This is a great and timely question, especially considering that most product/feature sets are evolving at an extremely rapid pace in a technology ecosystem becoming more expansive by the day as well (thanks, AI). One of the most important places to start is to consider what business objectives your product helps to serve, even if not considered critical to the customer's business. There's a reason your product is purchased across your customer base. What sets your product apart in the marketplace? Why are customers inclined to buy your product? How does your product drive business results in their organization - what is the value narrative? What happens when customers optimally use the product - what results do they see? Being able to effectively articulate this can allow you to then create measurable criteria to showcase progression against those objectives, thus proving customer ROI. Having a clear view into customer objectives also allows you to work with your product and marketing teams to align products and feature sets to these objectives, enabling your CS team to build success plans with customers anchored in these objectives, build strategies to drive product adoption/stickiness based on these use cases, and co-create a value narrative.

With a self-serve product, you probably want to stay away from some of the more product-based KPIs (e.g., product adoption or health score if it's largely adoption driven) but retention, NPS, etc. are still critical metrics for Customer Success. The business has a value proposition for why it's investing in Customer Success despite the product being self-serve so it's incumbent to figure out what that investment thesis is and tie you and your team's KPIs around it.

When directly correlating with pipeline generation proves difficult, consider alternative metrics such as engagement (website visits, email open rates), lead quality (conversion rates, lead scoring), brand awareness (social media sentiment, brand mentions), CAC, CLV, retention rates, customer experience, and customer feedback. These metrics provide insights into marketing effectiveness and overall business impact.

You can go two ways here with respect to metrics. 1. Use a metric they know and understand 1. Pros: They can engage with it, they have an understanding of why it may be going up or down and a sense of how they can help influence it. 2. Cons: It might not be the best measure of the health of the customer base or may be one of 5+ factors. 2. Use something new that you feel better represents the business. 1. Pros: You can have confidence (if you've done your homework) that influencing this metric will drive retention and growth 2. Cons: It can take several months of repetition to warm up the executives to what these numbers mean and how to influence them Frankly, I do a little of both. We have aligned the executive team on a set of metrics on which we have varying degrees of comfort and confidence. Here are a few examples * Adoption Health - defined by our data science team and shown to have a strong correlation to retention. A composite score that the executives have moderate comfort/understanding of but they're aware of the strong correlation. * Executive Engagement - % of accounts and ARR where we've had an intentional exec conversation in the past 90 days. * Onboarding Duration - # of days to take a customer from kickoff to launch. * ARR not yet launched - how much of our ARR is not yet in the Launched phase (meaning they're still in onboarding). Top questions from the exec team: 1. How is retention trending this quarter, next qtr, for this year? 2. Why do we have confidence that our renewal/retention forecast is accurate? [I demonstrate this through the other metrics] 3. Which customers need help from the exec team?

Here are some key roles onboarding plays and practical techniques for ensuring a smooth process: 1. Educating Users: Onboarding educates users about the core functionalities and value of the product, helping them understand how it can solve their problems or enhance their workflow. 2. Reducing Time to Value: Effective onboarding shortens the time to value, enabling users to experience the product's benefits as quickly as possible. This is crucial for retaining interest and commitment. 3. Lowering Initial Friction: Onboarding aims to reduce potential friction by guiding new users through setup processes, integrations, or initial configurations that might otherwise be overwhelming. 4. Building Confidence: By gradually introducing features and allowing users to succeed early, onboarding builds confidence in using the product and encourages deeper exploration. 5. Encouraging Habit Formation: Good onboarding guides users toward behaviors that will become habitual, ensuring that the product becomes a regular part of their routine. Effective Onboarding Techniques: 1. Segmented User Journeys: Tailor onboarding experiences based on the user’s role, industry, or experience level. This ensures the onboarding process is relevant and aligned with the user’s needs and goals. 2. Interactive Walkthroughs: Instead of just video tutorials or manuals, interactive walkthroughs guide users through the key actions they must take within the product environment. This hands-on approach helps reinforce learning and engagement. 3. Progress Indicators: Incorporating progress bars or checklists during onboarding shows users how far they've come and how much is left to complete. This can motivate users to continue through the onboarding process. 4. Immediate Value Delivery: Design the onboarding flow to demonstrate value quickly. For example, if your product is a marketing automation tool, help the user set up their first campaign during onboarding. 5. Use of Tooltips and In-App Messaging: Subtle tooltips and contextual in-app messages can provide additional information and reminders without being intrusive. They help users learn at their own pace. 6. Regular Feedback Collection: Implement mechanisms to collect feedback during and after onboarding. This helps identify pain points and areas for improvement, ensuring the onboarding process remains effective. 7. Personalization and Flexibility: Allow users to personalize their onboarding experience by choosing what to learn about or skip based on their prior knowledge and experience. Offering flexibility makes the process more user-friendly. 8. Integration of Support Resources: Ensure that help resources, such as FAQs, training links, community forums, and customer support contacts, are easily accessible throughout the onboarding process. Knowing help is at hand can reduce anxiety for new users.

