Inside Sales Expert

Taking new clients only on a referral basis.

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

CRO and Founder

SmartBound

Sales development is changing rapidly with the advent of artificial intelligence.

For most CROs and sales leaders, asking "How can I use AI to power my pipeline generation team" leaves more questions than answers.

The team at SmartBound have an answer.

SmartBound combine two powerful things that make pipeline generation easier and more consistent: AI tooling and a conversation-first methodology.

I'm excited to join them as a Strategic Advisor as they grow their business.

Strategic Advisor

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

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

Trellis Research

Advisor

Schmoop, LLC

Managing Member

Wonderway

Boldr

SEON Fraud Fighters

Hirect App

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

Kevin has made 1000s of mistakes but that has made him successful. After building, fixing and growing sales teams at 8 startups and 3 liquidity events, he loves sharing these mistakes and learning lessons from over 25 years at pre-IPO tech companies so that you can avoid these mistakes and see faster success.

With KG, you get experience, not inexperienced 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 have said about me. 👇

Kevin Gaither

I hired this woman to sell for me and let me tell you, she absolutely sucked in her 1st 90 days.

But then she made President's Club 🎉

I was thinking, "Boy, I think I've made a hiring mistake with this one. Maybe I should let her go."

In her first 90 days, she wasn't ramping like all the rest. Wasn't nailing demos. Wasn't closing sales.

But she kept working at it. Hard. REALLY HARD. Following the playbook.

And she was unbelievably coachable. We listened to calls together. She listened to her calls by herself. Whatever I coached her on, she put it into place on the very next call.

And then it started clicking for her and by the end of the year, she made President's Club!

Learning Lesson: There's 4 types of salespeople:

➡️ Not coachable, not hitting goals. Term quickly. Like ASAP.

➡️ Not coachable but hitting or exceeding goals. Leave them alone and don't let anybody else on the team try to emulate them. These are naturals. They don't know why they're successful but they are.

➡️ Coachable and hitting goals. These are the examples you use for the rest of your team.

➡️ Coachable/Hard-Working but not hitting goals. Keep working with them in a defined, limited window. You'll be surprised how many will make it through when you give them good, solid coaching.

In your experience, how long would you work with a coachable salesperson who is not hitting their goals? 

But if you really want to start hiring A-player salespeople like this, check out my Interviewing and Hiring Bundle in the the first comment.

(2) Feed | LinkedIn

li_at

JSESSIONID

Talks about #sales, #startup, #leadership, #insidesales, and #peoplehelpingpeople

CEO @ InsideSalesExpert.com Helping sales leaders avoid galactically ridiculous mistakes in all areas of building, fixing & growing their sales teams

6 of my sales reps forced me to hire a woman as their sales manager. 

Don't be so surprised. She was one of the best sales leaders I've ever had the fortune to work with.

But the way this all went down was crazy and a learning lesson for me.

We were ramping up our sales team and I started hiring a bunch of people from a failing daily deal site.

I personally do reference checks and I kept talking to this one sales leader, Lauren Delfino.

Finally, I had hired 6 reps that had worked for her and they finally came to me and said

"KG, you have to hire her. She'll be a game-changer for our sales team!"

And so I did. And she was. Grew one of our sales teams from 50 reps to over 150 reps. Helped open up a new sales office in AZ. Crushed it.

💡 Learning Lesson: When you're hiring for new sales leaders, ask your sales reps who were THEIR favorite former sales managers and start networking with them to recruit and hire them.

What are some creative tactics you've used to recruit sales leadership talent?

But if you really want to start hiring A-player salespeople, check out my Interviewing and Hiring Bundle in the the first comment.

This dude legitimately showed up to an interview with me for a B2B tech sales job with neck tattoos & sleeves. 

I actually hired them!

At first, I was shocked. Couldn't believe what I was seeing.

Really? This isn't very professional. AT. ALL.

But I stuck to the objective hiring process I had created. Asked all my questions and remained open-minded as I listened to the answers.

I was blown away. Behind all that ink was one of the most humble, hard working, positive and motivated people I had ever interviewed. Not cocky and assumptive.

I hired that person and they turned out to be one of the best salespeople I have ever hired in my entire career.

