Help Me Choose
Jordan Benjamin

By: Jordan Benjamin on March 31st, 2021

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Meghann Misiak, Founder, Path to President's Club



How’d you end up in sales?



Stumbled into sales 

Selling bathing suits at 15 in FL- getting people in suits they love the fit!

College- worked as leasing agent almost full time throughout college

Moved into COmmission only sales - ROUGH

BDR role is tough in tech, but can be a lot harder as commission only rep with NO resources, sink or swim environment- if you didn’t sell, you didn’t get paid and can’t pay rent

Need to learn from the best people, get hungry and get gritty

Sales training- getting into SaaS selling $30K deals vs. $30 swimsuits


Finding patterns, documenting them.  Was in a role as the only sales person after everyone quit ....”why can’t we attract and retain salespeople??” there was NO TRAINING



Wow love these thoughts and the journey through sales.  The vast majority of people I’ve interviewed don’t know what’s working or what they’ve done.  Such good points and a great sales story for us to unpack!



How do we build training for all of the types of sellers

3 different groups in sales teams, Middle of the pack, Still figuring it out & Peak performers

The beauty and challenge of sales it restarts every month/quarter/year

Peak Performers

How do we get the peak performers that edge? How do we get them to perform even higher?

As leaders, we see that person as good, making money and we realize they didn’t have upward mobility, thought they were happy but got complacent and they leave!

I went into sales training with a lot of assumptions to test and completely debunk

When I went into sales training, I thought everyone was LIKE ME- Hungry, eager to learn, gave them the training/tips/tactics/support that they would crush it….and that didn’t happen!

We have a new tool. It's going to be amazing, but why aren’t people using it?

First thing is understanding the mindset going into sales.  Are they open to training? Are they open to resources?

Give those sellers the WHY beyond; “you’re not going to get commission”

Sales people are really creative.  When you tell sellers to do something you find all the ways you can see how sellers get to acting like they did something. 

Give them their why? How do we understand their true motivation? It’s usually not money, because it’s a means to an end.  It could be Mastery. Family. Travel. 

Mindset is the first thing I had to rethink as I started building sales training programs. 

I did a lot of things that didn’t work and miserably failed myself and had to adjust. Many sales leaders don



So much training focuses on the tactic or the thing and yet most managers only tell their reps to dial the phone more and yet it’s not really effective at all because most hires realize and know that dialing the phone more will make them more $$. 



The thing around dialing and activity is one of the top reasons reps don’t trust their managers. 

So many times people are exhausted from hearing DO MORE DO MORE DO MORE, it really is the embodiment of the Hustle Culture. People are sick of hearing DO MORE

The best salespeople are problem solvers, they have natural curiosity. 

Exhausted of hearing do more and not seeing the results. They lose trust because they look at the numbers and see the best BDRs aren’t the one dialing the most. 

Clients come to me and say I hear do more and it’s not activity based. 

It’s a fine line, we know/studies show and natural intuition is obvious that we know if you do more, you will get more results

If you can get people to align with a strategy, most sellers want to learn WHY things work and it’s one of the best ways to motivate people.

I see you’re good on the activity and lean into the STRATEGY 

In QBRs with teams (QBR Meg) - Training on how to do a 10-K Report - running through office but top seller had a quick question about 10-K, found something interesting between training that give the seller a new strategy or new way to approach an account to motivate them to be better

To take someone from really good to great, having more moments of just being good and hitting quota can motivate, inspire and truly lead



100% is just doing your job



The story that inspired The Path to President’s Club

Mid-market team was between BDRs and senior sellers trained people. Manager quit right after a cycle of promotions, 5 people just got promoted and the manager quit. Took on a lot of responsibilities and learned a lot. 

Ask the team members, hey what do you want to achieve?  100% to quota… no what do you REALLY want to achieve?

Went to a former mentor from MSFT, who had a former manager who didn’t push past 100%. Created this coaching slide. 

Ask people - what’s your mission statement? Who are YOU as a person?  Not just as a seller.

Asking people they had never been asked before. What are your goals(not just quota)? What are the goals you haven’t told anyone because you’re scared they’re going to tell you is not realistic but really lights you up inside?

Because sales is so focused on lagging indicators of success, are you hitting quota or not?

HItting your quota isn’t a superpower

Started having really open conversation

3 up 3 down - after every sales call 3 things that went well and 3 things that could be better

Our conversations about feedback are typically about going on a PIP

One rep that would live at my desk, ask questions every single day, open o so many things….last company president’s club was Quota attainment based upon your number. I want to be the first person from this team ever to make it to president’s club 

$100K my first quarter---- a little crazy and let’s go for it!

Fell short, only sold $87K!  Now let’s readjust, hit 100% in October then started to focus on new post-it notes on his desk and had 2 new ones.  PC & SPOY - worked his butt off, hit PC, missed SPOY was 3rd

These incredible stories of motivation. It’s not that difficult if you have a framework.

Managers are so focused on quota/close rate


JB: You weren’t the manager, was it easier to have that conversation?



Lots of sales managers look at training/enablement to get the stuff done

I want to be in a position where you can work with people to have conversations I don’t have with the reps. 

I think the reason why a lot of managers struggle to enable people. A lot of times the way we train people is so SHADOW based- follow some people around and you’ll pick it up.  Most of the time it’s actually matching and mirroring. 

