Scaling Onboarding with Self-guided Pathways


Shareil Nariman is the Head of Customer Experience at Arrows. Previously, he led customer lifecycle management, including onboarding, at Sprout Social and previously led operations teams at In this guide, he explains how companies that offer lower-priced SaaS products can leverage cross-functional collaboration and automation tools to design high quality self-guided customer onboarding experiences.

Table of Contents

Why is good onboarding important?

Prevent churn – customers churn early in their life cycle if they don’t understand value. The “why” of onboarding is to explain to customers the true value of your tool for their needs and to do it as early as possible in their journey with you. You want to prime them to grow with your business and you’re acting as a catalyst for potential growth down the line. 

Make a good impression with the customer – it’s like your first date. They’ve agreed to work with you and they’ve paid, so they know it’ll be a longer journey, but this is your chance to make that first impression and reset or realign any mistaken expectations that the customer inferred from the sales process. You’d rather do that sooner instead of later.

What is an onboarding playbook?

Your company’s living, dynamic guide to successfully activating customers – people tend to treat onboarding like a checkbox; it’s often mistakenly viewed as making some phone calls that take a couple days in the early part of the life cycle. But a strong onboarding playbook is never done, because it’s going to be a living, dynamic tool that should have multiple versions for multiple products. 

How do you create an onboarding playbook for your organization?

Define what onboarding means for your company –  you need a definition that the whole organization can stand behind. Oftentimes that includes starting by timeboxing onboarding, whether that’s saying it’s X amount of days or X amount of time in their life cycle. As your onboarding process matures, you may stop viewing it based on time, then it becomes really important to define what success looks like for customers moving through your onboarding process. As time goes on, both you and the client will no longer view it this way. Therefore it’s important to define what “success” looks like once you start putting customers through your onboarding process. 

Define what “types” of onboarding do you have – and which customers quality for each. For instance, some customers might qualify for 1:1 white-glove onboarding, while others might have a more product-led experience. Each onboarding type should have its own playbook, however, they should supplement each other.

Determine the “why” behind onboarding – explain the background along with the “why now.” Talk about the ultimate pain that brought you to the point where you realized you needed to invest in onboarding, because that pain is often what gets other people on the team bought in to spend time improving the process.

Spell out details for each step of onboarding – outline the first call: what are the discovery questions on call one? Where are you capturing the answers to those questions? What are potential next steps depending on some of the possible answers to those questions? Determine the number of subsequent calls/meetings, and what exactly you talk about on those (what features, etc)?

Decide how to track and measure onboarding progress – that can be using a dashboard or a tracker, but you need an indicator of what data you’re tracking, and where you’re measuring the progress. If done well, this tracking should encompass all of your onboarding pathways in a unified way.

What are the different “levels” of onboarding service? 

Guided version – this is the most common approach to onboarding and is 1:1 with humans. It usually lives under the success or account management umbrella and is pretty straightforward.  

Self-guided version – this is everything else. It’s a more scalable approach. The self-guided version involves live webinars, on-demand content, and a help center. This can also include tours and education built within your product itself.

Make sure the guided and self-guided versions are aligned – the more aligned the milestones are within the different funnels, the more aligned the measurement of success will be. 

What levers can you use in self-guided onboarding?

One-to-many webinars – these are live, more scalable calls that cover some of the same content you might address 1:1 in guided onboarding. Sometimes webinars are sequenced (e.g. level 1 then level 2, then level 3).

Teaching through an LMS – you’ll want a learning management system that takes the concept of those webinars and breaks them down into smaller and digestible videos. It’s not often referred to as onboarding, but your help center is a big extension and branch of onboarding. The two should talk more closely then they often do since the help center is usually run by the support side of the business, but it needs to be more tied to sales and customer success. 

Product-led onboarding – this is the tool itself conveying to a customer how to reach that value realization point. Companies should have cues, videos, or modules pop up in the app to help move a customer through a workflow. 

How does onboarding evolve as you become more sophisticated?

Start with 1:1 – this is the traditional path, and it’s limited by headcount. You can stay with this model as long as you have the headcount to support it. Some customers (because they’re large, or strategic, or in certain regions) will always get 1:1 onboarding. Usually threshold aligns with account management segments that already exist.  

Use webinars to scale 1:1 – start to do this pretty quickly. For context, when I built out Sprout’s onboarding process, I started layering in webinars within about two months. Once you know enough from 1:1 interactions to know what the onboarding team says consistently, what lands with customers, and what content the team is spinning up, turn all of that into live webinars. If this offering is robust, you’ll notice that customers are taking more level 2 or level 3 type webinars or courses in your LMS, vs. just those entry-level types of courses.

Use in-app guidance to get personalization at scale – very few companies do this really well, because to do in-app guidance well takes a long time, and a significant cost investment in the tools. Completing this phase takes a lot longer than the first two (assuming you want more than just a couple of pop-ups in your tool). We’ve been working on the in-app onboarding experience for two years because we have multiple user types and personas, and there are so many use cases with so many different things you can possibly pop up there.

