Proactive vs. Reactive Onboarding: Strategies for Customer Success Managers

When a new customer signs up, you have two ways to approach their onboarding experience: guide them through the process step by step before they run into roadblocks, or wait for them to reach out when they hit a problem. Both approaches—proactive and reactive—have their place, but relying too heavily on one can lead to frustrated customers or an overburdened team.

Customer Success Managers (CSMs) know this struggle well. Set up a solid onboarding process, and customers see value faster. Miss key moments, and engagement drops. The challenge is knowing when to anticipate customer needs and when to step in reactively.

This blog breaks down the differences between proactive and reactive onboarding, their pros and cons, and how you can blend both approaches to create a better customer experience.

Defining onboarding approaches

Onboarding sets the tone for a customer’s experience with a product. It can determine whether they adopt the platform smoothly or struggle to find value. There are two primary approaches to onboarding: proactive and reactive. While both have their place, they serve different purposes and impact how customers engage with a product.

Proactive onboarding 

Proactive onboarding is about staying ahead of potential challenges. Instead of waiting for customers to ask questions, it provides structured guidance through automated walkthroughs, educational content, and predefined processes. 

This approach helps customers reach value faster by ensuring they understand key features and workflows from the start.

Reactive onboarding

Reactive onboarding, on the other hand, responds to customer needs as they arise. It typically involves answering support tickets, resolving product-related issues, and providing guidance when customers encounter obstacles. 

While it’s necessary in certain situations, relying too heavily on reactive onboarding can create inconsistent experiences and increase support costs.

A strong onboarding strategy doesn't rely solely on one approach. Instead, it blends proactive and reactive elements to create a seamless experience for customers while optimizing internal resources.

Key differences between proactive and reactive onboarding

Proactive and reactive onboarding aren’t opposing strategies—they complement each other. Understanding the key differences helps Customer Success teams strike the right balance.

Timing

Proactive onboarding aims to prevent confusion by guiding customers before issues arise. It introduces key features early and ensures customers understand their next steps. 

Reactive onboarding, on the other hand, happens after a problem has already occurred, often through support interactions.

Customer experience

A well-structured proactive onboarding process fosters confidence and encourages product adoption. Customers feel supported without having to reach out for help. 

Reactive onboarding, while useful for troubleshooting, can leave customers frustrated if they struggle to find answers on their own.

Efficiency

Proactive onboarding reduces repetitive support requests by providing customers with the right information upfront. Reactive onboarding requires Customer Success teams to manually address each issue, which can be time-consuming and resource-intensive.

Scalability

Automating proactive onboarding through guided tours, playbooks, and educational resources allows companies to onboard more customers without increasing workload. 

Reactive onboarding, however, often requires human intervention, making it harder to scale without adding more support staff.

While proactive onboarding reduces dependency on support teams, it doesn’t eliminate the need for reactive assistance. A hybrid approach ensures customers have the guidance they need while still having access to personalized help when necessary.

Benefits of proactive onboarding

Proactive onboarding sets customers up for success from the start. When done well, it helps them adopt the product efficiently, reducing frustration and increasing retention.

Shortened time-to-value

When customers receive structured guidance, they can start using the product effectively much sooner. This increases engagement and helps them see results faster.

Increased customer satisfaction

A clear onboarding process prevents common frustrations, ensuring customers don’t feel lost or overwhelmed.

Improved retention rates

Customers who experience a smooth onboarding process are more likely to continue using the product. They develop a stronger connection with the platform and are less likely to churn.

Lower support costs

By addressing frequent questions and challenges upfront, proactive onboarding reduces the number of reactive support requests, freeing up Customer Success teams to focus on strategic initiatives.

Despite its advantages, proactive onboarding doesn’t eliminate every challenge. Some customers will still need additional support, making it important to have a responsive strategy in place.

Benefits of reactive onboarding

While proactive onboarding helps prevent issues, reactive onboarding ensures customers receive the assistance they need when problems arise. There are several advantages to keeping reactive strategies in place.

Immediate issue resolution

Some problems can’t be anticipated. When customers encounter unexpected challenges, reactive onboarding ensures they get quick solutions.

Personalized support

Not every customer follows the same path. Reactive onboarding allows teams to tailor guidance based on specific customer needs, rather than relying solely on automated processes.

Better insight into customer needs

Direct customer interactions through reactive onboarding provide valuable feedback on where customers struggle the most. These insights can be used to refine proactive strategies over time.

How to implement a proactive onboarding strategy

Building a proactive onboarding strategy requires a structured approach that ensures customers receive the right information at the right time. Instead of waiting for them to ask for help, proactive onboarding anticipates their needs and provides guidance before issues arise. Here’s how to implement it effectively:

Define key milestones in the customer journey 

Identify the points where customers typically need guidance, such as account setup, feature adoption, and achieving their first success with the product. Create structured onboarding steps that guide them through these moments.

Use automation to deliver timely onboarding content

Automated emails, in-app messages, and guided product tours can help customers move through the onboarding process smoothly. Tools like Velaris allow you to set up trigger-based onboarding sequences that send the right information when customers need it.

Leverage playbooks for consistency 

Standardized onboarding playbooks ensure that every customer receives a consistent experience. Playbooks should outline key tasks, best practices, and checklists that your team follows for every new customer.

Monitor customer engagement and sentiment

Tracking customer health scores and behavioral data can help identify users who may be struggling. If a customer hasn’t engaged with a key feature or hasn’t logged in for an extended period, proactive outreach—whether through an email or a check-in call—can help get them back on track.

