A Guide to B2B SaaS Onboarding

Lessons learned about how high-touch customer onboarding goes wrong... and how to make it right.

A 9-part series — April 2021

Introduction

We researched 100+ of the best customer success and onboarding teams while building Arrows. During this process we learned how many of the best teams onboard their customers.

We also heard many of the ways customer onboarding breaks down. This guide will teach you how to fix your onboarding, keep everyone aligned, and get customers to value faster and more cleanly.

Part 1

Every company should define onboarding for themselves

Every company should define onboarding for themselves

The first step in improving your onboarding is to define it.

What does it mean when a customer is “onboarded” at your company?

Some people think onboarding is only about helping customers learn your user interface. For them, being onboarded means that the customer has configured their account and knows how to use it.

But if you define onboarding that way, you’ll graduate customers from your onboarding process before they start seeing the value of your product. This leads to confusion, lack of direction, and in the end, much higher churn.

Here's how we define onboarding:

Onboarding is the moment your customer experiences the value they expected to gain by buying your product.

It can be hard to nail down exactly when that moment is, and what it actually looks like. But getting clarity on this point can be a game-changer for both your product and your company.

When everyone in your organization is on the same page about what it looks like to be onboarded, it focuses every team around the same goal.

The sales team frames their pitch around a solution for a specific set of problems. When a new customer signs up, the CSM team reminds them that a successful onboarding will help them get to that solution faster. And the product team prioritizes the product changes that help customers solve those problems more easily.

Define onboarding across all teams

Sometimes companies call the moment the customer experiences value the "Aha Moment". (there can also be more than one—more on that soon…)

Those Aha Moments give the customer hope that they’ve made the right decision, motivating them to keep plugging away at the onboarding process.

Making sure customers see the value of the product before they churn is life or death for any company.

Once you have onboarding defined, then you can begin building your onboarding process.

Help your success team be awesome at onboarding...

...so they can help your customers be awesome too.

Start using Arrows

Part 2

Switching to a new onboarding process can be hard!

Switching to a new onboarding process can be hard!

Somewhere between hiring your 1st customer success manager (CSM) and your ~5th, you reach a breaking point with your ad hoc onboarding process.

Customers start churning. No one can identify why. And you really start feeling like you can’t keep up. You're relying on a mix of spreadsheets, project management tools, and email templates to guide customers through their onboarding steps. Things are beginning to fall through the cracks.

To ensure long-term success, it’s crucial to develop a high-touch onboarding process that every CSM can follow. Ideally, this process will provide high-level visibility into the progress of each customer as they move through the onboarding steps.

Typically, many high-touch onboarding processes involves some or all of the following phases:

  • 🤝 Sales Hand-off
    Transferring the relationship from sales to the success team.
  • ☎️ Kick-off Call
    Setting expectations around the onboarding process, due dates, work required by both parties, and points of contact.
  • ✅ Implementation
    Importing data / processes, setting up new hardware / installing new software, and testing systems.
  • 🎓 Training
    Helping the customer educate their employees, making sure everybody understands how to use the product, and final prep for launch.
  • 🚀 Launch/Rollout
    The moment the customer begins using the product in a fully live state and to solve real problems.
  • 🎉 Review
    Getting feedback from the customer about how the launch went, how they’re using the product, and their plans for further usage.

After interviewing more than 100 companies, the biggest barrier we’ve seen to creating an onboarding process is finding the time to do it while continuing to onboard new customers. Since most teams don’t realize they need a formal process until they’re feeling overwhelmed, any efforts to step away from day-to-day onboarding efforts will make them feel like they’re falling further behind.

But an investment in a formal onboarding process is well worth it in the long run, because it will help reduce churn and allow CSMs to automate many of the processes that take time away from building relationships and driving real value.

The second area of resistance we’ve noticed happens when CSMs feel invested in a process they have created, rather than the outcome of that process. When they are asked to change their onboarding process, they feel like their entire job is changing.

The key to overcoming this resistance is to shift the mindset of your employees so that they focus on the goal and not the process. One effective way to do this is to create financial incentives that are tied to successful onboardings with a compensation plan that includes base pay plus bonus or base pay plus commission. This doubles as a way to explain the process changes as well.

But you also should make sure any new tools or processes feel like real solutions to your team. Find out what the most painful and tedious parts of their jobs are and fine-tune them to automate or improve those tasks. After your team gets over the adjustment hurdle, they’ll be happier doing less busy work and spending more time proactively helping customers.

