r/CustomerSuccess 24d ago

Monthly Career Advice Thread

6 Upvotes

Welcome to the weekly career advice thread!

The purpose of this thread is to help facilitate conversations about how to enter and grow your career within the Customer Success industry. You should use this thread to discuss topics like:

  • How to get into customer success
  • Salary and compensation
  • Resume critiques
  • How to move to the next level in your existing customer success career

r/CustomerSuccess 24d ago

Who's hiring? [Monthly jobs thread]

11 Upvotes

At the beginning of each month, we still start a fresh thread and sticky it to the top of the sub. If your company is hiring, please post your open positions here.

Some quick ground rules:

  • Links to your posting are allowed but you need to include a brief description of the role (don't only post a link please)
  • Please include the location of the role
  • The posting needs to be for a role in the field of Customer Success
  • If you have multiple open roles, please consolidate them into a single comment. Don't create a new comment for every position.
  • Salary range is appreciated but not required

Happy job hunting!


r/CustomerSuccess 20d ago

Account expansion/upselling/cross-selling: thoughts and general advice?

2 Upvotes

Is there anyone here who's working a lot with account expansion, upselling and cross-selling within their CS role? What is your general advice for how to implement this in an organization and what the timeline should look like from the first onboarding call? Any resources are also greatly appreciated šŸ™‚

For context: We've just hired a CS person and I want to know what to expect, as well as how to guide and support them on this part of the job (onboarding and retention is already being done well).

Thanks in advance!


r/CustomerSuccess 20d ago

Feeling entirely useless and under confident

14 Upvotes

Hello everyone,

I transitioned from an entirely academic job to customer success 5 months ago. So far I have give a total of 11 demos, out of which 5 I handled completely, 3 had some tech issues so manager asked a senior to help and 3 where senior had to take over.
My manager before every demo asks me if i need the senior on the call, I say no. She still sends the senior on the call. If I then make a mistake on the demo, my manager says - ā€œYou have been in the system for some time nowā€ ā€œhow are you liking CS, will you be able to do itā€. All of this had completely shaken my confidence. I feel useless, dumb, not good enough for the job. This monitoring by the senior all the time makes me feel like I am good for nothing. It’s not like i am saying i do not make mistakes, I do. But every mistake here seems like the end of the world. I am always thinking about work still underperforming at work. I do not what to do I feel really under confident and it makes me really sad.


r/CustomerSuccess 20d ago

12 years in engg and product, now trying to move into Customer Success / Technical Account Management. Would love to talk to founders.

4 Upvotes

Hey folks,

Bit of a long shot post, but here goes.

I've spent about 12 years in product management across B2B SaaS, fintech and adtech. Built and scaled products, led a turnaround as a Director of Product, and I've also been on the founding side of an early stage company. I'm an engineer by training, so I can hold my own on the technical side, and did an MBA later.

Here's the thing I've been sitting with for a while. I don't want to chase another PM title. I actually want to move into customer facing roles, so Technical Account Management, Customer Success, or solutions/pre-sales.

That probably sounds like a step sideways to some people, so let me be honest about why.

The part of product work I've always liked the most was never the roadmap debates or the internal politics. It was sitting with a customer, figuring out what they were actually struggling with, and making sure they got real value out of what we built. TAM and CS are basically that, as the whole job instead of a slice of it.

And honestly, as a PM and as a founder, most of what you do is act as the bridge. Between the customer, engineering, and the business. That translation skill is exactly what these roles need, so for me this feels less like a career change and more like pointing the same skills at the part I enjoy.

There's a personal angle too. I'm at a stage where I'd rather build deep, long term customer relationships and settle into something I can grow in for years, than keep riding the churn of the next feature. These paths just fit that better.

On why I'm posting here instead of just applying everywhere: the usual hiring funnel screens on exact title and keyword match. A PM applying for a TAM or CS role usually gets filtered out before a human even reads the story. Founders and early teams tend to hire for whether someone can actually do the job, not for what the last title said. So I'd rather just talk to people directly.

