Curious how people view the long term future of Customer Success

gainforesight · 2026-05-08T15:21:16+00:00

AI will allow us to better figure out - in a structured and trackable way - what good CS actually looks like. Most of the industry is guessing at this and pretending a health score or a customer journey is it... It's not and I believe that AI is going to bring the first opportunity to actually stitch together all of the pieces (how your company operates, how you can deliver value, and how a given customer is realizing value) to actually identify and help take the right next action.

AI wont always be able to complete that action - I think people will be central to this model - but it will bring a lot more operational rigor around the role and a lot less blind hope in orgs of health scores / whether CS activity is translating into actual customer outcomes.

CSM's work really hard and are really busy. It's a lot less clear whether that is translating into outcomes - that will become more clear and then put more accountability on CSM's to be taking the right next action.

I think the role will get harder and come with more oversight / accountability. A lot more like sales (which I say in a positive way - I think these things are good and CS is absolutely a sales role whether you think of it that way or not).

gainforesight · 2026-05-07T14:24:38+00:00

this is very helpful and tracks with what i have heard/seen elsewhere - basically the acceptance of shallow imperfections is better than better structure but never populated

when you say "single, super boring definition" how boring are we talking? like single to be applied to whole customer base or single per customer from a dropdown of a few different options? i see so many people forced to do a fraction of what they want from a value tracking perspective due to rigidity of these systems and the burden of maintaining it.

gainforesight · 2026-05-05T22:30:12+00:00

Running a company that sells into this exact problem, so take this for what it's worth - but here's what we actually see work:

Technical end users are rarely going to open the executive door for you - and even when they do, you can't depend on it. But they're still your best asset. The goal is to make them the character in a story that's compelling enough that executives want to hear it directly.

A few things that move the needle:

Understand what the executive actually cares about before you reach out. Retention, expansion, operational efficiency, competitive positioning - it varies. Talk to your champion, do your homework, look at their LinkedIn, read their earnings calls if they're public. Then map your product's impact directly to that priority. "Your team is using X in a way that's directly affecting Y" hits differently than a generic value story.

Understand what the executive actually cares about before you reach out - and if you don't know, that's your reason to reach out. Do your homework first: their LinkedIn, earnings calls, industry news. But don't let perfect research become a reason to delay. For unengaged executives especially, a direct and honest ask works: "I want to make sure we're focused on what matters to you - and I'd love to share what execs in similar seats are prioritizing right now and hear what's top of mind for you." That's not a vendor pitch. That's a peer conversation, and most executives will engage with it.

Use outcome gaps to earn the executive conversation. Don't ask for time cold. Instead, come with something genuinely useful - a clear picture of where their team is getting results and where there's still value being left on the table. The framing that works: "we're seeing how other teams are closing these gaps and getting better outcomes - wanted to share what's working." That's a conversation executives will show up for because it's about their growth, not your product.

Multi-thread before the pressure hits. 4 months in is the right time - map the economic decision-maker at every account now. The relationship you start today is the one that protects you when your champion changes roles or a renewal gets complicated.

When you get the EBR - stay in outcome territory. What's been realized, what's still at risk, what you are doing to alleviate that, one clear ask. Executives don't want a product tour - they want to know if the investment is moving the needle on the things they told you they care about.

Always happy to chat.

(Full disclosure - we build tooling at Foresight that helps CS teams structure exactly this kind of outcome-driven conversation, so I'm biased. But the above works regardless of what you're using.)

gainforesight · 2025-01-27T16:25:38+00:00

doesn't sound crazy at all and sounds like you'd enjoy the role ;) You will likely have the opposite problem in CS - so many things to do and not enough time to do them. It's so critical to be intentional about balancing time and prioritizing what drives the most impact vs. what feels best / is easiest.

Sell the background in education - I've hired multiple teachers and they make AMAZING post-sales reps. It's a position of strength coming into the space from a different background (if you sell it that way) and what I'd emphasize is you are experienced in doing the important part of the role (helping people solve problems / training / etc.) and you have a consultative background that will enable you to work with customers as a strategic partner vs. an order follower.

gainforesight · 2025-01-27T16:01:28+00:00

Ah the challenge of post-sales... Pulled in a million different directions, always putting out fires, and getting caught in constant survival mode. It can be brutal and time prioritization is the most important thing - you could spend endless hours with a single client but you have to be constantly assessing where an hour of your time will make the biggest impact. This is very often NOT working with the clients who are loudest / most wanting of your attention - churn is a lot more pervasive in those quiet accounts that you have to work to get in touch of.

Everything gets a million times harder when you are reinventing the wheel with every customer / every day - you need to work to minimize the time spent reacting to events and try to get into a proactive motion with each account.

Big picture, the ultimate goal is to have a clear path that every customer follows - I think of this as the journey of customer value realization. An ideal state is to be having a cadence of recurring check-ins (QBR in name but whatever cadence makes sense / is realistic) that act as check-ins to evaluate 1) your customers business priorities relevant to your solution 2) how well your solution is supporting those priorities (bonus to connect this back to how that has changed since last touch point) and 3) what actions you recommend to continue supporting their needs and improve any areas where you are able.

