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10 Characteristics of a Sales Pirate

By July 10, 2023March 15th, 2024No Comments

“There is no passion to be found playing small –in settling for a life that is less than the one you are capable of living.” – Nelson Mandela

Steve Jobs was well known for being a Pirate. He used this mindset to run Apple, and he encouraged his people to adopt it as well. To Jobs, the Pirate mindset is that of an adventurous, “can-do,” free-thinking, non-conformist rebel with a startup mentality and a passion for action and results. His mantra was, “Strike quickly, break rules, and take risks.”

Adopting this mindset is a conscious decision that will vault you to higher levels of success and sales excellence – but it also can create friction. You have to expect that there will be a conflict with clients and internal personnel as a result – but the rewards far outweigh the pain. The Sales Pirate mindset is captured in Steve Jobs’s famous quote, “It’s more fun to be a Pirate than to join the Navy.”

You must always pick your battles as a Pirate, but approaching the sales job without fear means there is quite a bit of gold and silver in the journey. This is a list of the attributes of a Sales Pirate – review the list and determine if you have the qualities of a Sales Pirate!

  • Assertiveness and courage – Sales Pirates get out of their comfort zone and start moving forward with a “what if” perspective What would you attempt if you were convinced you cannot fail? Courage does not mean that you do not experience fear – it simply means you are willing to act despite the fear you are experiencing. “Fear is a liar” is a great way to create the proper context.
  • Sales Pirates are well-skilled in their craft and always seek to improve their skills to become a more valued member of the crew. What have you done to hone the edge of your “sword”?
  • Clever “rule breakers” – there are times when Sales Pirates may choose to beg for forgiveness rather than ask for permission. However, they always do this with the agreement of your Captain and the Crew involved in the mission! Never act without letting your crewmates know what you intend to do, but actively sell them on the risk/reward. Sales Pirates will always own the consequences if the plan does not work.
  • Unconventional thinking – Sales Pirates do not do what everyone expects them to do. They take actions that are bold and far different from their competition. Sales Pirates always seek to be unpredictable. Competitors never know where they are, what they are thinking, or what areas they are going to attack. Competitors live in fear of competing against true Sales Pirates.
  • Sales Pirates are calculated risk takers. Anyone can follow a “safe” plan – Sales Pirates weigh the risk/reward and know there is generally MORE risk in not taking risks!
  • Sales Pirates can navigate well (think about client relationships and politics). They understand where the obstacles are, learn and leverage personal agendas, engage their Partner Allies in collaboration, and are extremely effective in providing ideas to the right people. They chart their course and navigate accordingly. Sometimes, they must backtrack, slow their speed, and/or take a different tack. Proper navigation is a continual process – Sales Pirates never set their course and sails without evaluating their progress and direction.
  • Sales Pirates are extremely resilient. They understand that bold moves do not always work. They know there will be setbacks and disappointments. They remain optimistic in their search for gold and silver while creating new attack plans. THEY DO NOT QUIT.
  • Passion for action – Sales Pirates are not passive – they move fast; and think big – thinking big excites them and helps them keep their focus during disappointments from failed missions.
  • Strategic but opportunistic – Sales Pirates invoke strategy with targeted contacts. They leverage the proper relationships, messaging, and well-developed win plans – Sales Pirates understand that execution is important – but having a strategic plan is critical to sales excellence. At the same time, Sales Pirates are also alert for opportunities they can quickly address.
  • Sales Pirates have a strong sense of humor. They see the absurdity of both success as well as failure. They use humor to lift the spirits of their crewmates, and they use it as a means of building resiliency.

A common denominator for people adopting the Sales Pirate mindset is approaching their accounts and opportunities with that list in mind. You can pick Sales Pirates out of a crowd – they are FUN to be around, energize you, and spark imagination. Sales Pirates are people that will be successful in almost any company due to the way they approach their challenges. Review the list and ask, “How much of a Sales Pirate am I?” If you decided to do more of these things… would it make a significant difference? How much more valuable would you be to your crewmates, your Captain, and your clients? Strive to take all of them on these bold adventures while creating more value and relationship bonding.

Personal Challenge: Select one account or opportunity and determine where you can/should take more risk. Identify the actions you can immediately take to become bolder and more adventurous in your approach. Build and share the plan with your “Captain” to gain their support and buy-in. Once you agree– set your “sails” to increase your “sales!”



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