Behind the Scenes of the June 2019 Executive Insights Release


A conversation with TaskRay VP of Product and Marketing, Jamie Cole

With TaskRay’s June 2019 release came new groundbreaking capabilities for executives and leaders. The ideas behind this release have been in the works for the last year, and one of the people at the helm has been our VP of Marketing & Product Jamie Cole. In today’s blog, Jamie gives us a behind-the-scenes look at the ideation and product innovation processes behind this release. 

How did the idea behind the June 2019 Executive Insights release come to be?

Last summer, we began surveying our client base in an effort to help us better understand what our customers valued in our product, and what we could expand upon. One of our big “a-ha” moments in talking to our customers was a story that we heard over and over again.

Our customers had been able to go along with a sort-of cobbled together system, whether it was spreadsheets or Google Sheets or some off-platform, low-cost system for their onboarding and customer journey mapping. But the first time something went wrong and they needed to present information to an executive or a leader about what was going on, the pain of not having a true system with analytics built-in made them realize they needed to switch to something else. So we knew we wanted to introduce even more ways to give our customers access to the insights that they need. 

What is the product innovation process like at TaskRay, and specifically with this release?

It’s a mix of us really knowing the market and being a leader, but it’s also mixed with what our customers are saying. We are constantly working toward the goal of getting everyone to be able to do onboarding well. We are always listening. We get a lot of ideas from our ideas forum and customer feedback. This release, in particular, is very innovative and comes from us knowing where to step up and set a precedent of how it should be, but it’s still based on practical feedback and what our customers need.

Additionally, one of the interesting things about building TaskRay is that we also use TaskRay to onboard our own customers. We’re always actively using our own product. Whenever we do a release, one of the first things we do is get user feedback both internally in our own office and externally from our customers. And for this particular release, we actually interviewed our CEO and our VP of Sales and Customer Success about what metrics they couldn’t currently get access to and what pain points currently existed. We thought that if we could build something to solve their issues, it could solve other executives’ pain points as well.

What were the primary drivers of this release and how will it affect your customers?

This is the most strategic release that we’ve ever done. We are really building a tool that allows everyone at the organization to drive first-class onboarding, and each user persona now derives value from TaskRay. We had a lot of very important data that wasn’t readily available to the executives and leaders who need those insights to make business decisions about where to invest, when to hire and what areas they need to focus on if there's a problem.

The handoff functionality in this release was designed to generate the data that would feed the reports that allowed these types of people to get a 10,000 foot view of all their projects. It helps people detect the health of a business process and then drill down into where problems are and come up with solutions quickly.

There’s really this highly innovative duality at work in this release because the handoff functionality adds more built-in structure to people using TaskRay as an onboarding tool, while at the same time generating rich information and insights for executives.  

Three Reasons Why Customer Onboarding Needs Executive Level Insights

Onboarding is unequivocally the most decisive stage in a customer’s journey. It’s no secret that churn rates are the highest when onboarding is insufficient, nor is it that churn is bad for business. In fact, research shows that “for every 1 percentage point increase in revenue retention, a SaaS company’s value increases by 12% after five years” (SaaS Capital). 

So why is it that the same business rigor that is applied to other divisions, such as marketing and sales, isn’t also applied to understanding your customer onboarding? Just as marketing automation provides insights, reporting, and analysis for marketers, accessing an aggregate view of customer onboarding data provides crucial and otherwise untapped opportunities to a pivotal aspect of your business. 

Customer onboarding is more important than ever to a company’s health, but applying the same level of business discipline and technical capabilities to this process has too long been overlooked. Here are three reasons to stop overlooking the importance of aggregate customer onboarding data and start utilizing executive-level insights for your company’s gain.

Reason 1: Assess the Health of Your Company

Customer onboarding is, in many ways, the beating heart of your company. Your business’ success is presumably contingent on your customer’s success, and customer success is dependent upon the success of the onboarding process. The significant ROI from focusing on onboarding has been proven time and time again. 

63% of companies that prioritized customer onboarding were able to better anticipate higher-level customer needs. ~Harvard business review

A Harvard Business Review study found that 63 percent of companies that prioritized customer onboarding were able to better anticipate higher-level customer needs, compared to 30 percent of companies that didn’t prioritize an understanding of onboarding. Without visibility into data around customer onboarding and implementations, there is no way of pinpointing your company’s performance at any given time, including important performance metrics such as drop-off points in the onboarding process. This vital data provides improvement opportunities as well as feedback on successful initiatives. 

Reason 2: Expose Hidden Issues and Inefficiencies

Mitigate risks by tracking the effectiveness of your onboarding process in real-time.

Mitigate risks by tracking the effectiveness of your onboarding process in real-time.

In customer onboarding, the currency is time. And if your business is like most others, you have no idea if your current onboardings are performing to standards or have much advance notice of potential issues ballooning into major problems. Many teams are operating blind, only receiving feedback through customer churn.

With executive-level insights, business users can monitor processes on a summary level, exposing issues before they become larger problems. Head off potential lost business by analyzing churn rates at each step of the onboarding process and addressing those weak points. Mitigate the risks of customer onboarding by tracking the effectiveness of your onboarding process in real-time through a comprehensive view of this data. 