Help your success team be awesome at onboarding...

...so they can help your customers be awesome too.

Start using Arrows

Part 3

How to have a smooth hand-off between sales and success

How to have a smooth hand-off between sales and success

The way your sales team and your success team handle transferring a customer from one team to another sets the tone for their experience with your company.

Too often, that hand-off feels more like a toss over the fence. Customers notice instantly when teams are siloed.

In a successful hand-off, the customer knows who their new point of contact is and feels a sense of continuity in their relationship with your company. For that to happen, the sales team needs to facilitate a smooth transfer of both the relationship and their knowledge of the customer’s goals so the customer doesn’t feel like they’re starting over.

There are two ways to provide that sense of continuity:

  • Option 1:
    The sales rep joins the hand-off call for the first five minutes, introducing the customer to the success team and sharing a brief synopsis of the customer’s goals. Then the sales rep leaves the call and the success team takes over.

  • Option 2:
    Before a customer commits to purchase, assign a success team member to them and bring that team member into a later-stage sales call. The CSM can answer questions about how long the onboarding process will take, how much work the customer will have to put in to get up and running, and any prerequisite steps they should start before they even sign the contract. Then, after they sign, the success team member can take over the relationship seamlessly.

We usually recommend the second option, at least where the sales process allows it, because it can help build momentum toward a sale. That momentum is important for getting customers successfully onboarded.

Another way to improve the hand-off, which works in either option above, is to create a success plan or onboarding plan. A success plan is a shared document that makes all the little assumptions and hidden details in your onboarding process clear to both the customer and your team.

Included in the success plan, or in a separate implementation plan, is an outline the technical tasks to get your product set up. This includes timelines and due dates for those tasks, and assigns responsibility for each one. We’ve seen smart success teams share a basic success plan with prospective customers before they’ve even closed on a sale. The sales rep can send it to the customer as a nudge, or the CSM can get on the phone with the prospect and introduce the success plan to set expectations and help convince the customer to buy.

We’ve also noticed that compensation structures can impact the smoothness of your hand-offs. We’ve seen many SaaS companies achieve smoother hand-offs when the sales team has a blended compensation structure that includes bonuses for customers that successfully complete onboarding before churning.

Help your success team be awesome at onboarding...

...so they can help your customers be awesome too.

Start using Arrows

Part 4

Keep things moving with due dates and timelines

Keep things moving with due dates and timelines

A good customer success plan outlines all of the steps in the implementation phase of your onboarding process and pairs them with timelines or due dates for each of the steps along the way.


Let’s use an imaginary company, Acme SaaS, that serves CPA firms, with the following success plan:

  • ☎️ Kickoff
    (a few days or a week after purchase)
    • Create accounts (15 minutes)
    • Determine and document KPIs (30 minutes)
    • Pick first client rollout candidate (30 minutes)
  • 🧰 System Setup
    (starts in the days after kickoff and lasts 1-4 weeks)
    • Enable custom data connections (2 hours)
    • Import pre-existing data (1 hour)
  • 🚀 Rollout
    (as soon as system setup is finished)
    • Share portal with rollout client on call (60 minutes)
    • Forward FAQ to rollout client (15 minutes)
  • 👋🏻 Check-in
    (~2-4 weeks after rollout)
    • Gather feedback from internal users and rollout client (60 minutes)
    • Schedule check-in call with Acme SaaS (15 min)
    • Hold check-in call to review progress and KPIs (30 min)

The timelines provided in this plan are based on the average amount of time past successful customers have taken to complete each step. These timelines set expectations for the customer about how much time and effort it will take for them to see the value of your product.

But those averages are just a baseline. It’s important to come to an agreement with the customer about the due dates for each task. Some customers may want to push the onboarding timeline to get set up faster than average.

While you may want to capitalize on that momentum, you also need to make sure the customer’s timeline is realistic. Pairing each task with an estimate of how much time it will take to complete will help the customer commit the appropriate amount of resources to the onboarding process.

If the customer misses an agreed upon deadline, your success team can reach out within a day or two to find out why they are stuck and offer help.

On the other hand, if a customer knows they will need more time on each task than you suggest, they can request later due dates so that your team doesn’t nag them before they are ready. However, you don’t want to let a customer push the deadlines out too far or else you risk them losing momentum to finish onboarding.

