Developing Your Customer Success Career

I have many different questions and always include some scenario based questions to see how they would handle those. Often I start with a very fundamental question along ...

This depends on the type of product your company sells. However, I would say it's essential that CSMs deeply understand the product and its benefits. I would ensure I kno...

It’s been a number of years since I’ve been a CSM (which I still believe is one of the most difficult customer-facing roles!), but as a Leader, I think it’s wildly import...

I am assuming this is while maintaining an individual contributor role.Consistently meet and exceed your KPIs. Be the go to person for Customer Success within your organi...

I have hired over 100 CSMs so far in my career. I believe that competencies and attributes are what is most important hiring in CS vs. a typical career path. I've hired f...

I believe that these are the must-have skills for every Customer Success Leader:Being business minded: As your scope grows, so does your responsibility to monitor perform...

It's very feasible to break into the tech industry as a CSM without prior experience. The key thing is to understand what the tech provider is looking for from the role a...

You're going to want a well-rounded set of knowledge and tools to set you up for success in Success. These include the practice of Customer Success, business metrics, co...

Most PIPs are not recoverable. I know that’s hard to hear. The data inside companies is usually that 70-80% of PIPs end in exit. In 15+ years in leadership roles, I've do...

Depends on what you actually like doing. Here’s how I think about it:AM (account management): Right move if you love commercial conversations and relationship work but wa...

If your team isn’t there yet, it will be. The era of “CS is a cost center, sales owns the revenue” is mostly over at strong companies. The teams I’m building today own re...

Both paths are valid. They are not the same job, and a lot of people pick management because it sounds like the next step, then hate it. Don’t do that. Management isn't a...

This market is brutal and I don’t want to sugarcoat it. I’ve reviewed reqs with 600+ applicants for a single CSM seat. You have to be deliberate.What is actually working ...

Short answer: AI is replacing parts of the job. It is not replacing the job. The CSMs who get cut in 2026 are the ones whose work product looked like AI output already: c...

It depends on stage. The KPIs change as the team matures.Early stage teams (under ~$10M ARR): anchor on GRR and LRR. You’re proving the product is sticky and that custome...

The two areas I would recommend are 1) Sharpening your Sales skills and 2) Adopting some Product Manager mindsets.  When working with customers and the further upmarket ...

The future of Customer Success is evolving beyond traditional retention-focused roles into a strategic, revenue-driving function with deep technical expertise. Based on m...

While I have been at HubSpot for a long time (13+ years), many opportunities have come up over time that I have had to assess new opportunities. Here are the things I ten...

As a customer success manager, one of the most important skills someone can develop is setting the right expectations and getting alignment between internal and external ...

I have to say that there is a big caveat here - you MUST be clear on your company’s strategy around rewarding talent. I’ve seen many differences in how companies approach...

I think about risk in a couple different categories. If we're talking about the beginning of the journey, I tend to lean more on monitoring stakeholder behavior for signs...

One example of a Customer Success Operations framework is the "Customer Success Management Framework" developed by Gainsight. The framework includes five key components: ...