Reason 3: Gain Unprecedented Insight into Your Company’s Growth Track

Proactively drive growth through a focus on successfully onboarding customers.

Proactively drive growth through a focus on successfully onboarding customers.

The easiest way to proactively drive your company’s growth is to focus on onboarding. Increasing the visibility of your customer onboarding data, and using it strategically, can be transformative for your company’s trajectory. Access to high-level insights into your existing onboarding program helps teams to uncover both strengths and inadequacies—both of which are essential to sustainable growth. 

B2B and B2C relationships can be complex–which is exactly why, in order to strengthen ties and propel growth, it is crucial to start with a positive first impression during the onboarding process. Build a solid foundation for your customers and use the insights you get along the way to create a complete picture of your successes, failures, and what both are telling you. 

Part 2: Delivering Customer Success Through Optimized Communication

In business, both internal communication within your company and external communication with your customers are central to customer success. When communication is clear, concise and direct, everyone wins. But in crucial handoff times, when communication is the most important, businesses often miss the mark.

Research shows that 85% of consumers churn because of poor service. However, great communication, especially during the first few steps of the onboarding process, is at the heart of prevention: 67% of customer churn could be avoided if the business resolved the customer’s issue during their first interaction.

The Illusion of Communication

“The single biggest problem in communication is the illusion that it has taken place.” -George Bernard Shaw

For any business, the illusion that effective communication has occurred can be both toxic and tragic, leading to high churn rates and lost opportunities. If you’re confident that this could never be your company, you may want to think again.

A Bain & Company survey revealed that while 80 percent of companies believe they are delivering “superior experiences” to their customers, only 8 percent of customers agree with this sentiment. This staggering chasm between company and customer perceptions exposes a harsh but true reality that the experience for the customer might not be as good as companies imagine and often times this can be the result of ineffective communication.

How to Address the Communication Illusion

First, review your external communications, from the first touchpoint your customers have with your product and brand to their annual renewal emails. Ensuring a consistent message at each stage of the process is critical to providing those promised “superior experiences” for your customers.

Next, look inward. Internal communication often degrades during the handoffs from sales to customer onboarding and customer success (think of it like a bad game of telephone or one of those interminable forwarded email chains). Mapping out these processes and identifying breakdown scenarios will help support more consistent customer communication and potentially give insight into where new systems are needed.

Optimize Your Communication Systems

At TaskRay, we’re deeply invested in key customer success principles. When all eyes are on you to successfully onboard a customer, communication is crucial. One of the primary questions we receive about how to nail the handoffs is, “How do you do that at TaskRay?”. And the simple answer is, we drink our own Koolaid. We regularly review our own communications and how we’re nailing (or missing) the handoffs.

Interested in learning more? Download our free eBook at and stay tuned for Part 3 of this series on ‘Setting Your Processes Up For Success.’

Part 1: Be Our Guest - Secrets in Customer Success from the Hospitality Industry  


Imagine you decide to stay at a gorgeous, new hotel, in a city you’ve never been to for a long weekend vacation. Your enjoyment of the trip is largely dependent on your experience in that city and your hotel plays a major role in that. Sadly, many of us had bad experiences at hotels where from the moment we’ve checked in, the hotel ‘checks out,’ overcharging our rate, giving us poor directions to our room, even sending us to a room that’s not ready or in bad shape.

These disappointing first impressions immediately color our perception, not only of the hotel, but of the overall city we’re visiting in a negative light. But this poor ‘handoff’ experience is not unique to the hospitality industry, it is echoed in the B2B and B2C customer experience as well—and something we see regularly in our work with customer onboarding at TaskRay.  

The hospitality industry, hotels especially, (typically) understand that their brand and their product is the lived experience of a stay, a meal, or a perfectly curated moment. So it’s not surprising that the best guest stays are the result of a great customer experience from the moment you book to the end of your stay.

Let’s take a look at the tenets of a great guest experience and how that can translate directly into how your customers experience your SaaS product.

Anticipate Needs By Understanding Your Customers

One of the best things hotels do to allow for customer success is anticipating guest needs, then meeting or surpassing them flawlessly. For example, your hotel concierge may have asked you a bit about yourself and your travel plans when you arrived, then offered personalized guidance and recommendations for relevant attractions around the city. Or, say you are running late for your 7:00 pm dinner reservation that you mentioned to your concierge–you come downstairs only to realize that the valet has already pulled your car around. This proactive anticipation of customers’ needs or even pain points has an incredible power to ensure and drive customer success, as you’re creating successful experiences ahead of time.

While SaaS customer onboarding and success teams are typically more removed from their customers than hotels from their guests, there is still room for creating a better understanding of who your customers are so you can better anticipate and meet their needs. But similar to the hospitality industry, getting to know your customers begins the moment the deal goes closed/won (ideally before). Capturing information about your customers’ industry, use case, team structure, and what successful implementation and use of your product will look like is critical to anticipating what they will need from you along the way.

