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Common SaaS Onboarding Challenges and 15 Best Practices to Crush Them

Usha Vadapalli
September 5, 2023

It’s like encountering unexpected detours on a perfect road trip.

Naturally, every SaaS business wants to build a better product onboarding experience. But, where are we falling short?

Before sketching out an intuitive, efficient, and ideal onboarding journey, let’s look at the common challenges SaaS companies face in building onboarding from the ground up and improving the existing one.

Mapping Onboarding Journey Afresh

According to Ramili John, “The goal of the entire onboarding experience is to help users improve their lives” and we agree. Though the end target of any product’s onboarding is the same, building the onboarding journey from scratch and optimizing an existing one comes with their own unique set of challenges. Let’s start with a new product’s challenges.

  • Lack of User Familiarity: Unless you are in a red ocean environment where most of the competing products are similar in functionality, the onboarding process needs to introduce and educate users about the product's purpose, features, and benefits right from the start.

    Depending on the space you are in, providing comprehensive education about the product while speeding up time-to-value can be your biggest challenge.
  • Uncertainty and Evolving Design: With a brand-new product, the design and functionality may still be in flux. There may be uncertainties and changes in the product's features, user interface, or overall user experience.

    This can pose a challenge in designing the onboarding process, as it needs to be flexible and adaptable to accommodate any updates or modifications that occur during the development process.
  • Limited or No User Feedback: Gathering user feedback can be challenging due to a limited user base or lack of usage data for new products. This makes it difficult to identify pain points and areas for improvement in the onboarding process. User research and early adopter feedback become essential in understanding and addressing potential issues.
  • Establishing Brand Trust and Credibility: Hesitation in adopting a new solution due to unfamiliarity or concerns about reliability is a valid concern. If you are brand-new on the market, your product onboarding journey has to deliver what you promised while signing up on top of everything else to earn the user’s trust.

    Building a SaaS onboarding journey for a brand new product requires a stronger emphasis on education, trust-building, and adaptability compared to optimizing an existing product's onboarding process. It involves addressing uncertainties, limited feedback, and establishing a solid foundation for user adoption and engagement from the outset.

Improving the Current Product Onboarding

Optimizing an existing product's onboarding process comes with the advantages of familiarity and the availability of user feedback, but there are other challenges to overcome.

  • Legacy Systems and Constraints: The extent of changes or improvements that can be made can be limited unlike building from scratch, where there is more flexibility, optimizing product onboarding journey requires considering compatibility with the existing system.
  • User Resistance to Change: Users who are already using the existing product may resist changes or have certain expectations based on their product experience. They have developed habits and workflows around the current onboarding experience, and any modifications may disrupt their established routines.

    Overcoming user resistance and ensuring a smooth transition during the optimization process requires effective communication, clear explanations of the benefits, and a user-centric approach.
  • Limited Data Insights: While optimizing an existing product's onboarding, businesses have the advantage of user data and feedback. However, this data may be limited in scope or not fully representative of the entire user base. Analyzing this data for a comprehensive understanding of all user pain points or preferences and deriving actionable insights can be challenging.

    The optimization process needs to carefully consider available data while seeking additional and constant feedback through surveys, user testing, or customer support interactions.
  • Alignment and Cross-Functional Collaboration: Optimizing the onboarding journey requires collaboration across multiple teams, including product, engineering, customer success, and the leadership team.

    Ensuring effective coordination and alignment among these teams can be a challenge, considering they may have different priorities, objectives, and perspectives. It requires strong leadership, clear communication channels, and alignment of goals to facilitate collaboration.

SaaS Onboarding Best Practices

Let’s explore how to overcome some of these common challenges to optimize your product-led onboarding journey.

  1. Implement online signup to lower friction to using your product and increase your customers and users.
  2. Start thinking about automating the part that requires manual provision. Users are in the zone... don't add a blocking moment.
  3. Implement an in-app navigation guide or a product tour for your new customers to start using your account. You can also consider using an onboarding checklist for your users to complete. Check out Vidyard’s example.
  1. Implement and improve the onboarding assistance experience further by using proper in-product tours, tooltips, and help resources classified by factors such as the user persona, product role, and goals in the product.

    For example FAQs for System administrator, product tour for a Team Manager, How-To video tutorial library, and so on. Asana’s welcome email has a section that redirects Admin and Super Admin users to the relevant section to set up necessary settings.
  1. Start sending onboarding emails to your new users if you aren’t already. They are very important to reduce friction for onboarding and increase conversion rates.
  2. Create an automated welcome email to send within 1 minute of signing up outlining the next steps.
  3. Don’t forget to show timely reminders about the remaining time on a trial plan both in-product and via email. Check out Trello’s example.
  1. Time-based emails are sometimes useful for your users, but product activity-based emails are worth their weight in gold. Start sending product activity-based emails for a personalized onboarding experience.
  2. Kudos if you’re already sending product activity-based emails for onboarding new customers. Strive to personalize them further and optimize for better conversions. Grammarly’s onboarding emails triggered by product activity knock it out of the park.
  1. Use a person’s email as the sender address for all customer communications so that users know they can respond and get a real person.
  2. Help users see more value in your product and understand their next steps to guide them better. You can do this via in-app help, push notifications, onboarding emails, checklists, and other possible means to guide your users through an ideal onboarding journey. At, we send an email to move along in the onboarding process.
  1. In-app notifications can be a great way to guide users in your product to important differentiating features, missing setup information, and more. FigJam onboarding guide has 3 steps. If the new user doesn’t complete exploring the video guides on all three topics, a notification on the bottom right corner reminds the user to do so without intruding in their workspace.
  1. If your product needs a complex setup, assign a product expert, CSM, or account executive to help guide the user through when they are stuck at a step for too long.
  2. Avoid combining upselling with onboarding campaigns. Let the users experience value before you ask them to pay or upgrade.
  3. If your product delivers more value with network effect (more value as more users start using it), for example, Slack encourages users to invite their friends and colleagues to the product by making it easy to connect with anyone outside your workspace too.

Embracing Onboarding Challenges

You're not alone in this quest for seamless onboarding. Every successful SaaS trailblazer has faced their share of roadblocks, refining their strategies to create experiences that captivate and convert. Put yourself in the user's shoes, evaluate your onboarding, anticipate their needs, and lead them with clarity.

If you are embarking on your journey to revamp onboarding, we’re happy to walk with you. Grab a 1:1 with our expert for a free onboarding consultation.

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