CS Management

Annual Planning for Customer Success

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By Kristen Hayer

It’s a little too early to start planning for 2019, right? Wrong. If you’re a customer success leader, now is the best time to get started. You have a lot of ground to cover before the end of the year. For most industries summer is slow, so you can get a bunch of the analysis and process redesign done in July and August. Here’s a 6-month plan that will have you and your team ready for the new year:

July: Review Customer Data

Find time this summer to review the data you’ve collected on your customers, and decide if you need to make any adjustments to your program going forward. Look for areas where customer behavior is changing. Are they purchasing more, on average? Are they taking longer to onboard? Are they giving you different reasons for churning? Use this information to determine whether you need to make any changes to your customer journey map, segmentation, or processes. You’ll need to watch for additional changes throughout the rest of 2018, but you’ll have done the heavy lifting in July.

August: Evaluate Tools and Processes

The work you did in July leads right into an assessment of your processes and tools in August. Can you track all of the data you need? Are you maximizing your existing tools? Do you need to add processes to create a better customer experience? If you noticed a lot of customer behavior changes in your July analysis, you may need to completely revisit your customer journey map and team processes. If you suspect that you aren’t using your tools to the fullest, schedule demos with your vendors and have them review best practices. This is also the month to evaluate new tools.

September: Align Metrics and Goals

Once you have your program outlined you can think about what makes sense from a metrics standpoint. Consider metrics in 3 key areas of customer success: retention, expansion, and satisfaction. Think about the tools and measures you already have in place, and create a plan that leverages that data. If you need to add new measurement points, add those now so you have a 3-month baseline going into next year. Once your metrics are established, use those to draft department and team goals. Again, these may need to be adjusted over the next 3 months, but doing this work now gives you a solid starting point.

October: Build Hiring and Comp Plans

Use data from sales, combined with your own churn expectations, to determine how many customers you’ll be serving in each segment every month. This will indicate when you need to hire. Don’t forget about managers and operations staff. Think about compensation as well: most customer success roles now include variable comp. Create a compensation plan that is tied to the goals for each role on your team. Clear role descriptions will help you align the existing team members to their roles, and help you hire new CSMs who are top performers.

November: Develop a Budget

Some organizations are great about getting their annual budgets finalized early. Unfortunately, most end up pushing final approval well past the end of the year. This makes it tough for you to get the resources you need to hire, equip, and train your team in the early part of each year. You can get around this common issue by developing a working budget ahead of time. Talk with your finance team about the format they use, and develop a draft budget that includes headcount, variable comp, tools, training, and team events. Ask for approval to use this working budget until the official company budget is finalized.

December: Communicate and Train

At this point you will have done a ton of work on your program, but you probably haven’t included your team in every part of it. You need to clearly communicate any changes that you’ve made to the program, roles, goals, and compensation plans. You’ll also need to train the team on any new processes or tools that you’ve decided to add. December is also a good time of year to develop skills that the team will need for next year, so consider adding skill-building workshops to your training plans. Keep in mind that different people learn in different ways, so be sure to communicate both in meetings and in writing to cover your bases.

By following this plan you’ll be less overwhelmed with planning in the fall, and your team will be ready to hit the ground running in January. Of course, if your business doesn’t run on a calendar fiscal year, adjust this plan as needed to match your company’s operating schedule. Good luck as you begin planning for 2019 (now!)

Need some help? The Success League is a customer success consulting firm that helps leaders build and develop top performing customer success teams. We offer short-term consulting engagements that can kick-start your planning efforts, as well as coaching for leaders who need some weekly advice. Check out TheSuccessLeague.io for details.

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Kristen Hayer Kristen believes that customer success is the key to driving revenue, client retention and exceptional customer experiences. Her areas of expertise include developing success goals and metrics, designing the optimal customer journey, selecting technology, training teams, and building playbooks. Prior to founding The Success League, Kristen built and led several award-winning customer success teams. Over the past 20 years she has been a success, sales, and marketing executive, primarily working with growth-stage tech companies. Kristen has her BA from Seattle Pacific University and her MBA from the University of Washington.

Supporting Success in an Early Stage Startup

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By Steve Schwartz

I’m often asked about my transition from technical, enterprise customer support into B2B SaaS customer success. I had the amazing opportunity to experience support, implementation, and account management, all at one company, and I came to see how disjointed these customer-facing teams can be. Customers struggle when there isn't alignment between teams. I thought, there has to be a better way, which led me to customer success. Here are three strategies early stage startups should consider when starting a customer-facing team.