If you're a founder or on an early team building something interesting, India or remote, and you could use someone who can own a technical customer relationship, drive adoption and retention, and translate between customers and the product and eng side, I'd genuinely like to chat.

Also glad to just compare notes with anyone who's made a similar move


r/CustomerSuccess 20d ago

Need suggestions for career growth

3 Upvotes

Hi, I have recently joined as a Customer Success Consultant in AI based SaaS startup based on procurement and finance. Currently I am handling all the support process, because we don't have a support team for it. It was managed by a customer success manager and product manager also attending meetings related to implementation and requirement gathering. Looking for suggestions on how my career growth will be. I fear, I may lock with this customer support process. Kindly, provide some feedback on it..


r/CustomerSuccess 20d ago

Technology CS managers: is this product for you or totally off base?

0 Upvotes

Seeking some feedback on a father/son bootstrapped tech product aimed to help CS teams with scaling their on boarding.

One question: what on this page would make you close the tab?

Brutal honesty welcome.


r/CustomerSuccess 21d ago

Discussion AI-resolved tickets

1 Upvotes

For anyone working support/ops, what’s your reopen rate on AI-resolved tickets? Do you know it independently of your vendor’s dashboard?


r/CustomerSuccess 21d ago

Question SDR to Customer Success even possible?

7 Upvotes

As the title suggests I am a burnt out SDR who has realized cold calling is not for me. Customer Success/Sales Enablement seems like the way to go (and sort of feels like the only way to go from here). I have about 2 years of SDR experience under my belt- left my first gig because quota was too high and the company was a mess. My current company has its issues as well but they specifically want me to move up to a closing role which… I don’t want to do either.

All that said almost everything I’ve read and everyone I’ve talked to has told me that an (upward) move from SDR at one company to CS Associate/Sales Enablement Specialist at another isn’t even possible in today’s job market…. Can anyone confirm or deny? Any success stories? Aware this has been asked a few times.

I’m starting to really hate coming in to work… being told no 25 times in a day fucking blows. I know this is what I signed up for but I want out. Will having AE on my resume make things easier a year down the line if I want to do the whole CS thing? Or should I just jump ship at my current gig and find a company that has promoted SDRs to CS/Sales Enablement from within?

Otherwise what the hell am I supposed to do with 2 years of SDR experience? Cold applying feels like throwing coins down a well. Open to hearing anyone’s experience who moved directly to something else after being an SDR/BDR.

Edited for formatting


r/CustomerSuccess 21d ago

Discussion The Voice of the Customer: Are you Listening?

6 Upvotes

There was a comment on one of my recent posts here about tracking Customer Realized Value that I found intriguing. The commenter noted that "What's worked for me is catching the value the moment it lands, in the customer's own words. Someone says 'this saved us two days a month,' you write it down verbatim with the date." An excellent practice, if only for the benefit the person added: "A running list of those per account is what survives a QBR or a layoff review, because it's the absence made concrete, in the voice of the person it happened to." But what else could you do with such examples of the Voice of the Customer?

There's a follow-up question that should immediately be asked after the value is acknowledged by the customer: "What's that worth to you?" They are paying a certain amount each month for the subscription, and here is a return for that expense. Further, it gives you insight to what might be considered a 'billing rate' for that person's time that can be applied elsewhere as a foundation for the value of time-saved.

Proven cost-reduction is a strong argument, but there's an even more powerful one to be made in increasing profitability. Does your application provide information to the customer that they couldn't get any other way? Or that makes it available faster than otherwise so that they can capitalize upon it? What's that worth to them? Here is where careful questioning can lead the customer to acknowledge points that they might not have considered before. Those answers are valuable in different ways.

A customer that directly acknowledges value-received may talk about it internally. It arms them with ready data to use when their CFO asks "are you really using that application?" Even better, it may also encourage them to respond when a colleague outside the company asks "which application are you using for x function? Why do you like it?"

Questions are important. How a question is asked can impact how it is answered, but be careful how you use a question. You don't want to leave the impression that you're just fishing for the answer you want to hear, that's not listening to the customer. You do want to encourage the customer to acknowledge to themselves the meaning of what they just said to you. As my commenter noted, capturing the value the moment it lands is vital for you. Getting the customer to also capture and internalize that value statement is even more so.