How do you scale onboarding when you’re adding customers fast?

One option is just to hire more people – I’ve done that, just hired 20-30 people. It doesn’t not work. It may be what you have to do if there’s no cross-functional collaboration, because if marketing doesn’t know how to help you with customer communication and if the product or design teams are never going to redesign key flows, you’re never going to improve the onboarding experience, and you’re going to need more people. Because nothing else is learning or getting better or improving.

Self-guided onboarding helps you add more users than you can touch – with fast growth, every month you’re adding more users than the previous month. If your headcount is capped, figure out how many new subscriptions your team can handle, and what percentage of new customers that accounts for – that’s the number that you can plan to do 1:1 onboarding for. The goal then becomes getting everyone else to consume one-to-many and in-product onboarding.

For lower-end customers, 1:1 wouldn’t be a good ROI even if you had headcount – you can do a cost analysis on the impact of hiring one onboarding CSM: they can touch X amount of accounts a month, and they’re technically impacting X amount of revenue. If it costs $50,000 to employ one person, and they’re each impacting $150,000 worth of revenue, you can probably add a couple more. But when you do the same math with a $99/month subscription, you’ll see quickly that you can’t afford to have many 1:1 calls.

Who owns onboarding?  

An onboarding program manager potentially with the support of an “onboarding guild” – this person should oversee all onboarding at your company. They’ll probably sit under the customer success umbrella. I also see tremendous value in bringing together an “onboarding guild” of cross-functional stakeholders (read more about that in the “Creating a cross-functional onboarding guild” playbook).

What are some typical touchpoints for 1:1 onboarding?

Set-up – this includes login and billing, setting different permissions, and helping to connect API’s or upload tags and other content.

On the first call, address their main pain point – ask what they’re trying to solve, and then show them how to take care of it.  Get them to figure out how to use the functionality of the tool in that first call, and how to start to tackle whatever they tell you is their main pain point. 

Between calls, assign homework – between check-ins, give your customer something that you know they need to do. That helps to make the calls more impactful. 

Make subsequent calls hands-on – instead of demoing, have the customer show their screen and walk you through what they’re clicking on. You can help them from there. 

Introduce the CSM (at different times) – for an enterprise customer, a CSM might be on all the onboarding calls. For smaller customers, a CSM might join the last call to a live handoff.

What are some typical touchpoints for self-guided onboarding?

Triggered communication – it’s mainly emails that are sent on a certain date. For example, they could be from the time of subscription, time from first course digest or time from first login. 

Invite to webinars (sequential or not) – customers should all have access to your learning portal for webinars and other training materials. In triggered emails, invite new customers to the next series of appropriate courses. We run webinars on a fresh four-week cycle, and we advertise them that way.

In-app guidance you can tailor in-app messaging based on whether this is their first time using the app or if it’s a “repeat” session. It can also be based on the user’s role. Based on those variables, craft different pathways to take customers down with automated in-app communication. 

What tools/resources make onboarding easier?

The basics:

  • A CRM – e.g. Salesforce for tracking customer data
  • Marketing/email communication – e.g. Marketo or Pardot for email automation
  • Docs and spreadsheets – for internal knowledge such as playbooks, spreadsheets for tracking, and decks for sharing information.

The next level of sophistication:

  • In-app communication – e.g. Intercom or Pendo for delivering guidance and messages within your application
  • An LMS – e.g. Skilljar for housing scalable courses and webinars
  • Data storage and visualization – e.g. Redshift for data storage, Tableau for data visualization to analyze onboarding data

Tools for greater scale:

  • A call recording training tool – e.g. Gong to track and learn from 1:1 onboarding calls
  • A whiteboard visualization tool – e.g. Miro for designing flows and journey mapping

How do you measure onboarding success?

% of customers who are taking advantage of onboarding – if you don’t 1:1 onboard all of your customers, it’s really important to see what portion of your new customers are taking advantage of the self-guided onboarding pathway you offer. 

User’s behavior in the tool I care about what they do after they finish a pathway of learning. For example, if they attended a webinar that has a very specific topic, are they doing that behavior afterwards?

Revenue retention – are the customers who are completing your program reaching net dollar retention targets. If it’s over 100%, great. If it’s under 100%, what can be improved?

What is an “onboarding guild”?  

A cross-functional collaborative team – good onboarding is a company-wide effort. An “onboarding guild” is a cross-functional collaborative team that makes sure you have the right stakeholders around the table to craft a successful onboarding playbook.

An onboarding program manager coordinates the guild – unlike others in the guild, this person’s full-time job is onboarding.

Who makes up the “onboarding guild”?  

