Help Me Choose
Jordan Benjamin

By: Jordan Benjamin on May 12th, 2021

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Building Tools to Help Sellers


JB: How’d you get into sales?



Came from engineering and always loved building things for people and adding value. 

Building websites for people, 2nd hand cell phone business as a student in university

They wanted me to spend all my time behind a computer, lots of interviews and went to Business school→ got into marketing position → Biomedical engineering → Pharma -typically go through sales in Pharma, was a really boring thing with no freedom and possibility to change things 

Make sure sales people knew how to use it, went to marketing consultancy, became Account manager and learned a lot about sales there from finding leads to book meetings, learn about issues, create proposals budgets and full customer responsibility 


JB: Cool to bring a different background to leadership and sales product development


JC: Don’t remember much of the engineering anymore - gives some background to go deeper in technical conversations. 

The mindset and way of thinking is helpful 


JB: How do you think about goals and growth now leading your company?



We don’t focus totally on numeric goals, it’s hard to reach these things. 

We transform end goals into the things we’ll do on a consistent basis 

Now we can consistently check off the tasks 


Sales Quota Salesflare

It’s nice to have an output sales quota but it’s really helpful to have input level habits to get to the output



James Clear - Atomic Habits, it’s about the systems and activities you have in place that drive the output



2nd year we’re now working with these habits/systems vs. just tracking towards goals

Numbers of links, marketing shares, external visibility

Keep track of habits and deliver the consistent input = lower churn, increased conversion 

Inbound funnel that we put as much in at the beginning


JB: In sales we can miss the goals/habits/outcomes. How do you bounce back?



First it's important to acknowledge things aren’t going well

See there is a problem, and call it out

General team meeting every 2 weeks - What are the negatives? How will we solve them consistently? Then look through the positives to see what we have done well.

Demo moments for everyone to show off what they have built and then get feedback.


JB: What went well and what can we improve on? Personal habits and routines that you have to show up at your best?



Running, exercising every 2 days, and sleeping 8 hours/night, which is more important than exercise for me. Eating good food, just started watching food, whole foods plant based not.  Not totally vegan but taking control of his health. Lower the chance you get sick and up your overall well-being. 

Mindfulness off and on with the meditation

Sometimes his wife will turn on meditation before bed, I personally don’t really need it 

7 years of leading Salesflare they all seem like ups and downs that aren’t that scary


JB: You’ve seen the ups and downs and can handle them more effectively.  Sellers, especially early on can go really up and really far down.  Stoic philosophy is a great one to maintain level-headedness through sales. 



Focus on the stuff you can control. It doesn't make sense with your mind being busy for things you can’t control

Visualize the worst thing that can happen and realize it probably isn’t going to happen.

Whatever state you land in between is fine, we’ll try to avoid it and can accept 

You can invest in crypto and understand the ups and downs


JB: Visualize worst case scenario in Sales and still have the courage/bravery to push through it anyway. 



Psychology of Money - people more likely to consider you intelligent if you are pessimistic about something - we are programmed to stay safe. More likely to see the possibility of failure, it hurts more when we lose than have fun when we win. 


JB: How do you think about the psychology of the sellers that you work to build your products for? The habits they’re trying to build and how to support them?



Built our tools specifically for making follow-up easier, you may have hundreds of leads and it’s really hard to follow-up perfectly

Make the system so that it doesn’t fall apart.  Typically you don’t do the full data input 99% of the time. That means your system will start falling apart. No data in the system and it starts to fall apart. System will pull the information from where it already is and do automatic data and then adapt it manually. 

Build better relationships. Don’t disappoint people or lose relationships

Help people stay up to date, notifications to ensure you’re on top of everything and gamify things a bit 

Notice in initial onboarding people didn’t complete extra steps, when they complete steps will work them to open up extra days in their trial. If you’re doing this as a team and you complete a step, get a notification for the rest of the team that there are additional days and to keep the vibe going


JB: Gamification is a powerful force and we are tribal as humans so that makes sense for how it can drive increased engagement. I’m excited for the future of sales and seeing tools built to help the seller vs. being built for the EVP or IT team. 



Companies go after the big $$ which removes the practical aspect for the seller or end user because the buyer with the dollars is removed from the end user.

Software goes wrong and starts with the right intention

We just avoid making the decision to go after the big companies we aren’t building for the huge companies 


JB: Love winning or hate losing?



Hate Losing


JB:Top Qualities you’ve seen in leaders that you try to emulate or look up to.



Empathy- listening to the other person and what their context is. 

Communication skills- be able to clearly explain something, 

Willingness to learn and improve. 

Creating a culture where these types of things can live -- People need to have willingness to live and learn, important on a general level and want people to be able to express that. 

Communication - everyone says what they think is wrong with things. Everyone can speak up and say this is BS or really bad!

I’m not the only one that needs to look for things that are bad. 

I don’t know everything and you need to unleash all the thinking in a company


JB: What does success mean to you?



If you can make an impact for other people- that is business success- seeing that your offering is improving and helping more customers, seeing the team be more effective and can be better people. Seeing the people that may have left and are doing great. 

We’re not just building a product, we’re also growing a team in a sense that the people in it are growing!


JB: Where can people find you?




LinkedIN - connection requests please include a personal message 

Sales Flare Blog

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.