A lot of times people copy others vs. understand the STRATEGY/why. 


Work with sales teams and define the top strengths and weaknesses we should be building in people

What are the competencies for reps, BDRs and senior sales people moving towards management

Build custom coaching frameworks that give them the list of all the things they can choose form and can self-assess

What I see happening a lot of times in interviews and conversations with sales reps. They think they are doing a lot better than they are because they are only looking at sales numbers when managers have fears about the person’s ability to lead, have EQ, manage up.

Performance falls into 3 buckets. 

  1. Lagging indicators, performance metrics
  2. How are you evaluating organizational values - how do we build more inclusive and supportive sales cultures
  3. Competencies and skill sets - leading indicators of the leggings KPIs

Imagine if sales leaders had a more cohesive and comprehensive way of assessing performance

What if we had more direct conversations with reps about those things?


JB: What has prevented this from happening in sales conversations in the past? 



Been with sellers who don’t feel support

Most sales leaders are not going into sales thinking they don’t want to help their team, they are doing their best

Walk into work 1 day, have a territory, have a quota

Promoted, now walk into work, new desk, now 7 quotas, 7 different people -- but most people aren’t getting MANAGEMENT training

Most training is for tactical individual selling

Need to build empathy for managers - managers are managed and reported in the exact same way with lagging indicators 

The strategy piece is the 110% 

In today’s sales management world actually training and supporting your reps is seen as going above and beyond...that needs to be totally flipped on its head. 

Lots of HR background but HR is not Sales, they are not sales training, they don’t know what it’s like to hold a quota over your head and start over every quarter. 

Create resources for the seller that I’ve been. I also know what it’s like to walk into a sales leadership meeting and look at all the challenges that other teams tell you and see you’re not hitting goals without knowing your own weaknesses, very similar challenges that aren’t talked about

Better coaching, better support and better performance


JB: Talk to me about humanity and vulnerability in sales



It’s so challenging to train people.  It goes back to that HUMAN element - BDR had been in the role for 2 years, CRUSHING it and just moved to a partnership role, go to all SMEs ask for resources, get a lay of the land, the rep learned a lot about management and mentorship by making a mistake. 

1 year into the role, had templates and had people asking for her help. She just gave them the resources, the templates she was using. Started talking to these people and they were using the EXACT same template form a year ago, but she hadn’t taught them the HOW AND WHY for them to create their own approach. 

We don’t know what we don’t know!

Most managers struggle where they’re not trying to NOT train or coach and don’t get why it’s not working

Vulnerability piece is SO hard and it’s so easy to get frustrated.  But we as sales leaders need to recognize that Humans are Humans. 

Curse of Knowledge- as you get more advanced in your career it’s really easy to forget what it’s like to be that person who doesn’t know

We need to have more empathy. WE need to make it OK to make mistakes. We need to encourage curiosity and empathy. Just as much as we encourage competition and collaboration as well as Grit.

Vulnerability is the human trait I would like to see the most moving out of 2020 into 2021



Wow I’ve definitely seen this in the best leaders I’ve got to work with. 

What are the top qualities in leaders that you’ve worked with and want to emulate?



  1. Vulnerability - our current sales culture doesn’t leave space. It’s constantly so defensive (why aren’t you hitting? What’s missing here?) 

We are typically not met with empathy as a sales leader

  1. Empathy & EQ - should the manager be authoritarian - i want to be the person you come to with fears and challenges - Emotionally intelligent leaders go through to different leaders and progress in their careers and then come back to the leader with the emotional intelligence
  2. Transparency- without it, there’s no trust. We had to tell people I don’t have all the answers. Transparency is required to be vulnerable and to have high EQ. They see inherent risk involved in being 


JB: How do you bounce back?


Even as a consultant I have a business coach, I have mentors. A lot of people think entrepreneurs do it all on their own. It’s impossible to do it ALL on your own. 

I would encourage everyone to seek external mentorship, it’s very easy these days. RevGeniuns, Revenue Collective, Clubhouse making people really accessible (go find that person on LinkedIn and reference what you heard) 

Addicted to sticky notes, probably 40 around me at all times with Mantras that I’m working on. Little things. 

AND THAT’S OK. I’m not perfect, this was not ideal, or this didn’t work…..AND THAT’S OK!

On my coaching sheet I have helpful quotes and mantras with mentors you can work with in specific areas

5 Minute journal and gratitude journal to start everyday. Surround myself with people that lift me up and get me in the right mindset to get through tough months. 


JB: Morning routines and habits



I’ve heard a lot of people share ideas that don’t work for me. And I believe discipline is important.


I struggle with focus - 50 things I would LOVE to do but I’m always looking at - Mantra-- will this get me to the next $50K?

List top priorities everyday

REST- in such a hustle culture of sales, rest is critical, practicing self-love and healing to start everyday fresh

External mentorship group she runs. Text community with 3 women in a similar position to me, talking to them about my challenges. Another one for a mixed group of entrepreneurs  and do it externally so you can be super transparent. 

Those are routines that I’ve built during quarantine that are much different than my pre-covid




Path to President’s Club- Tues/Thurs free geek out sessions for specific questions and challenges

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.