How To Set An Early Path To Customer Success
A lot of what’s written about customer success focuses on structuring and hiring teams, retaining customers, up-sell and usage. While all these areas are important, there’s little reference to a critical topic - onboarding your customers.
Onboarding is a hot topic right now for low touch freemium products as companies realise the huge impact it has on short and long term user retention. This focus shouldn’t be any different for higher touch customer success teams.
In this post I’ll focus on 5 ways to set yourself up for onboarding success by -
- Aligning with sales teams
- Ensuring customers have a fast start
- Doing your research
- Optimising for time to value and
- Reinforcing goals
1) Enable sales

A great customer onboarding experience starts with sales. The expectations set by the sales team about what will happen in the first few days, weeks or months can greatly help or hinder onboarding progress and time to value for your customers.
Misaligned expectations can be as simple as how quickly the customer will speak to someone after they buy to something as large the time investment required during the onboarding period. A major reason for onboarding going off course is a disconnect between what is promised, customer expectations and reality.
In order to ensure there is no disconnect here I advocate spending time working on pre-sale content, speaking to prospects and regularly training and reminding sales teams about what your onboarding and customer success programs look like. It sounds simple but requires consistent time and effort and it gets much harder as you grow and scale.
Create Content
A scalable way to set expectations about what your onboarding and customer success services look like is to create web pages, downloads and tools that explain it. Companies invest a lot of time and money into content to market their products and this should be no different for your onboarding.
If you are creating content my advice is to keep the resources as visual as possible. GANTT charts, timelines or other visual resources will avoid any wrong interpretation your team or the customer.
Here’s some common pitfalls of creating content for your services to watch out for -
1) If your onboarding process is new or in flux it can be a significant time suck to repurpose that content on a regular basis. If this is the case aim to house your content on your website rather than in PDFs so it can be updated easily and you don’t have out of date content circulating.
2) If your onboarding process is highly customised it can be difficult to easily explain what you do for a wide variety of customers and industries. In this case keep it high level and use the “average” use case to create your content.
Speak to prospects
I’m always surprised how little I see this happening in the customer success world. Speaking to potential customers before they even sign up is a great investment of your time. It builds credibility, helps set the right expectations and gives onboarding teams a greater sense of the concerns and hesitations customers have before they sign up.
But there can also be a hesitation from sales to invite customer facing teams to meetings/calls. There’s a sense you might distract from closing conversations or be “too honest”. There’s a fine line to walk here so I’d advise meeting with the sales rep before hand to go over strategies and your approach to positioning onboarding.
Build customer success modules into your sales training
Your new sales hires should be exposed to the work your onboarding teams do. Training doesn’t need to be formalised but reps can join/shadow meetings and calls with the onboarding team.
Balance the training with the types of conversations your team has, success stories as well as roadblocks and problems you run into early on. If you position your onboarding services as a value add that sales teams can lean into to help sell, you’re much more likely to build their trust.
2) Optimise for time to start

When a customer makes a purchase, we’d like to think they are happy and excited about that decision. To capitalise on this excitement and keep momentum going post sale, you have to make some sort of connection with the customer in the first 24 hours. Otherwise that motivation can dwindle and other projects and priorities may come across your customers desk. In the worst case that customer may even experience buyers remorse and start to question their decisions.
Build “new customer welcome time” into your CSMs or implementation teams schedules
Initially this requires digging into numbers. By looking at the trends and numbers of customers you sign up each month or quarter you can predict how much time needs to be put aside on the teams schedule to welcome new customers.
Where possible always default to prioritising new customers. With existing customers, there’s at least some level of trust and they may understand if you need to reschedule. There’s zero trust with new customers and if you let them down early it can take twice as much effort to get them back on track later on.
Automate some of the process
Scheduling calendars across your team and your customers teams can be time consuming and an unproductive way to spend time early on in your customer’s lifecycle. When a deal closes an automatic welcome email should be sent to the customer that includes - next steps, their points of contact and information about how to book time them.
There’s a whole host of tools out there to help with this kind of automation. If your marketing team uses some sort of automation tool, see if you can tap into that and create your own customer onboarding campaigns.
Some other tools include -
3) Do your research

When I started working with customers I received some advice that has stuck with me since - whatever amount of time you plan to spend with your customer during your first interaction, spend an equal amount of time preparing.
New customers have not built up a trust in your service in the early days. By researching their business, industry and team you can ease any concerns or doubts by speaking their language, showing you understand their industry/business and relating to the people on their team.
With the rise of professional networks like LinkedIn, company profile sites like Crunchbase it's easier than ever to quickly get detailed information on the companies and people you're working with -
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Go through your customer's website in detail
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Research the team on LinkedIn
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Look out for CurnchBase pages or similar profiles for their company
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Do a Google News search for their company
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Use tools like SimilarWeb to find companies, competitors or websites similar
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Speak to your sales team
Use this information to prepare an “ideal world plan” in advance of the meeting in case things go off course or you need to be more prescriptive.
4) Get value in the first 30 mins
When we discuss onboarding in the freemium world we often talk about the “aha moment” and getting your users there as quickly as possible.
This shouldn’t be any different with higher touch onboarding. It might not possible to arrive at the full “aha moment” when we’re working with more complicated tools or enterprise software but you need to look for opportunities to show “micro value” as quickly as possible when your customer signs up.
I’ve seen way too many customer success teams spend their first onboarding sessions simply welcoming the customer, discussing goals and schedule next steps and calls without getting something tangible done. Those topics are of course important but even if you can complete something as simple as turning on one tool or ticking one basic task, the feeling of making progress can put the customer at ease.
5) Continuously bring it back to the customers goals

This one sounds obvious but when a customer starts working with a new tool it can be confusing as to why they are doing certain things in certain orders. Without a lot of context it can be difficult to see how everything ties together when you start using new software.
On the other hand, CSMs usually know exactly why they are recommending certain tasks or action plans because they know what it takes to make a customer successful. With that in mind, every task you assign or work on with your customer during onboarding should be backed up with the “why”.
This is why it’s so important to understand your customers short, medium and long term goals and priorities. The ability to justify your actions by falling back on those goals helps build trust and reduce a lot of anxiety in the beginning of your customer’s lifecycle.