Help Me Choose
Jordan Benjamin

By: Jordan Benjamin on May 26th, 2021

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Failing Forward, Lessons on Sales Leadership



How’d you get into sales?



Always fun to reflect on how you got here as you extrapolate out your career

When I finished school- got a shiny piece of paper and asked Now what? 

You feel proud, excited, that you have enough and pretty quickly can become deflated trying to get your career started

I probably sent out hundreds of applications - had the fortunate timing graduating in 2008 during the recession

I figured out how to learn different skills

Traveled for almost 2 years after school, I found work, worked in Nicaragua for a few months teaching econ and learning Spanish

I remember calling my bank to check my balance and told me I had $25 left, I was PUMPED!

I had $25 to start my career journey, a lot of problem solving and skills I learned from traveling on how to get from here to there.

Grew up in New Hampshire and had a friend hiring for a sales role selling merchant accounts

I had no idea what I was getting into, day 2/3 I knew it wasn’t the job for me but decided, If I’m in this I need to figure out how to be GREAT at something. So I stayed there for 1.5 years.

I figured how to connect with the customers, the flow of a sales call. 

I would set goals for myself to see how quickly I could close the deals

It wasn’t the most sophisticated sale but I decided I wanted to gain a higher degree of mastery 

Reached out to Forrester research - some of the best experiences of my early sales career- Thrown into the deep end with tech buyers who had been purchasing tech & research for decades!

Thought I knew what I was doing as this junior guy and I stumbled my first few months

Had a great leader who was a great motivator and great coach, Michelle Allen

Put me into an underperforming  territory of Chicago and she bet on me to turn it around!

Ended up #1 in the company in sales, got to fly private with the CEO 

Could see the impact I had on businesses, thought it was amazing and wanted to see what’s next?!

Heard about HubSpot and never had any research on them, but hadn’t been covering the market for HubSpot 

Found a friend as a recruiter at HubSpot, wanted to learn SaaS and engage with these higher level buyers, and follow a great leadership team. 

It gave me an opportunity to learn something new and I was struggling my first 4-5 months and I couldn’t figure out why? 

Why aren’t my playbooks that had worked time and time again working, I realized I needed to be open to learning and bringing my history with me. Don’t just bring your old playbooks but look to learn and be curious.

A lot of great people from HubSpot alumni are doing great things NOW! 

Was able to step into my time as a leader at HubSpot, you think you’re taking off in your career and you stumble and fall, but hope to FAIL FORWARD

When I first stepped into leadership it was incredibly humbling, you have to stop and reflect, What am I doing right? What am I doing wrong? How can I reach out to peers and mentors to improve and find guidance?

VirtueDen- reached out to build their go to market, 2 guys with an awesome tool that didn’t have a big sales background. I love building things.  I love figuring out how to get from here to there!

Got to dive into the inner working of the machine which opened up the Compass opportunity, it’s adding all of these pieces together from my past experience.  Going from how customer learn shop and buy to align in an industry I haven’t worked in before. 

Connect with people across the entire organization, each new role is more challenging than the last and has been great, great to celebrate heading into the public market with the team of course.


JB: What an awesome sales journey over multiple years with the past view into being a young grad and traveling that all culminates to give you a unique perspective on leadership.  Multiple times struggling and failing forward with new challenges each time.  



I'm so grateful for the experience. There’s nothing to make a career easy.

A Career is a hard thing to build

I remember Mike Volpe coming in saying “ when you look back at your career it’s going to look like this steady up and to the right, but when you’re in it it’s going to feel like a staircase”  You figure something out you go up, and plateau a bit, then do it again 

It’s so hard to wrap your head around when you’re in the trenches everyday. 

It’s really important that you don’t give up on yourself, developing yourself and leaning into being better everyday because it compounds. 

JB: Compounding tiny changes is so powerful over a career to move into a leadership role. Everyone is making things up every day along the way you need to be open to learning, to feedback to continually improve.  So much motivation and inspiration 



Hitting quota for the month/year, the great note from your manager are all so fleeting

It can be exhausting to reach for those milestones. 

Reaching for those milestones is important, it’s a part of it but there has to be more, you won’t find joy/pleasure if you’re just shooting for the number.milestones it will lead to burnout


JB: How do you think about setting goals and defining the bigger goals?



Every year at the start of the year around Christmas to the start of January I take 2 weeks off, totally disconnect and spend time with family.

