Richard Benavides on How Crew Reinvented Its SMB Onboarding From High-Touch to Self-serve

Richard shared his experiences with onboarding, the reasons for Crew’s switch to a low-touch customer onboarding model, and more
Kirthika Soundararajan
April 22, 2021
Implementation Stories
Main Illustration:
Krishna Kumar

Richard Benavides on How Crew Reinvented Its SMB Onboarding From High-Touch to Self-serve

Richard shared his experiences with onboarding, the reasons for Crew’s switch to a low-touch customer onboarding model, and more
Kirthika Soundararajan
April 22, 2021
Implementation Stories
Main Illustration:
Krishna Kumar

In This Post

In this session of Implementation Stories, we spoke to Richard Benavides, Onboarding Manager at Crew App. With over five years of experience in handling onboarding for SaaS apps, Richard’s expertise lies in leveraging automation and technology to create onboarding experiences that deliver the brand promise quickly and effectively. At Crew, Richard single-handedly manages onboarding for all customers across foodservice, grocery and retail, healthcare, long-term care, and lifestyle sectors. 

Crew is a digital workspace similar to Slack and connects distributed workforces comprising frontline workers to their managers and corporate leadership by unifying communications, streamlining scheduling, and making operations easier.  

In an hour-long chat, Richard shared his experiences with onboarding, the reasons for Crew’s switch to a low-touch customer onboarding model,  their current approach, and the one thing to focus on in onboarding. 

 Let’s get started. 

Note: We’ve edited the conversation for brevity and clarity.

Please tell us a bit about yourself and your work at Crew.

I’ve been in onboarding for nearly six years and with Crew since 2019 and am currently the one-person onboarding team here. 

You can think of Crew as Slack for shift workers or dispersed workers. It has schedules, shift coverage, a repository for workers to access resources, etc. Our users are mostly from the fast food, retail, or healthcare industry. Basically, any place that has distributed sets of field workers. 

What did the onboarding process at Crew look like when you joined? What is the core methodology like?

It was a high-touch approach, no matter who the customer was. On average, every customer got about three hours of live training sessions, live check-ins, etc. through online meetings. 

Since Crew is fairly easy to use, we focus on the leaders to drive onboarding. 

The first call is a kickoff one with the leadership team at a high level. Then, there is a meeting with, say, the department leaders, to understand their requirements and configure the app for them. During this time, they submit the information that shows us how to create the setup for them—this is mostly through Excel templates that they fill for us. 

By Week 3, the training is complete for everyone. 

During Week 4, we invite everyone to check in with them, and this happens once again, after another two weeks.  We introduce the CSM after about 60 days.

What was the first thing you decided to change and why?

At a progress tracking meeting for a smaller company, I realized that progress was stuck because it was hard for their team to organize the meetings. But I later found out that the end-users were still using the product. I realized we were manually doing things that we didn’t need to; there were too many meetings.  

That’s when I started turning to automation and self-serve models. I started creating training modules in the form of short videos using Thinkific. I found that these videos were only around 35 minutes long—half the duration of my training sessions.  

I found that most customers needed these videos as safety blankets, and not everyone needed or used them. 

What were some of the other tools that you used and experimented with? 

There are tools like Skilljar which make sense for bigger companies. Since we are smaller, simpler ones work well enough. I use Adobe Suite, Premiere Pro, and After Effects to create videos and GarageBand to work on audio.  

For the delivery of the training, it was initially through templated emails. We then moved on to ActiveCampaign and HubSpot, and then Zapier which connects them both. We also use G-Suite and TypeForm connected with HubSpot.

What kind of customer has this low-touch approach best worked for? What level of automation do you use for different kinds of customers? 

Our automation tools are used throughout for all customers. 

For customers with ARR less than $2500 who have fewer than 100 employees, our automated approach involves the sales team filling out a Google form and firing off a HubSpot campaign, with reminders, follow-ups, etc. built-in. 

We use a hybrid approach for customers with ARR between $2500 and $10000 who have between 100 and 600 customers typically. We send out a personalized email and ensure that they have access to someone from our side. The rest, such as training modules for employees at say, the store leader level, is still automated. 

For customers with ARR over 10K and 600 to 3000 employees, we provide consultation and training for their leaders in person, with the rest still automated in the form of recorded training sessions. 

For customers with ARR over 50K, we work with the entire team: our Director of Customer Success is involved, there is more leadership team involvement for integrations, etc. We still use the automated bits, but because they’re designed to be modular, we customize what we finally offer to the customer by excluding some elements, adding some others, etc. 

No matter what kind of customer we work with, I’ve seen that all of them benefit from the automation we have put in place. 

How do you configure the tools to make sure the customer is serviced correctly and that the right people within the organization are sent the right resources based on their needs? Is this done by Sales? 

The initial determination is done by the Sales team. Sales fills a questionnaire for us so we get all the details. Sales and Onboarding work very closely together.  The Sales team has also moved away from pitching high-touch post-sale service and instead, talks about the benefits of the automated on-demand experience that we offer. 

Did you face any internal challenges when you tried this low-touch approach? Have onboarding roles within your team changed since these changes were made? 