Gather feedback and adjust

Onboarding isn’t a one-size-fits-all process. Use surveys like NPS or CSAT to understand how customers feel about their onboarding experience, and refine your approach based on their feedback. 

With Velaris, you can build and analyze surveys in one place, making it easier to track responses and improve onboarding based on real customer insights.

A proactive onboarding strategy helps customers reach value faster, reducing frustration and reliance on support. However, no onboarding process can anticipate every customer’s unique needs, which is where reactive onboarding plays a role.

How to implement a reactive onboarding strategy

Even with a strong proactive approach, customers will still encounter challenges that require immediate assistance. A well-structured reactive onboarding strategy ensures that support is efficient and that customers get the help they need without unnecessary friction.

Provide multiple support channels

Customers should be able to reach out in a way that suits them best—whether through email, live chat, or a support ticket system. Offering flexible options makes it easier for them to get help.

Use event-based triggers for real-time assistance

Set up alerts for key moments when customers may struggle. For example, if a user attempts an action multiple times without success, trigger an in-app message offering help. If a critical feature remains unused after a set period, send a check-in email with guidance.

Prioritize urgent issues with AI and automation

AI-powered tools, like Velaris’s AI copilot, can categorize incoming communications based on sentiment. Communications with negative sentiment can be marked as high-priority onboarding roadblocks.

These should be escalated immediately, while routine inquiries can be managed with automated responses or self-service recommendations.

Maintain a centralized record of customer interactions

Ensure that all onboarding progress, past support conversations, and product usage data are stored in one place. This allows Customer Success teams to provide informed, context-aware responses without requiring customers to repeat themselves.

Offer live onboarding sessions for complex needs

Some customers benefit from direct guidance. Hosting office hours, onboarding webinars, or one-on-one calls can address unique challenges and provide a more personalized experience.

Analyze recurring issues to improve proactive onboarding

If multiple customers face the same problem, adjust onboarding content or product documentation to prevent similar issues in the future. Data from support tickets can highlight gaps in the proactive process.

Follow up on unresolved issues

If a customer reaches out during onboarding but doesn’t follow through with suggested solutions, send a follow-up message to check if they need additional help. This ensures no one gets stuck without support.

A strong reactive strategy ensures that when customers do need help, they receive it quickly and effectively. When combined with proactive onboarding, it creates a seamless experience that helps customers stay engaged without frustration.

Integrating proactive and reactive strategies

The best onboarding strategies don’t favor one approach over the other—they integrate both. A hybrid model ensures customers receive structured guidance while still having access to support when needed.

Developing a hybrid approach

A hybrid approach to onboarding ensures customers receive structured guidance while still having access to responsive support. This means automating the most common onboarding steps while maintaining a support system that customers can rely on when needed.

For example, a SaaS company might provide automated walkthroughs to introduce new users to the platform while also offering a live chat feature for customers who need clarification. This combination allows customers to learn at their own pace but still access personalized help when necessary.

The key is to structure proactive onboarding in a way that minimizes confusion while keeping reactive support readily available for unique or complex cases. This ensures a smooth experience without overwhelming either the customer or the Customer Success team.

Using behavioral triggers for timely interventions

Not every customer will reach out when they experience friction. Behavioral triggers help identify when a customer might need support by analyzing their actions (or lack thereof) and responding accordingly.

For example:

• If a customer has created an account but hasn’t logged in after a few days, an automated email can be sent offering help or a quick-start guide.
• If a user repeatedly tries and fails to complete an action, an in-app message can be triggered, linking to a relevant tutorial or offering a support chat.
• If a customer has stopped engaging with the product after initial onboarding, an automated check-in email can encourage them to reconnect.

By implementing behavioral triggers, Customer Success teams can ensure that proactive support reaches customers at critical moments, reducing the need for reactive troubleshooting later on.

Offering self-service resources to reduce friction

Customers prefer to solve problems on their own when possible, making self-service resources an essential component of onboarding. A well-organized knowledge base, in-app tooltips, and video tutorials help customers find answers without needing to contact support.

Self-service resources should be easily accessible and structured in a way that anticipates common onboarding questions. For example, if a product requires multiple configuration steps, a step-by-step guide should be available within the onboarding interface.

While self-service tools contribute to proactive onboarding, they also improve reactive support by allowing customers to quickly access solutions when they need them, reducing the need for one-on-one assistance.

Maintaining a support safety net

Even with a strong proactive strategy, some customers will still need real-time assistance. Ensuring that reactive support is accessible and responsive is key to a balanced onboarding experience.

A good safety net includes:

• Multiple support channels, such as live chat, email, and a ticketing system.
• AI-powered support suggestions that provide automated recommendations based on customer queries.
• A dedicated escalation process for critical onboarding issues that need immediate attention.

Customers should always feel like help is available when they need it, but the goal is to ensure that they don’t have to rely on reactive support for every step of onboarding.

A balanced onboarding approach reduces friction, enhances customer engagement, and improves overall efficiency.

Conclusion

A strong onboarding strategy doesn’t rely entirely on either proactive or reactive methods—it blends both. Proactive onboarding helps customers get started smoothly, reducing confusion and support requests, while reactive onboarding ensures they receive the help they need when unexpected issues arise. 

Using automation, playbooks, and customer health tracking can make onboarding more structured and scalable. Velaris helps Customer Success teams automate onboarding workflows, track customer progress, and stay ahead of potential issues. 

If you’re looking to build a more structured and proactive onboarding experience while ensuring customers still have access to support when needed, book a demo today.