The core group includes the onboarding program manager, plus representative from teams like:

  • Customer success
  • Marketing
  • Product
  • Design
  • Growth sales

Guild members are functional leaders – ideally, these members are at the proper level within the organization (usually Director level and above) to allow them to decision-making power, teams, and resources (at a smaller company, the head of marketing, head of sales, and the head of product would be in the onboarding guild).

The guild is supported by cross-functional analysts – data analysts, data engineers, Salesforce engineers, and Tableau engineers. They’re needed more when it’s time to figure out attribution to these pathways and when it’s time to figure out what is and isn’t working. 

How often does the guild meet?

Guild members meet bi-weekly or monthly – the core team meetings include check-ins on progress on projects that different members are working on.

Wider stakeholders get monthly or quarterly updates – we send a monthly newsletter that goes to the whole company as well as a separate executive newsletter that goes to the C-suite, VPs and director levels to inform them of the progress of onboarding, who’s going through it and what updates are happening with it.

How does the guild get work done to improve onboarding?

The guild doesn’t spin up its own roadmap, work gets prioritized within teams – we don’t have to change anyone else’s projects that are already in play, which is a pro. The con is that you don’t always have full-time resources. 

How can an onboarding guild drive early value realization?

Don’t start with the onboarding steps – when siloed, too many onboarding teams try to document every bell and whistle. When you do that, you tend to try to train on every feature of every tool. The reality is that your customers aren’t ready for that level of mastery yet and that might not be their learning style. 

Pull pain-point insights from customer-facing teams – work backwards starting with what your customers are trying to do. What are the pain points customers are coming to you for? What does the customer need to do to do that job? You need to know what your customer needs to do to be able to do their job or to do the thing they want to accomplish with your tool. 

Work with product to identify the highest value features or actions in your tool – you don’t need data science from day one, but you need to understand what are the couple things that, if the customer can’t do them in your tool, then there’s no value. Hold customer interviews and focus groups and ask, “do you care about this feature?” When you’re in the role for a little while, you start to figure out what you need to tell the customer early on and what you don’t.

Partner with growth teams to design onboarding with future expansion in mind – premium add-ons won’t be right for every customer, but onboarding needs to understand what will trigger them – whether that’s seeing ROI, or the addition of a user, or some kind of monetization that increases with growth. 

Figure out what you won’t cover in onboarding and who will cover it – tell success, growth or support teams what you did or didn’t talk about with the customer, so they’ll be able to better manage their relationship down the line. 

What are some of the ways a cross-functional approach transforms onboarding?

Get and share feedback across teams – during onboarding you get feedback “with good intent.” Customers have just chosen that they want to use your tool, so what you hear is genuinely intended to help improve the tool, design and process. 

Solve problems upstream – instead of training around a clunky design, re-design the product to be simpler and more intuitive. Instead of having a bunch of support tickets later on, review the tickets to identify issues that need to be included in early onboarding. Instead of over-promising, make sure the sales team is setting the right expectations.

Better capture and hand-off information – you can engineer the layout of Salesforce fields or objects or account pages so that as the onboarding team captures information there’s an easy way to translate that and pass it off to success or support.

Flag what new customers are most excited about – onboarding can help inform marketing campaigns based on what we are seeing is a sticky feature. When onboarding talks about something with new customers and there’s excitement there, that can be fed back to marketing.

The onboarding team gets told “no” less to requests – to be successful, onboarding needs help from other teams on data requests, engineering needs, tooling needs, etc. When the team that’s being asked for the help better understands why onboarding is important, it becomes easier for the onboarding team to get that help.

For what types of companies or products would an “onboarding guild” approach be valuable?

If you bill monthly – any SaaS company should consider cross-functional onboarding, but especially ones that have a monthly subscription because it means that every month you have the risk of not showing somebody value and them leaving. 

If you’re seeing churn – especially among smaller customers, engage your product and design teams to drive toward a solution. If it’s your largest customers are churning, then you probably need more 1:1 service.

What are the most important pieces to get right?

Get your “why” and definition right – if you don’t, you might not see the support and buy-in you truly need to build this out. 

Aim for progress, not perfection – there’s no world in which you build all of this simultaneously. You can’t build certain pathways until you’ve learned the lessons from the other pathways.

What are the common pitfalls?

Trying to pack too much content into any one interaction – this could be a webinar, live call, or any other touch point. 

Make sure your content keeps up with your onboarding program – don’t simply record trainings, and send those recordings out, but never update anything. As your onboarding program develops and as the look and feel of your app changes, make sure the rest of your content is keeping up.

Keep your pathways aligned – this is especially important as you build more pathways (e.g. 1:1 vs. self-guided). All pathways should be leading customers to the same end result – which is using your tool more effectively.

Shareil Nariman
Shareil Nariman

More Resources

Activation (PLG)Customer OnboardingCustomer Success

Want free guides?

We feature guides every month in our newsletter

Newsletter Sign Up