When I hire my first Customer Success Manager, I’m looking for a teammate who can span the breadth of roles that I expect I’ll need on my team. In my last two companies, those roles included customer onboarding, training, documentation, support, and success. I also look for a high level of empathy, a natural curiosity, and someone who questions the status quo. Starting with a generalist gives your customers a single resource that they can turn to at any stage of their lifecycle, and gives your CSMs a deeper connection to their customers. Early focus on customer success ensures that you can learn quickly whether customers will be effective in using your solutions or not. As important as your first customers are as references and case studies, they can be equally detrimental if they receive no value from your company.



A customer success generalist who juggles all of these roles will ultimately get overwhelmed by one or more areas, which can make them less effective in the rest. As an example, if your number of customers doesn’t grow significantly, but your end user count does, it can lead to a significant increase in inbound support requests. If you’re in a business where responsiveness to these issues is critical to your success, then a CSM will need to be able to drop everything to address them in a timely fashion. While this may be possible when the CSM has two or three customers, it certainly gets harder when they have more. When you can no longer deliver the quality of support that you strive to, it’s time for your first customer support hire. Likewise, when implementations start to bog down your customer success team, considering splitting the roles of CSM and Implementation Manager apart.



The best way to stay ahead of your need to specialize is to constantly measure your CSMs based on how they’re allocating their time each week. A quick way to do this is to periodically have them self report roughly the percentage of time they are spending in each area. Alternately, if you use a CRM or CS tool to track customer success activities, you can have the team bucket activities by category. If you trend this data against the increase in customers or end users, you can start to build a predictive model for when you’ll need to create the next specialist role within your team.

By starting with generalists, and using data to determine when to specialize, you'll be able to create a consistent customer experience from early through the growth stage of your company. I'd love to hear more about your startup journey, and I'm happy to share more about mine!

Need help planning your customer success team? The Success League is a customer success consulting firm that offers online training and workshops designed for success leaders. Topics include Planning a Team Structure and Hiring Top Performers. For more information on these and our other classes and workshops, please visit TheSuccessleague.io


Steve Schwartz - Steve is a customer success leader who enjoys starting and building high-performance teams at early-stage startups. He has worked in energy startups for the past 10+ years in a variety of customer-facing roles. By engaging with customers during the sales cycle, he ensures customer expectations are fully understood and can be exceeded. When not writing for The Success League, Steve is leading Customer Success at FreeWire Technologies. He holds a BS from Tufts University and an MS from Virginia Commonwealth University, and spends his free time with his wife and two kids exploring the Bay Area.

High Touch Customer Success + Automation = Focus


By Kristen Hayer

Doesn’t high-touch customer success mean that the Customer Success Manager is running the show? Absolutely. Doesn’t that mean that there’s no room for tech-touch tactics? Absolutely not. Customer success automation and a high-touch program aren’t mutually exclusive. In fact, incorporating technology into high-touch customer success can result in improved focus for your CSMs as well as a more engaging customer experience. Here are 5 things to consider as you think about adding automation to your high-touch customer success program.

Different People Prefer Different Approaches

First, let’s consider the customer: Different people prefer to have different kinds of connection with your organization. While many clients enjoy and respond to regular outreach from their assigned CSM, others will never respond. Some CSMs find it surprising and slightly offensive that non-responders will attend a webinar or engage with in-app messaging. The reality is that different people learn in different ways, and respond to different types of messages. If you vary the format of your messages, you’ll appeal to a broader audience.

CSMs Should Focus on High-Value Activities

Customer Success Managers are busy. They have to balance their valuable proactive work with inbound customer questions and scheduled meetings. This can create time-management issues, unless in-person work is supplemented with some automated communication. Automation can free up CSM time for personal touch-points that drive real value. If your CSMs are having a hard time getting to all of their customers, automation can help them expand their reach. If they are currently reaching everyone, automation can expand the number of customers they can effectively handle.

Repetitive Messages are Easily Automated

There are some parts of any job that are repetitive, and that includes some of the messaging that high-touch customer success teams deliver. Think about where this lives in your customer lifecycle. Is your introductory email the same for each client? Do your CSMs send out notifications about billing issues or reminders about executive business reviews? Look for every message that is consistent from customer-to-customer, and you’ll find places to automate. The messages can still look like they come from the CSM, but they don’t require your valuable resource to push a button.

Customers Like to Learn from Other Customers

Customer forums, advisory boards and events not only provide an efficient way of communicating with customers, they allow customers to learn from each other. An effective, high-touch CSM is seen a trusted advisor, but they are still an agent of your company. Other customers are seen as a neutral source of information about your solution, your company and best practices. Leverage your (happy) customers by inviting them to events that supplement your high-touch customer success efforts.