Actively Participate In Your Customers’ Success  

The very heart of your hotel experience is often how the staff made you feel valued. Every hotel guest wants to feel special, as if their stay is personalized just for them, and great hospitality staff go out of their way to make their guests feel important.

Making your customers feel valued may look different when it comes to technology, but the basics are the same: keep track of your customers’ information, know where they are in their customer journey, and don’t make them repeat themselves.

Following these three basic rules can make any B2B or B2C customer experience feel as smooth as a stay at the Four Seasons.

Listen To What Your Customers Aren’t Saying

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Great hotels know that it’s essential to listen not only to guests’ initial requests but also to what they don’t say out loud. If you’ve been lucky enough to stay somewhere that your drink never seems to empty or your room is somehow always made up and the flowers in the lobby are never droopy, you’ll recognize this silent hospitality magic. There is a very well-rehearsed formula to this type of service that can be similarly applied in other industries: listen to what your customers aren’t saying.

With customer success, especially in SaaS, your customers may not be able to articulate what they “need” from your product or what they wish it could do for them, but it’s critical for you to read between the lines. How? Review your customer's usage data—are they even using the product? Do they have new users who haven’t been onboarded properly? Are they aware of new features and functionality that fits their needs? What are their growth goals for the next 3,6, 12 months? How can your product help them reach those in ways they hadn’t anticipated?

When broken down, the five-star hotel guest experience is comprised of the same basic elements any customer experience should include:

  • First impressions matter.

  • Anticipate customer needs.

  • Actively demonstrate interest in the customer experience.

  • Listen to what your customers aren’t saying (and of course, what they are saying!).

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For more details on how we’re applying these customer success fundamentals at TaskRay, download our free eBook — 

Stay tuned for Part 2 of this series on ‘Delivering Customer Success Through Optimized Communication.’  

Three Tips on Scaling Your Customer Onboarding Program - Part 2

This is part 2 of a two-part guest blog post by by Elizabeth McAuley-Italiano of WnTD Partners. You can read the first post here.

So now that we’ve gone through the importance of onboarding and described approaches on how to scale it across your customer base, let’s review some best practices you can put in place and how you can leverage each engagement method to help improve your customer’s onboarding experience. This will ultimately help to increase their value to your business over time.

Onboarding Best Practice #1
Create a prescriptive setup and implementation process. When designing an onboarding program that will help your customer get started on the right path to be successful long-term, determine what the exact steps are that your customers need to take in order to ‘go live’ and realize time-to-value as quickly as possible with your product. Be prescriptive about what steps and actions need to be completed. Once you have those steps outlined, put them in a customer facing format and share with all of the appropriate stakeholders within your customer’s organization that are involved in the onboarding process.

High Touch – Create pre-defined onboarding calls and training sessions that are designed to get your customers set up and using the product properly. These sessions should all move the needle towards getting your client to the first time to value. Provide setup assistance and training sessions on your platform that includes best practice tips. Educating the customer on both product and industry best practices can set them up for long-term success and sets the tone for your CS organization to be seen as a true partner and not just a point of contact.

When creating your onboarding program ensure that your training is conducted in a way that empowers the customer to use the product themselves. Make sure they are hands on. You want to avoid scenarios where the CSM does all of the work for your clients as this is not scalable across all high touch clients. Empower your customers to take ownership.

Low Touch – This can be a combination of tech touches and 1:1 interaction. Educational material and tech touches can augment and bridge the gap between less frequency proactive 1:1 communication. For example, provide helpful onboarding collateral such as a ‘Getting Started’ kit that provides the customer with a comprehensive map of how to set up and use your product successfully. Provide content in easily digestible chunks that provide the right level of information for each stage of setup and learning. At the point of purchase, it’s also important to inform your customers of all available resources and provide clarity on what resources to use and when. For example, when and how to contact Support vs the Customer Success Management team.

I’ll add a caveat to this approach – how low touch you go depends on the complexity of your product and on your customer base. We highly recommend reviewing your customer segmentation and requirements before deploying this model. Consider the Required Customer Journey your customers need in order to be successful.

Tech Touch – Contextual guides and in-app tutorials are arguably the most effective approach. Contextual guides allow your customers to learn your platform, with the help of educational content, without having to leave your product. As the name contextual guide implies, it educates your customer based on the context of where they are in your platform and what actions they are taking. For example, if they are setting up their account information, then a contextual guide may direct them to add the correct user permissions for each account user so the customer group has the appropriate access and experience. Again, as with low touch, the complexity of your product may have an implication on how far contextual guides and in-app tutorials will take a user and of how prescriptive you can be in a tech touch. Ultimately, it’s best practice to have a user friendly design but if that is not the case and if it will take some time to become more user friendly then it’s important to consider how much tech touch is appropriate.

If you do not have the resources to implement contextual guides an alternative is an automated email journey. There are two popular approaches to this method. One, is triggering emails based on product usage (or lack there of) or secondly, triggering emails based on a time frame. In  approach number one create a series of emails that get triggered to customers based on what stage they are at in their product setup and onboarding journey. Alternatively, you can create them based on certain days within their onboarding journey if you are unable to tigger emails from product usage. For example, day one could be a welcome email with instructions on how to login and change their settings, day 3 could be how to import data, and so on. This approach does make some bold assumptions that each user will onboard at the same pace. In order to avoid frustration with this approach, include a full onboarding guide (such as the Getting Started Guide mentioned above) with your welcome email so users can go at their own pace if that is their preference.

