I work for an entertainment software startup, and I’ve watched for five years as my CEO has focused the company on creating demos to get investment, and short term deals with large companies using what we have. This has resulted in burnout, attrition, and massive tech debt.

There is a time and place for this, but five years in, we haven’t invested our resources in making an MVP we can build a customer base on. The board is finally asking that we have a revenue plan, but in a recent conversation, the CEO told me he has no plans to make money over the next year or attempt to scale users. His vision is high level, without details on strategy. At this point, the CTO and head a product are pretty much in my corner, sharing my concerns.

I don’t want to just assume he’s an idiot. He’s a gifted talker, but there’s a kind of reality distortion at play that I just don’t get. It’s like he’s ignorant to how software development works, yet is the CEO of a software company. Maybe he just hopes we’ll be purchased.

Point is, how can I help right this ship as a non-founder, but senior level early employee? What should I be empathetic to? What’s a sign that he really doesn’t know what he’s doing?

  • founderscurve@alien.topBEnglish
    1·
    1 year ago

    I working VC, helping the companies post-investment, i’ve see several of these archetype founders. they’ll call it ‘product led growth’ (LOL!)

    basically the premise is, if i build a shiny object that the company (inevitably a big whale with thousands of employees) i’m talking to wants - they’ll for sure sign me up (despite having no clients for case studies or previous business history.

    when you suggest, why not got for smaller clients, that will close faster and can use our out-of -the-box solution, the founder with laugh a hearty laugh and say something like ‘we’re not here for play time boyz, we’re here to make millions and we can only do that if we get in with the big fish, huzzah!’

    For me, the issue is these founder want to run before they can walk, its not that going after big fish isn’t the goal, its more they want to skip the foundational steps, too inspired by the weworks and sequoia backed rocketships, to see that pre-sequoia all companies start at the bottom and grind their way to scale.

    what can you do, run the numbers and show him how if you get smaller ‘deer’ clients with a product designed to scale it’ll be more efficient… it probably won’t work, since the founder will think it takes too long, but maybe if you have enough pressure… worst case, the CTO and product lead like it, and lobby the board to make you CEO.

    • AffineChianti@alien.topOPBEnglish
      1·
      1 year ago

      Thank you for the constructive advice. There have been glimmers of hope where it seems like we’re moving toward something worthy of a release cycle with time to dev a stable set of features, but it usually dissolves as the next big deal shows up and he values elevating the relationship (and a demo to make it happen) over prioritizing a robust long term feature set.

      I said we don’t have an MVP, because we don’t have a viable product. We have lots of fragile code and services on multiple platforms that would fall over in a moment outside of a demonstration.

      I’m not interested in being the CEO at this time, and just want to get us pointed in a rational direction, with the right people making biz decisions. I’m here for the tech vision end execution (which is an interesting thing to say given the lack of support for either).

      • founderscurve@alien.topBEnglish
        1·
        1 year ago

        well, one thing you can try and do, is to point out that no large mutli-national with thousands of staff is going to integrate a core-tech that will affect their millions of dollars of revenue and give that over to an untested, unverified prototype from a new startup, even the corporate insurance wouldn’t cover them if it went wrong, and those are the kind of errors that would result in ppl on your client side getting fired. (i’m being melodramatic)

        the point is, most large companies with multi-levels of leadership dont want to take risks on prototypes, they want something working perfect with zero errors on day one. don’t get me started on the procurement process and the payment process which is already enough to kill a business with 3 months of runway left (not suggesting thats your situation)

      • OrangeSunset86@alien.topBEnglish
        1·
        1 year ago

        Y’know, it probably feels like most of the commenters here aren’t giving you the advice you’re looking for. Everyone says leave, but that’s not what you asked, right?

        I’ve been in your shoes before. Not exactly, but similar situation with CEO problems. I was in leadership there. We *all* tried to talk to the CEO. Actually, it was our impulse to help, and the feeling of importance from trying to save the day, that kept us chained to the sinking ship. Every glimmer of hope meant another six months wasted. That may be why folks aren’t giving you viable routes within the company.

        But, maybe that’s not respecting your question enough. Here are a couple things we tried or could have tried:

        1. Talk to the CEO respectfully with the best argument you have. Given his personality, it could be a “motivate by challenge” conversation. Like “I’ve always wanted to learn about how startups work, and I’ve learned so much being here. Lately I’ve been reading [esteemed author] and I realized how hard it was to do [steps we should be taking that are also glorious]. Most people fail at that stage. Have you thought about how our company could handle that situation?” (one such book is Crossing the Chasm, but maybe there’s a closer match?). Or the wake up-threat angle, or your best facts-loaded arguments.
        2. Rally the troops and try to have an intervention with the boss, where everyone says the same thing. This can also backfire spectacularly.
        3. Rally the troops and talk to the investors. Share the dirty secrets. Propose alternate leadership, and if you have the legal leverage, try to stay in charge of the new CEO selection process.
        4. Everyone jumps ship together and starts a new startup together in that space, building the thing that the CEO should have been building.

        Noting here that each of these options has potential legal risks, risks to your reputation and hire-ability in the future, or risks in giving yourself false hope and wasting your time.

        What do other posters think? Assuming OP is dead set on not leaving, what options would folks recommend?

        • AffineChianti@alien.topOPBEnglish
          1·
          1 year ago

          Thank you also for your advice. Everyone who says that I should leave isn’t wrong. But I’ve grown with this company, and leaving needs to be a process that I’ll feel good about in the end. Trying to help is my therapy I guess. Presently, I’m gunning for somewhere between points 1 and 2.