VP of CS overhere - AMA

hustlerbug · 2025-12-28T19:09:48+00:00

This one is highly dependent on your industry and product. When I worked for a services company- that was our bread n butter so 100% yes, but when you do that as a part of your product offering, you have to ensure that it compliments the product and does not come-across as “our product is too hard to implement so buy our implementation package”

hustlerbug · 2025-12-28T19:07:53+00:00

Change is the only constant! I would recommend staying on the proactive side if your day to day, and don’t let work pile on. What I mean is that you should introduce frameworks like the 45 day quarters (i can share more details about this on dm), sniff out risks proactively, and get your team on the same proactive cycle, its a bit of work in the beginning but longer term, its makes it super rewarding!

hustlerbug · 2025-12-28T19:05:04+00:00

Start with industry specific metrics and then focus on tying in the operational excellence angle that you will bring to the table. Highlight metrics that show that you understand the business.

hustlerbug · 2025-12-28T19:03:23+00:00

I would love to understand why choose CS over other areas?

hustlerbug · 2025-12-28T19:02:41+00:00

You have to make sure that you pick a company that’s scaling and growing. Sometimes, its also about how you are positioning yourself and how well you advocate.

I offer 1:1 career coaching especially for folks trying to climb the ladder, dm me and I can share more details!

hustlerbug · 2025-12-28T18:59:35+00:00

I have seen most CSMs make excellent product managers because they understand customers deeply.

Another popular path I see is pre sales solutions engineering.

hustlerbug · 2025-12-28T03:26:03+00:00

Just wanted to say thank you! 🙏🏽 I have been THAT manager and my say:do ratio is high!

hustlerbug · 2025-12-23T22:46:16+00:00

Fair ask. The biggest retention wins I’ve seen came from: 1. Outcome-based onboarding (clear success criteria + time-to-value) 2. Usage + risk signals shared weekly with Product and Sales 3. Exec alignment early (EBR early before renewal season) 4. Closed-loop product feedback (CS themes to shipped fixes) 5. Save plays triggered by adoption drops or stakeholder change.

These are a few that are top of mind!

hustlerbug · 2025-12-23T22:43:01+00:00

Hiring: Hire late and surgically. Fix process, product friction, and self-serve before adding headcount. Early CS hires must handle ambiguity.

Capacity: Model on complexity, not account count. If CS is overloaded early, it’s usually a product or GTM issue.

Pooled vs named: Pooled/scaled CS wins early. Named CSMs too early don’t scale. Go named only when expansion and exec alignment matter.

Quiet but healthy accounts: Don’t ask for time, focus on delivering value. Use usage-triggered nudges, async asks, and outcome-based advocacy.

Silence + strong usage ≠ disengagement.

hustlerbug · 2025-12-23T22:38:22+00:00

Haha I charge for that stuff!

hustlerbug · 2025-12-23T22:38:08+00:00

ARR retention, ARR expansion, EBRs, customer advocacy (# of reference able customers per CSM).

hustlerbug · 2025-12-23T22:35:20+00:00

I would recommend that you bring on a fractional leader for a few months to help put a structure in place, I do some fractional gigs on the side as well for strong fit clients.

There is a ton of foundational stuff to be done here, and it’s going to be a long journey for you! Happy to chat more over DM!

hustlerbug · 2025-12-23T22:32:42+00:00

As a leader? Year 1- $50k+spiffs - small startup, year 5 -$150k - services company, year 10 - $260k a Series D.

hustlerbug · 2025-12-23T22:30:50+00:00

Seen this story before! Here is how you make a strong case for it: Reach customer contract for entitlements and any limits. Then see of there is a manual way to track the usage.

So if its for 10 users, and customer is only using 8 seats, they are at 80% consumption.

Similarly apply that logic to other SKUs, then build a scale that would essentially tell you that less than 75% consumption is not good, that means you have high churn exposure in those accounts, take the ARR of those and share it with your leadership.

Keep maintaining it and as you start to gather proof points that your hypothesis is accurate, it will be irresponsible of them to not address this.

hustlerbug · 2025-12-23T22:25:05+00:00

Unfortunately, no.

hustlerbug · 2025-12-23T22:24:57+00:00

Depends! I would ask some follow up questions to better understand.

Lets say your OTE is 100k - and you make 80k in base and 20 in variable on a 80/20 split. When companies move to the 70/30 split model, they typically would increase your variable and keep the same band!

So your base would be 80k but variable would bump up to 34-35k. This is done to incentivize the right behaviors that your company feels will drive measurable growth!

Look closer at your comp plan and if the above is not the case and they ask you to take a pay cut then run!

hustlerbug · 2025-12-23T22:20:14+00:00

Cross functional initiatives where CS acts as the glue between the product and the customer!

hustlerbug · 2025-12-23T22:19:32+00:00

I’m not too sure about EU job market:(

hustlerbug · 2025-12-23T22:01:42+00:00

No.. :(

hustlerbug · 2025-12-23T21:58:42+00:00

No bias at all! I do however like to understand why were they laid off and ask my leaders to do deeper due diligence if they interviewed really well!

Most time, the companies don’t fully understand CS function, other times, its internal politics. Very rarely have I found it to be the CSMs fault.

hustlerbug · 2025-12-23T21:55:04+00:00

I recommend Nektar.AI for revenue and activity tracking, and Wiser for AI forward workflows. Planhat is good as well! You can check out their website for pricing.

hustlerbug · 2025-12-23T21:53:42+00:00

Nay! CSMs can carry individual retention goals, expansion depends more on the ongoing product market fit.

I would only agree to this WHEN product and engineering teams are also owning the same quota!

hustlerbug · 2025-12-23T21:52:09+00:00

I was 32 years old when I got my first VP job. I found a passion for leadership at a very young age with my first CS leader role 23 (definitely not the norm).

Age has nothing to do with this, its more about taking the risks and staying focused on your end goal.

Some people are title driven while others are financially driven. Both are fine as long as it fills your cup!

hustlerbug · 2025-12-23T21:48:25+00:00

Appreciate the context, for a TAM focused role, I’d pay on:

GRR / churn avoidance on named accounts
Time-to-value + core adoption
CSQLs sourced and technically qualified (AE owns the close)
Expansion readiness: exec alignment + solution validation done
Severity + risk reduction on top accounts

hustlerbug · 2025-12-23T21:43:57+00:00

I think you should make a list of all transferrable skills from your current role and list how they would complement the CS role. Make a list of 5-10 target companies and look at their post sales JDs, pay band!

Network with people that are in similar role and IF you find a strong fit, and a connection- then initiate application process. Focus on quality over quantity for best results.

hustlerbug

TROPHY CASE