How do you choose whether or not to engage with a start-up or younger companies relative to their more mature peers?

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CIO in Software, 501 - 1,000 employees
It can be very difficult to get to a CIO if you're a start-up. You have to think from the CIOs perspective, how many start-ups are trying to get to the CIO? I can't remember the exact number but it's in the 10s of thousands.  If I took a 15 minute meeting with each of those companies every day, I would be doing nothing for the rest of my life. Clearly, that's not what scales it. 

The first thing to understand is you have to come up with a different approach. The other thing you have to think about is how many solutions can an enterprise actually support? If you are a really large company, maybe you can have a few thousand if you're ambitious. If you are a small to medium sized company, you can maybe support a few hundred at the most. Usually if you add one, you have to rip something out. Most vendors don't think like that. They just think “look how cool this idea is, wouldn't you like to use it for this?” But that is not a business idea. You have to show me it's valuable to me within my finite resources (budget and people). Can you even help me put this into my environment? To help me fund it, I'm going to switch something off or maybe multiple somethings. 

But then, if I have to invest in creating a new skill set to support this tool that is also expensive for me because I have to retrain my people or I have to hire in some new people and sometimes that is even more difficult even if I have the budget to do that. If I can repurpose existing skill sets it's much easier for me to adopt something.  Then, if it's something that my end users can consume and manage themselves, it's even better. 

There are multiple things I'm looking for but let's go back to the first one. 10s of thousands of vendors are trying to get to me, typically it's through some trusted referral or connection that I have. So, if it's someone on my team telling me “hey have you come across this?”, that is something I'll pay attention to. If it's through another CIO who I know and trust, then I'll look at that. 

The third is the VCs. They will have days where they spend time with CIOs to bring them up-to-date on what is happening in the portfolio. Sometimes, if I'm close to certain VCs I might be advising them on their portfolio companies. That's another great thing. I would say those are typically the ways to get to a CIO but don't waste your time with spamming me or inviting me to events or anything because I have more invitations than I could ever take up in my life. They need to persuade me that it is a business problem that I have and they can solve and then to make it easy for me as well.
Senior Security and Compliance Auditor in Software, 1,001 - 5,000 employees
When I have a problem that needs fixed my ears tune in when I get an email, call or drive-by on the topic.  If the solution meets my needs I look further into the features, company, pricing.....  Some problems require a mature solution while others, that are less critical or sensitive, can be met with a startup offering.  Word on the street helps as does any early adopters in key or related industries.  Sometimes the agility and innovation that startups can offer will offset their shortcomings enough to still make the short list.  
Chief Information Officer in Manufacturing, 10,001+ employees
I don't look at the age of the business, I look at the features, services, cost, value add, and attitude of the employees behind the name.  I look at my needs and who would be able to support the successful completion of those objectives. I've worked with a start-up and will well established companies, the bottom line is have their lost their ability to build a relationship or are they just in it for the revenue?
CTO in Software, 11 - 50 employees
I've engaged with a fair number of startups and found it very beneficial when we were trying to solve for something that no one else had done before. Working with an early-stage company you typically have a fair amount of influence on the prioritization of their roadmap and how that fits in with the desired solution and outcomes. This agility goes a long way for future sustainability instead of getting locked into an incumbent's solution, licensing model, etc...
Founder/CTO in Hardware, 11 - 50 employees
First I'm looking for at what they offer and can it solve my problem. If so then I look at the company as a whole. You want to look at their credit rating, can they provide you with sales and revenue data? Do they have reference customers? Lastly what is the risk to your business if you use them and they go out of business? 
Senior VP, Global CTO Hybrid IT in Software, 10,001+ employees
It might be helpful to think of yourself as a VC from two perspectives. If a VC was to buy your company what are its strengths and weaknesses and how would they grow the business in the current and adjacent market segments?If you did that on your application stack where are your holes or modernization efforts, what do your competitors have that you do not? With that in hand, a VC would go out an look at interesting companies to fill those gaps and engage them to understand, to help shape or potentially purchase now or in the future. Think of yourself as a VC and spend 5-10% of your time on those efforts. My experience is that we easily spend that time with existing partners and wonder if we're really getting the return.
IT Director - Data & Development in Telecommunication, 1,001 - 5,000 employees
I evaluate my needs with the services provided.  Startups want to please by satisfying your requirements and not theirs.  Some established entities want to do things their way, but perhaps there's a good reason for that.  I've worked with both successfully.  No reason not to give companies a chance.  Your evaluation and experience should select the best opportunity regardless of who the service provider is.  

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Director of IT in Manufacturing, 5,001 - 10,000 employees
I sorry I never found the AI tools to conduct assessment of IT Contract, I suggest to you , you can create customize internal tools to screen it contract
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