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?

  • OrangeSunset86@alien.topBEnglish
    1·
    10 months 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·
      10 months 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.