“The decision to renew is made in the first 90 days of the post-sale journey,” says Shari Srebnick, a Principal Analyst at Forrester.
Customer onboarding matters, regardless of your target market. But nowhere is it more important than with those enterprise accounts you fought so hard to win.
“It's a unique pressure you don't see with smaller accounts,” reflects our own Customer Success Lead, Madison Kochenderfer.
Enterprise clients expect a white-glove, personalized onboarding experience—easier said than done if you’re running a lean CS team.
In this article, we’ll break down:
- How to create a high-quality onboarding program that will help your enterprise clients get to value as quickly as possible and encourage those all-important renewals.
- How to keep your onboarding and implementation journey as efficient and low-lift as possible internally while still providing the white-glove, customized experience your enterprise customers expect.
What makes the enterprise client onboarding process different?
Madison worked as a Senior Customer Success Manager at Lattice before joining us to lead the CS team at Dock. She explains that onboarding large accounts isn’t necessarily more challenging than onboarding SMBs:
“With smaller accounts, you're fighting for bandwidth at times—you're fighting for attention. With larger enterprise accounts, hopefully, there are more people you can tap into to get the job done more quickly.”
But while there are more hands on deck, Madison says it can take some practice to learn how to leverage them. With so many stakeholders potentially involved, it’s critical that you nail down exactly who you should be talking to early on, or your implementation process ends up being everybody’s responsibility—and nobody’s.
Introducing a new tool into an enterprise account also requires a higher level of change management.
Getting 20 people to use a new tool can be done with a couple emails, but getting 2,000 people to use a new tool takes a full change management program.
Finally, as Gillian Heltai, former Chief Customer Officer at Lattice, explained on our podcast, “Your biggest customers are the ones stretching your product.” Large accounts will expect “a different level of attention, a different cadence of attention, different product workarounds.”
You’ll need solid processes in place to capture and respond to enterprise customer feedback. You may also find that CS has to step in to fill the void, says Gillian:
“A lot of times, CS augments the product and does the things the product can’t do—things like reporting, or configuration design, or data entry[...] You want to fill the gap with a service intervention, rather than putting that burden on the customer or having their needs go unmet.”
The challenge, especially for smaller CS teams taking on enterprise customers, is to figure out how to ensure that enterprise customers feel heard and supported while not overloading the CS team or neglecting smaller accounts.
7 enterprise customer onboarding strategy best practices
“If you don't deliver a great onboarding, it's like a trough of disillusionment where it's like, ‘Oh, I thought it was going to be this. And now this is so sad,’” says Gillian.
To keep your enterprise customers out of the trough and keep the initial excitement high, our CS experts advise you to:
1. Look hard at your CS team structure
As you move upmarket, your CS team structure should evolve to support changing customer needs. This isn’t just about adding more people—it’s about adding a greater degree of specialization.
As you start to take on enterprise accounts, make sure that you have coverage for the following functions:
- Customer Success Managers (CSMs) to build initial customer relationships, measured by net revenue retention and churn rate.
- Technical support to resolve technical issues, measured by customer satisfaction and resolution rates.
- Implementation and onboarding to guide customers through initial product use and accelerate time to value.
- Professional services to offer tailored solutions for enterprise accounts.
- Customer success enablement and operations to provide resources, training, and tools to CSMs.
- Renewal managers to focus on retaining and expanding customer accounts.
In the early stages, your CS team is probably made up of generalists who are doing a little bit of all these functions. But you’ll likely need to specialize as you bring in larger accounts. Here are a few different options to consider:
- If you’re still on the smaller side, start by creating a separate team to handle onboarding and implementation and keep the rest of the team as generalists.
- If your product is complex and/or highly customizable, you’ll need a professional services team to support enterprise accounts.
Joseph Schmitt, VP of Customer Success at UpKeep, says that separating professional services allows the “CSMs to focus purely on proactive engagements around gross retention activities.” Meanwhile, the new professional services team can “guide customers through the implementation and fill in skill or resource gaps to ensure a successful deployment that leads to long-term customer retention.”
- If you’re hitting the growth stage of your business, it’s a good time to move renewals and upsells from Sales into Customer Success, and start setting revenue targets for your CSMs.
