Inside Sales Expert

Helping leaders at early stage tech companies avoid mistakes in all aspects of growing their sales team in the US.

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It Happened on the Sales Floor-100 Sensational Stories About Sales Leadership Screw-Ups and Big-Wins

📢 Exciting News! 🎉 My audiobook "It Happened on the Sales Floor: 100 Sensational Stories About Sales Leadership Screw-Ups and Big Wins" is now available on Audible! 🎧📚

In this audiobook, I share 28 years of sales and sales leadership experience at tech startups. Learn from mentors, my countless mistakes, and the resilience that led to success in building sales teams. Topics covered include hiring, training, coaching, firing, sales processes, leadership challenges, and more.

This audiobook is an easy-to-read companion, not a heavy instruction manual. Pick it up with your morning coffee, read a couple of stories, and gain valuable takeaways for the day. I wish I had this book 20 years ago to avoid mistakes and achieve success quicker.

Get your copy on Audible and learn from my sales leadership mistakes: https://www.audible.com/pd/B0C6FRZ1MC/?source_code=AUDFPWS0223189MWT-BK-ACX0-353065&ref=acx_bty_BK_ACX0_353065_rh_us 🎧📖

#SalesLeadership #AudiobookRelease #SuccessStories

Audiobook Author

IVP Paragons are hand-selected operating executives with unique skills and a willingness to advise IVP portfolio companies become enduring market leaders. Paragons are experts at their craft, have a desire to give back, and actively want to participate in the start-up community (anywhere from Series B to newly
public companies).

(Full Disclosure:  I do not work FOR IVP.  This is an advisory role for their portfolio companies)

Paragon Advisor

Wonderway

SEON Fraud Fighters

Lensa

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Web Scribble

Helping leaders at early stage tech companies avoid mistakes in all aspects of growing their sales team | Advisor

I love helping leaders at early stage tech companies avoid mistakes in all aspects of growing their sales team.  I love sharing my experience and expertise from over 25 years.  You get experience, not inexperienced opinions.

Experience not Opinions

✅ 3 startups I’ve been with have had liquidity events (none fire sales)

✅ Helped build 3 businesses into Inc 500/Deloitte Fast 500 companies (that means fast revenue growth)

✅ Built sales teams at 8 Startups since 1997

✅ Built teams of 30 salespeople - 550 salespeople with GREAT gross margins

✅ Built multiple Inside Sales, SDR/BDR, Account Management and Enterprise Sales teams.

✅ Been in Sales Leadership since 1997

✅ Started 3 of my own businesses (Recruiting, Advising, Real Estate)

✅ Named to the AA-ISP Top 25 Most Influential Inside Sales Professionals 6 years in a row

✅ Made lots and lots of mistakes

Check out the recommendations section below to read what other people/clients have said about me. 👇

RFPs suck. 
 
Don't let your salespeople get enamored with completing one of these pieces of garbage. 
 
Waste of resources for your entire company. 
 
And the process is usually rigged anyway....against you and FOR the preferred supplier. 
 
Prove me wrong.

Kevin Gaither

If you're an a$$hole as a boss, your days are numbered. 
 
A world with loving and caring bosses is the wave of the future. 
 
And I love it. Why? 
 
The payoff for leaders who show love and care is creating a legacy of other great leaders. 
 
It's not about the money. If you're getting into leadership because you want to make more money, you're doing it for 100% the wrong reasons. 
 
It had better be a calling and a vocation you're driven to where your goal is to teach and lift up the people working for you. 
 
It's messages like the one below that make it all worthwhile. 
 
Now go be a loving and caring leader and leave that shitty boss that's dogging you.

graphical user interface, text, application, email

Old habits die hard. Thank you ZipRecruiter for all you did for me. 
 
I'm truly blessed, greatful and honored to have been chosen to join the ride early on.

I asked one of my top sales women to apply for sales manager but she refused. 
 
But her reason for not wanting to apply for the job took me back. 
 
👎 "KG, I'm the #11 rep on the team so clearly I still have a lot to learn before I apply." 
 
We were at TopGolf in AZ and I was introducing her to others on the sales leadership team because I WANTED her to apply for sales management... 
 
But I couldn't believe what I was hearing. She was 11th best salesperson out of over 200 salespeople and because of that, she didn't feel she was ready for sales leadership? 
 
I was confused. Thankfully, I was having dinner with the great Lauren Bailey the next night and here's the pointers she gave me: 
 
➡️ Women won’t apply until they meet 100% of requirements. Men will apply if they meet just 60%. Reduce the amount of requirements in your job description. 
 
➡️ Check to make sure that women are represented on your company leadership web pages already. 
 
➡️ Make sure the language in the job description doesn't contain overly male-dominated language like "aggressive" and "quota crushing." 
 
➡️ Make sure the hiring process has an interview team that ISN'T all white males. 
 
