Tim's Saasiness

Defining Your Customer’s Journey

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How Not to Plan a Journey

Between my junior and senior year of college, I decided to study Kung Fu with Shaolin Monks in China.  I Googled a westerner-friendly school, bought a flight, notified my parents, touched down in China, and hired a driver to take me to a mountain school east of Mongolia – all in the span of about two weeks.  Needless to say, my parents freaked, expedited their passports, and stood ready to make my extraction.

I could have better prepared them for my journey by mapping out the entire summer, managing their expectations at each stage and ensuring timely check-ins.  Instead, I came back to harried parents with my Steven Seagal ponytail – not good looks for any of us… but I learned from both mistakes.


Make or Break

Mapping your customer’s journey is imperative for long-lasting business relationships.  Far too many SaaS companies continue in the delivery rut that was first formed and don’t take the time to understand where they can deliver value faster and more often.  Your customer journey understanding will make or break your company growth.

Customer Segmentation

Not all customers will follow the same journey.  You may have SMB, “bread and butter” customers that completely understand your offering, have zero integration nor data transformation concerns and can get to value rather quickly without much effort.  As you expand into the Enterprise level customers, you will find not only a complicated technical integration to deal with, but also many layers of bureaucracy that complicate the sales, implementation and communication phases.  It is imperative that you identify customers journeys for each of your customer segments.

Suggested Customer Journey

My suggested customer journey starts by involving CSMs in the sales process and keeps them as main point of contact throughout the life of the customer.  However, by deploying a 1:1 and 1:M interaction approach, you can provide a scalable, yet highly specific customer journey.

Figure 1: Suggested Customer Journey (Larger Version)


The key to Pre-Sales Customer Success involvement is a good Lead Gen and Qualification Team.  This means making sure that when a CSM is brought onto the sales call, the prospect is warm and interested in what you have to offer.


Many C-level decision makers hate investing in new software.   Chances are they have a large technical debt that is full of underutilized software packages.  CSMs can help assuage this fear by expanding upon the Customer Success departments’ ethos to ensure proper implementation and continual usage.

Contract Signing


The CSM first assigned during the pre-sales stage should conduct the kickoff call to introduce all of the members of their team as well as bridge the gap from Sales to Customer Success.  A basic timeline should be established and customer points of contact identified.


This auto-triggered email should come from C-level executive welcoming the client to your company as well as detailing brand promises and reinforcing the value proposition .  If you have a long-lead period between contract signing and implementation, this should be a welcome email series that showcases past wins, testimonials, case studies, and capabilities in order to retain decision maker interest prior to kickoff.



Implementation is often the key phase to ensuring customer profitability.  Your services team must fully comprehend the needs at all levels of the organization and design an implementation to best meet those needs on time and on budget.  Constant communication of status and health monitoring metrics must be deployed to ensure a great launch.


During the implementation phase, your 1:M efforts should be focused on training on capability of your software.  As the final requirements are not known, you must use generic use cases and train on best practices through Email and In-Application messaging and video training.



The Adoption Phase is often the second most important phase in ensuring longevity of a customer.  It is here the training becomes much more granular and applicable to the actual day-to-day tasks of the end users. CSMs must pay extra close attention to usage metrics to ensure license saturation as well as key/sticky feature usage.  Any attrition during this stage will likely shorten the lifespan of the account.


Bootcamps are typically used to bring a large section of users up to speed quickly.  These training sessions make use of real world scenarios to show how the software can meet those needs.  Users are typically then introduced to the user community portal as a quick and easy way to find answers to common problems and or questions.



The key to Retention is value realization.  The CSM must be able to demonstrate continual objective value to ensure continual usage as well as contract renewal.  This requires meeting the needs of the power users, but also communicating ROI to client upper management on a periodic basis.  When properly done, CSMs can identify areas for expansion and/or product penetration and achieve negative churn.


Your customer base must be continually trained as new sticky features are deployed and customer employee additions are made.  A great way to approach this is through In-App callouts and training.  These can be tailored to the usage of a particular set of users to ensure messaging is in context and a welcomed value addition.

Drive Value

Here is the bottom line: Customer Success must drive value at every stage and with every communication.  Approach your customer journey mapping with this primary objective and you can’t go wrong…  unless your journey ends in a ponytail.  Then start over.  There is no value there.  None.

timschukarDefining Your Customer’s Journey

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