Customer onboarding challenges from Seed to Series B

From real scenarios at Chili Piper, learn what to do and what not to do when scaling from Seed to Series B.
March 18, 2022
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In this fireside chat at Propel22, Gemma Cipriani-Espineira, CCO at Chili Piper, and Gaines Murfee, Manager of Customer Implementation at Chili Piper, discussed overcoming onboarding challenges from Seed to Series B.

Gemma and Gaines talked about how they improved time to value by over 30% in the past year. They also talked about how you can unlearn bad habits that prevent you from scaling and how data-driven metrics can be used to justify a change to the leadership team.

Quick background on Chili Piper and its growth

Note: Things that work for you when you are a smaller team may not necessarily work when you begin to scale and grow. So, a lot of it will have to change.

Chili Piper started 2016 with an angel round, similar to many other startups. In the summer of 2017, when Gaines joined Chili Piper as an account executive, there was only one CSM who was handling customer onboarding. And as they progressed into a seed round in April 2019, everybody wore lots of different hats at that period. By August 2019, they had added quite a few people and realized they needed to split up the onboarding responsibilities between the CSMs and the account managers as they were all trying to do renewals, etc. CSM account managers were to hold the business side of things, while the CSM would hold the technical side. They hired their first full-time support agent, which everybody loved because debugging things can take a lot of time and a lot of effort. 

They got a Series A round in 2020, hired a few more resources, and in December 2020, they got a CS resource. And in April 2021, they received their Series B funding. 

What makes Chili Piper onboarding uniquely involving?

The Chili Piper product is pretty involved with onboarding because it integrates with your website.

  1. Chili Piper’s scheduling product integrates with three very business-critical aspects: your contact request website form, the CRM, and the sales reps’ calendars.
  2. The ‘Demo Request’ or ‘Contact Us’ leads are the lifeblood of any sales team.
  3. Sales reps get paid commission based on the number of meetings booked with Chili Piper. 

Improving time-to-value

Chili Piper has reduced the days to launch from signature to being live on the client's website by 30%. While maintaining an 85% NPS, they have also increased monthly active users year over year by 83%. Gemma has implemented a weekly scorecard called the Center of Excellence, where they are tracking metrics, including onboarding metrics

Anyone coming in at a leadership role for a startup will be tasked with improving retention. And while everyone slices it into logo retention, net retention, and so on, at Chili Piper, it was ensured that time to value was one of the key activities they were obsessed about. And in doing that, they've been able to get a lot of this improvement both in the experience and the amount of time to launch customers. And as it happens, the rest of the company enjoys hearing about which customers have recently been onboarded and what they had to say about that experience. So all around, it's a great way to scale with onboarding, measure it, and share the progress as you're going on a weekly cadence.

Maintaining the onboarding excellence at scale

A. The people, process, and platform

  1. Google Docs for onboarding works but does not exactly scale. Adopting a dedicated CSM tool is the best way ahead. This helps with the standardization of playbooks for clients, especially when your company grows or has different products, etc.
  2. Team enablement: One-on-one works for a small team. But, as you begin to scale and grow adoption, you have to find more automated ways to do it. The time it takes to onboard a new hire, particularly a new CSM, is something to pay attention to, as much as the time it takes to onboard new customers because the two are inherently linked. So onboarding doesn't just include the customer end of things; it's ensuring that your staff has the right onboarding to deliver those experiences.
  3. Team structure: We were once all one, wearing many hats. But, it's really nice to have more specialized staff, as they can train teams and don't always have to come from the same one or two people. Lots of experts, specialists, and knowledgeable members allow for more efficient delegation all around. 
Chili Piper changed the name of their Support team to Department of Customer Love!

B. "What got you here may not necessarily get you there"

Bad habits to unlearn if you want to scale:


CS can be seen as a call center. But they are the ones helping retain customers who ultimately drive tonnes of revenue in the world of SaaS. Therefore, getting the hiring right is essential. Measure the number of hours it takes to onboard a customer, the number of customers you expect to close (when you are growing at a specific rate), and the time required to do other activities that you need to do to be a successful CSM team. These data points help you get your hiring formula right. It helps you calculate and justify to your executives the headcount you need to expand resources. And every CEO is going to want that growth. 

