There is no silver bullet - it's a grind. Some broad thoughts:
First, identify the exact buyer persona for the product. Get to this level of clarity: Person X at company type Y making Z revenue has A problem and our product solves that with a clear B ROI and we have a list of C people to vouch for us.
Without that clarity, you'll be shooting in the dark. You can make as much noise as you want but unless your existing customers are rave about you to their peers the engine won't start....
Next, figure out where these people hang out. Are there conferences they go to? Groups they participate in? Twitter handles they follow? Do they have any influencial customers or organizations they look up to?
You can get a sense for this by talking to your existing buyers and doing research.
Then, try all niche marketing channels to get to them. Examples: conference emails or booths, influencer marketing, Twitter ads, etc.
In parallel, A/B test the heck out of your landing page. Hash out the exact words and visuals and make it easy for them to request a demo.
Keep experimenting until you find something that works. Then double down on it and scale.
First, get a sense for why the middle managers are against the system. Are they afraid of losing their jobs? Do they believe that it will add more friction to their process? You can do this by getting the stakeholders on a call and asking them to explain the why (which will make them feel included and important). Or if you can, visit them and say you want to shadow them to understand the process and in doing so get into their minds.
Once you get that clarity, work with them to design a solution that works for them, and make it look like it's their idea not yours. Make them look brilliant.
Much of success in hostile environments boils down to identifying the motivations of people and making new ideas theirs not yours.
The key question is if you're critical to the ramp and success of the new businesses.
If the answer is no, then message that to all investors (existing and new): We're pivoting, here's why the new direction is good for the company, and, to make sure we have the right leadership on board, you will transition out and your co-founder will bring in a new leader who is critical to the businesses.
If the answer is yes, think hard about what you want to do. If you love the team and want it to succeed, then gulp it, stay on, raise, help out for a year or so until the business is in motion, and then leave. DO NOT leave a month or quarter after the raise.
If you really don't want to be there, then be honest about that with your co-founder and investors and let them decide the best path. DO NOT lie or hide with investors. It's not only unethical, it could be illegal and they could sue you for misrepresentation.
Companies aside, money is aside, this is a testing time for your personal values as a leader. Decide what they are and stick to them.
First, try to understand why he is shy and how exactly is his shyness preventing him from contributing to progress. Is he shy by design, even outside work? Or does he feel like he does not have the psychological safety to speak up? You can get a sense for this by spending some time with him 1:1 outside work and getting to know him as a person.
Second, examine your own relationship with him. Does he trust you as a manager? Is he open to your feedback? If not, you should work on building that relationship - you know how you can/should do that.
Finally, once you have that relationship and understand the root cause, give him constructive and candid feedback. If he's shy by design, you could have a constructive conversation about it - does he perceive it as a weakness? Does he realize that it might be holding him back? Make him think and align on a plan to help him overcome it. If he's not seeing psychological safety in the team, dig into how the team works and make a plan for yourself to fix that.
Then make this part of your regular 1:1s and track progress. Important that he sees that you are vested in his success and are genuinely helping him.
Needless to say, this assumes that you want him on the team and help him become a better version of himself.
First, identify the exact buyer persona for the product. Get to this level of clarity: Person X at company type Y making Z revenue has A problem and our product solves that with a clear B ROI and we have a list of C people to vouch for us.
Without that clarity, you'll be shooting in the dark. You can make as much noise as you want but unless your existing customers are rave about you to their peers the engine won't start....
Next, figure out where these people hang out. Are there conferences they go to? Groups they participate in? Twitter handles they follow? Do they have any influencial customers or organizations they look up to?
You can get a sense for this by talking to your existing buyers and doing research.
Then, try all niche marketing channels to get to them. Examples: conference emails or booths, influencer marketing, Twitter ads, etc.
In parallel, A/B test the heck out of your landing page. Hash out the exact words and visuals and make it easy for them to request a demo.
Keep experimenting until you find something that works. Then double down on it and scale.