Disappointing CS roles at Startups. What do I do?

Kienan Member Posts: 3 Navigator
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Quick Promotions

After 6 years at a FAANG company, I was excited to join the startup world where I would have more autonomy and could gain experience quickly. That worked out! I've since worked at three small startups and progressed from CSM to Senior CSM and now Head of CS. But I've moved up quickly and I don't totally know what I'm doing. 🤦‍♂️

The Problem

Startups usually don't work out. Most fail, we know this. Given the lack resources and traction, I don't have a ton of customers to work with and I've struggled with the lack of data. Now, my current company is running out of money and will likely fold. And I'm left with the Head of CS title on my resume without the deep experience to show for it.

What do I do about the lack of deep experience?

Do I downshift to become a CSM at a larger company?

Does anyone have a similar experience?

Connect with me on LI - I want to learn from you all!


  • Jeffrey Kushmerek
    Jeffrey Kushmerek Member Posts: 96 Expert
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    Kienan. -

    I have always said that I prefer a CS leader from startups that didn't have all the money and budget in the world. Its kind of like comparing sports teams that have unlimited budgets- I love seeing when a small market team wins the championship, as they had to do a better job with less.

    I am happy to chat- gone for a week, but connect and set something up

  • MarkStagi
    MarkStagi Member Posts: 3 Navigator
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    Hey Keenan,

    Keep learning and finding ways to network with others (like you are doing here). I’m sure at 3 startups you’ve learned a lot more than you think.

    What’s your longer terms goals? Do you want to be back at a larger company or do you like building at a small company?

    Happy to chat anytime, you can find time on my calendar here (https://book.avoma.com/avoma/mark/mark-office-hours/)

  • ianwelles
    ianwelles Member Posts: 17 Navigator
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    I feel you. I am reading a lot of Head of, Manager of, CS Lead, and Director of CS job postings this past month. The requirements and expectations listed are wild.

    Here are some examples:

    • 8 years of experience growing revenue in [very specific, new industry]
    • Proven track record (already a negative keyword for me) of building high-performing (duh) CS teams at scale-ups with demonstrable (another negative keyword) success
    • 10 years of account management experience in [even more specific industry]
    • Sales oriented account manager with decades of experience managing managers of Customer Success Managers at Fortune 500 consultancies

    They do not take into account the recent development of Customer Success as a practice, nor the recent creation of totally new industries. Then they fluff up the job descriptions with so many buzzwords that they mean nothing at all. The confusion in the TA market between CS and Sales is very apparent. Many CS leader job postings read like Sales Enablement or Senior Sales positions.

    It is discouraging when your "demonstrable" CS experience is 2 years but your relevant experience is 20 years. By the way, how do we demonstrate these things? All my past work is the IP of my past employer and covered by NDA. All of my past companies will only give a "yes he worked here" reference.

    What have I been doing? I put myself forward for all of them. I do my best to pass the screening, unless it is just a really bad mismatch. Then I find out what they really really want in the hiring manager stage. 

    I have a 50% hit rate so far in finding companies and opportunities that are genuinely interesting or could be a fit. I have had several great conversations. When I get through a full process with the next interesting company, I will be coming right back to the job descriptions and TA education to help improve this.

    Sorry to everyone out there looking for CS leaders, but until job descriptions get better and tea TA learn what CS really means, there are going to be a lot of wasted 45 minute interviews.

  • Marc Phillips
    Marc Phillips Member Posts: 13 Contributor
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    All great stuff already shared here. While you're going through this, it's often helpful to make a concerted effort identifying those things that are absolutely under your control and make sure you act on them in the time that you have, where you are right now. For example, do you have a list of things you want to try or learn that you can do in your current environment (even as it may be winding down)? What stories/examples do you want to share with a future interviewer that you don't yet have but could still get in some fashion in your current role if you focus on getting them? Obviously there are constraints and limitations here, but also likely there are a few experiences you can still make happen.

  • Heidi Schmidt
    Heidi Schmidt Member Posts: 7 Navigator
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    This is great comments and really resonates with me as I am having a similar issue. I've been a long time IC and team lead and moved up to VP of CS but am still feeling my way as a leader. I'm not sure I fit the job descriptions list of responsibilities and it leaves me wondering if I should downgrade the title to Head of, Team Lead, etc.

    I liked Ian's comment about the CS job descriptions sounding like Sales roles. I like his suggestion to just apply, see what they are actually looking for and decide if it's right for you instead of ruling it out.

    Thank you for the good ideas!


  • ianwelles
    ianwelles Member Posts: 17 Navigator
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    Maybe a senior leader here can share job description tips that worked for "Managers of" or team leads? This could help other senior leaders and also those of us that are looking to fill those roles.