Some Customers Expect Technology

There’s technology, and then there is TECHNOLOGY. If you have a highly technical solution, you are probably engaging with very technical contacts. IT professionals, engineers, product managers and sometimes even C-level technologists will expect a lot of automation and in-app communication from you. In-person communication can be foreign or even unwelcome to them. This can be disconcerting for your high-touch CS team, so teach them patience and build up automated communications that echo your brand message.  

Does all of this mean that a high-touch program isn’t right for your company? No. Most organizations benefit from a high-touch program for their top customers, even if those customers don’t always resonate with it right away. By supplementing your high-touch program with automated communications, you’ll be addressing different communications styles, aligning with your brand promise, and freeing up your CSM team to focus on developing relationships that offer value to your customers.

Need help segmenting your customers and aligning your success program to your client base? The Success League is a customer success consulting firm that works with executives to develop top performing customer success teams. Let us help you design your program. Visit TheSuccessLeague.io for more information on our consulting services and training programs.

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Kristen believes that customer success is the key to driving revenue, client retention and exceptional customer experiences. Her areas of expertise include developing success metrics, designing the optimal customer journey, selecting technology, training teams, and building playbooks. Prior to founding The Success League, Kristen built and led several award-winning customer success teams. Over the past 20 years she has been a success, sales, and marketing executive, primarily working with growth-stage tech companies. Kristen has her BA from Seattle Pacific University and her MBA from the University of Washington. She currently resides in Silicon Valley with her family and an energetic German Shepherd puppy.

Developing a Scalable Success Team Structure

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By Kristen Hayer


One of the questions we often get from our customers is how to build a customer success team that scales from a budget and business-model standpoint, while still providing a customer experience that is consistent with their brand. Many teams are either understaffed to provide the customer journey they want to deliver, or are being asked to cut costs or headcount.

To have a smart, data-focused conversation with your leadership team about these issues, I recommend performing both a top-down and bottom-up analysis on your customer success program. If you have your client base broken into segments, evaluate each segment separately. At this end of this article I’ll also cover a few other things to think about as you plan your team.

Consider Top-Down Budgeting Issues

Unfortunately, a number of industry benchmark numbers get thrown around, typically a specific amount of revenue per CSM. CEOs and CFOs love to refer to this, and often push for this number when budgeting for customer success. I won’t mention a number here because I don’t want to perpetuate this problem. As you’re figuring out the ratio of customers/CSM it is important to consider a variety of factors beyond budget, including price point, brand promise and segmentation.

If you’re being asked to plan your team with this revenue/CSM benchmark, go ahead and calculate the number of customers per CSM that benchmark recommends. Then look at the number. Does it make sense? Can you deliver the program you’ve promised your customers with that ratio? Do you have very different numbers across different segments? Ask yourself these questions and then…

Balance with Bottom-Up Activities

If your CSM program is well-structured, this should be an easy exercise. Figure out how much time it takes to serve one customer over the course of a month with your current program. Divide the number of hours a CSM is available to customers by the first number and, again, you’ll arrive at a number of customers per CSM. Compare this number to the number you got from your top-down analysis.

Do the numbers match? Fantastic! You’ve arrived at a ratio of customers/CSM your finance team can get on board with and you can use for budgeting. Is the top-down number substantially larger than the one from your bottom up analysis? You need to have a candid discussion with your finance and leadership team about what is realistic. Either the revenue/CSM will need to be reduced to match the existing customer success program, or the CS program will need to be scaled back so that it aligns with the budget. Doing this planning and analysis will prepare you to have a discussion about the trade-offs.

Don’t Forget…

As you’re planning your team you’ll want to consider a few other things. First there’s segmentation. Most customer success teams have several different models in place, from tech-touch through high-touch. Before you do this analysis be sure that you’ve broken your customer base into segments that represent groups you want to interact with in different ways.

Next, consider automation. Without tools to automate, you’ll need to keep your customer/CSM ratio fairly low. As you add automation you can decrease the amount of time it takes a CSM to serve their customers, and increase the ratio. Tools cost money, so you’ll need to make some budget decisions, but automation is critical to building a scalable team.

The bigger your team gets and the more tools you add, the closer you’ll get to needing a customer success operations person or team. This function can run your tech-touch program, serve as the administrator for your tool set, and perform analytics for your team. Just like the sales operations function, this role is critical to growth.

Customer marketing is also becoming an important, behind-the-scenes part of a customer success effort. With 75-90% of revenue coming post-sale, it is surprising that this is a relatively new role on most CS teams. Email campaigns and other one-to-many communication vehicles serve as the foundation for tech-touch programs, and can drive expansion opportunities as well.

