Help Me Choose
Jordan Benjamin

By: Jordan Benjamin on March 17th, 2021

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Michelle Benfer, VP Sales North America, HubSpot


JB: How’d you get into sales?


I come from a sales family

Mom was in sales working from home, BDR type role at home and in-office, hyper competitive always wanted to be #1. Saw her hustle and there was always a chance for jobs working in sales

Dad had analytical background from finance

Didn’t think she would get into sales, thought she would be a lawyer or politics, working for Kennedy’s in college

First job out of college- Route 1 Automile in Boston- get away from waiting tables, try that out and then got the sales bug, commission check and being $$ motivated could quickly eclipse what her peers were making as college grads

Got in Sales department at Harper’s Bazaar, Vogue and top women’s fashion magazines in NYC before transition to tech

Family had a budget, we can’t afford this or that, if you want to buy XYZ, you’ve got to get a job

14 years old started working at McDonald’s & delivering the Boston Globe in her neighborhood

Had to figure out how to make $$ and be in control of her own purchasing power

Now $$ motivated is a lot different = sending kids to school, plan for retirement

JB: Realizing this need for motivation in sales and drive to get to your ultimate goals.  I’m always curious about when things don’t go your way in tough quarters, months & years.  How did you handle that early days as IC? And now leading teams?


Bouncing back from tough times - IC early on, see you might miss and don’t have a path- lots of pipeline from scratch or your activity isn’t working

That FEELS like Crippling anxiety and at times is paralyzing - whether in personal or professional life, some sort of paralyzing anxiety.

This has happened as an IC, VP, Director

         Realize it’s a problem and What is the solution?

Remove emotion and the EGO Look at this as a business problem

Leverage people around me that do it well with their knowledge

Seek out other top performers

Mark Roberge - “top performers look at failure as an ITERATION NOT an Endpoint”

#1 thing I’ve seen with resilient leaders, Failure is part of our everyday, maybe once a month/quarter.

Sometimes failure is just not getting the most out of a day - if it’s not as productive as it can be - we are all here to continue to grow

JB: Can you talk to us about routines or habits you have to perform at your best?


New role- calendar is chock full - has an EA to help out, but need to be playing Offense AND Defense with her calendar

  1. Find thinking time, Fridays at least 2, hopefully 3 hours to get into flow state where I can sit, digest, read.

Hard to build strategy and long-term planning in short, 1 hour blocks

Yamini, CCO @ HubSpot - takes 1st day of the month off to decompress and have prep time

  1. What kind of micro-breaks do you need? I know I need at least 1 hour and then 30 minutes to get lunch and take the dog for a walk

Every day 30-40 min walking dog with doggie crew every morning, chit chat, talk about life and say goodbye to kiddos

  1. Shut off in the evening


JB: You mentioned some things that surround your desk, the environment you create and you mentioned a poem from your grandmother.


Michelle’s the family historian - cultivates and curates family history - Found a poem typed by her Grandma who Michelle never met. 

Don’t Quit

When things go wrong as they sometimes will

When the road you're trudging seems all uphill

When the funds are low and the depths are high

And you want to smile but you have to sigh

When care is pressing you down a bit, 

Rest if you must

But Don’t You Quit!

Resiliency, overcoming adversity, growth mindset, my family is really positive and optimistic people and they have definitely taken their lumps. We’ve always had this sense of resiliency and facing adversity with a positive attitude.

Dont Quit

JB: Knowing your core values and principles can help come back to those areas when times are tough. We talked a lot about mindset, attitude and beliefs.  When did you realize attitude and belief was a critical part of sales and sales leadership?


Attitude- I had crippling anxiety, self doubt- Remove my ego from the problem solving and getting myself out of the way.

Make is less about me and more about My Work - helped me improve my overall attitude 

Always want to iterate to reduce anxiety and improve myself and do that in a way that initiates change

Mindset- working at AOL, Manager → Director, fellow manager had the BIGGEST deals one after another after another. 

How is this guy closing such bigger deals?  He didn’t have Self limiting belief that it was a BIG DEAL

Present the best solution and see it as possible

She had Seed & Grow mentality which was a self-limiting belief

New sellers come in and don’t have Self-limiting belief holding the line on the sale, discounting, ASP

It’s really interesting to see how mindset plays into your sales game. 

Something she still works on, always looking to iterate and improve

Always checking in on my mindset and my own self-limiting beliefs to see where I can iterate and improve even as my role changes. 

JB: Interesting to see how those fundamental mindsets of sellers can lead to performance in any industry, role, etc. 

Some resources and books that you’ve looked at throughout your career that have been instrumental in helping you build this belief system that leads to your success. 


Books and resources - 

Worklife with Adam Grant podcast- what makes really great teams?

