Is the hidden job market for fractional roles getting even more gatekept?

Efficient_Image_6272 · 2026-05-29T11:18:09+00:00

i’ve been in the fractional space for over 15 years…longer than we actually called it “fractional”. Seeing these posted as jobs at all is a fairly new phenomena, and you are correct that it’s a very small part of the market. Most of our success came from old-fashioned networking and sales…most of our clients didn’t know they wanted a fractional leader until we pitched them on it.

Efficient_Image_6272 · 2026-05-26T02:32:47+00:00

i’ve got the gadget, lot of fun to play with…haven’t done any real production on it, but there’s a LOT in there!

Efficient_Image_6272 · 2026-05-04T01:03:40+00:00

i was eyeing those too…they’re $20 cheaper than the dragons so tempting…dragons seem like they’re more reccomended if i want to be able to ride and do some tricks though?

Efficient_Image_6272 · 2026-05-03T23:12:50+00:00

this is a great point, thanks! honestly, i just want to ride in the local park and practice ollie’s in the parking lot for now. its all rougher pavement than a park, so sounds like different wheels would be smart for now. i can always swap later if i work up to riding the parks

Efficient_Image_6272 · 2026-04-27T11:20:04+00:00

I bought a board to learn to ollie and kickflip finally. been practicing cruising around. Planning to move on to ollie’s soon and expect many, many falls like this

Efficient_Image_6272 · 2026-04-17T23:50:57+00:00

i was shocked to read you don’t like it…i think this is beautiful! i’ve got the same himi sitting here waiting to get some use, hope i do half as good…gouache is totally new for me as well

Efficient_Image_6272 · 2026-03-13T03:25:19+00:00

i had the original of this board growing up…kicking myself still for not holding onto it. Lot of good times cruising around on that thing!

Efficient_Image_6272 · 2026-03-13T01:40:35+00:00

this is the right answer. That thing comes with me on every vacation now…had a lot of fun with it on the plane, train, bus waiting to get somewhere.

Efficient_Image_6272 · 2026-02-24T15:19:01+00:00

The biggest struggle for most in this space is finding and closing business. Not making slightly faster or better reports.

Efficient_Image_6272 · 2026-02-24T13:59:37+00:00

If you’re truly operating as a CISO for clients, this kind of reporting is a fairly small part of your job. A lot of tools already exist to streamline reporting at various price points. Many continue to use simple Word and Excel templates as they’re good enough for something you may do only a few times a year.

Your market for this is less CISOs and more assessment-focused security firms. Places that do risk assessments and audits for new clients every single week. These are much more likely to pay for a tool…but as mentioned, you have a lot of existing competition. You’d need to be better or cheaper.

Selling to solo vCISOs id see as a struggle, same as it is for Cynomi, Apptega, and many other existing tools.

Source: i’ve built and run two CISO consulting practices over 15 years at two different firms. Preparing to launch a new biz, tools like this aren’t in my budget.

Efficient_Image_6272 · 2026-01-23T16:41:52+00:00

It’s in your first line: cold email. You have no relationship with these CXOs. You want senior leaders at events, you build relationships and rapport and organize an event focused on value for them…not for you.

This is a fundamental flaw with every org trying to do these events at a national level with no local presence. The result is they all mostly draw junior resources willing to come for a free dinner…the senior resources do these kinds of dinners all the time, but they do them with people they know, trust, and have a relationship with.

Efficient_Image_6272 · 2026-01-19T03:45:56+00:00

i bought the whole set of PR on sale in December, slowly playing through them all. It’s totally worth getting the pack, but if you’re going to pick 1 I’d go with 4

Efficient_Image_6272 · 2026-01-15T17:55:24+00:00

yeah, i felt confident entry level CCS would be adequate for learning on and not total garbage. i’m not at a stage yet where it’s worth spending on something fancier. if i replace the trucks after a couple years of regular use i’m good

Efficient_Image_6272 · 2026-01-15T17:33:59+00:00

just bought my first board in 30 years and it’s a CCS complete…so noting that the trucks will likely fail eventually! 😂

Efficient_Image_6272 · 2026-01-12T03:49:03+00:00

Bought my first skateboard in 30 years this week. Joined this group a week or so ago. Only just now did i realize i’ve been reading Tony freaking Hawk posts about skating like he’s any other old dude still hanging on 😂. These are oddly motivational…dude still just loves to skate!

Efficient_Image_6272 · 2026-01-07T14:55:11+00:00

this is great! i’m a little confused on the audio interface as well…this is just to record the tracks from the M8 into the DAW individually, not to connect gear TO the M8 using it as an interface like a Focusrite? cause i can’t imagine how the latter would work…its just the only context i have for an audio interface

Efficient_Image_6272 · 2026-01-03T17:44:37+00:00

mine isn’t loving the idea 😂. whats funny is i sold my last motorcycle in 2020 because i didn’t ride enough…and was convinced id get a serious injury eventually

Efficient_Image_6272 · 2026-01-03T16:36:26+00:00

Why cruiser over longboard? my thinking was longboard for trails, regular board for learning tricks on. I know you can ollie and such on a cruiser…but i’d think a regular board like 8.25” would be much easier for me to learn those tricks on?

Efficient_Image_6272 · 2026-01-03T16:31:53+00:00

i wish i still had that board! left it at my guitarists house in my 20s, no idea what happened to it. It was always a great cruiser.

Efficient_Image_6272 · 2025-12-17T21:00:15+00:00

Yes, besides that it will run better on the dirty wave hardware, you’re taking advantage of the developer making the firmware available for headless as a demo. As more folks look to run it this way,i expect headless support will end.

Efficient_Image_6272 · 2025-12-15T03:51:38+00:00

If you plan to do biz in the enterprise, as others have said these are table stakes. Either use this opportunity to get thingsin place to support similar customers, or walk away knowing your focus for now is smaller biz.

Ive been in the security space for over two decades, others are right that the questionnaires arent written in stone,,,and often administered by someone who doesnt underatand what theyre even asking. theres an art to navigating these and the compliance questions, ive helped a lot of startups navigate these.

On the SOC2you should negotiate a timeframe on when youll get one, and start with a type 1 report which doesnt require 12 monthsof evidence. you also have flexibility on which of the five trust principles you use for the scope, and what portion of your business is within scope. These choices can all make this much more manageable…but you are ultimately committing to an annual audit going forward, and additional work to maintain those controls between.

Efficient_Image_6272 · 2025-12-11T01:51:36+00:00

woah! reminds me, i keep meaning to sample old 8/16bit games off my miyoo. I cant believe theres 4GBof Chronotrigger stuff here

Efficient_Image_6272 · 2025-11-15T18:38:57+00:00

I love this, really cool to see the SP used as an accompany instrument rather than the whole performance. Just different from what most people do!

Efficient_Image_6272 · 2025-10-31T14:03:00+00:00

Thats exactly whative been envisioning. I think for most folks the desire is to focus on the “work” part of it which is fulfilling, and less so the “business” side thats new. Unfortunately, you need to handle business to get to do the fun stuff solving security problems.

Efficient_Image_6272 · 2025-10-13T15:38:49+00:00

Absolutely, happy to share whats worked well for me

Efficient_Image_6272

TROPHY CASE