- You may also decide to segment your CSMs by enterprise account, industry, or customer profile to ensure they develop specific expertise.
- Finally, make sure you’re still taking care of your lower-ACV (annual contract value) accounts with a scaled customer success program.
📖 For detailed examples of CS org charts at Lattice, Deel, and Meister, check out our guide to Customer Success team structures.
2. Build in guardrails for feedback
One of the challenges with enterprise customer accounts is negotiating product feedback and new feature requests, says Madison.
“With smaller accounts, it's easier to be firmer in terms of how often you're engaging with them, the level of support you're giving them, and how you react to feedback you're given. It's easier to say, ‘That's just not on the roadmap.’”
Enterprise customers, understandably, expect to be able to influence product development, which presents a challenge for CSMs.
“You have to have boundaries in a different way,” Madison explains. It’s about treading a fine line—being receptive to feedback while also explicitly addressing what they can expect to see on the roadmap, what won’t be on the product roadmap for the foreseeable future.
Madison advises CS teams to partner closely with both Sales (to make sure that enterprise accounts come in with a realistic understanding of what product changes they can expect) and Product (so you know which changes are easy to accommodate and which aren’t on the horizon).
Madison says that great CSMs sometimes over-identify with the client: “You’re right, I’m going to get this fixed for you.”
Instead, it’s wiser to position yourself as a partner and an advocate for the customer without overpromising: “I'm going to advocate for you as best as I can, and I'll let you know what the Product team says.”
3. Support your customer’s change management process
Brittany Soinski, the Manager of Onboarding at Loom, recommends that you play a proactive role in your new customers’ change management strategy:
“Our job in customer success is to package everything up really easily to help our admins, champions, and stakeholders to communicate this change effectively.”
For example, Loom provides their enterprise customers with a ready-made communication plan:
- "Here are the five times you're going to communicate at your org."
- "Here's who should send the message. Here's what it should say. Here's the channel you should share it in. Here's how long it should be."
- "Here are some really effective talking points when you are introducing Loom to your organization and this new way of working."
- "Here are some values and benefits to communicate.”
4. Refine the sales-to-success handoff
Working closely with Sales ensures the customers’ needs are communicated to CS, so you can work to realize value as quickly as possible.
To nail the sales-to-success handoff for enterprise accounts, our experts recommend that you:
Bring in CS early in the deal
Eloise Salisbury, Chief Customer Officer at AutogenAI, is a big believer in bringing in CSMs before the deal closes to showcase the quality of support customers can expect from working with you.
“Customer success doesn't start, at least in my mind, when somebody signs a contract. I typically go into pre-sales calls and say, ‘You're thinking about investing heavily in our product, but you're also going to be investing heavily in the people that sit behind and support the product.
“So, whilst it's really important for you to go through the sales motion with technical consultants and talk about commercials, it's also really important that you understand and put a face to the name of the team that will be helping you onboard and see value.’”
In terms of when exactly to bring in Success, Eloise recommends that they join as soon as you’ve done the technical validation and well before the deal closes.
Make Sales part of the onboarding process
It’s worth having the Sales rep present at the first post-sale meeting with CS to reassure the customer that both Sales and Success have a clear grasp on their goals, needs, and expectations.
Sales and CS should also meet for regular account reviews to stay on the same page and identify opportunities for expansions, cross-selling, or upselling.
Repurpose your digital sales room into a customer portal
If you use Dock as a digital sales room during the presales process, Sales should have already capture these key details:
- Customer background
- Key stakeholders
- Customer priorities and goals
- Pain points and challenges
- Mutual action plan
- Notes on the sales process
- Contract details
Then, instead of introducing a new tool or process when the customer is handed over to CS, you can easily transform your Dock sales room into a customer onboarding portal.
Just unhide the onboarding content when the customer is ready for it, and they can keep working with your team using the same link.
CS has all the information they need to provide a white-glove customer experience, and the customer doesn’t have to learn a new tool or find and read a bunch of emailed links.