Onboarding Best Practice #2
Establish milestones that you know the customer must achieve in order to be successful. The prescriptive steps mentioned above should lead customers to these milestones. For example, if you are setting up a CRM an important milestone in your onboarding journey would be adding customer data. Assuming part of the setup process is uploading data via a spreadsheet then one of the prescriptive steps could be: ‘Format the data in <this> specific format as it will allow for cleaner data once uploaded.’ This leads to the milestone of having all data imported and ready to use in the CRM.

Once you’ve established what your first time to value is you have to ensure your customer realizes that value. Your prescriptive steps should lead to milestones and your milestones should result in your customer achieving their first point of value.

High Touch – Have your CSM setup regular calls with the customer. During the onboarding stage we’d recommend weekly or bi-weekly calls, but as mentioned above, this depends on your coverage model and complexity of your product. But it’s not enough to simply set up calls. Create agendas centred around milestones that lead to first time to value. Work with your customers to establish measurable goals then create timelines and additional milestones as required. Clearly align outcomes from your solution with their goals. This is a very proactive approach that requires CSMs to act as an advisor to their customers.

Low Touch – The low touch approach is best done with some human interaction. Low touch doesn’t equate to no human touch. Calls in a low touch model can be done on a monthly or quarterly basis. However, with calls scheduled this far apart you need to supplement their onboarding journey by leveraging technology. One example is implementing product usage alerts that get sent to CSMs that inform the team of low usage or inactive users. This can be set up through your software or through a CSM platform. If the CSM receives an alert or notices product usage is low, this is their queue to jump in and intervene. This is more of a reactive approach when customers fall off track in their onboarding and are not following the prescribed steps and best practices as outlined in your quick start guide and educational content but can help get a customer back on track and prevent churn.

Other tactics are to create campaigns through email or messaging platforms that get sent out via automation in a 1:Many fashion. You can have these emails come from a CSM so it appears 1:1. And to be honest, there are some that would argue that this is too impersonal. However, when a customer responds to a 1:Many reach out it truly does become 1:1. It’s making the most out of your time when sending relevant information by leveraging technology rather than repeating a task over and over again. This leaves more time for meaningful conversations that will have a big impact and drive value. Think of it this way, the 1:Many communication can be to inform and guide customers. The 1:1 communication time is dedicated to conversations that put CSMs in the advisor seat where they are providing product and industry best practices, helping to establish goals and answering more complex questions.

These platforms and methods can also be leveraged to educate customers on recommended goals, milestones and how to track them. You can create webinars for customers to attend, provide YouTube training sessions or even create a user community and facilitate discussions amongst a group of customers. 1:1 interactions can then be used to dive into topics more deeply as the concepts and ideas have already been introduced.

Tech Touch – The low touch model described above already started to introduce some ideas for tech touch so let’s look at a few requirements for implementing tech touch. One requirement is that you must have the appropriate and relevant content to serve up to your customers. It has to provide some value to them and lead them down a prescriptive path to milestones. Your content should have three main objectives.

  1. Educate customers with prescriptive content on the exact steps and actions they should be taking. The content should be detailed enough for the customers to self serve but not so detailed that it becomes overwhelming and scares them off. The Getting Started Guide is one example of how to provide this, as it’s essentially a map from step one of ‘sign in’ to the final step of implementation and achieving value.

  2. Provides milestones and goals they should be looking to achieve. It helps clients to visualize their progress towards realizing value.

  3. Promote product adoption so the customer becomes ‘sticky’.

You also have to have the necessary tools in place for tech touches, such as a chat system, in-app messaging, a customer success platform, and/or email automation. Chat and automated in-app messages and tutorials provide flexibility in how you connect to customers. Customer Success platforms can provide the ability to trigger messages and alerts based on product usage, and an email automation platform allows you to send html marketing campaigns or 1:Many plain text campaigns from a specific CSM.

With the right tools and content in place your organization can create a very effective and helpful tech touch model.

If these approaches sound familiar, they should as they were discussed above. While you do want the engagement model to differ depending on customer segments and their Required Customer Journey, you want the outcome to remain the same, which is successful product adoption. I felt this was a point worth repeating to confirm it’s importance in each approach.

Onboarding Best Practice #3
Have a variety of training resources that both your customers and CSMs can leverage. In our experience, the way customers prefer to learn can vary greatly from person to person. Some people prefer hands on step-by-step training, where others like to learn on their own. For those that learn on their own their preferred method varies once again. Some select to learn by video, where others choose written step-by-step instructions. With this in mind, consider implementing the following as part of your customer education options:

  1. In-app tutorials

  2. Contextual Guides

  3. Live Training Sessions that both trialing prospects and customers can sign up to and attend together.

  4. Recorded Training sessions.

  5. A YouTube channel with training videos

  6. Quickstart Guides

  7. Knowledge Base Articles and ‘How To’ Guides

  8. Paid Professional Services Offering

  9. Onboarding email journey

  10. Customer community that is monitored by a Customer Success Manager or Support team member.

High Touch – For your high touch customers the training resources are often a supplement to your 1:1 communications. We recommend it as being part of your overall customer engagement framework.