➡️ Keep actively encouraging females to apply for the leadership roles even if they don't meet ALL the requirements. Seek them out on the floor and ask them directly. 
 
I'm not sure how many bottles of wine that Lauren, Steve and I consumed that night but the learning lessons were out of this world. 
 
💡 Learning Lesson: If you want to get more women into your sales leadership team, you're going to have to evaluate several aspects of your recruiting and hiring process to make it a place where women will WANT to apply. 
 
Oh and one more thing, if you're reading this and thinking, "why are we always talking about getting more women into leadership?" Get with the program. Lack of diversity will kill your company. 
 
What else can we do to get more women into Sales Leadership roles?

After hiring 1000s of salespeople in 10 years, we figured out, "does a college degree matter or not for sales performance?" 
 
The question of whether salespeople need college degrees or not has been a hotly contested debate for decades. 
 
When I first started hiring salespeople in 2002, I was faced with this question and couldn't find anybody that had any ACTUAL DATA to support the decision. 
 
👉 But I had a hunch: Why the hell would having a college degree matter towards sales performance? 
 
But the question still nagged at me because all I could find was opinions and no real data. 
 
Should you hire a salesperson with a college degree? 
 
Does their education have any bearing on their ability to do their job? 
 
I finally worked at a company that had the analytical horsepower, coupled with the sheer quantity of hires to answer the question once and for all. 
 
🎓 Bottom line: After evaluating 1000s of hires over many years, we determined that there is NO correlation between even minimum levels of quota attainment and having a college degree. 
 
What made me especially happy was that we could finally put the debate to bed because we used real data and weren't relying on mere opinions. 
 
I'd love to hear your thoughts and experience on this. 
 
PS:  this isn't published research where there's a paper or a url to cite the research. This was an internal study done at one of my previous companies.

We're going full speed here at Trellis Law! And our sales team is continuing to contribute significantly to our company’s growth. 

That means I'm back on the recruiting trail looking to add more account executives to a star studded team. Specifically, we're adding Strategic / Enterprise level new business AEs, that like to hunt.

Beyond that, here are a few things an ideal candidate will need for this role: 

* Experience using MEDDICC or some variation of sales qualification method.
* A.B.C..."Always Be Curious" with a major bonus if Sandler Sales trained.
* Not afraid to prospect...Mostly cold outbound with some warm inbound.(70'ish/30'ish) 
* Need to have a "win or learn" mindset.

If you or anyone you know sounds like a fit, please reach out! #hiring #salesroles #startupgrowth

There's a right and wrong way to lay people off. Unfortunately, I've had to do it 4 times in my career. Here's SOME OF the right and wrong ways to do it. 
 
Wrong way: take weeks and weeks to make the cuts. 
 
Right way: Do it quickly. The team senses it's coming and the rumor mills are distracting. 
 
Wrong way: so surgical and sanitized that people are wondering what the hell happened. 
 
Right way: take time to explain what's happened, what's happening and what will happen next. They deserve it. 
 
Wrong way: once they door hits them on their butt, you never see them again. 
 
Right way: Do your best to try to help them find new jobs through your extensive network. When things pick up again, you might even be able to hire them back! 
 
Just like breaking up with a significant other, there's no PERFECT time to do it or perfect way but there are certainly right and wrong ways to do it. 
 
Anybody else have any personal experience with this? 
 
With all the layoffs happening, it would be great to let leaders know how to do it properly right?

I did this 1 dead simple thing each morning when I walked onto my sales floor. 
 
🤝 Walked up and down each aisle of my sales floor and greeted each and every salesperson by name. 
 
At first when my teams were smaller, I just did it because it was usually an open office and it was polite. 
 
But then I realized that by greeting each salesperson and using their first name, or sometimes their last name ( "Good morning Ms. Ben-Ari" ), 
 
❤️ salespeople usually want to feel connected to sales leadership and I was developing a bond with each and every one of them by using their name and giving them a fist bump in the morning. 
 
🤜 BTW, I'm a germaphobe so I prefer the fist bump over a handshake. It's not a bro thing when I do it. 
 
Years later, reps that used to work for me would recount to me how they liked it when I walked through teams of 100s of salespeople and greeted nearly all of them by name each morning. 
 
💡 Learning Lesson: Take a moment to greet your salespeople by name each morning. It will help you develop a mutual bond with the salespeople you're leading that can pay dividends down the line. In my experience... 
 
Since Remote Work is the Future Of Work, any tips on how to do this when your entire team is remote?

I've lost 52 lbs since Feb '22. But I lost the weight doing the same things that I've done building sales teams at startups 👇 
 
✅ Measure Inputs: I've logged over 2,000 meals in a row. Tracking all food. Tracking all steps. Tracking all calories. 
 
