This sounds a little nutty but if you want to be a bootstrapped Rippling, it's possible.
A trick I've found repeatable is to find an enterprise that doesn't shy away from big budgets (where six and preferably seven figure budgets are fine even for unproven vendors, because what's big/existential for you is negligible/experimental for them), and is willing to buy a product from you that requires "integration" (they love to spend money on integration, plus that means it doesn't work on day one!), where the "integration" cost is enough to bootstrap the product AND integration (and your ramen!) at your internal rates.
To avoid the bootstrap money going to overhead, to keep the money for product build (engineering instead of paperwork), you need to avoid getting "risk managed" like a mature vendor. Its best for you to be a pilot, or proof of concept, or pet project for a sponsor to show a concept they want the enterprise to do.
Pick your customers and product integrations carefully where the work will pay for the enterprise capabilities most likely to win your next sale. Use these big contracts like lilypads to cross the pond to the other side of Geoffry Moore's "chasm" between early adopters and early majoriy.
Impossible, unless you already have an in with someone high up in the management chain to approve your $1m/3months proposal.
Enterprises that don't shy away from big budgets have a constant stream of multiple suitors all thinking the way you are, many of them more experienced with doing this as well.
In case anyone was wondering how to make such connections: attend a top 5 MBA program or have a long history in management consulting, preferably both.
Contrary to sibling replies, it's possible to find.
For example, when these mega enterprises realize they're behind, they undertake "Transformations" or strategic initiatives to "Digitize" this or that.
Look at enterprises that could use your product, see if any are making noises in the press about landing a Transformation Officer or Digital Officer or similar roles. Or work the other way, search for hiring announcements around such titles, and see if the firms hiring them are ones that need you to pull off that change.
Either way, when they land that new leader, then look for hiring announcements for their directs or in their product or technology areas related to what you could help do. If you see they hired from "outside", particularly if they hired from Silicon Valley, the Magnificent 7*, or other "Fast Company" cultures, you may be able to cold contact those new hires (LinkedIn InMail, standard email address formats, etc., there are hustle guides to this step).
Do not form mail at this step. You get one tight clean shot to hook them that you might have a genuine way to help them, it's worth a conversation. Make having that conversation cheap, meaning, offer to make time convenient for them, 30 minutes is fine to just talk to see if your idea fits, etc. They don't want a dog and pony show. Be painless for them to check if you can help. (Note: Be completely unlike Oracle, Salesforce, Snowflake, or any other vendor where if your desired sponsor takes a call or email they'll be hounded by dozens of sales people for months, and that's just to start a 9 month procurement cycle. In contrast, your sponsor guesses a small firm could ship by then, and they wouldn't have to waste time ...)
If what you have could legitimately help them deliver on the Transformation or Digital initiatives' goals, they may get back to you**, because the last thing they need is to deal with even more enterprise vendors, they need some small fast vendors to help them actually put wins on the board.
** I have been that guy, and I have gotten back to small firms. (I also occasionally reach out to startups here.) Peers at similar roles have gotten back to people too. It is much more common to get introduced through VC-hosted field days, senior exec or board room referrals, and the like, but this path can work with enough hustle.
yes, i was part of doing something like this at a small elearning startup for one of the largest publishers in the world circa 2010.
Exactly as you say, brought in to provide the tech platform for a strategic initiative involving a transformative shift to digital-first courseware and content.
A trick I've found repeatable is to find an enterprise that doesn't shy away from big budgets (where six and preferably seven figure budgets are fine even for unproven vendors, because what's big/existential for you is negligible/experimental for them), and is willing to buy a product from you that requires "integration" (they love to spend money on integration, plus that means it doesn't work on day one!), where the "integration" cost is enough to bootstrap the product AND integration (and your ramen!) at your internal rates.
To avoid the bootstrap money going to overhead, to keep the money for product build (engineering instead of paperwork), you need to avoid getting "risk managed" like a mature vendor. Its best for you to be a pilot, or proof of concept, or pet project for a sponsor to show a concept they want the enterprise to do.
Pick your customers and product integrations carefully where the work will pay for the enterprise capabilities most likely to win your next sale. Use these big contracts like lilypads to cross the pond to the other side of Geoffry Moore's "chasm" between early adopters and early majoriy.