Establishing timelines for your onboarding process can also help your sales team drive to a close. During a late-stage conversation with a prospect, they could say, “It takes most customers two months to get fully onboarded, so you'll want to sign the contract now if you expect to go live by your deadline.”

Help your success team be awesome at onboarding...

...so they can help your customers be awesome too.

Start using Arrows

Part 5

Designate a point person to coordinate multiple stakeholders

Designate a point person to coordinate multiple stakeholders

An onboarding process can quickly go off the rails if there are multiple stakeholders on the customer’s side. Especially so when they're not on the same page about what tasks need to get completed and who is in charge of getting them done.

We’ve seen companies run into issues with customers of all types and sizes. For example, when dealing with schools there are often siloed departments and layers of bureaucracy. With larger enterprises, the person in charge of purchasing is often different from the person who needs to pull the data or graphics to get the product running. And ultimately, that person (or team) is often not who will end up using the product.

To make sure your success manager doesn’t have to track down all of those stakeholders individually when a task is overdue, it’s important to designate a person on the customer’s end who will be the single point of contact during onboarding. That person will be the champion for your product on the customer’s team, and we often call them the "point person".

Reserve time on the kick-off call agenda to designate a point person. You can do this as simply as asking them to choose someone on the call, making sure there's total agreement from everyone on the customer’s team. Appointing a point person from the customer is possibly the most important objective during kickoff, since it ensures everything else continues running smoothly into the future.

The point person needs to be someone who feels a sense of ownership over the project. Ideally, the point person is someone whose job depends on launching this product (to be blunt). They will need a strong incentive to coordinate all of the players on the customer’s side to get the product running.

If you’re using a project management tool or a B2B onboarding tool like Arrows to share the onboarding task list with your customer, you (or the point person) should assign tasks directly to the people on the customer’s team who need to accomplish them. Then you can set up automated reminder emails around the due date for that task so there’s no chance of confusion about who is supposed to do what.

Help your success team be awesome at onboarding...

...so they can help your customers be awesome too.

Start using Arrows

Part 6

Suggestion: stop using email during customer onboarding

Suggestion: stop using email during customer onboarding

Emails get lost like it’s their job.

Email was not built for sharing information that needs to be referenced over and over again. But too often, companies rely on email for sharing their success plans and next steps with customers. It’s no surprise that customers are often unable to find the information they need to understand what happens next during onboarding!

How many times received an email from a customer asking "Where are we on this?" Usually this email arrives because you're waiting on the customer to do something, but they lost track of what they were supposed to do next.

To avoid communication problems during onboarding, make sure any resource your customer will need to reference in the future is stored at a website they can bookmark. This could be a Google Doc, a Trello board, or a custom success plan in Arrows. Having that information in a link will prevent you and the customer from digging through old emails to figure out what information has been shared.

The ideal success plan lets you manage the whole onboarding process without using email at all—except for automated alerts. To do this, you need a plan that’s stored in an editable format so that the customer can update the plan as they check off tasks.

It’s also helpful to be able to add comments to each item of the plan so that any notes discussed during your calls or any discussion about an item can be added directly to the relevant task. And to make sure your success manager doesn’t have to send reminder emails, your plan should be able to assign tasks and due dates to individuals and send automated reminders. (p.s. did we mention Arrows helps with this? 👀)

A good success plan provides accountability for you and the customer, and emails get lost. If the onboarding process slows down, it should be easy for both parties to figure out why and get back on track.

Help your success team be awesome at onboarding...

...so they can help your customers be awesome too.

Start using Arrows

Part 7

Have high-level visibility across all of your customers

Have high-level visibility across all of your customers

When you start onboarding multiple customers at a time, it’s important to be able to quickly assess where each one is at in the process. That's why you need high-level visibility into the status of all of your customers' onboarding processes.

We see it all the time: every CSM on a team has their own ad hoc processes or tools, and the only way see status across all customers is to call a meeting or have everyone manually update a shared document. But meetings are time-consuming and gathering the info to fill out an update takes time too (and, let's be honest, is likely out of date).


Gaining visibility into the status of each customer in real-time is a crucial step to improving your onboarding process. You can’t improve what you can’t measure. And if you don’t know where your customers are at in the onboarding process without checking on each one individually, you won’t be able to measure any data about your onboarding process.

When you can see all of your customers’ statuses at once, you can gather a lot of data about your onboarding process. That data can help you quickly triage which customers need the most help. It can help success managers direct their energy toward the customers who are closest to hitting an "aha moment" or a milestone, especially if it's tied to a bonus.