Since our director had been a CSM herself and we had started focusing on enterprise companies, she loved the idea. 

Thanks to this automated onboarding, I have been able to hand over some people directly to support teams. We’ve had cases where I have had up to 50 customers all getting onboarded at the same time. It worked just fine with automation working just as it was supposed to

Automation lets you get out of the monotonous work so you can focus on the customers who need help. This has allowed me to standardize a lot of processes and made me more effective in getting customers to value faster.

Do you have any advice for people who want to move towards automation but don’t necessarily have the tech/automation skills themselves?

Lean into what you’re good at. If you’re good at writing emails, there are a lot of marketing automation tools, like HubSpot and ActiveCampaign. That is already a good start; you can use this time to learn tools. Don’t let the tools worry you, you can accomplish most things with even basic tools like iMovie. 

What factors, would you say, determine if automation or manual or hybrid onboarding models will work for a particular customer?

Understand your end user. For instance, in our case, the senior leaders are not digital natives, so we sometimes have to simplify the process for them. But at this point, emails and videos on YouTube work for everyone. Our frontline workers are digital natives, but we have to be careful not to bore them with over-touch. 

In the end, it boils down to being honest with your end user. 

How are the training videos typically delivered?

We host our videos on Thinkify where they can access the transcript too. Thinkify makes sure it’s already set up for mobile viewing. Our HubSpot landing pages have videos there as well. 

The previous company I worked for, had Wistia and YouTube channels. 

How did you ensure that your end users accessed these videos, given that they are on other platforms?

That’s why you need the senior people from the customer team on your side. It’s important to let the leaders like district managers or anyone with enough clout within the organization know how the training happens, how the sign-up happens,  and get them to push the end users towards your training modules. 

What are some tell-tale signs that indicate high-touch is not working for a particular customer? 

The difficulty of organizing meetings. 

The second thing to look out for is the level of engagement during meetings. It’s important to read the room, have check-ins, and ask questions that can help you better understand what’s not working.  

But if adoption numbers are high, don’t worry about meeting every single person to train them. 

Any closing advice or inputs for onboarding teams?

Everything boils down to how fast you can deliver your brand promise and how effectively you can do that. The hard part happens when you equate implementation with onboarding and try to show them everything. Most of the time, your customers are buying your tool for a purpose. Make sure to ask your sales team exactly what the customer wants out of the product. If you focus first on that one thing your team promised, you’ll be more effective and take less time to show them value. Other than that, it’s just about making sure that they know where to find you if they need you. 

Focus on adapting based on the context and the customer’s level of maturity. Instead of having a program approach, have a customized personal approach that you can insert the programs into. 

Summary 

We couldn’t help but notice how Crew’s journey from a meeting-intensive, high-touch onboarding to a low-touch one was triggered by something as simple as paying attention to the end user’s usage patterns. In customer onboarding, it’s easy to get carried away with processes, plans, and training, but onboarding is successful only if your end user uses your product and sees value in it soon enough. 

Here is a quick summary of the rest of our takeaways from the session with Richard:

- Figure out the right amount of support that customers need during onboarding. For simpler products or smaller customers, make sure that you don’t overwhelm them with too many meetings/touchpoints. 

- Automating training and making them available on-demand can help turn possibly repetitive and forced training sessions and meetings into self-serve solutions that users could use and learn from at their own pace.

- The right way to look at automation: Instead of looking at automation as a risk to your job, look at it as a way to free yourself from repetitive tasks and use that time to help your customers. No matter what the size of your team, it is possible to automate some processes.

- Using a combination of tools and platforms such as Thinkify, HubSpot, TypeForm, Adobe Suite, etc. can help you design, develop, and host videos, training sessions, and webinars. 

For different kinds of customers, Crew uses:

- A fully automated approach for customers with fewer than 100 employees

- A hybrid, semi-automated approach for customers with 100-600 employees. In the hybrid approach, they provide personalized emails and touchpoints, but collect information manually, and automate the training. 

- A personalized high-touch onboarding process for enterprise customers with 600 to 3000 employees. This includes personalized consultations and live training for senior executives but automated training for local managers. 

- A whole team approach for enterprise customers with more than 10,000 employees, where the whole onboarding team with Crew’s Director of Customer Success and a few C-Suite executives join hands for onboarding and training.

Advice to people who want to automate their processes but lack the skills to do so: 

- Lean into what you’re really good at and find the tool that will help you automate that.

- Use the time saved to learn to use advanced tools that can showcase your content more professionally if needed. However, in most cases, simple tools get the job done. 

- Understanding your target audience and especially your end user is crucial. Knowing what they want and how comfortable they are with digital tools is important.  

- Lastly, focus on understanding why a customer is buying your product. Remember that they don’t care about everything your product can do. They only care about what they want to achieve with your product, so make sure your onboarding delivers on the promise you’ve made to them. 


If you found this useful, consider joining our private, invite-only Slack community and attend the next Implementation Stories session or just access more such resources. You will also gain access to peers and share knowledge on customer onboarding, implementation, and customer success.

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Kirthika Soundararajan
Content Marketer @ Rocketlane

All things content at Rocketlane. I run on coffee and cat videos. Follow me on Twitter @kirthikasrajan

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