Daily Show - psychological safety

The Problem with All-stars- Great teams may have B players that make A Players better

ScaleUp With Reid Hoffamn

Tim Ferris Sometimes hot and cold - but focus on peak performance, what do people do to be their best selves?

Oprah Super Soul Sundays

Tony Robbins

It’s all about my own Self-iteration

JB: Talk to me about your other groups you connect with as a woman in sales. So many people that helped me as a seller were amazing women, I’m curious to hear more about how that has developed for you.


So much available now which she didn’t have any women in sales, women in business. 

Had to figure it out on her own and now she wants to Pay it forward!

Revenue Collective - There are other people to learn from.  Often thought where HubSpot is in our growth and where she is in her career, she has to learn from other larger companies; LinkedIn, Zoominfo, Google, Etc. 

You’re always learning.  What’s working well? What’s not?

She can also learn from folks that have much smaller orgs and teams

Hearing challenges other people go through helps her rethink what is, isn’t working. 

Always learning and over the last 5-7 years of her career, separate Ego from her worklife, be a student of learning from others 

Women in sales, raising children, being a working professional, navigate working up the ladder 


These aren’t separate from what men work on, it’s just nice to have a separate space for women to connect. 

JB: With work/life and covid especially it’s been really tough on working moms.  What have you found helpful with work life integration to show up for your teams and your home team/family as well?


Aunt who fell, that Michelle is healthcare proxy, had to go to hospital until 2AM. 

She had to help support her, you need to open space to be a human, Sometimes life just happens

At a certain point you just have to realize Life Happens and we’re all humans

We Work to Live, not always LIVE TO WORK

Letting go and knowing you can take personal time as needed. Working at a company like HubSpot that allows you to take the personal time really helps, and is where people can help you pick it up

The ebbs and flows of life just happen 

My colleagues know when kids lose a tooth, my dog barks and everyone knows

We’ve all had to become more intimate with our colleagues as they have a view into our homes

We all need to let our guard down and realize we have lives outside of work

JB: It hasn’t been as acceptable in the past to show up fully to work. Many people have a work self and home self that are very different and makes it difficult to be fulfilled in work.  

Empathy comes up in sales a lot lately.  What has led to a change in how we show up in sales?


Employee retention makes a big difference. Happy employees= more productive employees = happier customers = employee retention = bottom line impact

Create a culture where employees bring their best selves to work

First daughter 8 weeks off, 12 weeks off for 2nd - worked in the middle of it - was attending something the first week after having her daughter- had fear she would lose her job or progressing her career. 

I’ve been very lucky to work at companies that I know support my wellbeing and what my direct manager says to me and how they support me as well as the team around me

As a woman and the only female leader, felt like the outlier where other people had to pick up her slack when she went on leaving

Having leaders that say “we’ve got your back” Empathy and support 

You can have empathy but if you don’t pair that with support you’re in trouble

JB: What are the qualities you look for in the best leaders you’ve spent time with?


  • Support, knowing that somebody believes in me and is there for my development. 
  • Psychological safety and a partner for your success knowing you are there to help me
  • A high bar and expectation of performance 
  • Working smarter, not harder
  • Resiliency
  • Leaders who build great teams, not just the people that report to you. Your cross-functional partners and key stakeholders. Can you create a team environment?
  • Personal connection, we are humans. Checking in when you hear something personal, not just because it’s a checkbox, it’s because I know they are actually invested in my personal life

JB: Do you love winning or hate losing more?


This is a tough won, I  enjoy winning and hates losing

I hate losing more, that eats at me -- you can taste a win then on to the next one

JB: What is your favorite interview question?


Where could you be better? Find someone with a growth mindset- the future for someone.  Trying to get wisdom, tips and best practices. To hear someone working on their growth and where they are going.  What are their gaps and how can she help create a plan or partner with them.


JB: Any tips or advice for folks moving into a leadership role?


Be a student of iteration, constantly learning and evolving. Looking at yourself leading a team and where you can do better.  HOW WILL YOU CHECK ON THAT? Hold yourself accountable every 30 days, every quarter, bi-annual and annually moving towards your own personal growth, development and measuring it.

Super helpful separating ego from work! A lot of anxiety came from taking it personally when work wasn’t going well. Sometimes it IS personal, other times may be rough business model or external factors. Removing the emotion/ego from solving a work problem has really helped my growth and development. 


Links from the episode:

Michelle Benfer on LinkedIn

Worklife with Adam Grant- what makes really great teams?

Daily Show - psychological safety

The Problem with All-stars- Great teams may have B players that make A Players better

ScaleUp With Reid Hoffamn

Tim Ferris Sometimes hot and cold - but focus on peak performance, what do people do to be their best selves?

Oprah Super Soul Sundays

Tony Robbins

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.