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Successful Customer Onboarding: Best Practices From Insight’s Portfolio

Insight Partners | November 24, 2021| 1 min. read

First impressions are lasting impressions. Onboarding is the very first experience the customer will have with your product, and it’s critical to get it right. If you fail to demonstrate value and support for your customer at the very start of your relationship, it will directly impact their success long term.

“Renewal happens in the first 90 days of the customer journey, not in the last 90 days.”

Donna Weber, recognized customer success leader and author, shared this impactful quote in our recent “Driving Customer Value at Scale” onboarding webinar. In fact, Donna noted that customers who struggle through their onboarding experience are “50% less likely to renew compared to those that had no issues.” She reinforced how important onboarding is in the customer’s journey with your product – if they are not successful at the start, future adoption, growth, and even retention can be significantly impacted. 

So how can you avoid friction from the very beginning and ensure long-term customer retention and growth? Having a strategic approach to onboarding will ensure alignment across teams and set your customers up for success. SkillJar, a leading customer-education platform and Insight portfolio company, created an excellent Guide to Customer Onboarding that demonstrates how to build a successful onboarding program and create a value-based approach from the start. They emphasize that companies who can “understand onboarding as a strategic process with a direct impact on customer success” will be “better positioned for long-term product adoption.” By approaching onboarding strategically, you ensure you’re aligned with the customer on how they define success with your product. Once you’ve achieved the first success milestone, you can then switch on the “value drip” and start scaling to maximize customer lifetime value and accelerate the adoption of the product.

As a part of the webinar, we also hosted an interactive discussion with 110 customer success leaders from our portfolio companies to share best practices and exchange tips and tricks related to common onboarding challenges. The sessions focused on three onboarding themes: 1) optimizing time to value; 2) scaling the process, and 3) achieving “value drip” through phased deployments. We are now sharing the key takeaways from these conversations:



What are you doing to accelerate time-to-value for your customers? 

  • Showpad – First we track adoption, but adoption does not mean we are always providing value to the user yet. We need to be able to demonstrate value based on the original buyer’s use case. You should define the framework of how to measure value. What are the metrics to track value? This should be consistently defined and used throughout the entire customer lifecycle. 
  • Hootsuite – We leverage success plans in our enterprise and low-touch models. We work closely with customers to get them through a first success plan, then advance them to different success plan phases. We also decoupled our renewal function from our CSM team to allow them to focus solely on their customers. However, what we are seeing on the commercial side is that CSMs don’t have as much time to spend with customers because they are overwhelmed with the number of customers they are covering. It is important to be more prescriptive with the commercial customers and describe what value should look like for them. 
  • Quantum Metric – Building out a maturity model has helped us accelerate time-to-value, from a first-stage use case all the way to a future sophisticated outcome. The value should be defined at the beginning of the engagement, which will also help your company understand how to best package the product. 
  •  Recorded Future – Make sure to have many lines of self-service customer enablement tools to help decrease the time to value. Some examples include in-product interactive walk-throughs, recurring client-wide training webinars, video-based learning platforms, a detailed support site, and how-to buttons. Make sure you are covering all the different types of learning preferences.   


What scaling strategies and technologies are you leveraging to reduce onboarding cycles and effort?

  • Versatile – We break out our onboarding into phases – launch, implement, mature. We also use a project management tool called Monday.com to streamline the information we have from sales to onboarding, all the way downstream to the customer success team. 
  • ParcelLab – A project management tool that helps us identify risks that are put up by not delivering against dependencies. We use this to speed up implementation and improve communication with our customers during the onboarding process. 
  • Camunda – We use SkillJar to create content that helps us differentiate based on various roles, as well as make the information bite-sized and digestible.
  • OwnBackup – Establishing an implementation department will help take work off the CSMs’ plates, so they can focus on adoption. We also use Calendly for scheduling touchpoints with customers, so we can keep them engaged.
  • E2Open – Splitting out onboarding from the professional services team really helped us optimize, especially as a first step to getting away from the really high-touch engagements and building a scalable process.


How can companies phase deployments to improve the customer experience? What approaches have worked for you? 

  • 6sense – Ask your customer – how is value defined for you? Logging in is not always valuable! A shared understanding helps you align on objectives and timelines. We try to be as prescriptive as possible during onboarding, so we can bring our customers to value. A lot of times customers want custom things, which can be challenging for successful onboarding. 
  • Within3 – We immediately start educating from the point of signature. This gives customers time to learn and be fully prepared to easily transition throughout the onboarding process.
  • Tigera – It’s critical to define “done” – you should understand the endpoint on what is being delivered for the customer. For the onboarding value drip, we use 3 things to measure success: 1.) if it’s demonstrable in the environment/use of the product; 2.) enablement; and 3.) operation of the platform and use on other applications.
  •  LeanIX – Done is a strategic objective. An example of this could be: If the adoption rate is 90%, your customer has used the products, and they are engaged in an opportunity, then you could consider this successful.
  • Automox – It’s important to remember that we are still catering to each customer to some extent. We do try to cater the experience slightly, so we know what each customer is getting. This needs to be controlled so that the customer doesn’t become a “snowflake.” 
  • VNDLY – If a “snowflake” customer has a need that helps add value for our other customers and aligns to our product roadmap, we will say yes! 
  • Hootsuite – Implement a success plan for your onboarding. We give customers a checklist of things to do; for example, online content to view. However, it’s easy for them to get distracted. We try to do scheduled check-ins on feasibility, making sure they can be held accountable for getting certain things done within a certain time period (such as 30 days).

If done well, onboarding can create a solid foundation for your customer relationships. There is a substantial risk to the growth and success of your business if customers aren’t introduced to your product successfully.

Remember to always tie your onboarding strategy back to the customer experience – know what value means to them, how to measure if it’s successful, and how to generate more as they grow.

Use these best practices to help optimize the customer experience from kickoff call and beyond, and you’ll retain customers and secure substantial growth down the line.

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