I think one of the biggest 'surprises' was that regardless of the maturity level of the CS organization, some of the same considerations held true in both cases: * The role of CS is constantly evolving alongside other customer facing roles. Even if you have the ability to build a strategy at the start, the need to commit to regular check-ins on how CS strategically fits within the broader organizational goals remains present. Examples include: Are the measurements and incentives the right ones to drive behaviors that lead to ideal customer and business outcomes? Do we have the right skillsets within the CS team to drive results? How quickly will we be expected to scale? * Cross functional relationships were very key in both places to maintain a value-based customer journey and agility in creating value for the customer - across product, engineering, sales, marketing. One notable difference in this respect is the proximity to which CS teams find themselves with these other teams in each scenario. For example, when a CS team is being built, there's often a necessary and natural deep partnership between CS and product/engineering to understand customer response to product features, gather continuous feedback, iterate on that feedback, and maintain product quality. This often creates a much more nimble and fast feedback-to- action process than you might find in a more established organization where CS is one input in a more complex feedback collection network. * Consistently investing in building and refining the CS impact narrative is key in both cases - when establishing a CS function, it's critical to think early about how impact and value will be measured so you can build perspective around headcount modeling and resourcing, so you can talk confidently about how the team contributes to business outcomes, and so you can think in the right ways about scaling outcomes. When moving into an org where CS is already established, you often have to consider these same things, but for slightly different purposes and within different constraints. In this case, you are working within the bounds of existing processes and measurement models, so it becomes important to assess current state, determine where gaps in impact and potential exist, assess the ideal pace of change, and build step-work plans to evolve.

The best Customer Success candidates demonstrate a genuine interest in the industry they are supporting, whether it’s a passion for enhancing the customer experience, like at Zendesk, or a strong enthusiasm for technology. They excel in communication and problem-solving, building lasting relationships while thoroughly understanding customer needs. A proactive, solution-focused mindset is essential, along with the ability to navigate complex situations with empathy and clarity. Top candidates also thrive in fast-paced, ever-changing environments, showing adaptability. Last but not least, the best customer success candidates must have a commitment to continuous learning.

When bandwidth is extremely tight, focus on high-leverage KPIs that align with essential business outcomes and don't create unnecessary admin overhead: 1. Must-Have Metrics * Critical account retention rates * Revenue at risk identification * Core product adoption milestones * Basic customer health scoring (simple red/yellow/green) - AI generated and not CSM-owned (NO MANUAL SCORING!) * Minimum touch frequency for key accounts 2. Efficient Activity Metrics * % of proactive vs reactive work * High-risk account coverage * Essential QBR completion (top accounts only) * Response time to critical issues * Key milestone completion rates Crucial Adjustments: * Segment customers ruthlessly - focus metrics on top/strategic accounts * Simplify reporting - weekly numbers only for what's truly critical * Automate what you can (basic health scores, usage alerts) * Cut nice-to-have activities entirely * Accept "good enough" on non-critical accounts What to Skip: * Detailed activity tracking * Complex scoring systems * Non-essential customer touchpoints * Granular feature adoption metrics * Extensive documentation requirements The key is choosing 3-5 metrics maximum that: * Have clear business impact * Are simple to track * Don't require manual data entry * Focus team on highest-value work

If you enjoy what you do and why you do it, you’ll do it better and you’ll do better. Here are some questions to ask yourself when consider a new role: 1. Do I feel good about what I would be doing in this role? Do I feel good about the company I would be working for? Maybe it’s in an industry that you’re interested in, or maybe it’s something that helps shape the sort of world you want to live in - whatever it is, make sure you feel good about it. If you believe in the company you are working for, you will have much more energy at work and in your life. 2. Can you feel good about who you’re working with? What are the leaders and peers at the company like? Did you feel good during the interview cycle? Do the publicly stated values of the company align with yours? You’re going to spend a lot of time with these people and it needs to feel like a good fit. 3. What is the product like? If the product is weak, CSMs, almost more than any other role, are exposed to this. Will you be spending most of your time dealing with product issues to retain your customers, or will you have a chance to be more strategic? An early or imperfect product is fine, but I would try to validate what the short to medium term prospects are. Is the company early-stage and rapidly improving the product or is the product imperfect because it’s not being invested in properly? 4. What are the business prospects like? What is the industry or business space like? Is the industry growing or are its best days in the past? It can be very hard to retain your customers if there are macro economic issues at play.

