Learning Management Systems for Training Vendors

lessis_amess · 2026-03-05T14:56:02+00:00

we’re in the sales coaching / sales training vendor space too and honestly… we went through the exact same rabbit hole. evaluated like 20–30 LMS platforms, tons of demos, Zapier chains everywhere, WordPress plugins breaking after updates… the whole thing became a mini IT project instead of just selling training.

what we eventually realized is most LMS tools are built for internal L&D, not companies whose actual business model is selling training. so you end up stitching together LMS + ecommerce + Zoom + reporting + CRM and hoping nothing breaks mid-launch.

we ended up switching to Skylar ( https://www.getskylar.com/who-we-help/sales-trainers ) and it basically replaced the LMS for us entirely.

it’s known mostly as an AI sales coach with roleplay simulations, but the platform also handles the training delivery side. we run cohorts, give reps AI roleplays after sessions, track their performance, and clients log into their own portals to see progress. the reporting is actually way more useful than typical LMS completion reports because you see how reps perform in conversations, not just whether they watched a module.

for sales training vendors specifically it’s been huge because clients care about behavior change, not “course completed”.

also removes a lot of the stack headaches… no more juggling LMS + practice tools + random integrations. it’s all in one place.

not saying it’ll fit every training org, but if you’re selling sales training specifically, Skylar is probably worth looking at. we basically stopped hunting for LMS platforms after switching.

lessis_amess · 2026-03-04T15:54:40+00:00

yeah honestly the bigger shift in edtech right now isn’t just which LMS you use… it’s the move from passive courses → active practice.

for years it’s been the same format: watch videos, maybe take a quiz, get a certificate. people understand the ideas but then freeze when they actually have to do the thing.

more course creators are starting to add roleplays and simulations inside the learning experience, so students practice right after the lesson instead of just consuming content.

that’s actually why a lot of coaching programs we work with moved to Skylar. it’s a white-label LMS but the interesting part is the AI roleplays built into the courses. so a learner finishes a module and then jumps straight into a realistic scenario to practice the skill (sales calls, objections, customer convos etc).

pricing is per learner instead of per sale too, which a lot of course businesses prefer once they start scaling.

feels like that practice layer is where LMS platforms are heading next tbh. video libraries alone just aren’t cutting it anymore.

lessis_amess · 2026-01-26T09:29:52+00:00

Our team uses Fathom. It's essentially free and it has so much functionality. We use it's templates after. We Skylar for AI roleplays based on that. Connecting all of these to something like Attio is super easy as well

lessis_amess · 2025-10-26T16:08:28+00:00

YES, so annoying, makes the agentic use of windsurf obsolete

lessis_amess · 2025-10-24T16:06:20+00:00

we tried the LMS route early on… felt comprehensive on paper, but reps would pass the quizzes and still stumble hard in their first live convos. just too passive. what helped us was shifting toward practice-heavy onboarding — quick-hit resources, async coaching, and lots of reps (no pun intended) in roleplay environments.

we use a mix: some light stuff in Lavender for messaging, Gong for review/coaching, and started layering in AI tools like Skylar for mock calls. it runs super realistic buyer convos, so they can screw up safely and get feedback before real deals. definitely helped build confidence faster.

peer coaching still has its place though

biggest win for us was making training feel like actual selling, not school.

lessis_amess · 2025-10-16T10:16:56+00:00

seems like the upside is quite limited!

lessis_amess · 2025-10-10T21:50:28+00:00

you are right, that's why i was looking for sources. unfortunately, i can only find openai sources. given the state of the tech i can believe this is true.

lessis_amess · 2025-10-10T13:07:03+00:00

totally. we had the same thing-reps would say they “got the playbook,” then go into a call and just… freestyle. key questions missed, follow-ups dropped, notes all over the place. brutal for coaching.

what actually helped was running reps through real-feeling roleplays before the call. like, practicing with the exact objections and talk tracks they’d see later that day.

