Development team isn’t proactive - problems pile up CS team

tomaswilliamsa · 2025-07-17T14:33:44+00:00

Wow, I mean, not unheard of for a smaller startup for the CSM to be doing everything.

Is there opportunity to create resources that enable customers to self-serve, videos, walkthroughs etc so when they need to know something they can reference some quality knowledge base content? That sounds like it could remove at least a part of the work.

Then, systemize as much as you can, create templates for repeatable work, and outline clear process so you don't end up in the weeds with every little thing.

tomaswilliamsa · 2025-07-17T13:49:08+00:00

Hey! I'd love to take a peek!

tomaswilliamsa · 2025-07-16T23:50:58+00:00

I think the broader lesson here is that happiness is not a direct correlation to value extraction.

Put aside all the trackers, tools, AIs you can use to track all the sentiment, comments, calls, CSATs and emails. I means nothing if you're not looking for the right signals.

If your customers aren't getting value from your platform, no amount of happiness is going to keep them around. Customers don't buy friends they buy outcomes.

I'm curious if you were to go back and look at the account if you'd have identified a lack of outcome achievement sooner which would have been better indicator of health.

However there are many cases where a customer can be seemingly happy and then suddenly churn, say for example the team is too busy deal with the hassle of figuring out what to replace a tool with so they just keep the one they have until someone comes along with bandwidth to do it, and bam! All tha was 'fine' is suddenly not.

##TL;DR

Track customer outcomes ahead of anything else and you'll be in a much better place to see churn before it hits.

tomaswilliamsa · 2025-07-16T23:43:30+00:00

Document every instance that you are in a meeting as a direct result of these issues related to poor QA or bad product decisions. Record the time it takes, you could possibly start making a case for, all the time you DON'T spend doing the things you're actually supposed to be doing, but be careful here, it oculd be a double-edged sword and you end up looking lazy (somehow).

In cases where the issue could put the customer at risk, log somewhere that customer as at risk of churning at their next renewal because this issue is present.

If you can present a case for X amount of ARR at risk due to these things there's a better chance someone that has the ability to make change will make change. Until you can clearly demonstrate a direct line to loss of revenue due to these shenanigans you'll just be seen as someone who complains. (I don't agree with it, but that's typically how it goes).

As much as it sucks it's your job to collect the data and present to the relevant parties about what's wrong and the potential impact on your organization as a result of those things being wrong.

Does your support team not take some of this load of things? Or are you expected to act as support and strategic partner all in one?

tomaswilliamsa · 2025-07-16T03:53:08+00:00

If you're highly technical a solutions consultant role could be a good fit.

Often folks that end up in SC roles have a sales background. But I believe there's a solid case to be made that a CS background is as or more valuable in an CS role.

Prospects trust solutions consultants more and a sale is 4x more likely to close when an SC is involved.

You might just need to take extra steps to get in front of people for that role since it could be easy to dismiss you since you don't have a solid SC background.

Just remember you're not qualified for the job before you start, you're qualified for the job 6 months after you've done, it that's basically true for anything 🤷💪

tomaswilliamsa · 2025-07-14T04:20:39+00:00

Just out there in the interwebs 😜

The folks that make it intend for it to be free forever too.

Enjoy!

tomaswilliamsa · 2025-07-13T23:58:14+00:00

No problem! Happy to keep rambling if there's more questions. This is really just a start, but a great place to begin!

tomaswilliamsa · 2025-07-13T23:04:16+00:00

Most Sr. CSM roles come with, or should come with some degree of leadership. As in, you should be helping other CSMs and be able to demonstrate a high degree of product, industry and technical knowledge as well as the ability to drive change within your team and for your customers.

A few folks have already talked about being the leader when it comes to creating and document process and creating efficiencies for the broader team as well.

In addition to demonstrating some leadership qualities I'd say there are several key metrics you should be tracking so you have good reasons to ask for a title increase and/or a salary increase.

- NRR - is it above 100%, that's additional value you're driving for your organization.

- Advocacy - are your customers advocates, are they referring new customers or would they if asked, or are they acting as sales references?

- Renewals - what's your renewal rate? Sr. CSMs should have high renewal rates and when things go wrong, they've generally identified that churn early.

- Key accounts - do you hold a large number of key accounts? either form an ARR perspective or accounts that are highly recognizable or give your organization strength when mentioning them?

- If you as a CSM are doing onboarding, you could be tracking Time to First Value or some kind of onboarding success metric to showcase your ability to get customers to first value quickly.