5. Consider all your customer personas
When working with enterprise accounts, you support at least three different personas:
- the economic buyer
- the admin(s)
- the end user(s)
To make sure you’re engaging the right stakeholders, our experts recommend you:
Define which personas you need for an effective onboarding
To make sure you have the key players engaged, start by defining which personas you need to work with post-sale, advises Eloise:
“What was really important for us at Iterable was that, in that kickoff call, we had the customer identify who in their team would be against each of those personas.”
“So we had the executive sponsor, then we had the marketing lead. We also had the TAP or the data lead as well. Then, occasionally, depending on the organization, we would have an operations lead. And so we identified right at the outset who they were.”
Get them all on the kickoff call
“Tell the customer exactly who you’ll need in the kickoff call—and, once you’re on the call, double-check to make sure you’ve got the right group,” says Madison.
“I typically say something like, ‘Please introduce yourself and tell me what your role is in the implementation.’ So I kind of throw it at them to start and see what their responses are. Quite a few times, it will be, ‘I'm not really sure why I'm on this call.’”
Create metrics for each persona
Eloise recommends the concept of the “triple metric” for your onboarding and implementation:
“Think about a pyramid. There's three different layers of that pyramid. The day-to-day users of your tool are at the bottom. You need to identify the KPIs they're tracking and that they care about. Then you do the same for that mid-layer of management at the company. At the top of the pyramid are the execs. Then we link how the KPIs from the day-to-day users would roll up to the middle management and up to the execs.”
Set a regular engagement schedule for each persona
Eloise recommends you set up a schedule to make sure that you’re engaging with all of your enterprise stakeholders:
“In enterprise, we had weekly or bi-weekly calls with the day-to-day users. Then, we would typically schedule separate monthly calls with our executive sponsors.”
“And yes, to a certain extent, we wanted to make sure our day-to-day users were able to feed up what they were working on to the business and the value that they had derived from our product. But it was also important that we were sharing that higher-level triple metric with the exec sponsor when we met with them on either a QBR or on a monthly basis.”
Educate admins to drive adoption
To quote Brittany from Loom, “Engaged admins are key to engaged users and driving adoption.”
This is crucial in enterprise onboarding, she explains:
“Our role in customer success during onboarding—as opposed to product-led onboarding—is really partnering with our admins to make sure the account is set up for success. We're working with our admins on the technical setup: ‘Here’s the order you need to set things up. Here’s how to consolidate your workspaces. Here’s how to turn on your SSO.’
“We're providing a lot of information for them, so the onboarding period is a really important time that we both educate them and enable them to be able to administer their workspace moving forward.”
For instance, Loom’s CS team uses Dock to walk admins through every step of onboarding:
“We use Dock on the first kickoff call with the customer—our Joint Success Planning call. We give them an overview of onboarding and align on what they want their onboarding journey to look like and what success ultimately looks like for them.
“It's really nice to be able to show them everything we're going to be doing together visually in the Dock onboarding template. And I'm able to take notes and edit on the fly. After our first call, I embed the recording from that call into the Dock template.”
6. Map out the implementation journey
Eloise explains that “enterprise implementation is all about adoption and engagement.”
Your priority has to be to capitalize on their initial excitement to drive toward value as quickly as possible.
“The most important thing is to sit down and plan out that customer journey. Right from the handover with Sales to the graduation from implementation and handover to account management, what does that look like?
“If you can break it out into phases and ask yourself: ‘What are the things that we want our customers to be doing within a certain timeframe?’ That helps you get that initial project plan and timeline together. Share some of this information with the customer in a pre-sales process, so they know what to expect.”
Eloise suggests breaking implementation into phases based on product feature adoption. That way, you can steer customers to use your stickiest features first.
Alternatively, you can design the journey around adoption milestones or simply work from a task-based onboarding checklist.
Then, you’ll have to decide how much you’ll be doing for them and how much they’ll be doing themselves. Will you have an obligatory implementation package for your enterprise accounts? Or will you play a consultative role?
Regardless of the decisions you make, Eloise says, “At the end of the day, you should be asking yourself, ‘What does a customer of ours need to be doing to ensure that they are sticking in the product, that they see value in the service that we provide, and that coming out of the implementation, there is a likelihood for them to renew?’”
