Help Me Choose
Jordan Benjamin

By: Jordan Benjamin on December 9th, 2020

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Cierra Steiner


Cierra Steiner 4+ years in SaaS sales. 1 year in brand management, CPG, and retail sales for well known brands like Hormel, ZenDesk, HubSpot.

2019 Presidentโ€™s Club Winner, achieved #3 rep in global revenue @ Zendesk

Dog lover, amateur comedian, cheese curd enthusiast, world traveler, & sales mental health advocate.

Quotes I try to live by every day:

๐‘ฎ๐’†๐’• ๐’„๐’๐’Ž๐’‡๐’๐’“๐’•๐’‚๐’ƒ๐’๐’† ๐’ƒ๐’†๐’Š๐’๐’ˆ ๐’–๐’๐’„๐’๐’Ž๐’‡๐’๐’“๐’•๐’‚๐’ƒ๐’๐’† - Jillian Michaels

๐’€๐’๐’–'๐’“๐’† ๐’๐’๐’๐’š ๐’„๐’๐’๐’‡๐’Š๐’๐’†๐’… ๐’ƒ๐’š ๐’•๐’‰๐’† ๐’˜๐’‚๐’๐’๐’” ๐’š๐’๐’– ๐’ƒ๐’–๐’Š๐’๐’… ๐’š๐’๐’–๐’“๐’”๐’†๐’๐’‡ - Andrew Murphy

๐‘ญ๐’๐’“ ๐’˜๐’‰๐’‚๐’• ๐’Š๐’•โ€™๐’” ๐’˜๐’๐’“๐’•๐’‰... ๐’Š๐’•โ€™๐’” ๐’๐’†๐’—๐’†๐’“ ๐’•๐’๐’ ๐’๐’‚๐’•๐’†, ๐’๐’“ ๐’Š๐’ ๐’Ž๐’š ๐’„๐’‚๐’”๐’† ๐’•๐’๐’ ๐’†๐’‚๐’“๐’๐’š, ๐’•๐’ ๐’ƒ๐’† ๐’˜๐’‰๐’๐’†๐’—๐’†๐’“ ๐’š๐’๐’– ๐’˜๐’‚๐’๐’• ๐’•๐’ ๐’ƒ๐’† - F. Scott Fitzgerald

๐‘ป๐’‰๐’†๐’“๐’† ๐’Š๐’” ๐’๐’๐’•๐’‰๐’Š๐’๐’ˆ ๐’†๐’Š๐’•๐’‰๐’†๐’“ ๐’ˆ๐’๐’๐’… ๐’๐’“ ๐’ƒ๐’‚๐’… ๐’ƒ๐’–๐’• ๐’•๐’‰๐’Š๐’๐’Œ๐’Š๐’๐’ˆ ๐’Ž๐’‚๐’Œ๐’†๐’” ๐’Š๐’• ๐’”๐’ - Hamlet

  • Fell into sales - went to school for Business Admin because she had no clue what she wanted to do. Speciality in sales and marketing, didnโ€™t see many entry level marketing positions
  • Liked being creative mixing art and math- thought maybe Marketing would be a career 
  • Spent time as a BDR, was pretty introverted, didnโ€™t take a lot of risks growing up, so sales was really scary for her! 
  • Cold calling people was her worst nightmare, she doesnโ€™t even like answering her own phone
  • Got outside of her comfort zone in uncomfortable situations that helped her grow, wins and losses, while learning to deal with rejection
Getting into sales broke her out of her shell 
  • Spent time trying to be a type of seller that Iโ€™m naturally not
Understand how to be yourself and make your own personality work for you in a sales process
  • The negotiation process has always been a struggle for her being, from the midwest, quiet, introverted.
How do I come into my own in sales and be who I am? And not pretend to be who someone else is
  • Sales is a grind, you have wins, you have losses. Feel great and feel horrible. Itโ€™s an emotional rollercoaster on a daily basis
My biggest enemy is my own mind. My biggest thing holding me back from being successful is myself
  • Bad month you can get down such a rabbit hole of not believing in yourself and it affects how you are on calls, on demos and drags down your own progress
Mindset, self confidence are the keys to success
  • Bounce back, reasoning with yourself as to what can happen
Remind myself that my only job today is to help somebody and do the best I can!
Go into this day and take my best attitude and effort to make sure I am doing my best to help somebody
Not focus on the number, but focus on doing your best work everyday
  • Then look at HOW you do your job. 
  • First 3 years at ZenDesk did well, didnโ€™t have much adversity, life is easy
  • Then all of the sudden hit a tough quarter and realize what might have worked in the past might not work in the future
Be willing to change, take a step back and adjust
Ask for feedback even if youโ€™ve been there a long time
  • Be honest and see if a manager can help listen to calls, give you new insight and have humility 
  • Quote to live by: 
โ€œThereโ€™s nothing either good or bad, but thinking makes it soโ€ - Shakespeare
    •  your interpretation is what will affect you 
    • Somebody could come into your life with your circumstances and thinking you have the best life ever while you donโ€™t
  • Traits of top performers- not an expert, just working at improving on these everyday
    • Consistency in your process in what youโ€™re doing day after day
    • Confidence in themselves!
People that are consistent and continue to put the effort in even when they arenโ€™t seeing results are the ones that win
  • Do they trust you, do they like talking to you?
  • Being confident even when you donโ€™t know 
Gotta feel good about yourself before you can help others
  • Becoming more self-aware
This year thinking about ME, how am I feeling today? What can I do to change that? What can I be proud of myself for? What are the things that I need to work on?
  • Donโ€™t focus on just what Iโ€™m bad at 
  • Itโ€™s a confidence thing
  • Check yourself before you wreck yourself
In a bad place take a pause and step back to get yourself back to a good place
  • Getting better at prospecting
  • Leadership
    • Know yourself
    • Control Yourself
    • Know Others
    • Do Something for others
  • Traditional sales culture, smile and dial pretend that everything is fine 
Taboo subject in sales is mental health, does that make me look weak? What will my employer think?
It affects how you do your job
  • Appreciate managers, coworkers, companies to ask how someone is doing, care and take action based upon that
  • Care about you beyond a just the number that you brought in and see you as a full human
  • Be at a good company that understands the human aspect of things
  • Sales Mentor program - working with a solutions engineer- talking about mental health, building good habits for yourself and working on myself
Building a morning routine; going on a walk every morning, listening to a podcast, let the sun hit your face.
Colleen Hayes - Presenz
Take some time for myself, take a midday break and after work find a way to decompress
Change your hours to help you be your best self
Hate losing
Success= happiness, feel good about what youโ€™ve done. Used to be how much $$ am I making, my car, materialistic things
Was VERY achiever driven in the past and now realizing there is more to life. Am I happy? Do I like what I do everyday? Do I love the people Iโ€™m around?


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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.