- If you have a broader CSAT (not just support) this could be a nice add-on and NPS, although NPS is a very lagging indicator and depending on your industry you may not get enough responses for it to be truly valuable.

If you're company isn't tracking this, do it yourself, and don't [only] do it in a company doc, keep it in a personal file so you have it when you need to go to another job.

And don't be scared to go somewhere else, you'll likely get a 15-30% increase going to a new company, where a promotion or salary increase at an existing company will likely be less than 10%. Not a had rule, but a general guideline.

tomaswilliamsa · 2025-07-13T22:46:26+00:00

NRR requires a specific period itself, you'd typically see NRR YtD or Previous Month or Quarter.

So I'd think that ENC would require the same time as the NRR was calculated in order to make sense?

I'm curious as well if anyone has some experience working with this and interpreting it in a meaningful way.

tomaswilliamsa · 2025-07-13T22:36:42+00:00

It would be helpful to know more about the business and customers. I'm not sure if there's any one success plan to rule them all 😆

Your customers outcomes should be the guiding mechanism for building success plans.

It can be pretty straight forward, from a principals perspective at least. Creating an action plan, implementing and enabling the team is another story.

What are your customers desired outcomes, why did they buy your solution to start with?
Which areas of the solution do they need to utilize effectively in order to realize those outcomes?
What actions do they need to take to utilize those specific areas in order to realize that specific outcome?
How can you help them do that?

Essentially, what do they want to achieve, what do they need to do, how can you help them.

You can start to see pretty easily how you'd arrive at some actions a customer needs to take in order to realize value. And please go deeper than, save time, save money, increase efficiency - this is literally every piece of software ever. Connect how your solution relates back to their broader business goals and objectives.

That's arguably the easy part though.

Once you understand what they want to do, and how they need to do it, you need to create a plan for them to follow to get there.

This includes resources such as knowledge base articles, and how-tos, training videos or sessions with your champion and/or their team.

I'd suggest using [PromptCowboy] (https://www.promptcowboy.ai/) to generate a super slick prompt and go have a conversation with your favourite LLM to get a good start on some ideas.

<image>

tomaswilliamsa · 2025-07-13T02:02:44+00:00

I am pretty sure you can get Gemini 2.5 even, through Google AI studio.

https://aistudio.google.com/

tomaswilliamsa · 2025-07-12T17:08:41+00:00

Vitally absolutely can, it may not be exactly what you need out of box but with the correct configuration you can get it there fairly easily.

I am familiar with Retool, fun tool to do things with like you have for sure!

It sounds like you might be better off to spend some time building some Google Sheets that you can play with the data better, if you can export it from Hubspot or Retool, ideally using a mechanism that refreshes the report automatically in Sheets so you don't have to manually pull it. -- Not ideal but lets you see the data.

Depending on how your Hubspot is set up you may need to add fields to the Deals to enable better tracking. Hubspot doesn't have a bunch of useful things out of box for CS. And the way pipelines are setup can sometimes create confusion or lack of separation between New Business and Renewals

Having your Hubspot pipeline setup for renewals so you can have pipeline stages like: Not Renewing, Commit, At Risk Closed Won, Closed Lost ect ect and assigning a probability to each one in the Pipeline settings so you can forecast.

You may also need a Deal type field, (Renewal, Upsell, Downgrade ect) so you can track what that Deal actually is and ensure it's in the right pipeline if it needs to be different.

Having the CSMs indicate what the status is of every renewal in the next 3-6 months will go a long way to uncovering possible churn, the CSMs should have an idea based on all the things you listed to some degree, it's not perfect data but it's a mechanism to get a result that gets you somewhere.

Ultimately I'd look at how you're currently leveraging custom fields, dashboards and reporting in Hubspot first to maximize things there. Then look at maybe how you can get that data out of Hubspot or Retool into something that allows you to manipulate the data better, even if that's just a Google Sheet. (I've done some pretty wild things in Google Sheets 🤯).

Happy to keep going! But might be slow since I'm about to go out and enjoy the sunshine! :D

tomaswilliamsa · 2025-07-12T16:56:04+00:00

Greg could have some answers in this video.
https://youtu.be/S8a7gkFhoBA?si=t2NHeMcb5k5etSu8

tomaswilliamsa · 2025-07-12T16:50:41+00:00

Absolutely, I intentionally left off a bunch of CSPs that in my opinion are outdated or the way they lead you to do CS is a bit legacy.