Low Touch – When engaging with your low touch customers, your 1:1 interaction is often providing the most appropriate training resources for that customer. It’s about enabling them to be successful with your product by putting them on an easy to follow path with the resources that best suits their needs. These resource can in some cases allow a CSM to have a larger customer portfolio as customers are provided the necessary tools to self onboard. It also gives the CSM capacity to not only manage more complex customer questions but also to operate in a more proactive nature.

Eventually (and ideally) your content and onboarding process should be so fine tuned that you are answering common customer questions, before they even have them. This is when you proactively enable your customers at scale.

Tech Touch – The above customer education list is your tech touch strategy. Through 1:Many reach outs and the tools listed above, your organization can provide customers with all of the tools and content required for a successful setup and achievement of first time to value with your product.

In order to put these best practices in place you need to have a solid understanding of your customer base. Complete a customer firmographic analysis and you will be well positioned to create an onboarding process that incorporates high, low and tech touches.

Not sure where to start? Or questions on implementing this model? Comment below or contact us and let us help.

About the author

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Elizabeth Italiano is the Founder of WnTD and the creator of the Customer Success Master Class Series. Previous to starting WnTD she worked for organizations such as Xerox, Salesforce and Vend POS. Her career and passion for Customer Success began 10 years ago. Elizabeth’s expertise encompasses creating and implementing Customer Success strategies that start at the go-to-market strategy, through to renewal and expansion sales. She helps organizations increase revenue, reduce churn and decrease the cost to serve. The combination of her experience and passion for CS allows her to help create customer-centric cultures that scale across the entire business. She is a firm believer that Customer Success is a business imperative that’s quickly becoming one of the most important business disciplines to master, which is why she created the Customer Success Master Class and WnTD. 

Three Tips on Scaling Your Customer Onboarding Program - Part 1

A guest post by Elizabeth McAuley-Italiano of WnTD Partners.

Building your organization for scale is one of the most critical factors in the long-term success and overall health of a business, particularly for SaaS businesses. One area that we are most commonly asked about at WnTD is how to scale the customer onboarding process. Customers are often won over or lost in the first 90 days of their post-sale journey. It’s a crucial step to get right and it can have a massive impact on your customer’s success and your organization’s bottom line.

Particularly in today’s subscription economy customers can come and go with relative ease. When customers have a smooth onboarding period that results in realizing value from their purchase the following outcomes are likely for your organization:

  1. They are more likely to spend additional money with your company by adding users or upgrading their license. At the very least they are more likely to renew.

  2. They require less ongoing support over the long term. They start using your product correctly and effectively right out of the gate.

These two benefits will improve your revenue and your cost to serve.

I’d like to dive a little deeper into one of the points made above. I talked about customers ‘realizing value from their purchase’. CS professionals often call this, the first time to value. This is a critical component to think about in your onboarding journey. You want to have deliberate steps that will get your customers to not only use your product but use it to the point of achieving value. Your organization should be asking what is the Required Customer Journey that will get our customers to realize their first time to value?

This is the first step towards successful product adoption and creating a pattern of usage. CS professionals often talk about making customers ‘sticky’ in order to reduce the potential of churn. However, expecting customers to move towards becoming sticky without a solid onboarding process is kind of like expecting to steer a rowboat without paddles. You are at the mercy of external factors and that’s not a good place to be.

Ok, so we now know that onboarding and achieving first time to value is important … But you may be asking yourself ‘how do you scale this thing!?’.

Glad you asked! Let’s dive into how.

Our evaluation of the customer journey often has a heavy focus on the onboarding process because it lays the foundation for ongoing customer communication and the engagement framework. To have an effective engagement framework it’s important to evaluate the makeup of your customer base so you can determine the best way to engage with them. Scaling your onboarding process sometimes requires reviewing your customer segmentation. If your customer base is varied from small business owners with a single user to enterprise customers with hundreds of users you will likely need to tailor elements of your onboarding process for each customer segment. This will help to inform your customer engagement framework. We often break our engagement framework model into three segments and methods:

  1. High touch

  2. Low touch

  3. Tech touch.

Breaking out your engagement model into these distinct categories of engagement methods is one of the most effective ways to scale onboarding. Let’s start with describing each in more detail:

  • High Touch is a 1:1 engagement model and is generally aligned with your high-value target market customers that require frequent 1:1 proactive communication. These are the customers you want to establish a partner and advisor relationship with. An example, of when this is the Required Customer Journey is when you have a client with a large user base, integrations that make setup and onboarding more complex, and numerous use cases.

  • Low(er) touch is typically for customers that represent a large volume of your customer base, but with relatively lower contract amounts. Individually these clients are a small portion of revenue but cumulatively make up a material portion of your monthly or annual recurring revenue (MRR/ARR). Low touch is where the designing process for scale is most critical. It is a combination of proactive tech touches (often referred to as 1:Many reach outs) with less frequent 1:1 communication with a CSM.