Thinking all customers are equal

This is similar to Donna Weber's special snowflake idea where you want to provide the very best service to all customers. It works well in the early stages when you don't have many customers. But it becomes tough to maintain and scale. Instead, create clear customer segments of SMB, mid-market, and enterprise customers. And create different playbooks for them at all stages of their customer journey, particularly during onboarding. This allows you to scale while improving numbers.

Manually assigning onboardings

Always depending on a human to go about clicking buttons will not be fruitful. Instead, automate this within a few seconds of a closed opportunity. Bam! Everything's assigned, and it fires off an email to the CSM team and account managers. The aim is to let them know who to do a warm handoff introduction with and allow them to schedule their kickoff call. That's really what will help you speed up the onboarding and reduce human intervention with the stuff you automate.

Expecting to have high-value conversations during the kickoff call

This is something that anyone responsible for onboarding would like to have. But not everyone is necessarily prepared to have it; sometimes the customer is not in the right mindset to have that conversation. During the kickoff, customers just want to get started and get as many technical configurations done as possible. For instance, Chili Piper implemented a ‘Big Six Initiative’ across the company that ensured that they were capturing the six main reasons as to why a company chose Chili Piper in the pre-sales stage as early as possible. And they are ensuring that all that information comes into an automated handover to the CSM so that they do not have to ask the customer the big six questions, which are on:

  • The customer’s business objectives
  • Their user personas
  • Their use cases
  • Their KPIs
  • The baselines of those KPIs
  • Milestones they are trying to achieve

This ensured that they were kicking off equipped with the information and tailoring content that will get customers started as quickly as possible.

And, of course, if you need to verify anything or if something's changed, then you can have that conversation. But refrain from using the kickoff as a high-level scoping call because that's not what customers want to do during kickoff; they just want to get started.

Thinking self-serve onboarding is too complicated 

Sometimes, your offering might be complicated. But thinking it's too hard for customers to self-serve is not going to move the project along. Provide customers steps or help guides to take home and work on their own. Have playbooks instead of plain docs. Setting up video repositories also helps customers learn and do some of the setting up by themselves; you can then go to meetings with questions about what they've set up. This moves the ball quicker by speeding up the onboarding cycle.

Thinking onboarding ends with user training

Sometimes, the users attending these training sessions would only have their first view of the product. They wouldn't know why they are in training. They wouldn't have an incentive to adopt the product. They would feel like it was all the bells and whistles of what your offering could do for them, rather than being very specific to the reasons why it had been purchased and how it was going to make them more effective.

So rather than ending onboarding with end-user training, put in two new meeting types:

  1. One is a launch meeting, which is technically the end of the onboarding. You have gone through all Q&A, all checks, and all user accounts are ready to go. A launch event, gamification, and incentivizing help get users to adopt it. Set targets to achieve and work towards them.
  2. The second one is a successful meeting that happens 30 days after the launch meeting. At this point, you are assessing whether the licenses that have been purchased have been utilized, so we're truly taking the customer from onboarding to adoption. We're not leaving it to chance. This is also an opportunity to ensure that the onboarding has succeeded in its mission. You can now go into deeper use cases. Chili Piper has this concept of 'almost ever boarding customers', rather than just setting them up with the product and forgetting them at the point where the users have been trained.

Driving change using data-driven metrics

One specific example of using data to drive decisions would be  Jeff Bezos's concept of decision memos. You make a document beforehand that outlines the context:

  1. What you want to do
  2. Why you want to do it
  3. What your options are
  4. What the pros and cons are

You share it with the team to make a decision. Do this between tools, process changes, product decisions, headcount adjustments, etc. Introduce this and map the data behind it in a scalable format that outlines the problem you need to solve.

More resources from industry leaders and experts

  1. Propel22 recordings
  2. Implementation Stories
  3. Preflight Conversations
  4. The Launch Station - a podcast for all things customer onboarding
  5. Customer onboarding resources from Rocketlane

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Shuvedha Subramaniam
Content Marketer @ Rocketlane

Marketing analyst @ Rocketlane. An Advocate by choice and a penwoman for the love of it. When the world zips, I like to zoink. Also, being happy by being kind.

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