizing it creates its own friction. For too many teams we talked to, information lives in spreadsheets, shared docs, email attachments, and someone’s memory. There’s no single source of truth. For them, onboarding plans get rebuilt from scratch for every new customer, and a lot of work that could be templated just isn’t.

78% of the teams we spoke to are still running implementations on spreadsheets, despite managing (sometimes) multi-million dollar implementations. The word we hear most often to describe it is “unmanageable.”

The downstream effect is three-fold: inconsistent experiences across customers, inefficient projects, and processes that are inherently not customer-facing (more on that later). Because spreadsheets aren’t flexible to different customers’ needs, each customer can get a materially different experience. They also aren’t dynamic. Spreadsheets don’t react when timelines slip, dependencies change, or new stakeholders show up. Nothing advances unless someone remembers to update it. Many teams default to managing the sheet instead of managing the onboarding.

Standardized playbooks and reusable project templates are the most direct fix here. GUIDEcx’s approach allows teams to use these features to start from a proven structure and dynamically adjust to the specifics of each customer, rather than building every onboarding project from scratch. Automated task creation from milestones can take that even further. For example, when a project reaches a certain stage, the platform automatically kicks off the next set of tasks. 

The less your process depends on individual team members remembering the right steps, the more consistent your output gets across the board. That consistency matters both for customer experience and for your ability to identify what’s actually causing delays when things go sideways.

Problem 4: Inception churn

This one actually doesn’t come up in most onboarding discussions, which is part of the problem. Inception churn is what happens when a customer decides, during onboarding, that they made a mistake buying your product. The product could work as described, but because the experience of getting started was confusing, disorganized, or made them feel like they were on their own, the customer lost confidence in it solving their needs. 

64% of the teams we spoke with have identified a direct line between poor onboarding and losing a customer too early. One onboarding leader we talked to called this “inception churn.” He said this was their biggest challenge. He also said it was their most controllable.

Teams that manage this problem well do it through structure. They focus on keeping the customer deeply engaged through the process through guided onboarding paths, real-time visibility into progress for the customer, and early health tracking that lets them catch at-risk projects before they become at-risk relationships. 

Clear communication sets expectations before anxiety has a chance to take hold so customers know the plan, who’s responsible for what, and what good progress looks like. Customer-facing progress visibility removes the “black hole” feeling that drives so much early churn. And health tracking in the first weeks means your team is looking for warning signs proactively, not waiting for a customer to surface frustration in a QBR.

Problem 5: Disparate, siloed tools

Most onboarding teams are running their operations across a combination of tools that weren’t designed to work together. Project management is supported by one tool, customer communication by another, and data in a CRM that doesn’t talk to either. When they need to report on performance, they need to pull data from multiple sources and reconcile them manually. 

80% of the teams we analyzed cited CRM integration as a mandatory requirement for an onboarding platform. But we don’t think that’s enough. Your onboarding platform should be a single system of record. 

Here’s what that looks like in practice. In GUIDEcx, a team can automatically initiate an onboarding project with a tailored project template after an opportunity is marked closed-won in Salesforce. Then, relevant automated emails are sent to kick off the project. From there, leadership can monitor performance with clear, accurate project forecasts and advanced reporting dashboards. Everything the implementation team needs, consolidated in one place. 

Problem 6: Inability to scale without headcount

Onboarding operations tend to grow linearly with customer volume. More customers means more implementation managers, more project coordinators, and more capacity to follow up. At some point that relationship becomes unsustainable, mainly because the economics just don’t work.

75% of the teams we talked to feel like they’re already at or near that breaking point. The language they use is telling: “treading water,” “bandwidth constraints,” fear that things will “combust” if volume increases significantly.

Breaking this pattern requires standardizing and automating the parts of onboarding that are high-effort but low-value, like automating routine tasks, customer reminders, status updates, and templated communications. When those things run automatically, your team’s time goes toward the work that actually requires human judgment. 

Another important solution is the ability to self-serve. When your customers can complete tasks, upload documents, and check progress on their own without needing to email someone, you’re effectively expanding your team’s capacity without adding headcount.

Problem 7: Lack of internal and external accountability

When an onboarding project isn’t moving, someone owns the delay. The problem is that in most onboarding environments, it’s not immediately obvious who. Finding the answer requires digging through email threads and asking around to piece together a timeline.

85% of the teams in our analysis are actively looking for what several of them called an “objective scoreboard,” or a way to show stakeholders exactly where delays are coming from without it becoming a blame conversation. One onboarding leader described it this way: “This report email would have saved a couple of awkward conversations.” 

Solutions like clear task ownership with deadlines and audit trails change this because they make accountability a feature of the system rather than a conversation someone has to initiate. When every task has an owner, a due date, and a timestamp on every status change, the question of who’s responsible for a delay has an objective answer. That removes a lot of the political friction that slows down escalations. Externally, when customers have their own view of outstanding tasks with deadlines attached, they self-manage in ways they simply don’t when accountability is communicated through periodic emails. They can see they’re blocking progress. They don’t need you to tell them.

That second part is underappreciated. A customer who has clear visibility into their own outstanding tasks and deadlines is far more likely to complete them proactively than one who gets a periodic email from their implementation manager. 

And one more thing. Adding multiple customers to a project is great for keeping them accountable. See below:

Conclusion

These aren’t new problems. Implementation leaders have been wrestling with most of them for years. What’s changed is that the tooling to address them has matured significantly, and the teams that are investing in that tooling are pulling ahead in measurable ways: faster time to value, lower churn in the first 90 days, and more capacity without proportional headcount growth.

The gap between how leading implementation teams operate and how the rest operate is getting wider. Most of it comes down to whether these problems have been structurally addressed or are just being managed around.