Finally, don’t forget about leaders for your scaling CS organization. As you move up into Director and VP roles, you'll need to delegate some people management. When hiring and promoting, keep in mind that experienced leaders can typically handle 8-12 direct reports, and new managers shouldn’t have more than 6. As you build your headcount plan, be sure to add leaders when the time is right.

Need help developing a scalable customer success team structure? The Success League is a customer success consulting firm for executives who want to build and scale a top performing team. As a part of our Leadership Training Program we offer a class in Planning a Team Structure that includes tools, group discussions and best practices. For information on this and other programs for customer success leaders, please visit TheSuccessLeague.io

Building My First Customer Success Team


One of our customers, Russ Olsen, has joined us as a guest blogger this week to share his perspective on starting up a customer success team. Enjoy!


By Russ Olsen

I recently had the wonderful, and challenging, opportunity of building a new customer success (CS) team from scratch. Earlier in my career I was involved in a similar project, but not as the manager and therefore not responsible for navigating all of the complexities of such an endeavor. Throughout both projects I learned valuable lessons that I hope will help you as you build your new team.

1.  Your Mission, Should You Choose to Accept it

When my manager approached me with the opportunity to create a CS team, I immediately accepted and started down the path of learning everything I could about the CS movement. That being said, the opportunity may not always be right due to any number of conflicts. If you do accept, however, get ready for a wild ride! I found that building out a new team requires intense effort, dedication, and perseverance. There were times I felt lost or stuck, and my initial commitment to the mission was the guiding force that helped me break through the proverbial brick wall.  

2.  Prepare for Victory!

I had a manager who would walk in each day at 7:00am and shout, to no one in particular, “Prepare for victory!” I often thought of this battle cry as I began preparing to launch my new team. I have an insatiable desire to learn and I began researching all the information I could get my hands on about CS as it was a new subject for me. I read countless books and blog posts, attended multiple industry events, engaged consultants, and watched hundreds of webinars. I also emulated many of the actions of the successful leaders I came across.

Throughout this preparation phase I began to gather important data that helped me paint the picture of the status quo for our business. I utilized, and still do utilize, the data to analyze trends, formulate goals, structure compensation, and to create metrics to measure the effectiveness of my new team.  

3.  Create a Game Plan

With so much information available related to CS I nearly got stuck in the preparation phase trying to achieve a perfect expertise in the discipline. Fortunately, I had a wise mentor who told me, “Done is better than perfect. Good, fast, and easy to learn from is perfect.” I was forced to put pencil to paper, creating a plan for what I wanted to accomplish, when I was going to accomplish it, and what successful completion looked like.  

4.  Prioritize and Execute

Once my plan was in place, I began to take the steps to accomplish it.  At times I found it difficult to remain on task in this phase but I knew the success of the launch depended on my ability to prioritize my efforts and to see the plan through to completion. Not surprisingly I had many competing demands for my attention (e.g., my day job, coworkers, my boss, etc.), all of which had the potential of delaying the completion of the project. I really had to remain disciplined to deliver the project on time.

I also found that effective communication with the various key stakeholders in the project is key to successful completion. At first I did not fully appreciate how much overlap my team had with other departments within our business. The relationships I had already established, and the ones I was forging during the project, made my team rollout a success. I used every opportunity to share my vision and passion with them, letting them know how my efforts would benefit them in some way.  I quickly realized how the buy-in of key stakeholders would either enhance or detract from my ability to execute the rollout plan.

I absolutely loved the experiences I had in building out the CS team. Many times I felt unequal to the task but, fortunately, I had several great mentors and leaders who helped me see the project through to completion. I made many mistakes along the way, but the steps outlined above helped me launch the team and set us up for lasting success!

Are you a new Customer Success Leader, or do you want to improve upon your Leadership skills in the new year? The Success League is a customer success consulting firm that offers online training and workshops on core CS topics like hiring top performers and planning a team structure. Check out our 2018 Customer Success Leadership program for class options and more details.

Russ Olsen - Russ is the architect and current manager of the customer success team at Henry Schein Practice Solutions. He is driven to succeed in all that he does, including further developing and refining the customer success program he has built. He is also very passionate about developing the team members with whom he works.
Russ holds a BS from Brigham Young University and MBA from Westminster College. Prior to Henry Schein Practice Solutions, Russ spent six years in the private wealth management industry working with clients in the private wealth management industry. He currently resides with his family in Salt Lake City where he loves to spend time in the outdoors.