Help Me Choose
Jordan Benjamin

By: Jordan Benjamin on December 2nd, 2020

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Rob Barnes


    • Accidentally got into sales while working for a global PR firm
    • Had to start cold calling - didn’t even think it was sales initially
    • Moved into startup life with a Freemium sales model
    • Didn’t have much awareness about what sales was
    • Sales roles vary by industry - Manufacturing (order management & procurement), Commercial printing - Tradeshows and outreach 100’s of days per year different than Tech sales
    • Sales is changing significantly in the last 10-15 years
    • Startup vs. Scale up -> Specialization in scaling up now looking for deep over broad vs. jack of all trades “wear many hats” in startups
  • “Take what you’re good at, what you like to do and do more of that!”
    • Larger org, challenging to know what others are doing - hard to do now not being in the office around others. Call recordings have been very powerful to share ideas and best practices
      • Highlight recording of particular recordings that is indexable & searchable is so powerful to get better and improve
      • Give the rest of the group as much ownership as possible of where they want to focus their time = They are Bought-In!
      • Pick a challenge or theme you will run with for a month and then take a 60 minute meeting listen to 5-10 min chunks of call 
      • White hat/Black hat format-  highlight what went well and then also focus on constructive criticism
    • Rode in the PMC 7.5 times! - Check him out!
    • Performance is measurable against myself and others in an event similar in sports
  • Pick what motivates you in sales - is it yourself? Beating others? 
    • Know your personal bests, have that mark to reach for and work back from there
    • Setting Short, medium and long-term goals
    • Personal Finance- answer isn’t just save it all or use it all. Need to find a balance in the extremes
    • Work backward from knowing what you need to do and break it into expected time frames
    • Sales pro’s should be comfortable talking about money and should be able to plan ahead for things like cash flow
    • How do you bounce back from a tough month?
      • Work back to see what went wrong, what could have been improved?
      • Context & perspective- why did the bad month happen? What can I control?
    • Pre-covid didn’t spend much time on mental health, now realizing that he really loves being outside and doing things like walking meetings
    • Listening to more audio books
    • Read 1 book/week for all of 2019- fell a little short and trying again this year 
    • Tracks everything Maniacally! What did he read? What did he think about it? When was he reading it? Look at it in realtime and then reflect back on it
  • Just start tracking even if you don’t know what you will do with the data
    • All of his tracking is online/digital in things like Google Docs
    • Sales Data - tracks Activity as a leading indicator, can learn a lot relative to your peers, Spreadsheet of all his sales historically.
    • Focus on ASP - top performers have lower discount rates, Average Transaction is higher
  • “Is there a behavior that I can change where I don’t have to fundamentally alter my workflow to make an impact?”
    • “Top performers have a certain Go With The Flowitiveness” - a lot of people can have a big month/quarter or close a big deal but it takes a lot to sustain
      • They focus on what’s in their control and what is within the realm of reality for them to shift
      • The GSD factor & Adaptability
    • Qualities of Leaders
      • Way behind on a project and Exec VP at 8PM at night sat right down with them and got in the trenches to see them in action
      • Someone in the crow’s nest scanning the horizon to see what you need to pay attention to next - as an IC you have a relatively short-sighted view
    • Success means - Making those who believe in you look brilliant - Dharmesh Shah Employers, managers, parents, etc.
    • Hates losing more, wants to say likes winning more but when falling asleep or restless, not dwelling on the wins, but focusing on the losses
  • In sales you can have a pretty meaningful impact on an organization without having to do the heavy lifting. B2B business acumen can go so far if you can understand the business impact it makes on them and their organization
  • Seeing the impact/teams can help solve for


About Jordan Benjamin

Jordan is the founder of My Core OS. After spending years in sales, working with sellers and studying peak performance he found an opportunity to help sellers level up to not only build peak performance at work, but to also create harmony between work and life so you can sustain performance over the long term.