On top of all the usual traits of being a great CSM, I think of 3 things when I think of great Enterprise CSMs: Stakeholder engagement: To me in Enterprise CS this is the ability to confidently communicate with the C*suite, the ability to multi-thread across an organisation and the ability to achieve the buy-in of multiple stakeholders towards a common objective. Change management: As an Enterprise CSM you're usually dealing with much bigger and more complex organisations, and so you can't take all the action items yourself. This means you've got to get out of the weeds and focus on the bigger picture; driving a change to meet the customer's objective. You've got to be much better at both holding your customer accountable to executing their actions AND guiding them through what they need to do to drive this change. Project management: Essentially, being great at tracking all the strategies and corresponding actions that need to be completed in order to achieve the customer's objective, as well as being able to communicate this in a clear and concise manner to the customer. Your goal here is to keep everyone on track.

I've found two KPIs to be difficult to commit to: 1. Customer Health. If you have a robust algorithm to measure customer health (influenced by a number of inputs ), it can be hard commit to a certain outcome. To frame this another way, I've often observed customer health scores as being a bit of a black box where it's hard to tie the actions you take to specific outcomes when there could be a number of variables outside of your control that influence the ultimate score. I much prefer to commit to lead measures that are directly within the control of the team. KPIs related to customer engagement are a good example of things that are more directly within the team's control. 2. Upgrade rate. Many CSM teams are measured on Net Revenue Retention. As part of this, your CSMs may be responsible for identifying growth opportunities within the install base of customers. I find it's effective to measure the team on how many growth opportunities the team identifies but not the close rate or upgrade rate, especially if the Sales or Account Management team owns the closing motion. 

There are so many career paths for a Customer Success Manager! I don't view the CSM's path as necessarily linear, but a "typical" one might be: 1. Customer Success Associate 2. Customer Success Manager 3. Senior or Enterprise Customer Success Manager 4. Strategic Customer Success Manager 5. Manager of Customer Success 6. Director of Customer Success 7. Head of Customer Success That said, there are a lot of different specializations, such as Customer Success Operations, Renewal Management, or large-scale Customer Success (sometimes called 1:many or "digital"). These specializations are great goals for someone who has been in Customer Success for several years and would like to advance in paths that are not necessarily management. 

Technical Support response targets! We’ve all been there, and being the first Success Hire is super exciting. You get to wear many hats, get involved all the way through the customer lifecycle and be scrappy to get customers what they need. For us at the beginning, that meant taking on a lot of Technical Support tickets for our EMEA customers, especially in the morning before our then US-based tech support team was online. On the one hand, this gives you a lot of valuable product knowledge that can help you be an impactful CSM, but on the other hand, it can mask the business need to expand technical support teams and can hurt your focus in the long term. If you can, explain early the difference between CS and Tech support KPIs and ensure that anything you take on is temporary!

There are two questions I always like to ask during an initial interview with a candidate: 1. Tell me about a problem you have worked on and how you solved it? - In full transparency, I actually borrowed this question from an article I read about Elon Musk's interview questions. I found the reasoning behind this question to be extremely interesting. First, you gain insight into the types of challenges the candidate has come across and their thought process for overcoming those challenges. Second, Musk says that this question shows him if the candidate truly worked on resolving this problem. Someone who was integral in the solution of a problem will know all the details and be able to explain in length what they were thinking was during the process. I have found a lot of success in asking this question. 2. I ask candidates to share with me a time they had to articulate value of their product/solution to a customer. As I mentioned in another question, showcasing your company's value is one of the most important responsibilities of a CSM. If a candidate does not have experience with this, how can I expect them to articulate value to our customers?

This can vary wildly. Areas It depends… 1. CSM/Pooled CSM 2. Digital 3. Renewals 4. Support 5. Professional Services 6. Implementation 7. Education 8. Operations/strategy 9. Enablement So when you look at all those, a CS org structure could be complex even with a small team! My recommendation is to start small, ensure your definition of success and annual strategy is clear for where you need to go based on your product/service, is aligned with other teams, avoids the errors of 1) being overly complex, 2) being non-ambitious (thinking small), and 3) shooting for the moon and demoralizing yourself and the team. The biggest piece of advice I can give is to: 1. Establish your long term strategy 2. Seek wise counsel around you for what you should pursue and how to organize it given your long term strategy If you're looking for general org structures, there are many images on the internet that you can use to get started.