  • Tech touch is leveraging technology to communicate to large groups of your customers with a 1:Many process. For example, this can be done through campaigns to inform of a new product feature, or by emails that are pre-written and triggered to send to customers based on product usage, or webinars put on by a CS team member for a group of customers. It is used in a combination of scenarios, which we get into in more detail in our best practices below, but for now suffice it to say it’s a 1:Many customer outreach model that helps you scale across a broad customer base. It is also particularly important for customers that are not within your ideal product-market fit. It allows you and your CSMs to focus time and attention on your customers that are within your target market fit that can be successful with your solution over the long term. You should be selling to the right customers anyway, but we’ll leave that topic for another day.

It’s important to note that low touch and 1:Many engagement models and methods are not for the purpose of avoiding speaking to customers. If time was not a finite resource we could offer the same level of 1:1 communication to all customers, however, that is not the reality. That’s why it’s so critical to evaluate each customer segments’ Required Customer Journey and provide an engagement framework that is a variety of high, low and tech touch methods that have the explicit purpose of helping customers achieve first time to value and product adoption.

Want to learn more about WnTD Partner’s recommended Onboarding Best Practices? Tune in next week for Part 2 of this blog series!

About the author

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Elizabeth Italiano is the Founder of WnTD and the creator of the Customer Success Master Class Series. Previous to starting WnTD she worked for organizations such as Xerox, Salesforce and Vend POS. Her career and passion for Customer Success began 10 years ago. Elizabeth’s expertise encompasses creating and implementing Customer Success strategies that start at the go-to-market strategy, through to renewal and expansion sales. She helps organizations increase revenue, reduce churn and decrease the cost to serve. The combination of her experience and passion for CS allows her to help create customer-centric cultures that scale across the entire business. She is a firm believer that Customer Success is a business imperative that’s quickly becoming one of the most important business disciplines to master, which is why she created the Customer Success Master Class and WnTD. 

You Don't Want Happy Customers

A guest post by Donna Weber, President of Springboard Solutions and Principal of KickStart Alliance.

Last month I attended a customer success meet-up in Palo Alto, Calif. At the event, there was a lot of discussion about how to “make customers happy.” I left thinking, “Do we really want happy customers?” While happy customers sound like a nice idea, engaged customers are more important to your success.

According to Merriam-Webster, happy means “enjoying or characterized by well-being and contentment.” Wouldn’t it be fabulous to create a killer product, deliver it to customers, and then everyone feels happy? The assumption is that happy customers result in all sorts of good outcomes, such as easy implementations, reduced support tickets, and of course less churn. The happy customer theory appeals because it should make your life easier, and that you can be happy as well.

There is a happiness craze, illustrated by the 23,000 books available on Amazon in the 'self-help' genre on the subject of happiness. While the focus of these books is primarily personal happiness, the craze highlights the elusive pursuit of contentedness and well-being in our culture. Yet, aiming for happy customers sets you up for failure. This is because ongoing customer happiness is unattainable and unsustainable.

The definition of engaged is "involved in activity," which is exactly where to focus your efforts. Engaged customers are more successful than happy customers. This is because they attend Webinars and take training. Engaged customers meet their Customer Success Managers (CSMs) regularly. Engaged customers log support tickets because they actually use your product. Engaged customers also complain and challenge you. This is important, because they want you and your product to be better, so they can be better as well.

When I built a CSM program at a company, I reached out to customers to listen to their needs. One of the sales reps told me, “Don’t ask customers that they think, you’ll just open a can of worms.” He was right, but the “can of worms” is customer engagement.

Engagement is the sign of a true relationship.
— Donna Weber, President of Springboard Solutions

Happiness studies reveal that when negative events happen to you, immediate happiness decreases. Yet, despite this decrease, there is an increase in the amount of meaning in your life. This means that negative feedback and stressful interactions are necessary because difficulties and obstacles keep you striving to improve. So, how does this relate to customer success? Those complaining customers are actually good for you. They are engaged, and they challenge you to be better. While happy customers leave you alone, they don’t grow with you. They might be nice and friendly, but they don’t push you to innovate. An internal champion might cheer for you, but they don’t demonstrate the huge impact you have on their success.

You get engaged customers through two methods: design thinking and an orchestrated onboarding journey.

  1. Design thinking. Don’t use hope as a strategy to engage customers, instead, leverage design thinking. Design thinking simply means listening to your customers. Find out what they want and need before you build customer-facing programs and services. Find out what their desired business outcomes are so you can partner to reach them. It is especially valuable to learn from your successful, green accounts. Explore what’s unique about how they implement and use your product. Then, share these best practices with all your customers.

  2. Orchestrated Onboarding. You can’t afford to expect customers to figure your product out on their own. While you might think you want happy customers who leave you alone in those first 90 days, you are wrong. Without guiding and involving customers through a successful onboarding, you might find renewal likelihood dropping to as low as 10%. It’s critical to connect with new customers immediately. Start the relationship right with a handoff call, then guide customers along an orchestrated onboarding journey, which includes milestones, timelines and deliverables to reach in the first 90 days, and to keep your customers accountable.

