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There are No Second Chances for First Impressions

Allyson White | June 05, 2017| 1 min. read

Allyson White is a Vice President at Insight Venture Partners. She works with software companies on customer success strategy and how to structure for best-in-class retention rates.

In this blog, Allyson emphasizes the importance of a well-designed customer onboarding process, providing helpful advice for improvement. In summary, Allyson shares the following tips for customer success leaders:

  • Your onboarding process sets the tone for your customer relationships. Remember: You never get a second chance at a first impression.
  • While new customers may be willing to provide some slack to young startups that offer inspiring products but lackluster onboarding, established companies have to put their best foot forward with each new customer. 
  • Onboarding processes should always be customer-centric, not developed around internal interests and deadlines in mind.
  • Being transparent and honest with your customers, establishing goals, and celebrating achievements are essential to a successful onboarding process.
  • Refine your customer onboarding process over time for continual improvement.

Onboarding is all about first impressions.

As a customer, you know that’s true. Think of a company that you admire or a product that you proactively recommend. Try to recall when you first used that product, chances are that you either don't remember it because the process was seamless and uneventful - or you remember a specific instance early in the relationship where the company exceeded your expectations. It’s unlikely that you had a negative early experience with a brand or company that you advocate for today. 

Since you never get a second chance at a first impression with your customers, invest upfront in customer relationships with world-class onboarding.

No Grace Period 

Young startups and innovators initially may be able to grow with lackluster onboarding. Their customers are early adopters inspired by a novel product or fresh approach. Thus, there’s a built-in grace period for newbies. Scaling software companies, however, receive no slack from customers. Insight’s portfolio companies find themselves striving to operate successfully at scale – onboarding more and more customers each month with higher stakes of losing customers as a result of a poor experience.

Improvement starts by standardizing your onboarding process. For growth stage companies, this requires designing a quality onboarding experience by customer persona.  To start, interview and learn from your most engaged current customers. What worked well in their onboarding? For example, for a cross-functional roll-out did they include a team lead or product champion by team? What internal processes did they create or leverage during onboarding? For example, did they create a weekly metrics dashboard or did they create a template for first-time users? Customers build workarounds when onboarding is not sufficient, and these workarounds are a good source of ideas on how to adapt your onboarding.  Also, ask customers what information they wish that they knew on Day 1 and which product features were difficult or not intuitive to use.  Incorporate the feedback from these experiences to improve your onboarding process. For example, create a best practices document with tips from peers and include in an early email to a new customer.

Common Missteps

The most common onboarding mistake that growth stage software companies make is designing the onboarding process around internal activity metrics and checklists instead of designing around customer personas. Customers become frustrated by friction in the process and struggle to crisply communicate the value of your product.

While good onboarding programs ensure customers quickly feel confident using your product, the best onboarding programs also shine a light to illuminate for customers the value your product creates.

Common Traits 

The most effective customer-focused onboarding processes have common traits. As yourself how many of these are being utilized in your customer onboarding practices? 

  • Adopt customer lingo – Ask your customers how they define success and then speak their language. Incorporate their definitions and terminology into your meetings, emails, and dashboards. 
  • Be transparent and share benchmarks – Show the customer the onboarding plan and paint a picture of what to expect, including timelines and check-in points. Then benchmark their performance against peer customers.
  • Be a coach – Don’t be afraid to highlight customer habits that may harm outcomes. Coach customers on tweaks to their processes or systems that will improve results. 
  • Set achievable, incremental goals – Establish goals before the end of onboarding and monitor progress to help keep your customers and your team on track.
  • Celebrate small victories – Recognize onboarding milestones with your customers and your company. Positive feedback motivates and will help build a better experience for your customers and your team (especially in a long onboarding or implementation). Find ways to automate these messages in your product, through emails or other communication channels.

Ultimately success is making your customers or stakeholders shine in front of their bosses; if you're in the B2B space, always remember the person you sell to has someone to whom they report. Empower them to show early wins during, and at the end of, onboarding.  


Retention rates – especially in multi-year deals – are lagging indicators. Instead of focusing on retention rates, look for early signals that your onboarding process is succeeding.

Three important metrics to consider are net promoter score (NPS), usage, and pace of expansion.

  • Measure NPS at the end of onboarding, both from users and the product sponsor/ buyer.
  • Track the usage of a sticky product feature or workflow that indicates successful product adoption. Strive to have customers consistently use that feature earlier in their tenure, for example, in the first month instead of the second.
  • Finally, if onboarding is strong, customers are more likely to expand or rollout faster, resulting in more upsell opportunities earlier in the customer’s tenure.

If these three metrics are trending positively, it is likely that high first-contract renewal rates will follow. World-class onboarding is a pillar of strong customer success functions. Investing heavily in a customer-centric onboarding program will pay dividends in the form of high retention rates and viral advocacy. And done correctly, world-class onboarding differentiates you from the pack.

Remember with customer retention – “it’s what you do in the first 90 days, not the last 90 days before renewal, that matters." Send us a message or tweet @insightpartners and share your onboarding tips.