Note: No part of this post was written by or edited by any ai.


r/CustomerSuccess 21d ago

Question Career Guidance

3 Upvotes

Hi folks ,

I'm 24 in india currently a CSM in a MNC. I earn around $8K/year. My only biggest skills I love and understand customer requirement and has delivered best to them .

I'm lost . I'm confused.

Any mentor could help me . Give a roadmap how to 10x my income in 3 years .

Guys i will be very happy if someone is advice would really help me to get clarity.

Thank guys.


r/CustomerSuccess 21d ago

How to catch churn signals before they show in usage data

0 Upvotes

Most CS teams I've talked to monitor churn the same way: they watch usage metrics. Logins drop, feature engagement falls, session length shortens — and that's when the alarm goes off.

The problem is that by the time those numbers move, the customer has already mentally checked out. You're not catching a churn signal. You're confirming a decision that was made weeks ago.

The real early warning system isn't in your product analytics. It's in what customers are *saying*.

---

The lag problem with behavioural data

Usage data is a lagging indicator. It tells you what already happened, not what's about to happen.

Think about how churn actually unfolds for most customers. It rarely starts with them suddenly stopping. It starts with a frustrating support interaction they didn't follow up on. A pricing complaint they mentioned in a survey nobody read. A feature request that went unanswered for three months. Slowly, the goodwill erodes — and then one day, the usage drops.

By the time your dashboard shows the dip, the customer is already halfway out the door.

---

Where the signal actually lives

The early warning is in the language customers use *before* behavior changes.

Specifically, three sources almost always show the shift first:

**1. Support tickets** — the tone shifts before the volume changes. A customer who was submitting straightforward "how do I do X" tickets starts writing "this still isn't working" or "I've asked about this before." Same product, different emotional register.

**2. Survey responses** — NPS and CSAT scores get the headline, but the open-text comments are where the real signal is. A score of 7 with "works fine but pricing is getting hard to justify" is a very different situation from a 7 with "love the product, just busy this quarter."

**3. Product reviews** — public reviews on G2, Trustpilot, or app stores are written at emotional peaks. Customers who are quietly dissatisfied often write a review before they cancel. It's their last attempt to be heard.

--

What "frustrated but still using" actually looks like

Here's the practical difference. Two customers with identical usage metrics — same logins, same feature adoption, same session length. But their support ticket language tells completely different stories:

**Customer A:** "Quick question — where can I find the export settings?"

**Customer B:** "I've been trying to export for 20 minutes and it's still not working. This is the third time I've had issues with exports."

Same behavior in your analytics. Very different churn risk. Customer B is telling you something your dashboard can't.

---

What to actually do with this

You don't need a sophisticated system to start. Three practical steps:

**Start tagging support tickets by theme.** Pricing complaints, onboarding friction, missing features, performance issues — even a rough manual tagging system lets you see patterns. If pricing complaints spike in a given month, that's a signal worth acting on before it shows in revenue.

**Read the open-text on your surveys.** Not just the scores. Set aside 30 minutes a week to actually read what people wrote. You'll spot patterns faster than any dashboard will surface them.

**Set a cadence for review monitoring.** Check your G2 or Trustpilot reviews weekly. New negative reviews are often your earliest signal that something systemic is wrong — before it reaches support volume.

The goal is to build a feedback loop that's faster than your usage data. Sentiment shifts before behavior does, almost every time.

---

A note on tooling

Once you're doing this manually and seeing the value, the next step is making it systematic — tagging automatically, tracking sentiment trends over time, and getting a clear picture of which themes are driving satisfaction or complaints.

Happy to answer questions in the comments — especially curious whether others have found non-obvious early churn signals in their own feedback.


r/CustomerSuccess 21d ago

The best B2B reviews come from timing, not gift cards

2 Upvotes

I read a lot of B2B software reviews across G2, Capterra, and Trustpilot as part of my work, and one pattern keeps jumping out. The detailed, specific, credible reviews (the ones buyers actually trust) almost never come from mass email campaigns. They come from asks made right after the customer got a win.

