J. Pierrepont Finch, a young window washer in New York City with large ambitions, reads the book How to Succeed in Business Without Really Trying. The “Book Voice” tells him that he will be successful in the business world if he follows the book’s advice. Excited, Finch enters the World Wide Wicket Company searching for a job (“How To Succeed”).
Finch bumps into J.B. Biggley, the president of the company, who sends him to the personnel manager, Mr. Bratt. Rosemary Pilkington, a pretty, young secretary working at the company, is impressed buy Finch’s boldness and helps him meet Mr. Bratt. Bratt is originally very brusque to Finch, and so Finch tells him that Biggley sent him and that they were friends. Bratt gives him a job in the mailroom, where he works with Mr. Biggley’s lazy, arrogant, and nepotistic nephew Bud Frump. Rosemary who dreams of married life and has taken a liking to Finch, fantasises about him to her friend Smitty. (“Happy To Keep His Dinner Warm”). A coffee break is called, but the machine has run out of coffee. (“Coffee Break”). Finch is frustrated about being at the company for a week and not advancing. Through Rosemary, he meets Miss Jones, Biggley’s secretary. In the mailroom, Finch earns the respect of long-time head of the mailroom, Mr. Twimble, who is moving to the shipping department and must choose his successor. He tells Finch the secret to longevity at the company (“The Company Way”).
Twimble announced Finch as his choice to head the mailroom, however the book warns not to stay in the mailroom too long. Finch recommends Frump for the promotion instead of himself, for the good of the company. Twimble is reluctant to promote Frump because of his laziness, but Frump promises to be a good employee (“The Company Way (Reprise)”). Twimble and Bratt are both impressed by Finch’s selfless decision, and Bratt offers him a job as a junior executive in the Plans and Systems department, headed by Mr. Gatch, much to Frump’s dismay.
An extremely attractive but air-headed woman named Hedy LaRue, Mr. Biggley’s secret mistress, is hired as a secretary. Her entrance attracts the attention of all the men in the office, prompting Bratt to explain the office policy on flirting (“A Secretary is Not a Toy”). Finch learns from Mr. Biggley’s secretary, Miss Jones, that Biggley is a proud graduate of Old Ivy college. In the elevator at the end of the day, Rosemary’s fellow secretary Smitty helps her and Finch set up a date (“Been A Long Day”). After they leave, Frump runs into Biggley and Hedy and realises the nature of their relationship. He blackmails Biggley into giving him a promotion, by threatening to tell his mother (“Been A Long Day (Reprise)”).
Finch arrives early Saturday morning and sets up the office so it looks like he has been working all night, knowing that Biggley is coming in to the office soon. Finch convinces Biggley that he is also a proud alumnus of Old Ivy and they sing the Old Ivy fight song (“Grand Old Ivy”). Biggley demands that Finch be given his own office and secretary, and Bratt assigns Hedy to him. With the book’s help, Finch realises that Biggley must be Hedy’s advocate and sends her on an errand to Gatch, well aware that Gatch will make a pass at her. Gatch falls for the trap and is sent to Venezuela, and Finch is promoted to his position as head of Plans and Systems.
At a reception for the new Advertising Department head, Benjamin Burton Daniel Ovington, Rosemary hopes to impress Finch with her new dress, a Paris original. However, all the other women arrive at the reception wearing the same dress (“Paris Original”). Hedy, who has had too much to drink, goes up to Biggley’s office to shower. Frump schemes for Biggley to catch Finch kissing Hedy in his office, but after LaRue blackmails Finch into kissing her, he realises he’s actually in love with Rosemary and proposes to her (“Rosemary”). As Rosemary is about to accept, Hedy comes out of the bathroom in a towel which angers Rosemary. She leaves, but returns to tell Finch that Bud and Biggley are just outside. Frump and Biggley walk into the office just as Finch embraces Rosemary. Ovington is forced to resign after Finch prompts him to reveal to Biggley that he is a graduate from Northern State, Old Ivy’s bitter rival. Biggley names Finch Vice-President in Charge of Advertising. Biggley leaves as Finch and Rosemary declare their love for each other, and Bud Frump vows revenge to stop Finch’s meteoric rise (“Act I Finale”).
Two days later, Rosemary feels neglected by Finch and decides to quit. Smitty and her fellow secretaries convince her to stay because she’s living their dream of marrying an executive (“Cinderella, Darling”).
The book warns Finch that because Vice-President of Advertising is a dangerous position and that to save the situation, he needs a brilliant idea. Bud Frump slyly tells Finch his idea for a televised treasure hunt. Finch loves the idea, unaware that Biggley has already heard the idea previously and rejected it. Finch tells Rosemary the idea, who responds by telling Finch that she loves him. (“Happy To Keep His Dinner Warm (Reprise)”). Hedy tells Biggley that she is unhappy as a secretary and is quitting. Biggley begs her to stay and tells her he loves her (“Love From a Heart of Gold”). In the executive washroom, Finch gives himself a pep talk before the meeting while, behind his back, Frump ensures the other executives Finch’s presentation will flop, and they plot against him (“I Believe In You”).
Finch presents his idea of the televised treasure hunt to Biggley: he will hide five thousand shares of company stock in each of the ten offices around the country and give the audience weekly clues as to where they are located. Biggley does not like the idea, until Finch explains that each clue will be given by the minimally-dressed World Wide Wicket Treasure Girl: Hedy LaRue.
During the first television show, Hedy is told to swear on a Bible that she doesn’t know the location of the prizes. Biggley had in fact told Hedy the locations the previous night and Hedy panics, revealing the locations to the entire television audience. This prompts all the Wicket employees to tear apart the offices looking for them. The book tells Finch that if he is the cause of the disaster, to re-read the first chapter on how to apply for a job.
The executives, including Chairman of the Board Wally Womper, are waiting in Biggley’s office for Finch to hand in his resignation. Finch tells Rosemary that he will probably return to washing windows, but Rosemary assures him that she will still love him no matter what (“I Believe in You (Reprise)”). Bud arrives to take Finch to the office. Just as Finch is about to sign his letter of resignation, reveals to the executives that he was in fact a window washer before coming to the company. Womper is drawn to Finch as he, too, was a window washer. Finch skilfully blames the treasure hunt on Frump, also mentioning to Womper that Frump is Biggley’s nephew. Womper is about to fire all the executives when Finch steps in on everyone’s behalf, telling Finch him that even though the business world is a place filled with betrayal and competitiveness, the World Wide Wicket staff is like a family to him (“Brotherhood of Man”). All the executives are spared, Bud Frump, however, is fired.
Biggley remains president of the company, Womper retires to travel the world with his new wife, Hedy, and Finch becomes the new Chairman of the Board. Rosemary stands by his side and inspires him to become President of the United States. Frump gets a job as a window washer, swearing revenge against Finch and reading How to Succeed in Business Without Really Trying (“Finale”).
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