Anyone ever gone from *management* to a senior IC role?

Long time lurker, first time posting :)

So my background has been in working with early stage start-ups as a head of sales but I'm considering going "up market" as an individual seller. My prior roles were with seed stage / pre-revenue startups.

In the less successful instance, I lead sales from pre-revenue seed round to Series A. (Mind you, this was a Series A back in 2018 before massive liquidity / funding inflation, ahem! ;)) In the most successful instance, I lead all sales efforts from pre-revenue through $10M ARR, from seed to Series B. That company still exists today as a market leader in its category and is currently raising a Series E.

In both instances I acted as an initial sales hire, without a team in place, without a lead gen or marketing program started and built the sales process as the initial products were developed, and finding product-market fit. This was through pivots, hiring and managing sales teams, managing customer success, and of course, closing the initial cornerstone deals with the CEO that got us profitable and able to raise subsequent rounds. While I loved selling a product that I believed in and geeked out about it, if I'm honest with myself I was not an effective manager. I exceled at the sales hustle, but motivating others to do what what I was naturally passionate about wasn't my forte.

After a long sabbatical I'm beginning my job search and I'm looking to apply as an indiviual contributor for senior / MM / enterprise AE roles for companies Series B and beyond. I have the following concerns:

1. My experience has exclusively been in first sales hire / head of sales roles for SMB / MM. How can I tailor my resume and search with that background? (i.e., my accomplishments are in overall ARR milesones, funding rounds company closed, number of SDRs/ AEs / CSMs managed -- whereas a senior / enterprise AE resume will typically list quotas obtained, deals closed, etc.)
2. How should I present my preference to "downgrade" to individual seller when I've already been a manager / director of sales?
3. Is it realistic that I can jump from having been the head of sales for an SMB / MM product to an IC selling MM / Enterprise? I suppose it's just a matter of a good pitch to a VP Sales willing to take the risk / jump with me. One possibility I've thought of is working as an IC for a more well-established startup that it looking to build a sales team for a new product offering. (i.e., Figma's recent launch of new product "Figjam" - a startup within a more mature company)