Stop striving for happy customers. Your harshest critics might actually be your most engaged and loyal customers – and far more valuable than your happiest ones – so dive into those challenging relationships. Partner with customers to innovate and to grow, and leverage challenging encounters to make you both better. Proactively engaging customers with design thinking and an orchestrated onboarding journey leads to both of your success.

Engagement is the sign of a true relationship, and relationships are the key to customer success.

More about Donna Weber:

Donna Weber, President of Springboard Solutions and Principal of KickStart Alliance specializes in the post-sales Customer Success journey. With over 20 years of experience, she has a proven track record helping hi-tech firms create customers for life with customer onboarding, enablement, and education programs. Her clients range from startups to well-established large companies, with a focus on the open source and SaaS arena. Colleagues know Donna as a leader who makes a difference. When she’s not springboarding customers to success, you might find her white water kayaking the rivers of California and beyond.

What International Women's Day Means at TaskRay

This year's campaign for International Women's Day is #BalanceforBetter, which acknowledges that a gender-balanced world is a better world.

Balance drives a better working world.

At TaskRay, we are proud to have a female founder and CEO. We are also proud to have a team made up of 50% women and 50% men—all of whom work hard to support each other’s success.

In the last year, the women of TaskRay took the main stage at Dreamforce 2018, Pulse Europe 2018, and a number of other high profile events. These stage presences were nerve-racking, challenging, exhilarating, and illustrative of the shift towards better representation for women across the tech world.

TaskRay CEO Blakely Graham on stage with fellow CEOs at Pulse Europe 2019

TaskRay CEO Blakely Graham on stage with fellow CEOs at Pulse Europe 2019

Outside of the TaskRay walls, we’re excited to now see female CEOs of major corporations like Pepsi Co. (Indra Nooyi), Lockheed Martin (Marillyn Hewson), and ORACLE (Safra Catz), among others. We’re happy to see more women serving on corporate boards, and to now have 121 women serving in the 116th Congress. We’re also proud sponsors and attendees of the Witness Success events and emphatically support the women who are driving change across our industry.

I believe our focus on balance at TaskRay provides us all with a better perspective and truly creates a better working world.
— Blakely Graham, TaskRay Co-Founder, CEO, Salesforce MVP

We applaud the strong women around the world today as they take on leadership roles from which they were previously excluded. We also applaud the quiet bravery of women who take on the roles that aren’t broadcasted on the news—the colleagues who challenge our thinking, support our customers, and push us to do better work each day.

The theme of #BalanceForBetter is true everyday at TaskRay as we celebrate and support every member of our team—regardless of gender—because we know it takes a village to build anything worthwhile.

So today we say a huge THANK YOU to the women in our workplace, to our customers, friends, families, and all those working towards creating a better and more balanced working world.  We can’t wait to see what 2019 holds.


To learn more about International Women’s Day, please visit:
To learn more about TaskRay’s core values, please visit:
To learn more about Witness Success, please visit:
To learn more about the Salesforce Equality movement, please visit:

We went to SaaStr 2019: Here's what we learned

This week, TaskRay co-founder and CEO, Blakely Graham and VP of Sales and Customer Success, Mike Davis, attended the SaaStr 2019 conference in San Jose, California. They brought us back these notes.

Customer Success > Sales

As tough as this one can be for sales teams to swallow, research tells us (and the world of SaaStr agrees) that retaining customers and supporting their success is less expensive than acquiring new ones.

We noticed (and appreciated!) that conversations about “scaling” are now focused on customer success and not just the sales funnel alone. In fact, we tend to believe that sales might just be the foreword in the customer success playbook. Because if our customers aren’t finding the success we promised, nobody wins.

Diversity and inclusion create a better workplace for everyone

Inclusivity is making strides in the tech world and the positive impacts are apparent. At the inaugural SaaStr 2015, Leyla Seka (EVP of Mobile at Salesforce) was the only female speaker. At SaaStr 2019, the speaker lineup represented a significantly more diverse set of perspectives.

Start with success and think backwards  

No, that’s not a typo. In her session, Sandy Carter, VP at Amazon Web Services, laid out a compelling argument for working backwards from customer success through onboarding and end with sales. She asked, “What if you wrote the press release before you built your next feature?”

Sandy Carter, VP at AWS

Sandy Carter, VP at AWS

She challenged us to think about how to present a new feature or product before we even start building it. Who will this feature impact? How will our customers derive value from it? And what will the FAQs be? This level of clarity isn’t often available until well after new features are released, but thinking about the impact this thought process could have is exciting!

Connection is (still) everything

Connection has been one of our founding principles since day one and it remains a critical part of our TaskRay DNA. Connecting with our customers is key to understanding their needs, challenges and helping to map new solutions.

Overheard at SaaStr: Remember its ‘Software as a Service’, not Software as a Subscription. We need to remember our customer wants us to deliver a service.

Its exciting to see the SaaS world pick up on the oft forgotten part of customer journey—deriving long term value from the service!  