If your team has multiple success managers, they can use the data to benchmark themselves against their peers and learn from the team members who are completing onboardings the fastest.

And when you have high-level visibility into each customer’s onboarding journey, you can begin to notice patterns of where customers get stuck and why some customers churn before they’ve even finished onboarding.

Help your success team be awesome at onboarding...

...so they can help your customers be awesome too.

Start using Arrows

Part 8

Keeping customers on-task during complex onboardings

Keeping customers on-task during complex onboardings

How do you keep a customer on-task during high-touch SaaS onboarding?

One of the most frustrating experiences for a CSM is when a customer drags their feet on the tasks necessary to move to the next step in the onboarding process.


There are two big reasons why customers stall out during onboarding:

  1. They lose momentum
  2. The onboarding tasks are too complicated

It's a simple rule:

Customers lose momentum when they lose track of the end goal of integrating the new product they just bought.

Everyone has a natural resistance to change and learning new processes, so it’s important to keep the “why” behind a customer’s investment front-and-center. We recommend including a visual reminder of the end-goal of the onboarding process on the success plan.

In Arrows, all success plan templates include a space to write a summary of the customer’s goals next to the task list. We’ve also noticed that it’s important to start every onboarding meeting by re-emphasizing the outcome you’re working toward. This keeps the customer focused and motivated and also provides a chance for the customer to let you know if their goals have changed.


How do you know when a task is too complicated?

An onboarding task might be too complicated when you notice many of your customers getting stuck in the same place.

You also need to have visibility into how often tasks are overdue to recognize this in the first place. But when it happens, it’s time to dig into that task and find ways to simplify it (or maybe move it to a different point in the process).

Maybe you’re asking too much too early. Find the most essential part of a task, and save the other elements for later on in their onboarding journey. Your customer needs to have multiple "aha moments" on the way to experiencing the full value of your product in order to stay motivated.


This actually happened to us at Arrows with some of our earliest customers. We noticed customers were getting stuck when we asked them to tell us their current onboarding process. In our minds, that meant “tell us whatever you’re doing now, even if it’s kind of a mess.” But many customers thought we were asking for their ideal onboarding process, and they felt like they needed to do a strategic planning session before they could even use our tool.

But the goal of Arrows is to help customers build and improve that process over time, so we had to make a change. We shifted the task to say “Gather your existing onboarding documents.” This simple prompt allowed customers to quickly grab whatever checklists or templates they already had. It gave us a place to start because we realized as they got more familiar with the tool, they would discover ways to improve their onboarding process organically.

Help your success team be awesome at onboarding...

...so they can help your customers be awesome too.

Start using Arrows

Part 9

Segment customers to give the best onboarding experience

Segment customers to give the best onboarding experience

The goal of onboarding for SaaS companies is to get the customer using the product and seeing its value as fast as possible.

If your company serves a wide variety of customers, the onboarding process can become bloated with tasks that are only relevant to some customers. Eventually, most SaaS companies will need to break their customers into segments and create separate onboarding processes for each segment.

But it’s not always obvious how to segment your customers. A three-person team and a 300-person team might need to go through the same process if their use-case is the same, so company size isn’t always the right metric. And two companies in completely different industries might still share a common problem that they’re solving with your product. There’s no need to create separate templates if the use-case is the same.

We recommend that companies start with one comprehensive onboarding template. Then customize the template for each customer before starting them on the journey, removing any irrelevant tasks and adding anything that’s missing. This adds some work before you send out each success plan, but it will streamline the process for the customer, which can get them to value faster.

If you find yourself needing to frequently edit your template in similar ways, try to find the commonalities across those companies (e.g. the product they bought, their timelines, their goals, etc).

Do the same for any tasks you frequently add or remove. Eventually, you’ll have enough data to break your customers into segments, and create separate onboarding templates for each segment.

In our experience, the segments usually end up being determined by things like the combination of products purchased, the number of custom features requested, or back-end details related to your product.

We've also seen many mature success teams use the Jobs To Be Done framework to segment customers throughout their entire lifecycle and build onboarding templates specific to each job. We hope to dive in deeper to this subject in future guides, as it's one of the things all scaling success teams start dealing with.

Help your success team be awesome at onboarding...

...so they can help your customers be awesome too.

Start using Arrows

Need help? Email a co-founder dz@arrows.to

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