In Death of a Salesman, success means different things to various characters. For the protagonist Willy Loman, success means wealth and professional respect.

In his early days as a traveling salesman, Willy enjoyed profitable trips and even forged a market in New England for the company where he worked. He was the "New England man…vital in New England." Not only did he establish this new territory for the company, but Willy also was somewhat famous up north. In a flashback he tells his sons Biff and Happy that "they know me, boys, they know me up and down New England." He brags that he is so well-liked that "I have friends. I can park my car in any street in New England, and the cops protect it like their own."

Wealth and respect illustrate the success of an old salesman named Dave Singleman whom Willy describes to his boss Howard; Howard—the son of the company's founder and Willy's former boss and friend—fires Willy for no longer bringing in sales. Willy tells Howard how Dave still made sales over the phone at age eighty-four and was "loved and helped" by people across twenty to thirty different cities. Dave was so respected that hundreds of salesmen and buyers attended his funeral. Willy admonishes Howard for viewing success merely in the terms of dollars and not in terms of valuable human relationships: "In those days there was personality...respect, and comradeship, and gratitude...Today, it's all cut and dried and there's no chance for bringing friendship to bear."

Willy wishes to teach his boys to strive for material success and imbue them with an entrepreneurial spirit. He reveres his older brother Ben who made a fortune in diamond mines; Willy describes Ben to the boys as "a genius," "success incarnate," and someone who "knew what he wanted and went out and got it! Walked into a jungle, and comes out, the age of twenty-one, and he’s rich!" Willy also ingrains in them the belief that success is represented by athletic prowess and popularity. During a flashback in act 1, Willy praises Biff for being a high school football hero who will not even allow nerdy Bernard carry his equipment. When Biff steals a football to practice (and feels justified in doing so), Willy supports his theft. He tells Biff that high grades and academic success ultimately do not matter because "the man who makes an appearance in the business world, the man who creates personal interest, is the man who gets ahead. Be liked and you will never want."

Yet in a reversal of fortunes, Bernard becomes a lawyer arguing before the Supreme Court while Biff flounders, failing to establish a career. Playwright Miller demonstrates that Willy’s view of success is flawed and limited—that success is not really material wealth but personal satisfaction. Biff confesses to Happy that he actually enjoys working on a farm and feels inspired by young colts. But because farm work is not sales, he feels "my God, I'm not gettin' anywhere." He eventually tells Willy to give up the "phony dream" of Biff being a successful businessman. Biff realizes that success may be personal satisfaction, not profits from sales.

To Linda, success may involve sales—she is delighted when Willy brings her expensive stockings from his trips—but has more to do with pride and respect from family. Her pride for Willy during his early successful days in sales is more about her admiration for him and less about the money he brings home. She also tells him that when the boys were young, they admired him: "Few men are idolized by their children the way you are." When Biff and Happy are older and Willy is less successful as a salesman, she focuses on his worth as a father, provider, and human. Linda admonishes them, "He’s not to be allowed to fall into his grave like an old dog. Attention, attention must be finally paid to such a person."

To Happy, success seems to be beating the competition—if not professionally, then sexually. When he is shown up by or passed over for promotions, he seduces his competition’s women. For example, he notes that when a coworker was in line for vice president, he "went and ruined her [the man’s fiancée], and furthermore I can’t get rid of her. And he’s the third executive I’ve done that to."

Depending on the character, success in Death of a Salesman means material wealth, ego, relationships, respect, and/or sexual manipulation.

In Death of a Salesman, the idea of success is examined through the lives of Willy Loman and his sons, Biff and Happy. For Willy, success means being personally popular ("well liked") and making a lot of money. The man who can amass a fortune, like his brother Ben, is deemed by Willy to be most successful. Throughout the play, these are the only definitions of success that Willy accepts. He places no value on honesty or personal integrity. He places no value upon his own life, except in those terms. This is seen most clearly when he commits suicide to secure insurance money for his family, imagining the crowds of people who will come from great distances to his funeral because he was so popular and important. Willy succeeds in killing himself, the money is paid, but the funeral is not well attended.

Willy's definition of success is passed along to his sons, both of whom grow up to lack personal integrity and to lead selfish, nonproductive lives. Of the two, Biff realizes their personal failures and rejects what his father died believing to be the truth about success.