7. Keep the enterprise onboarding process efficient
It can be challenging to create a white-glove onboarding experience with a smaller team. Here are our tips:
Make it as asynchronous as possible
Asynchronous onboarding lets your customers self-serve while still giving them a personalized experience.
Madison is a big fan of recording short videos in Loom: “I think that provides a nice white-glove experience without too much energy.”
For example, “I might give somebody a to-do item before we chat next. And I'll record a little Loom for a minute, just recapping why this is important and how to go about doing it so they don't even have to read an article. It's specific to them. I'm saying their name in it. It takes me 1 minute to record. I can do it between calls.”
She also likes creating a short introductory video that she’ll include at the top of the Dock onboarding workspace. Speaking of which…
Use a templatized onboarding workspace to streamline your workflow
Don’t have your CSMs reinvent the wheel for every customer. Madison remembers that before she started working at Dock, she was used to starting from scratch with each enterprise account:
“You might have a deck that you reuse, but most everything is built custom, like the email that you send and the follow-ups. And you create your own little Google Drive for someone, and you decide manually what resources you throw in there and what you don't.”
These days, Madison starts from a customer onboarding template in Dock and simply duplicates it for every customer: “Having a similar starting point for every single new client saves me a ton of time. It's usually just the conversation that's a little bit different.”
Check customer preferences
At Loom, Brittany’s team members use Dock to find out how much interaction their enterprise customers actually want:
“Now, in our onboarding guide in Dock, we have the steps of onboarding listed out, and under each, we started asking our customers, ‘Would you like to do this async, or would you like to have a meeting?’”
“This is a really good way to instantly show our value during onboarding. We’ll say, ‘We're going to do this asynchronously so that we can save us all 60 minutes from hopping on a meeting to walk through your workspace settings. We've pre-recorded this. You can watch this at 1.5 speed.’”
Make your resources easy to find
If you share key resources (like 101 webinars or how-to guides for admins) via email or as links in a spreadsheet, you can more or less guarantee that your customers will struggle to find what they need—wasting their time and yours.
Instead, you can use Dock to house your onboarding content in the same workspace alongside your success plan and to-do list.
5 steps to creating an enterprise onboarding program
Ready to build an onboarding program for your enterprise customers? Here are the steps:
1. Create an onboarding template
Don’t start from scratch every time. Instead, make sure your onboarding program is scalable by creating a customizable onboarding template.
With Dock, you can put together a template that anyone on your CS team can then modify with a few clicks to add specific resources, the customer logo, and any other information they need.
In your onboarding template, we recommend that you include:
1. A top-level summary showing the phases of onboarding, the onboarding team, the immediate next actions, and how to contact you.
2. A success plan, which you’ll finalize during the kickoff. In the success plan, include:
- Contacts and roles
- Use cases
- Success criteria for the implementation (e.g., 6 months from now, what does success look like for your team?)
3. An implementation task list, broken down by phases, with relevant educational content. For instance, in Dock’s case, the three phases of implementation are:
- Phase 1: Upload conten and create templates
- Phase 2: Set up integrations and dashboards
- Phase 3: Launch
Depending on how complex your onboarding journey is, you may want to show only the current phase of the implementation to avoid overwhelming the customer. With Dock, you can unhide each phase as soon as you see the customer is ready for it.
2. Schedule a kickoff meeting
Nailing the kickoff call is particularly crucial for enterprise accounts.
Make sure your customer knows who you’ll need on the call—at a minimum, the executive sponsor who’ll help set the strategy, the admin who’ll be completing the onboarding tasks, and someone with the technical skills to help with the integration.
According to Madison, the kickoff should have four main goals:
- To make sure that you’ve correctly identified and engaged with all the stakeholders you’ll need on the customer side to successfully implement your product.
- To introduce the customer to your CS team and make sure they’ll feel comfortable with where to go with questions.
- To give the customer the big-picture view of the implementation timeline—how long it will last, what they’ll need to do to get it done, the phases of onboarding, and what support will be available to them.
- To agree on a success plan.
