• Josh @ Replexus

What Makes a Good Customer Success Manager

The late management consultant Peter F Drucker told us that we, the workers of the 21st century, have to manage ourselves, manage our work and manage others. Customer Success Managers (CSMs) are essentially called upon to do all three every day, as they also straddle the space between technology and relationship building. The most challenging of these three tasks is managing the work because our role requires us to sell via proxy – to get customers to influence others in their organization to adopt a product they neither understand nor appreciate the benefits of.

Influence without authority

CSMs often operate with little or no formal authority. However, our work requires us to exercise inordinate levels of influence every day in order to succeed. Your ability to evangelize requires this.

Nothing happens if you cannot get your customers to take action. Little happens if you cannot convince your initial users to help you find other avenues for adoption within the company or enterprise.

In their book, Influence Without Authority, Alan R Cohen and David Bradford cover a broad set of topics that are extremely applicable for success in this realm. This is a top book that I recommend to customer success management practitioners who are looking to level up. Even if they only read the summary, it puts them into the right mindset about the top soft skill that a CSM needs to ensure a customer’s success.


Empathy is the next key skill for customer success because it aligns the thinking of the CSM with that of their customers’. Empathy often comes from shared or similar experiences. This is also why people subconsciously gravitate towards other people whom they perceive to be similar to themselves.

When working in application security (appsec) I look for CSMs and Solution Architects that have in some way lived the life of whomever they are likely working with. This helps them craft a message that constantly answers the most important question in a recipient’s mind: WIFM – What’s In It For Me?

Understanding what motivates people is key to getting things done. Failure to do so can get in the way of productivity. In trying to understand others, we need to be careful about the assumptions we make about everyone and their needs, desires, and motivation.

For example, when promoting the implementation of a software code vulnerability detection tool at various companies, it is often assumed that the typical developer wants to write secure code faster. In reality, the average software developer wants only to write code faster but with enough security so that they don’t have to come back and rework it at the Security department’s request. Knowing this comes from being able to empathize with the software developer.

A pithy plan you can easily modify

Another important skill of a CSM is the ability to draft a pithy plan. It needs to contain enough detail to convey the idea without it seeming too difficult to enact, so as to gain customer buy-in.

We must always be ready and willing to modify said plan as the situation changes.

In the past, customers expected complex and problematic installation of on-premise software. Today, software is expected to install in the enterprise instantaneously and smoothly just like we add apps on a phone. This is especially true with software as a service (SaaS) offerings. Customers expect painless implementations.

Adoption, however, remains the sticking point.

Too often I hear people talk about having the customer sign a project plan to get buy-in. The irony of this only becomes obvious with experience.

The purchaser may sign the contract, but the people implementing it may have many competing priorities. These easily get in the way, especially as you lack that authority to drive your agenda. For most implementations that includes efforts in adoption, the CSM has no real recourse if dates aren’t met. You need flexibility and adaptability to makes things happen because dates will slip and deadlines will languish due to competing priorities as resource inputs get delayed.

You are dealing with humans, and this is tricky especially in the aspect of adoption. All the more reason to add plenty of flexibility and contingency into your plan.

Being multi-threaded is critical

It is important to be able to deal with multiple customers concurrently, and also to find multiple concurrent avenues to adoption at each customer.

This is especially important in deployments at an enterprise, where you may need movement with one group if others are delayed. This is part of your stakeholder management. You are deploying your power and influence across boundaries to get results. People who cannot shift tracks and gears nimbly rarely make it far in customer success.

Multi-threading is also relevant to working with multiple clients. Customer success management is often about mastering the art of “hurry up and wait”. You want to be ready before you are asked for something and then “leap and linger”, for you may get great movement initially and then languish until an opportunity for movement becomes present.

One of my solutions is to schedule a standing meeting to hold time on everyone’s calendars, to keep the project top of mind and even to do work together or individually. These “Office Hours” are prioritized for scheduled topics but are open to anyone at the customer who wants to show up. Sometimes they lead to another avenue for adoption. At others, the meeting is spent connecting personally to build the relationships you will draw on later when if a sizable problem arises. In both situations, you learn how to use downtime in one project to achieve progress elsewhere.

Continuous improvement - Kaizen

Kaizen – continuous improvement – is a Japanese approach to management. Kaizen is a mindset that is based on the idea that big change can happen as the result of a series of small, ongoing positive changes. Kaizen is what makes some teammates stand out.

Those who have a Kaizen approach will continually improve the process. They will try to tweak every possible improvement they can identify within and contiguous to their purview. The hard part is knowing how often and how far to push.

Recognizing patterns and using a modular approach

Recognizing repeated activities and looking for ways to automate or answer them proactively is a great quality in a CSM team member.

In this vein, reusability is key. You can become much more effective and productive when you seek to create template presentations, scripts, plans, and even emails.

As a CSM, you know what your clients want to know. You know the most frequently asked questions and the topics that flummox most client staff. Consider investing your time creating a knowledge base. Your knowledge base can be intended for internal use by coworkers or external use by customers or prospective customers. It can also be built on many levels.

For example, it can be an add-on to the FAQ section on your website. You can add a very short (30 seconds, say) tactical video series on YouTube that solve common configuration issues. You may add longer videos that focus on strategy for improving return on investment (ROI) from your tool and longer demo videos to your online resource base.

It does not matter if you get only a fraction of your audience to use your resources. Any use increases efficiency.

Making and strengthening relationships

Building relationships with the initial individuals is vital in your journey to “land and expand”. No matter how efficient your processes are, do something personal for someone to reinforce your connection with them.

Make a phone call to understand how a customer is doing with the problem your product solves. Inquire into any other concern you know they had from your previous interactions with them. Ask them about their upcoming vacation. No matter how technical, we are all humans and want to be connected to people who care.

Making this effort goes a long way towards enhancing people’s inner work lives, according to the Progress Principle: Using Small Wins to Ignite Joy, Engagement, and Creativity at Work, an excellent book by Teresa Amabile and Steven Kramer. This is another book I’d recommend to team leaders, whether in customer success or elsewhere. As you read it, you begin to appreciate how little things make a huge difference to people and of course, to productivity.


Keys to reaching success in Customer Success include the ability to: exert influence without authority, enact empathy, create pithy flexible plans, adapt, be multi-threaded, continuously improve, recognize patterns, and think modularly.

Keep the humanity top of mind. We have to work with other people to ensure a customer’s success. No matter how technical, we are all humans and want to be connected to people who care.



Josh Rosenthal is a Customer Success enthusiast. In 2019 he sold CloudSploit, the internationally-popular open-source cloud security SaaS, which he co-founded and then grew via automation, community building, and the gig economy.

Josh brings an amalgamation of technology, communication, and technical bottom-up sales. Years before technical customer success was a buzzword, Josh put together a curriculum for it: majored in Computer Information Systems and minored in human communication, spent years as a programmer before moving to sales engineering, and then studied operations research (statistics) for business data.

Recently, he was the Director of Solution Architecture at Contrast Security, where he designed and implemented technical customer success strategies for "expanding after Sales did the landing".

Read more about Josh at linkedin.com/in/citizen

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