✅ Measure Outputs: Stepped on the scale. EVERY. DAY. For better or worse. Those signals help guide the day's Inputs and behaviors 
 
✅ Continually Learn: On Noom, there's 9 minutes of educational lessons each morning. While I'm eating egg whites for breakfast, I'm gettin' learned up. 
 
✅ Forgive myself: Popcorn. Pizza. Beer. Pizza. Was I being bad? No. I can eat what I want. There's consequences to my actions. Does that ruin the journey? Nope. Tomorrow I get to start fresh. 
 
✅ Stay Disciplined: There's days I don't want to put in the work. Or log the food. Or take the steps. This separates those that will succeed from those that won't. 
 
✅ Learn New Habits: Turns out I like eating pickles in the afternoon instead of a boxful of Cheez-Its. I've learned to couple listening to podcasts and audiobooks with getting in 10,000 steps. 
 
See the similarities?

Outside sales is dead. 
 
A McKinsey study found that over 75% of buyers and sellers alike now prefer virtual sales meetings over face-to-face interactions. 
 
If you're a leader at an early stage start up, keep leaning into building and scaling your inside sales teams because that's what most of your buyers want. 
 
Gone are the days when only the "grown up" salespeople are in outside sales or enterprise sales. 
 
Source: https://lnkd.in/gjtY59ez

I've learned that one of the most powerful phrases a sales leader can say to one of their salespeople is: 
 
"I trust you." 
 
And if you really mean it, watch out. That rep will run through walls for you. 
 
When you trust them and believe in them, they don't want to let you down.

I hired a DJ with no B2B sales experience for a B2B sales job. 😕 
 
I was starting to scale a new sales team and needed to make my first 2 hires. 
 
Once again, this was an experiment and my job depended on getting these first two hires right. 
 
So I hired one person who was referred to me and had B2B sales experience... 
 
But took a chance on another person who: 
 
🤷 Just graduated from Sac State a few months earlier 
 
🤷 Was a part time DJ 
 
🤷 And had an internship repping RedBull 
 
👉 Basically NO sales experience whatsoever. 
 
The "experienced" salesperson was meh. Solid B player. 
 
The newbie was one of the best sales hires I've ever made. Crushed it. Repeated President's Club. 
 
Scrappy. Coachable. Continual Learner. Organized. Flexible. Change Agent. Hard Working. Optimistic. Competitive. High Need for Achievement. 
 
All characteristics you can not teach. 
 
💡 Learning Lesson: When you're hiring your salespeople at your startup, 
 
✅ focus less on "experience" and current skills and 
 
✅ focus more on the behaviors, attitudes and beliefs (that you CAN'T teach) needed to be successful at YOUR startup. 
 
Anybody else had success hiring somebody who had NO B2B sales experience that ended up crushing it?

Be careful hating on salespeople. We're all in sales in some way or another. Prove me wrong.

Her male counterparts on the sales team were pounding their chests about how good they were to anybody who would listen but

Lauren Winer just quietly crushed her quota. But when it came time for promotions...

...she's the one that got the nod.

She then went on to help another startup grow and get acquired by Google.

Then she became the #1 salesperson at one of the largest global market research firms on the planet many years in a row.

So the next time you're giving out promotions, make sure you're looking at the women on your sales team that are not pounding their chests and appearing to be great.

You'll be glad you did.

Anybody else have any amazing stories of women on your sales team that quietly crush their quotas?

Despite what many people think about salespeople, the truly great salespeople never lie. 
 
They're not smart enough to keep track of their lies. 😳 
 
So they always tell the truth. 
 
It's easier that way.

I've made a mint helping people with no expectation of getting anything in return.

No, "I'll scratch your back if you scratch mine." Just helping.

And by doing so, I've been introduced to many, many people who END UP paying me to help them. 

Every once in a while, I help somebody with no expectation of getting anything in return and they send me a little gift.

It happened again today.

Thank you Marcin Malyszko and Mission Craft Cocktails 

What amazing packaging right? And the Margarita is literally award winning. #meetsexpectations

“Leaders are like tea bags: you only know how good they are when they land in hot water." 
 
Love this quote by Jo Owen. 
 
It was easy to be a leader in an expanding economy. 
 
The real leaders will emerge now that the economy has become tough.

have you ever built the desks from which your salespeople did the selling?

You know you're building a sales team from scratch when you have blisters on your hands on a Sunday afternoon in anticipation of new reps starting *in the office* on Monday.

It's a rite of passage few have experienced.

Mark Kosoglow knows what I'm talking about.

The worst kind of sales leader is one who refuses to admit their failures & blames others for what's gone wrong including their salespeople. 
 
Don't do that. 
 
Stuff goes wrong in life and in business. 
 
I know everything I need to know about you as a leader when I see you react and respond to an adverse situation. 
 
Do you blame others? 
 
Do you take accountability for it yourself?

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