I deserve a raise in the new commission-based pay structure.

I asked a similar question ages ago, though not commission related, just general salary. The best advice i got was something to the effect of "The correct answer(of what to ask for, and how to ask for it) is $0. Find a new job somewhere else". I did ask, and came totally prepared with not only several good arguments but lots of data, examples, and even a couple leads on much-more-fairly compensated jobs they were excited to interview me for(although, not hard offers). I did it because i liked working there. There wasn't a single coworker i disliked, i loved the flexibility, location, short commute, basically everything but the pay. They pretty much laughed at me. They offered to pay for some training, but said they couldn't give me even a tiny raise because they couldn't pay me more than a senior manager and blablabla bullshit bullshit bullshit. I really regret asking, i wish i just had freaking left. A raise is something you're given, or something you ask for if you're already making around the reasonable middle line for what you're doing and think you're performing good enough(or now have some seniority) to merit it. If your compensation is really that out of line with what the job should be paying, then they're obviously ok with fucking you and think you just don't know any better. No place like that will ever give you a real raise. They either deserve to realize they're fucked and pay the next person what they deserve, or can keep trying to wrangle in suckers or desperate people who will spear fish the chum bucket for scraps. Just move on.

Sales skills are transferable. If you can sell cars, you can sell software, or gazingus-pins, or widgets. Start looking at sales jobs with significant training. Something like http://att.jobs/careers/college/development-programs/sales-programs/business-sales-leadership-development-program Get into real estate or selling cars which is commission driven. There's no way you're going to get a raise from $30,000 to $110,000. None. You can request that the pay structure change, in such a way that you're getting a commission on your sales, but as great as you are at your job, they'd rather hire two schmoes at $30K and hope for the best, than pay you $110,000 for a sure thing. If they undervalue you this much, that enterprise is hopeless. So rather than ask for more dough there, find out where else you can make good dough and get a job doing that.

I think what's reasonable depends a lot on your local job market, and in particular how much it might cost the company to replace you with someone who performs at a similar level, and how much you could earn working somewhere else. It does sound like you are seriously underpaid, but you will have to work against the inertia of your current contract, which could be tough. Are you prepared to walk, if they say no? You might have to make that threat in order to be taken seriously, but then they might choose to let you go. I wouldn't start such a conversation without planning for this as a possibility.

What kind of packages are the competition offering? How are they structured? What kind of industry are they in? How does HR benchmark you in the industry? Making the jump from $30k to $60k may be achievable, but $30k to >$100k will likely get laughed at a unrealistic. You will need to work with your management to develop a plan that gets you to where you want to be with clear expectations of the deliverables that very you there. Is this the same job you've been asking about previously? If so, you will want to be careful about how you approach this. Using the conversation to vent will not be constructive. Do your research and go in with a plan.

At your level of retail, management is rewarded for having low expenses, and the higher sales are either expected as a given or regarded as transitory while they shore up in preparation for lean times. Even more, management probably believes that increasing sales are due to something they did, not something you did. Plus, paying you more money would raise a heckuva lot more red flags to their own upper management than any declining or stagnant sales caused by your departure.

It appears as if management thinks the product sells itself. They own the product. You are there in their minds and being paid as if you are just needed to do the paperwork on the sale. If all the sales force is making around what you do and are booking a $1 million in sales and you have increased your book by 25% to $1.25 million, even if they paid you 10% commission on all business above the average $1 million, you would get $55,000. They are better off hiring two sales folks at $30k and get $2 million in sales than pay you $55k for $1.25 million. Sounds to me as if they view sales as not something the seller (you) are doing, but as a function of time and capacity. If it were me, I would look for a different job at a company that pays a commission or in another industry that does. If you want to stick around this company, I would ask for benefits to supplement my salary and/or a commission on everything sold above $1 million. Have a plan in case (when) they say no.

Get a job offer at a competitor that offers 60 grand. Give two weeks notice. Companies don't give raises unless they absolutely must, and most managers will assume they can replace all but the very best of the top performers, and get away with paying the replacements even less. At least, that's how it works in my trade.

I think oceanjesse's right, you'd do better somewhere else. Maybe look at this negotiation as a way of putting another feather in your cap (shooting for the 5% commission / a bump in salary) before making your real move, and spend the time in between researching and networking.

See what other companies in the area are offering. If Other Company is offering $60k/yr + benefits, then you can casually mention that to Your Company and see if they offer up the goods. A better way of doing this is to have a job offer in hand so that if you get laughed at, you won't have to suffer working somewhere where they'll laugh at you.