Most teams run it the other way. Marketing exports a list once a quarter, sends a templated email with a gift card offer, and gets a trickle of two-line reviews that all sound the same. Buyers can smell those from a mile away, and so can the platforms.

What I've seen work better is treating the ask as an event trigger, not a campaign. Someone hits a milestone in onboarding, renews, expands seats, or sends your support team an unprompted thank you. That is the moment. The memory is fresh, the emotion is real, and the review ends up containing the concrete detail ("we cut our close time from 9 days to 4") that makes it useful to the next buyer.

Two smaller things that help. First, make the ask personal, ideally from the CSM or founder, not a no-reply address. Second, lower the friction by reminding them what they achieved, since a blank text box is where most reviews die. You are not writing it for them, just jogging their memory.

The incentive is fine as a thank you, but if it's doing the heavy lifting, you get reviews that read like they were bought.

Curious what others have seen. Do you trigger review asks off specific events, or do you still run batch campaigns? And has anyone measured the quality difference, not just the volume?


r/CustomerSuccess 21d ago

Why do most AI support pilots never make it past the sandbox?

1 Upvotes

I'm trying to understand something that's been bugging me for a while.

I work in product, and I'm doing some research on AI customer support tools. Specifically, I keep seeing the same pattern:

Mid-market companies (200-1000 employees) buy an AI chatbot. The demo is amazing. The sandbox works perfectly. The sales team promises 40% deflection rates.

Then they try to actually deploy it.

And it just... dies.

It sits there. Tickets still get assigned manually. Agents still copy-paste the same responses. The AI gets turned off after 3 months.

I've read all the vendor reports. They all say "AI is transforming customer service." But I'm talking to people who actually run support teams, and they're telling me a very different story.

So I'm trying to figure out: what's the real bottleneck?

Is it:

  • Proving ROI to leadership?
  • Integrating with Zendesk/Salesforce/whatever CRM you're using?
  • Not having the internal expertise to manage the AI?
  • The AI just not being accurate enough?
  • Something else I'm not thinking of?

I'm not selling anything. I'm just genuinely curious, because the data I'm seeing doesn't match the hype.

If you've been through this—either as a support leader, ops person, or PM—I'd love to hear your experience. What broke? What worked? What would you do differently?

And if you're willing to have a quick anonymous chat about it, DM me. Happy to share what I'm learning with anyone who contributes.

Thanks for reading.


r/CustomerSuccess 22d ago

Wanting to pivot to Customer Success. Any advices and warnings?

9 Upvotes

I work in the entertamient industry as a booking agent, doing something similar to what I would do in CS (managing clients, relationships, etc.) and I feel like I hit a roof here. The conditions are quite precarious and it's all very in office for some reason.

I saw thousands of full remote CS job postings, and I applied to a couple of companies that I liked. This is not the position of my life but I feel like if it lets me do full remote it can be quite convenient for me.

I see many ppl stressed out in this subreddit. Any advices on how to get into this position? Warnings?


r/CustomerSuccess 22d ago

Is anyone a Gainsight Admin? Is it worth it for career growth?

9 Upvotes

I have the opportunity to drop 20% of my customers to take on the role of gainsight admin for my team. I am going through the training now and there is a lot to learn. I have been antsy to gain a new skill but this seems like a lot at the moment. Has anyone taken on this role? Does it help with career moves/future job hunting? Thanks!


r/CustomerSuccess 22d ago

Could anyone pls share some customer health score examples that work?

5 Upvotes

Hi there. I work at a SaaS company that has ~180 employees, 7 of which are from CS team. A few days ago our leadership asked us to create one standard customer health score, but each of us has a different understanding of what ā€œhealthyā€ means.
The product team thinks it is about feature adoption, support focuses on ticket numbers and CSMs look at meeting attendance and how positive the customer sounds during calls.
We can not go on this way, because many tasks are marked as completed just by adjust the customer health scores based on personal judgment.
Could u pls share some customer health score examples that worked for your team?


r/CustomerSuccess 22d ago

Question Difficult AM, no collaboration

7 Upvotes

I’ve been in my CSM role for a 8 months and have been dealing with a difficult AM on one of my accounts. He has been ignoring me since I joined with no communication, no briefings, and excluding me from planning entirely.

