Sales is a Chess Game

By CEO National Master Evan Rabin

Before founding Premier Chess, I co-founded Pillar Sales, a sales outsourcing firm and closed deals upwards of 5 million dollars at Oracle and Rapid 7. When I would interview for new roles, hiring managers would often ask me the common question “Why do you like being in sales?” When I answered because I liked the analytical nature of it, my interviewers most often would not believe me, thinking I was just interested in the money. To the contrary, sales is analytical like a chess game. In both sales and chess, one should look for low-hanging fruit, recognize the process and review his games.

One of the biggest takeaways I got from my sales training at Oracle with Bill Petersen is that one should always look for the low-hanging fruit. When a sales representative first receives as territory, it can be overwhelming as he has lots of account and does not know where to start. While it may be tempting to go after the ‘whales’, the companies with the most revenue that may have a lot of buying power, it is best to go after one’s install base, identifying opportunities for his customers to upgrade where needed. Likewise, in a chess game, the goal of a chess game is checkmate, as that is the only way to win a game. However, one cannot blindly attack and aim for checkmate if the position does not justify such a plan. One should always look for his opponent’s weaknesses and determine an applicable plan.

For instance in this position, white would not go for a king side attack as black’s king is relatively safe. On the other hand, he would try to move his knight to c4 to put more pressure on the backward d6 pawn.

A chess game and sales both have distinct processes. In the opening of a chess game, a player develops his pieces, controls the center and castles to prepare for the middlegame. Likewise, in the beginning of the sales process, discovers budget, ability, need and timeline and identifies an opportunity. In the middlegame, a player  excecutes a plan, while a sales representative offers a proposal and negotiates. In the endgame, a player tries to increase his advantage to get a winning position, as a sales person tries to close a deal.

                                                                                                                                                                            In chess and sales, it is important to always analyze your mistakes and figure out what you can do better. The good thing about a chess game and a sales deal, is there is always another one. My former Vice President at Oracle Kevin Mcgee used to often say “there is only one way to overcome a lost deal- to go find another one.” To better on the next sale or game, one should objectively figure out his areas of improvement, whether it be in the opening, middlegame or endgame.

While there is no question one has to have a drive to make money to be sucessful in sales, an analytic mindset can also help. Whether you or sales person, entrepeneur or other revenue generating employee, chess can help. Off and on the board, look for the low-hanging fruit, recognize the process and review your games, and you will be sucessful.