r/CustomerSuccess

I'm in the customer success world. Managing 15+ accounts, mostly enterprise.

Early stage startup, immature product.

Every onboarding is riddled with blockers that require dev work from our product team.

Our product team resources are limited & only unblock the blockers when things are escalated (i'm not blaming them, they have their own roadmap and priorities to work on). Embarrassing bugs (incorrect data, loss of data confidence).

Custom one-off requests (e.g. back-end db exports) that take +3 weeks to get to customer (when it's only a db query on our side due to lack of resources & back-end folks juggling a million other things than random customer asks).

I'm finding the weekly sync meetings with customers brutal. Dead air. Going over the open items tracker with no updates to share (as everything is pending dev, no etas or committments from them). I try to zoom out & look for ways to make progress in getting them value outside of the blockers so we aren't stalled on ROI - but often the customers blocker's are preventing them from adopting & using the product to gain value.

I really want to make this job work. Despite everything I'm saying about my experience in the customer success realm, I view this as a very legit opportunity to work (startup, well funded, hot market, large enterprise customer base with impressive logos). Are there any mentoring programs or something similar where I could use them to advise & consult me on how to make this a successful venture? I feel like my current trajectory is imminent for failure (churning customers due to not being able to adopt the product due to product immaturity / lack of deliverables from product).

Hi everyone,

Posting here to try and get some ideas on how to handle a situation like this for a mock call that I have.

Here's the Scenario:

Your primary objective is to lead a 25-minute discovery meeting with your customer, Type Flow who is a a 150-person, Series C AI startup. Type Flow is eight months away from renewal, but they have shown low engagement, are underadopted with the platform, and their goals are unclear. This is your second meeting with them, following an introductory call where you met the entire team. Your objective for this regularly scheduled meeting is to understand what success looks like for them so you can create a strategic plan moving forward. Please be prepared for interviewers to act as your customer and ask questions during your presentation. You'll be walking into this meeting with minimal context, as the previous CSM provided a brief handoff, and your Account Manager counterpart is out of the office.

I have my ideas on how to handle this, but I want to make sure I'm not missing anything, or if there's anything I could add to my presentation. This presentation will also be using a slide deck.

Appreciate any and all help, and thank everyone in advance!

We deployed a chatbot for support and sales to save time and money.

Problem: Same question, 3 different ways = 3 different answers.

"How do I reset my password?" works.

“How do I regain access?" escalates.

"Password recovery?" gives wrong info.

We spent weeks debugging it. Is it the KB? The prompt? The configuration? We had no idea, so we kept guessing and throwing time at it.

For anyone who's hit this:

1. Did you ever figure out what was actually wrong?

2. How much time did it cost to diagnose?

3. How did you even know where to look?

Curious if there's a faster way to diagnose chatbot inconsistency.

I want to be clear that this wasn't some genius strategy we planned. It was mostly just doing things that felt too simple to actually work, and being too broke to do anything else.

When we started we had nothing. No website, no case studies, no social proof, no ad budget. just a service we were pretty sure we could deliver and a list of people who might need it. Most people in that position spend the first 2 months building a website nobody visits and designing a logo nobody cares about. We skipped all of that and just tried to get a client.

here is exactly what we did to get the first 10, in order

the first 2 clients came from direct outreach to people we already knew

not a mass email, not a linkedin blast. I made a list of every person I knew who either ran a small business or knew someone who did. There were about 40 people. I sent each one a personal message, not a pitch, just something like, I am starting to take on a few clients for x. Do you know anyone who might be dealing with that problem right now?

3 people replied with referrals. 2 of those turned into paid clients within the first 2 weeks.

The message was specific about the problem, not about us. that matters. Nobody cares that you started something new. They care if you can solve a problem they or someone they know actually has.

clients 3 and 4 came from a single facebook group post

There is a facebook group for small business owners in our city with about 4000 members. I posted something genuinely useful, a short breakdown of a common mistake businesses make with a specific type of marketing, no pitch at the end, just the information.

Two people called me the same day asking if we did this as a service. we did. both became clients.

The post took 20 minutes to write. It had no call to action. It worked because it showed we knew what we were talking about without trying to sell anything.

client 5 came from a reddit post

similar to the facebook group approach but on a subreddit where our target clients hung out. I answered a question someone had asked really thoroughly, like more thoroughly than anyone else in the thread. One person in the comments asked if I did consulting. We got on a call and they became a client.

This is the part people always underestimate about reddit. you don't need your own post to get clients. being the most helpful person in someone else's thread works just as well.

clients 6 and 7 came from following up with people who said not right now

When we did the initial outreach round, a few people came back and said they were interested but the timing wasn't right. Most people forget about those and move on. We put them in a simple spreadsheet and followed up 6 weeks later with something relevant, not a pitch, just something like, saw this and thought of our conversation, still open to chatting if the timing is better now.

2 of them converted on the follow up. The sale was already mostly done from the first conversation, the follow up just caught them at the right moment.

clients 8 and 9 came from doing one piece of work for free

This one is controversial and I am not saying everyone should do it. But we offered one small business owner a free audit of something specific, took us about 2 hours, and gave them a genuinely useful breakdown of what we found. At the end of the call they asked what it would cost to have us fix it. that became a paid engagement and they referred one more client about 3 weeks later.

The key with free work is that it has to be genuinely valuable and scoped tightly. not free ongoing work. a free specific deliverable that demonstrates what paid work with you looks like. if the free thing is mediocre it kills the sale. if it is really good it often closes the sale without you having to ask.

client 10 came from a linkedin comment

not a post. a comment on someone else's post. a business owner had posted asking for advice on something we knew well. I left a long detailed comment with an actual answer. They replied, then asked me, then became a client.

Linkedin comments are massively underused as a client acquisition channel. The people writing posts are competing with thousands of other people writing posts. The comments section is usually full of one line responses that say nothing. If you leave a genuinely useful 150 word comment on the right post you stand out completely.

what all of these had in common

• none of them involved us talking about ourselves first
• all of them involved being useful before being commercial
• all of them were personal or specific, nothing mass produced
• none of them required a website or portfolio or any credentials

The credentials question is the one I get asked about most. People assume you need case studies before anyone will hire you. in my experience that is backwards. People hire people they trust, and trust comes from how you communicate and what you know, not from a case study pdf. The first clients take a leap of faith. You earn the case studies from them.

The thing that slowed us down early on was trying to do too many channels at once. We were half attempting linkedin and half attempting cold email and half attempting content and doing none of them properly. The first 10 clients all came from doing one thing at a time with full attention. pick one channel, do it properly, get a result, then add the next one.

Once we got to about client 7 or 8 we started thinking about how to scale the outreach without it eating all our time. We ended up hiring a van through offshorewolf, $199 a week full time, she took over the research side, finding the right groups, the right subreddits, the right linkedin posts to comment on, tracking who we had reached out to and when. that freed us up to focus on the actual conversations and the work itself.

what i would do differently.

I would have followed up faster with the wrong people. 6 weeks felt safe but some of them had already moved on or found someone else by then. 3 to 4 weeks is probably better.

I would also have asked for referrals more directly after delivering good work on the first couple of clients. I was awkward about it and left referrals on the table that probably would have come easily if I had just asked directly after a good result.

The thing I am still not sure about is whether this approach works in every industry or if it is specific to service businesses where trust is the main thing being sold. I imagine if you are selling a physical product the dynamic is different. But for anyone selling a service, the website and portfolio first approach seems backwards to me based on what actually worked for us.

Anyone here who has tried these methods? Or got clients without social proof/website or anything?

Would love to hear more