I take that time to reflect, used to journal now on apple notes

I focus on the bigger things, more macro level and step back because one bad day shouldn’t get me down

Example:  Buy a new house this year. Read x  numbers of books in a year.  Then I can take my next step to find books and then they sit next to bed and I read them throughout the year

Personal goal setting is super helpful

The business stuff will come through the cadence of the specific organization and understand the Northstar to understand WHY I’m doing the specific things everyday

If you miss out on WHY you’re doing the calls, the emails, etc. Your customers also get a terrible experience when you don’t think about the why. You miss out on the ability to slow down to think “why am I sending this message to this person at this time?” 

It takes the connectivity between the end goal and the day to day activities that don’t feel transactional


JB: Everyone will have their own unique system that works for them. You mentioned setting goals but struggling many different times. How do you bounce back from the tough months/weeks?



“I can accept failure, I can’t accept not trying” - Michael Jordan

The failure piece is bound to happen!

Did Fail Fast Fridays at Compass for a year to share the things that we failed on over video that would be highlighted.

You have to be of the mindset, especially if you’re doing something new, you’re going to fail and if you’re uncomfortable trying new things or something, you get stuck there more than anything!

For me, I tend to not take myself too seriously, if you get overly caught up in the emotion of the outcome you’re aiming for.  You become reactive vs. proactive- as soon as you get reactive, you are dooming your future because you stop focusing on pipeline creation while you are too nervous about closing

If you’re working for leaders where they are emotional to all of the reactions and make decisions from an emotional state vs. what are our options to refine to a better path/outcome next month or quarter. 

You can work for those leaders that make decisions objectively

I want to know I’m going to show up to the same person everyday whether the business is running well or not and be in a safe spot where I try to be a steady northstar.


JB:  How do you manage yourself daily? What practices do you have?


Exercise is a good thing. I would always go to the gym on my travels or in the morning.  Last year I was reeling a bit through the pandemic. Was in Boston in Q2 and couldn’t do that normal routine. This last year was tough.  Are you just going to grip the wheel and grind it out or look for something new?

Typically it was running, cycling and some weights stuff. I ended up getting into yoga over the last year. Going into a classroom doing yoga wasn’t going to be possible in 2020. In the past I was doing long runs, trail runs, century rides and I would mix in yoga. But I forgot about the mental piece as much as the physical stuff is really centering. 

You forget everything around you when you’re in it. I would wake up early AM, roll out the yoga mat and go to the office and take a long walk 40 mins to the office. 

Then I’ve been looking for new hobbies to occupy my mind and separate me from work. Reading. Got into fly fishing and I’m terrible, getting caught up everywhere and LOVING IT. 

I’ve added 2 new things of Yoga and Fly fishing to my routine this year that have helped.


JB: I’ve talked to a lot of people that have been struggling, burned out, gripping the wheel tighter and still haven’t found the ability to find something new and get past the first few challenges where you find new opportunities and leverage a growth mindset to find the best in what’s going on now. 

The first key to mental health is physical health.  It’s really challenging to have mental health if you don’t take care of your physical health. 

Talk to us about some of the Top qualities in Reps?



How do you find the common denominator?

Lots of people go to Grit and tenacity, persistence and those things matter. But there are some unique qualities you find. 

The best reps tend to be incredible educators.  It’s hard to test for when interviewing. 

When you sell a product it’s important to know how to help people learn the product and go through the process. 

The folks that are excellent at educating the process and the why it matters of the product, tend to do very well. 

They will get you 80% of the way there, still need to drive urgency, can talk Sandler & Challenger and all these things. 

If it’s confusing for your buyer to understand the process for evaluating and WHY this purchase matters to them, you’ll lose every single time. 


JB: Love winning or hate losing more?



Never been asked this question, heard it many times and never able to just answer it. 

I love winning more than I hate losing, it’s rooted in my belief that losses are an opportunity to win next time. You may have taken my pawn, but we still have an entire game left. 

JB: Top qualities in leaders


RS: Great coach, I want to learn from whoever I work with. Teach me how to do what you’re doing and help me be better than who I was starting today. I want to know they’re invested in me.


JB: How do you be a great coach?



They need to know you’re authentic. New manager goes right to call shadow and giving feedback. 

If there isn’t a consistent culture of feedback across the team. Feedback can start to feel punitive.  You have to create an environment of learning across the team before you push into coaching. Maybe bringing the team together to talk about what it means to inspire this culture of feedback, who you want to be and your investment in helping them. 

You need a starting point to initiate the coaching.  It can’t just happen every now and then, it needs to be consistent. 

Continue, start, stop doing. Build a framework to make it easy to receive.  

When you inspire those things across the team, I’m always getting feedback, everyone is getting it and still working here! It’s an investment in me and my future


JB: To see coaching as an investment in myself and my future self. 

Learning how to get from here to there. 

All of these experiences help you go from where you are today and where you’re headed. 




Instagram @Rpspillla

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.