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by sdrinf 1178 days ago
> My #1 priority is to get the financing closed for the business.

> The strategy I would want to run as CEO is likely not something my COO or board will want to get behind

I'd argue that your #1 priority as a CEO is building alignment between all stakeholders -yourself included- on the direction to move forward; everything else is downstream from that. If you close financing at terms you're not aligned with, with boardmembers who are signing up for a strat you are not aligned with, the business will be pushed into different directions, and shatter at these cross-forces.

I've seen this before, and the deterministic outcome from it is you parting ways with the company in 6-12 months' time, at which point it will be in a significantly worse shape / position than it is now.

Presently you have some level of movement freedom. I'd start by sketching out a strategy you think have a high expected value X probability of working, and a roadmap to getting there. I'd look for investors who are okay with signing up for that plan, at valuation that reflects the business's true value given that strategy is successful. Get people aligned with that goal, and execute on that.

The second issue, "What's in it for me?" flows downstream from above. If your own expected value for a successful outcome is no longer motivating for you, your incentives are at odds with the company. To align these, one useful question is: "Okay, you fire me today, find a competent CEO. What would that CEO ask for to drive this?". Sell your board on this question, and take that specific package -with the advantage of the company being that they don't have to go through the C-level search process. Operationally, this can include: a bonus for achieving milestones on the strategic roadmap, and market-level salary.

In short, I'd start with alignment. Everything else -including what's in it for you- flows from there.

2 comments

I agree with much of this. Take the question to the investors and board, ie that your personal upside is being cratered and everyone is going to be pulling in different ditections.

If you have done and are doing a good job then everyone should want to put the right incentive plan in front of you.

Maybe you have to own the fact that valuations are down and the financing structure isn’t optimal, there is not really anyone to blame for that and a drop from the 20s to the 10s might be something you need to take on the chin. It’s still a good chunk of change.

Could you also look at pulling a some liquidity out during the next fund raise, with the above context set out. Most investors would appreciate the value of giving you some liquidity if you are still the guy to run it.

Thanks for this feedback. And maybe the pre-requisite to getting alignment, is to first get clarity on whether the new investor putting money in wants me as CEO to help get to the right outcome for everyone.