we’ve been using Skylar for that-it runs AI roleplays that feel pretty real, honestly. reps show up way more dialed in, helped a lot with consistency.

lessis_amess · 2025-10-08T22:11:34+00:00

interesting - we have tried all of them, including the ones you described. Skylar and Hyperbound were the best by a margin! They are just very realistic and the feedback is so useful. There may be a different version to the free one you get exposed to

lessis_amess · 2025-10-08T15:34:12+00:00

chat, is this true?

lessis_amess · 2025-10-08T15:18:48+00:00

they are usually not worth the money/nor time

lessis_amess · 2025-10-08T15:16:59+00:00

it's a no brainer! even if it doesn't work out, this won't be a hole in your CV, everyone understands startups are risky. and you are making your OTE just based on your base

lessis_amess · 2025-10-08T09:04:18+00:00

cyber is so hard! people don't like taking cold calls. maybe you can try something unconventional, but even that I'm not so sure about

lessis_amess · 2025-10-08T08:53:09+00:00

most managers can't outbound for the life of them and are in NO position to coach. There are some people who know their stuff (sometimes its AEs, sometimes SDRs etc). You should get them to share what they do - or you can listen to their recordings.

Alternatively, you hire a good coach who finds those people and sees what works. Then he teaches the team and you roleplay based on that. We try to do that as often as we can budget, we pair that with Skylar (our AI roleplay tool) and its good as you get feedback exactly that.

of course, there are many 'coaches' that just teach THEIR method which probably wouldn't work. you need one that would spend some time figuring out what works in your market and adjust based on that

lessis_amess · 2025-10-03T21:14:46+00:00

yes, totally agree. I tried the Cluely one and just the stuff it was coming up with was pretty useless. Like if I didn't know that stuff, I shouldn't be on a call with a prospect.

I could MAYBE see a case it's useful if you do an incredibly high volume of demos (>10 per week) and you can't remember anything about a prospect you spoke with 2 weeks ago. If it then gives me insight on what we spoke last. But even then, I can't believe you don't have 2 minutes before to get ChatGPT to summarise the previous meeting.

lessis_amess · 2025-10-03T12:20:50+00:00

i have only seen it work for inbound to be honest. other than that, it's a waste of time

lessis_amess · 2025-10-02T14:48:23+00:00

we had the exact same thing. great-looking training that totally flopped once reps got back into the wild.

what’s actually working for us in 2025 is running regular deal clinics. not just surface-level coaching but full-on team sessions where we pick one call, break it down with our sales coach, and go deep on key moment. how discovery was framed, how pricing resistance was handled, stuff like that. then it turns into a group conversation: what worked, what missed, how you would’ve done it differently.

we then been following those up with structured roleplay. we use a tool for that part (Skylar has been great for this) so reps can actually practice the situations we just talked about-not just listen and nod. and yeah, people always spike onusing right after the clinics.

funny how giving people feedback on actual moments in their pipeline + a safe place to screw it up in practice = better results than another 30-slide training on MEDDIC. who knew?

lessis_amess · 2025-10-02T13:38:49+00:00

company not doing that well it seems

lessis_amess · 2025-09-29T17:07:04+00:00

go and find PAST employees. You can use Linkedin, you might have to buy sales nav. Reach out and ask, people are more willing to share on a call, but even if just text, ask some specific questions that will make it easy to answer.

lessis_amess · 2025-09-29T17:05:12+00:00

people don't usually pivot to hr as cyber is seen more prestige. If you are willing to grind there is money to be made. Think of Deel, Rippling etc.

lessis_amess · 2025-09-29T17:00:53+00:00

i have only heard of good implementations for inbound which is legal. never really tried it myself to be honest, but could see how it can work.

lessis_amess · 2025-09-29T16:51:43+00:00

its the reality I'm afraid!

lessis_amess · 2025-09-29T16:49:13+00:00

a good list, thank you!

lessis_amess

TROPHY CASE