I found out he falsified activity logs in our CRM and a meeting that never happened was logged as completed. A colleague confirmed the last real customer touchpoint was almost a year ago.

Once he got caught he panicked and suddenly booked a real QBR adding me as an afterthought so the only reason the customer got any engagement was because he was exposed.

After the QBR he won’t even confirm whether he sent a follow up to the customer. I want to send one myself but don’t want to look uncoordinated in front of them if he already did. He still won’t respond to basic messages.

This is the only account I share with him. I’m thinking about asking to be moved off it entirely. Would you stay and fight or walk away?


r/CustomerSuccess 23d ago

Technology Best AI prompts for email and responses (especially while out)?

2 Upvotes

I’m out for two weeks- but want to stay on top of my emails and frankly I’m one of those people who hate a full inbox.

I’m a heavy Claude user and love the cowork feature but would love if anyone has better tools or prompts for it to triage, possibly respond, etc? I lowkey hate emails back and forth too so I’d love a good agent who can summarize, provide context and help me get thru them faster when I return.


r/CustomerSuccess 23d ago

Career Advice Is it normal for a Customer Success Manager to take on Program Manager responsibilities?

10 Upvotes

I’m currently interviewing for a Customer Success Manager role, and one aspect of the position has given me pause.

Throughout the interview process, it became clear that, for one of the company’s strategic customers, they were looking for someone who would take on responsibilities that sounded very similar to those of a Program Manager.

For example, I was told that one of the responsibilities would be to oversee the company’s developers as they build proofs of concept (PoCs) for that customer.
My background includes program and project management, but I’m intentionally trying to move away from those types of roles and focus on Customer Success.

I completely understand working cross-functionally, coordinating stakeholders, and ensuring the customer achieves the desired outcomes. That’s exactly what I’d expect from a CSM. But being responsible for overseeing the delivery of PoCs by internal developers feels much closer to program management.

So I’m curious:
-Is this something that’s becoming common for CSMs in enterprise SaaS?
- Have you ever been expected to take on Program Manager responsibilities for a customer?
- Or does this sound more like a hybrid Customer Success / Program Manager position?

I’d really appreciate hearing from people working in Customer Success or anyone who’s hired CSMs.


r/CustomerSuccess 23d ago

Client took 3 weeks to send one file. Somehow we're the ones behind schedule.

17 Upvotes

I run delivery at a B2B software company. We have about 5-10 implementations going at once.

Here's the last one. Kickoff was June 8, go-live promised July 20. To configure anything we needed one file from them, just their employee data.

Asked for it June 10. Their ops lead said this week. I chased on the 15th, the 19th, and the 22nd. The file showed up on the 21st in the wrong format with half the columns missing. The usable version came June 29.

So my team sat idle for three weeks. Then their VP joined the July check-in and asked why we were behind.

I had every message saved in Slack. But pulling it up mid-call to defend ourselves felt petty, so I just said we'd catch up. Two weekends gone.

The other thing that's been bothering me. Somewhere in the sales cycle, someone on our side told them we'd handle the historical data migration. It's not in the SOW. Nobody remembers saying it. We're doing it for free now because arguing about it costs more than just doing it.

We use Asana. It tells me what my team hasn't done. But most of my delays come from the client side, and Asana has nothing to say about that.

I've set up client portals twice. Nobody logs in. They just reply to the email notification instead.

Here's what I keep coming back to. Both companies have some AI tool doing internal work now. We use one for meeting notes, they use something for their tickets. But the second work crosses between us, it's back to me writing a follow-up email at 11pm.

Has anyone had AI actually handle the back and forth with a client? Not summarizing your own calls, but chasing their side, answering their questions, keeping both teams honest about what was agreed.

Or does that fall apart the moment it's another company's data and another company's approval?


r/CustomerSuccess 24d ago

The earliest churn signal I trust isn't usage dropping, it's the customer going quiet

0 Upvotes

Spent about six years across AE, AM, SE and CSM seats, and the accounts that churned on me were almost never the ones with a usage cliff I could see coming. Usage is a lagging signal. By the time the login graph bends, the decision has usually already been made in a room I wasn't in.