Sample agenda for enterprise kickoff calls
Madison’s loose agenda for kickoff calls with enterprise accounts goes something like this:
- A round of introductions—including that all-important question about the role each person will play in the implementation journey
- What the implementation will look like over the next six to eight weeks
- Three phases of the implementation
- A quick walkthrough of the resources included in the Dock onboarding workspace
- Defining what success will look like (the success plan)
- The tasks to be done before the next conversation
3. Co-create the success plan
Madison has refined her success planning process for enterprise accounts.
She used to put together a fairly comprehensive success plan before the kickoff, but over time, “we simplified it a little bit, so it allows me to have more of a conversation. In V1 of my template, I felt like I was leading the conversation too much.”
These days, the success plan she includes in Dock’s template is pretty bare-bones. Instead, she’ll spend a significant portion of the kickoff call defining with the customer what success looks like for them.
4. Add educational materials and implementation checklists
Make it easy for your customer to progress through the implementation journey with checklists and educational resources. Remember to include training resources for each customer persona. For instance, including technical specifications and integration guides for your technical persona and introductory tutorials for your end users.
With Dock, it’s quick and easy to embed personalized demos and walkthroughs, as well as pre-recorded videos and tutorials, links to articles, and interactive checklists.
5. Prepare a change management program
Support your customers’ change management by creating training resources and a sample communication program.
For instance, we have resources on How to introduce your customers to Dock, an employee training guide, video content on how to use Dock as an employee, and a sample training agenda.
You may also want to schedule internal training sessions, an all-hands Q&A, or regular check-ins to make sure the roll-out goes as smoothly as possible.
📖 Looking for a customer onboarding checklist? Here’s one we made earlier.
Enterprise customer onboarding software
Of course, managing white-glove onboarding at scale isn’t just an issue of processes—you’ll also need the right tech stack. If you’re relying on spreadsheets or a project management tool, you’re going to struggle to create a seamless onboarding experience.
To onboard enterprise accounts effectively, you’ll likely need the following stack:
Customer onboarding portal
An onboarding portal is a personalized workspace that makes it easy for your customers to find resources, to-dos, meeting notes, and timelines.
They create the quality experience that enterprise accounts will expect. The alternative—some combination of a to-do list in a spreadsheet or project management tool, plus emailed links to Google Drive folders—is clunky, spreads the information out across multiple platforms, and puts the burden on the customer to dig for the resources they need during onboarding.
Options for an onboarding portal include:
Dock
Dock lets you create onboarding templates that you can copy for each new account, making it easy to scale your enterprise onboarding program. You can drag-and-drop multimedia content, share onboarding checklists, collect feedback, answer questions, and upload new resources any time.
Here's a demo on setting up your customer onboarding process with our CEO, Alex Kracov:
Give your customers a single link (no login required), and they’ll find everything they need to learn about your products.
Even better, you can keep an eye on the onboarding process and make sure they’re making progress. With our detailed workspace and content analytics, you can see who’s looked at what, and how often.
Other onboarding portal solutions include:
Knowledge base software
Even with a personalized customer portal, you’ll probably also want to provide access to a separate knowledge base—or you’ll risk overwhelming your customers with TMI during the onboarding process.
Knowledge base software lets you create, organize, and distribute educational and support materials. Our top knowledge base tools include:
Customer success enablement tools
Your CS team will also need a platform that makes sure they can get ahead of the renewal conversation, record personalized videos, spot opportunities for upsell and cross-sell, identify customer churn risks, or even charm new enterprise accounts with swag. Our picks in this space include:
📖 For more detailed information, take a look at our Customer Onboarding Software Guide.
Create a scalable white-glove onboarding program with Dock
Dock makes it easy to scale a personalized experience across all your enterprise accounts. You can use Dock to:
- Create a visually appealing templatized workspace that CSMs can customize in just a few minutes.
- Build interactive checklists that make it easy for new users to work their way through the onboarding journey.
- Embed personalized videos to give the onboarding experience a white-glove flavor quickly and easily.
- Transition your customers from a digital sales room to an onboarding workspace seamlessly, all with the same link.
- Track customer engagement and win more renewals with our analytics tools.
- Skip the messy spreadsheets, clunky Drive folders, and endless email threads.
Ready to level up your enterprise onboarding?
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