You didn’t lose that customer at renewal — you lost them during onboarding. You just didn’t realize it yet.
In the race for growth, most companies are so busy chasing the next logo that they ignore the most critical moment in the customer journey: the first 90 days. When onboarding is slow, sloppy, or stitched together with spreadsheets, you don’t just frustrate new customers — you set a ticking time bomb under your revenue.
The customer onboarding software market should be booming. Instead, it’s stuck — crippled by political turf wars, lack of executive accountability, disconnected tools, and loud competitors who overpromise and underdeliver.
Companies that treat onboarding as a tactical afterthought will keep wondering why churn is climbing, upsells are stalling, and customer trust is fading. Meanwhile, the companies that treat onboarding as a strategic revenue driver will quietly eat their lunch.
Let’s break down what’s really holding back onboarding today — and why shortcutting it is one of the most expensive mistakes a business can make.
One of the biggest structural problems is that onboarding doesn’t have a natural “home” inside most organizations. Ownership is fragmented across Sales, Customer Success, Professional Services, and sometimes even Implementation or Product teams.
This creates a political tug-of-war for resources. Whose budget should fund onboarding improvements? Who’s accountable if it fails? Without clear ownership, onboarding initiatives often stall — or worse, get funded with scraps left over from other projects.
The result is predictable: onboarding remains underfunded, under prioritized, and incapable of evolving past basic spreadsheets and manual checklists.
Many executives say that onboarding is important, but few hold themselves — or their teams — accountable with hard KPIs tied to onboarding performance.
This lack of executive sponsorship signals to the organization that onboarding is “tactical” rather than “strategic.” It’s seen as the necessary plumbing to move a customer from sale to value delivery — not as a mission-critical function tied to net revenue retention (NRR), lifetime value (LTV), or customer satisfaction.
Until onboarding earns a seat at the strategic table with clear KPIs — time to value, onboarding CSAT, onboarding completion rates, early-stage churn — it will continue to lag behind other investments like sales enablement, marketing automation, and customer success technology.
When onboarding is underfunded and low-priority, companies fall into the trap of “duct taping” together their processes.
Spreadsheets, email chains, Salesforce tasks, scattered project management tools like Asana or Monday.com — this patchwork approach creates inefficiencies that bleed time and money. Teams waste hours manually coordinating tasks, chasing down dependencies, and firefighting issues that better systems could prevent altogether.
Most leaders don’t realize how much revenue is slipping through the cracks during onboarding until someone shows them the numbers: delayed implementations, slower time to value, and missed upsell opportunities directly impact the bottom line. Every friction point in onboarding slows momentum and weakens the customer relationship before it’s fully formed.
One of the trickiest challenges is that the ROI of better onboarding isn’t always immediate — and most executives are judged on quarterly results.
When you improve onboarding, the payoff comes in the form of:
But these benefits often show up months after the initial onboarding experience. Leaders focused on hitting next quarter’s targets may not have the patience — or incentive — to invest today for gains they won’t realize until next year.
This shortsightedness creates a vicious cycle: because the impact of onboarding improvements is slow to manifest, the initiative never gets prioritized, ensuring the organization stays stuck in reactive mode.
The customer onboarding software market has also suffered from identity confusion.
Some players — like Gainsight or ClickUp — market themselves as “end-to-end customer success platforms.” Others, like Rocketlane, focus specifically on onboarding. The messaging overlap creates noise for buyers, making it harder to find solutions purpose-built for onboarding rather than general project management or customer success. Clear definitions between the types of onboarding motions are critical for businesses evaluating solutions.
Do you need a Professional Services Automation (PSA) solution for managing complicated time tracking and billing? Does your business install hardware and software in the field and you require something that is built to enhance your field service experiences? Not all customer onboarding solutions are engineered to handle the unique complexities of different industry business processes or use cases.
This confusion often leads companies to choose broader tools that only partially address onboarding, rather than adopting specialized solutions that could drive real operational improvements.
In a market already suffering from fragmented ownership and unclear priorities, this only deepens the dysfunction.
When companies shortcut onboarding, they don’t just delay customer value — they actively damage their future growth potential.
A poor onboarding experience erodes trust early in the customer relationship. It sets the tone that your company is disorganized, hard to work with, and incapable of delivering on promises. And in today’s environment — where customers have more choices than ever and switching costs are lower than ever — a rocky start can be fatal.
The first 90 days of a customer’s journey often dictate their likelihood to renew, expand, and advocate for your brand.
If onboarding is mishandled:
No marketing campaign, loyalty program, or customer survey can undo the damage done by a bad onboarding experience.
The companies that win the next decade will be those that treat onboarding as a strategic revenue lever, not an administrative task. Especially with the emergence of AI, applying AI strategies to broken processes will not help you with long term success. You will need a foundation of data, processes, and work management strategies that AI can exploit to speed up time to value.
Winning organizations will:
In short: onboarding isn’t just “customer success’s problem” — it’s a CEO-level growth lever.
Companies that realize this — and invest accordingly — will build deeper loyalty, faster expansion, and higher lifetime value. Those that continue to treat onboarding like an afterthought will wake up to a shrinking customer base and wonder where it all went wrong.
The time to fix customer onboarding is now. Because in today’s market, you don’t get a second chance to make a first impression.
Ready to transform onboarding? Book a demo and see how TaskRay’s customer onboarding software can set your customers—and your revenue—up for success.