I love that you’re looking to break into tech as a CSM, here are a few strategies I would recommend: 1. Internal Promotion - Some of the best CSMs I have worked with have moved up internally from other roles in the company. Customer Support and Sales Development are two internal roles that I frequently recruit from. If you’re early in your career, look for entry-level roles in Customer Success-adjacent roles at a company that prioritizes internal mobility. A benefit to both you and your employer is you’ll already have a good understanding of the product. 2. Adjacent Industries - If you have experience elsewhere and are looking to make the switch, I recommend being strategic: Focus on companies where your previous experience would give you a unique advantage in understanding the customer. (eg: if you’re an accountant today, look at companies that make software for accountants). Don’t “spray and pray” - you’re better off focusing on a smaller set of companies that you think will be a great fit. 3. Entry Level CS Roles - I think this will be the hardest path for you, but it’s possible. I frequently receive hundreds or even thousands of applicants for entry level CS positions, so it’s important to stand out from the crowd. Network and attend CS meetups or events (meetup.org is a great resource) where you can. You’ll learn a lot and you’ll also start to meet people in your local CS community who can help you.

Understanding and quantifying the value customers receive is paramount for a new CSM function. Once identified, it facilitates the construction of a CS framework to expedite time to value recognition and provide tangible proof to the customer. Growth of this value becomes the cornerstone for aligning with stakeholders, conducting Executive Business Reviews, and other operational motions.

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.

Yes, it is absolutely possible for someone from a different field to transition into Customer Success. I have typically seen success from former Sales and Solution Consultants moving into Customer Success as well as former Support Reps being great in the role as well. The key when interviewing is to highlight experiences and abilities that align with the core responsibilities of Customer Success, such as communication, problem-solving, relationship management, and a customer-focused mindset. If you are interested in transitioning into Customer Success, I would start identifying overlaps between your current role and Customer Success. For instance, if you’ve worked in Sales, Support, or Solution Consulting, emphasize your experience managing client relationships, resolving issues, or delivering results. Next, invest time in learning about the field. Familiarize yourself with Customer Success methodologies, tools like CRM software, and strategies for customer retention and satisfaction. Consider earning certifications or taking courses on platforms like LinkedIn Learning. As I mentioned in a previous answer, networking is also crucial. Connect with Customer Success professionals to gain insights, ask questions, and seek mentorship. Tailor your resume and LinkedIn profile to showcase how your past experiences align with the goals of Customer Success, focusing on outcomes like collaboration, problem resolution, and customer advocacy. Finally, when interviewing, demonstrate your adaptability and eagerness to learn, which I love to see when I interview candidates. Show that you understand the value Customer Success brings to a business and that you’re committed to helping customers achieve their goals. With the right preparation, your unique background can be a tremendous asset in this field!

This question asks about balancing metrics focused on retention and expansion as if they're on opposite sides of a seesaw. They aren't. The path to expansion travels squarely through the metrics you would measure for retention. In other words, you have to earn the right to retain business before you should even fathom expanding. Large accounts are going to expand in two main ways: buying more product or more new teams buying what one team already bought. Both of these expansion paths can only be tread if you are delivering value to the original team for their original purchase. So green lights on retention mean you can then - and only then - run plays to expand the engagement.