We met so many great leaders and new voices at SaaStr 2019 and can’t wait to bring the lessons we learned to life with our own team and customers.

Don’t let Customers wander down dark alleys: Why you need quick wins

A guest post by Donna Weber, President of Springboard Solutions and Principal of KickStart Alliance.

As soon as the deal closes, your customers start groping in the dark. They dive into the technical weeds of implementing your product and end up lost down a dark alley. Seeking refuge, they desperately log support tickets, which your support team frantically tries to resolve, all because customers don’t know which direction to point. They shouldn’t be down that dark alley in the first place.

Avoid those dark alleys with quick wins. Quick wins are an important element of an orchestrated onboarding program. They start customers down a well-lit road and provide benefits for both customers and customer facing teams. 

What are quick wins?

quick: fast in development or occurrence; a quick succession of events

win: to succeed in arriving at a place or a state

With quick wins you rapidly guide customers to value in your product, even when the product isn’t fully implemented. When you chunk the implementation process into achievable components, you have a quick win. ServiceSource emphasizes that speed is of utmost importance during this time. This is because when customers don't see results in the first 90 days, and especially the first 30 days, their renewal likelihood drops to as low as 10%.  So, what happens when your product takes longer than 30 or even 90 days to set up? 

I had exactly that challenge at a previous company. The product, a complex analytic tool embedded into customers’ software, took six, nine, even 12 months to implement. How are you supposed to have a renewal discussion when the software isn’t even implemented yet? The answer: quick wins. Quick wins include clear deliverables to keep customers on track during the onboarding and implementation journeys. This means less wandering down dark alleys. 

When I shared this concept with a company I work with, they announced, “This is great. We’ll get customers to log in for our quick win.” Logging into your product is not a quick win. I learned from Mikael Blaisdell at SuccessCon West, that customers buy software for these three reasons: one, to save money; two, to make more money; and three, to align with regulations. So, while your product is likely incredible, I doubt customers save or make money just by logging in. Instead think about their use cases and goals. Reports and dashboards often provide immediate value, helping users make better business decisions; and automated workflows save time and money. 

When do quick wins occur?

Insert quick wins into the orchestrated onboarding journey. They belong after you nail the handoffs and before the implementation begins. I usually like to discuss quick wins during the kickoff or onboarding meeting. Review the options with customers and determine together which is most appropriate to work towards.

How to build quick wins

Rather than randomly picking an achievement, like navigating your product, listen to what’s important to customers. Find out the milestones and results they want and need in those first 10, 30, 60, and 90 days. You might provide a menu of quick wins that align with each customer segment or to unique use cases. You might have several quick wins along the implementation process, especially if it’s a long one. Your quick wins can also align with 10, 30, 60, and 90 day milestones.

Rather than randomly picking an achievement, like navigating your product, listen to what’s important to customers.

Start with one quick win and pilot it with a small group of new customers. Find out from them what worked and what needs to improve, then create assets and playbooks to make that approach as scalable as possible. Next, develop other quick wins, building on what you learned from the first one. Once you define quick wins, then work with Customer Education and Support teams to produce self-paced and instructor led content to guide customers to their quick wins. Now you have a solution that has impact.  

Examples of quick wins

To illustrate, here are a few examples. A company I talked to works with large property managers to build workflows for cleaning and renting their properties. Loading properties into the software can be time consuming and difficult. Rather than waiting for a customer to load all their properties into the system, I suggest they create a quick win to add one property into the system.

To facilitate this process, create quick-start guides and self-paced training to bring customers to a successful result without Customer Success Managers (CSMs) holding their hands. This means CSMs stay in the strategic zone. Once the first property is loaded, the CSM and customer review it together and determine the next milestone to aim for. Another example is from working with my client that thought logging in was a quick win. We determined that not just reports, but automated alerts generated from reports, would provide the most benefit quickly; that became the first quick win.

And finally, at my previous company, since the implementation was a long process, setting up a demo environment to highlight key functionalities that were most valuable to the customer's project was our first quick win.

Quick wins benefit both customers and the teams supporting them. Customer implementation teams get to show off their progress to internal teams and to stakeholders. This means they look good and celebrate successes along the way. Quick wins give them immediate satisfaction for buying your product which means their loyalty increases. You gain by keeping customers accountable, staying strategic, and avoiding unnecessary support tickets.

Quick wins are especially helpful when onboarding and implementations are long or complex. They break things down into achievable nuggets for teams to celebrate along the journey. What’s one quick win you can explore with customers this week? When customers feel accomplished right away in your product, you are on a well-lit road to customer loyalty and success.  

More about Donna Weber:

Donna Weber, President of Springboard Solutions and Principal of KickStart Alliance specializes in the post-sales Customer Success journey. With over 20 years of experience, she has a proven track record helping hi-tech firms create customers for life with customer onboarding, enablement, and education programs. Her clients range from startups to well-established large companies, with a focus on the open source and SaaS arena. Colleagues know Donna as a leader who makes a difference. When she’s not springboarding customers to success, you might find her white water kayaking the rivers of California and beyond.