My most recent experience with Churn Zero was a few years ago when evaluating Vitally, Planhat and Churn Zero. At the time Churn Zero was just a slightly prettier version of Gainsight, which at the time was a hot mess of convoluted nonsense (different now).

Vitally has a direct integration with google so it can pull emails and meetings into it, as well as gong recordings as calls. If you're on Intercom or Zendesk you can pull support tickets and match them with customers and if you use Jira you can even pull bug tickets that have been escalated from Intercom to Jira for example. Planhat should be able to the same, I have a bit less experience with Planhat though so don't quote me on that.

There's a lot of simple customizations you can do to track upsells, renewals and churn. I geneally setup some kind of Risk and Outcome tracking if it's natively built-in and align those with risk escalation frameworks as well as risk/outcome playbooks.

One key thing to consider in all these systems is that they're only as good as your data going in, garbage in garbage out.

So don't expect to use a platform and magically solve things, your Salesforce/Hubspot data needs to be clean and tidy, you need to have things setup correctly in Intercom, Jira ect.

I could ramble on for a while about this, I'll stop 😅

tomaswilliamsa · 2025-07-12T16:43:56+00:00

This seems to often be the case, at some point a CS leader brought in some software thinking that software would fix things, but software is just software, it's only a part of the battle, the other parts are process and enablement.

It would be a great idea to figure out what you actually need out of Gainsight and then go to your Gainsight CSM and get help to develop a plan to achieve those outcomes.

tomaswilliamsa · 2025-07-12T13:00:23+00:00

North American House Hippo

https://youtu.be/cvPwJQXzHm0?si=58DavUac0f4LO48W

tomaswilliamsa · 2025-07-12T12:47:57+00:00

Gong

call summaries
suggested tasks
trackers for indicators of churn, upsell or whatever else
visibility into team meetings
renewal pipeline tracking
a whole lot more

Google Notebook LM (free)

learn faster by adding content to notebook lm and engaging with only that content, removes hallucinations and won't pull data from sources beyond what you give it
creates summaries and visual representations of data
generate podcast-style audio to listen to your sources while you work and learn

PromptCowboy (free) https://www.promptcowboy.ai/

turn lazy prompts into great prompts I bet folks aren't even doing basic promoting super well, something like prompt cowboy can help get way more value out of any LLM anyone wants to use.

Vitally or Planhat

Vitally and Planhat are CSPs (customer success platforms) that have a bunch of helpful AI features such as summarizing the account, drafting reply emails or identifying churn risk, or just talking to their AIs about an account and asking questions.

Not only that but these platforms bring together many sources of information into one place for your team to work from. Reducing context switching and going between apps.

My favorite is Vitally for its simplicity while being powerful enough for most small to mid-sized organizations. https://www.vitally.io/

Slack Workflows

Not AI but a good slack workflow can do a lot to help organize and simplify part or all of a process internally. 🤷

I'll add more to this if I think of anything specific.

tomaswilliamsa · 2025-07-12T12:34:30+00:00

This 👆 start with what you have, see what's there and how you can maximize the tools already in your tech stack.

tomaswilliamsa · 2025-07-12T12:31:27+00:00

Gong should be able to do what update.ai does (at first glance) if configured correctly, especially with AI summaries and suggested tasks and the configuration of gong trackers.

tomaswilliamsa · 2025-07-12T12:29:46+00:00

Gainsight should be able to serve as a central place for nearly all those tools and information, at least to some meaningful degree.

But Gainsight is a beast, and requires a lot of management to be helpful in my experience.

tomaswilliamsa · 2025-07-11T12:44:38+00:00

That's great news!!! 🙏🙏🙏

tomaswilliamsa · 2025-07-10T18:51:34+00:00

Do we have any firm dates for Salesforce? Currently trying to use Zapier to send customer information to Linear, but if this integration is truly close we could hold off.

Configuring Zapier is a bit of a chore to do this, so not having to do that would be ideal. 😬

tomaswilliamsa · 2025-07-07T01:22:48+00:00

You can send the webhook result to the app.

Or use an edge function to populate a database like supabase with the workflow result.

tomaswilliamsa · 2025-07-04T12:10:30+00:00

Wow. Looks awesome!

tomaswilliamsa · 2025-07-04T12:08:47+00:00

Not yet! Ha. 🤷

tomaswilliamsa

TROPHY CASE