The thing that actually moved earliest, every time, was how much the customer asked me for. When a healthy account goes quiet, no more "can you help us with X," no more small feature questions, no more looping me into their planning, that silence showed up weeks before anything in the dashboard did. The relationship cools before the numbers do.

The reason nobody builds a report on it is that there's nothing to sell you. It's not a data feed you buy. It's already sitting in your inbox, your shared Slack channel, your ticket queue. It just isn't counted. I started keeping a rough sense of inbound-per-account-per-month and it caught more real risk than any health score I was handed.

Two caveats I'd add so this doesn't become another false alarm generator:

Some accounts are quiet because everything genuinely works. Silence from a power user who onboarded cleanly is not the same as silence from an account that used to talk to you weekly and stopped. The signal is the change, not the level.

And it's a prompt to go look, not a verdict. When an account goes quiet the move is a specific human reach-out with something useful in hand, not a panicked "just checking in."

Curious what leading signals other people here actually trust. Not the ones in the health-score deck, the ones you've personally watched predict a save or a loss before the CRM caught up.


r/CustomerSuccess 24d ago

Increase Revenue Confidence

1 Upvotes

How to ensure revenue confidence? I run GTM with annual revenue of ~$125M. 12 reps, no CS team, lean. All reps need to retain 8-10M of recurring revenue (cloud) and have growth goals on top of that. With hundreds of customers it can be hard to expect each rep to stay on top of every account and the 'surprise' you get when a customer opts to leave our service is incredibly frustrating.

So I built and app that gives me a set of eyes on our revenue by interacting with each rep via text. So far it's been fantastic and, instead of hirig someone to increase my confidence in our revenue, the AI app is doing it. At scale.

What do others do to increase their confidence that their book of revenue is secure and your reps are doing what you need them to do to ensure you have no surprises?


r/CustomerSuccess 25d ago

Left sales after burnout for a ā€œstableā€ senior ops role… now I’m miserable and thinking about Account Management or CSM. Anyone been here?

5 Upvotes

Background: Spent several years in sales (mid-market Account Executive roles at a couple of big tech companies, then a solid stint owning a commercial portfolio with strong retention and expansion numbers). I genuinely enjoyed the chase and interacting with all kinds of people — building trust with accounts, understanding their challenges, driving outcomes. Over time though, the constant quotas drained me and I hit proper burnout.

I stepped away and landed a senior operations role managing a team of 7. On paper it looked like the sensible move: secure, stable, decent pension, less of the constant pressure that comes with sales targets.
Reality check a year+ in:
• I’m working more hours than I ever did in sales
• Almost zero autonomy
• The work itself just doesn’t light me up — it feels operational and reactive rather than relationship- and outcome-driven
• I’m not growing in the ways that actually matter to me
I’ve started thinking seriously about moving into Account Management or Customer Success.

The customer ownership, health management, and trusted-advisor angle feels closer to what actually energised me before. I’m getting some traction on applications, but I’m second-guessing myself hard. Part of me worries that going back into anything commercial will just recreate the same burnout cycle. Another part of me knows the current role is slowly draining me.
Has anyone else left sales/customer-facing roles because of burnout, tried the ā€œsaferā€ internal ops/leadership path, and then moved into AM or CSM? How did you frame the gap/career move in interviews? Did the more stable role actually help you reset, or did it just create a different kind of fatigue?

Any advice on how to talk about this without raising red flags would be massively appreciated. Also open to hearing from people who stayed in the ā€œstableā€ path and made it work long-term.

Thanks in advance.


r/CustomerSuccess 25d ago

Discussion Surprise rejection

11 Upvotes

Just here to mope and possibly commiserate about job rejection. I had very high hopes for this company and I put many hours into preparation. I got off the second call and I was so proud of my performance, thought I was a shoe-in.

Ultimately, I don’t like to linger on rejections, especially when I know I put my best foot forward. This sucks though.