Actually, “loser” can be well defined as anyone who is involuntarily unemployed or underemployed for more than a short period of time, who cannot sustain his/her life (and that of any family/household whom s/he contributes support to) with the work that s/he can find (i.e. eventual bankruptcy), or who detests the work that s/he can find. And, in this context, “winner” is everyone else.
Note that this definition is not solely dependent on pay/benefit levels. To the extent that pay/benefit levels matter, they have to be in context of what the person needs to sustain his/her life. If two people are in the same job making the same pay/benefits, one may be able to sustain his/her frugal life, while the other may not be able to sustain his/her spendy life. So one may be a “winner” and the other may be a “loser”. In addition, the longer term career growth as it relates to longer term personal goals (common ones being raising a family, saving for the kids’ college costs, and retirement) also count toward whether the work is sustainable in the longer term.
But the bottom line is, most people do not have to be a investment bankers, management consultants, orthopedic surgeons, or partners in big law firms to be “winners” by this definition.