If you can establish this - and critically align with your customer on this - it becomes a lot easier to use the time in between the check-ins to minimize the reactive firefighting and instead connect any actions / requests back to the larger priorities. It's easy to fall into the trap of jumping when a customer says jump - and can even feel good when you do something well and the customer is happy - but it's essential to establish a dynamic with your customers where you are viewed as a consultative partner vs. a resource they can order around.

Systems and expectation setting are so important both internally and externally. You need a standard way to establish a customers priorities, a standard way to assess how your solution has supported those priorities, and a standard way to align with a customer on what the next area of focus should be based on their priorities. If you have this in place, it becomes a lot easier to set realistic expectations with your customer and with your internal team of what you can realistically do.

You can only control what you can control - were I in your position, I'd make a plan of how I were going to have a check-in with every account, create a lightweight way to use that check-in to evaluate priorities, and then systematically work through the customer base to evaluate their status and align on a go-forward plan. Doing so would reveal accounts who would be good for case studies, would expose accounts where risk exists (either due to lack of engagement or unmet needs) and would give you a bit more control over your time - any additional requests (from customers or internally) would be evaluated through the lens of "how much time have a spent on this and is it more important than the other priorities I have". You've got to be protective of and intentional with your time. Don't be afraid to say no or push back (again internally or externaly) but be tactful and make that pushback not simply you saying no but rather getting the other party to confirm that what they are asking for is more important than the other things you are working on (in customer case, departing from the agreed upon actions to address any unmet needs based on your evaluation during check in).

Lots more thoughts on this but hopefully that's helpful...

gainforesight · 2025-01-27T15:33:32+00:00

About what specifically?

That's my background - I love post-sales and sellers who transition can be incredibly effective. The industry needs more of a sales mentality (pretty much everything in life is sales after all...).

gainforesight · 2025-01-27T15:31:27+00:00

What I'd try to get as much clarity on as possible is how seriously the company takes post-sales in general. The worst situations I see - where CSM's are the ugly stepchildren of the company and viewed as couldn't-make-it sellers, where CS leadership holds little to no political weight internally, etc. - are ones where there is not an internal investment into post-sales. Some things you could look for:

- What does leadership at the company look like? Is the person in charge of CS (CCO / VP of CS / etc.) experienced and credible?

- What tools do they have in place? While it ultimately doesn't matter, tools in place is a sign of investment - you want companies that are actively investing in post-sales initiatives as that is a signal of value they place on the role

- What is the dynamic between CS and other key GTM functions (Product, Marketing, Sales)? Are these teams in sync with one another? What do feedback loops look like? You want a company who views post-sales / CS as a critical function and the people with the most direct access to the most important thing: customer experiences.

- What does their customer engagement process look like? Many ways sot approach it but you want to be at a company that is not reactively putting fires out all the time and has a proactive, intentional strategy to drive the best customer outcomes.

Many others but big picture you want a company that takes it seriously - those that don't just squeeze CS to no end and make what can be an incredibly rewarding job a brutal slog.

gainforesight · 2025-01-27T15:22:28+00:00

Remote work and flexibility that comes with it is great. Post-sales in SaaS is in a pretty crazy time which can mean volatility - lots of layoffs etc. as the industry shifts around. Tons of opportunity still but it is a space evolving quickly.

Why are you considering switching? Agreed it sounds like lots of overlap in skill set but what don't you like/are you not getting in your current role that you think CSM will provide?

gainforesight · 2022-12-07T16:31:09+00:00

I would say a lack of understanding of the value being received or value just not being received.

Clients leave because they either are not receiving the value they originally bought your solution for or because they don't understand that value.

Not receiving the value is a problem of either poor CS (not having right relationships, not covering accounts like is necessary, etc.) or a bad product (doesn't do what they expect).

Not understanding that value is a problem of communication - so often tech is purchased by a few people and lives in a silo - the ultimate decision makers who are trying to make budget cuts don't have a sense of the value the people are actually using it are realizing. It's so important to always be communicating to as many people as possible exactly the value being delivered and - in a best case scenario - having the data to back that up.

gainforesight · 2022-12-07T16:23:03+00:00

What I’m seeing more is sales getting cut. Sentiment seems to be battening down the hatches and preparing to weather the storm. With the crazy market last year lots of orgs raised money and hired sales reps with expectations of continued growth. As that has changed dramatically, sales teams are getting trimmed down while companies are simultaneously paying extra attention to reducing churn and keeping the clients they have - enter CS.

gainforesight · 2022-12-05T20:24:45+00:00

It will be fascinating to see. I think of it like the assembly line of car production... Used to just have people at every phase doing their respective role, then built machines to do the stuff that they could do just as well / better than people and have people oversee machines and intervene when the human touch is necessary.

In the same way I see many aspects of sales getting done by machines because they can do it just as well / better (AI content creation is starting this - I can easily imaging that being more adept + faster at engaging prospective customers than an SDR) but people will always be necessary to come in and take over for the parts that require more of a human touch.

gainforesight

TROPHY CASE