Good thing I didn't judge the book by its cover right?

💡 Learning Lessons: 

✅ Develop your salesperson hiring benchmark with objective characteristics, 

✅ judge them based on their answers and their actions and not by how they look. 

✅ Reserve judgement on the candidate for after the interview, not before.

Removing bias from the interview process is critical. You miss out on great hires when you introduce bias into the interview process.

But if you really want to start hiring A-player salespeople, check out my Interviewing and Hiring Bundle in the the first comment.

My rep laughed when she got hung up on. 🤣

I hired this rep whose only previous sales experience was selling lingerie at Nordstroms. No B2B. No phone sales. No tech.

But I observed that she scored very high on optimism, resiliency and coachability during the interview.

So I took a chance on her anyway to break into B2B tech sales. What a great hire!

We were all on an open sales floor. I had a low-walled cubicle right on the other side of hers. 

When she got hung up on, she would stand up, peer over the cubicle at me and laugh about how she got hung up on. "Their loss," she would say.

And then sit down and go right back to making more cold calls without skipping another beat. My word.

The learning lesson here: When you're a leader hiring for new reps, sometimes the ones with NO relevant experience can be your best reps if they are optimistic, resilient and coachable.

Make sure you build that into your interview scorecards.

But if you really want to start hiring A-player salespeople, check out my Hiring and Interviewing Bundle in the the first comment.

The last time this person worked for me was exactly 18 years ago and I just got this text from them a few months ago.

This kind of stuff makes me so happy to read. A salesperson who worked for me nearly two decades ago still wants to share their successes with me long after we worked together.

If you're a sales leader and you're having a rough time, getting messages like this from salespeople who used to work for you is extremely up-lifting.

Wanna share some messages former reps have sent you in the comments?

graphical user interface, text, application, chat or text message

I hired an "experienced" sales manager and boy what a mistake that was. 🙇

We were scaling my inside sales team and needed to hire a bunch of new sales managers.

And I was referred to a guy who was literally at a direct competitor.

Nearly the exact same product. Same sales cycle. Same inside sales motion. Same deal size. Why wouldn't that be a fit?

My word, what a mistake that was. This guy was a train-wreck.

👎 He was a micromanager

👎 Managed through fear and intimidation

👎 Wouldn't listen to me or any of his supervisors 

👎 Made excuses for why he behaved the way he behaved

I fired him in less than 90 days. 

💡 Learning lesson: Just because the sales manager came from a direct competitor don't assume that they will be a good fit for YOUR TEAM and YOUR CULTURE.

Include the cultural questions in your sales manager hiring benchmark such as...

"Tell me about the last time you had an underperforming rep, what did you do about it?"

But if you really want to start hiring A-player salespeople, check out my Interviewing and Hiring Bundle in the the first comment.

When I was an inexperienced sales leader, I used to think Urgency was something you could coach.

I don’t believe that anymore.

Urgency is either in someone’s DNA or it isn’t.
It shows up in their current and past actions.
It shows up in their business AND personal lives.
And you usually don't have to dig that deep to see it...when it's actually there.

The candidates who follow up without being told.
The ones who are closing for next steps at the end of the interview.
The ones who treat the job interview like a live deal, not some B$ chat.

You can’t fake that kind of pace.
And you can’t teach someone to care more than they actually do.

Yeah, you can force Urgency.
Riding the rep to get stuff done quickly.

But that's no fun, for anybody involved.

So if you’re hiring sales talent, I’ll say the quiet part out loud that many of you might object to (that's okay):

You’re better off hiring somebody with Urgency than hoping you can train or coach for it and then hope it shows up later.

That gamble will cost you revenue and it might even cost you your job.

My favorite interview question to test for it?

“Tell me about a time you were up against a tight deadline or quota. What did you do when it looked like you might miss it?”

What to listen for:

Do they take immediate ownership and problem-solve fast, or do they rationalize and delay?

Do they talk about proactive actions (calling prospects, re-prioritizing pipeline, staying late, asking for help) or passive reactions (“waited to see what would happen”)?

And then ask them to tell you about ANOTHER time.

Urgency, in the truly urgent, shows up consistently and recently. Not every once in a while.

If they can't show you that they already have urgency, you’ll end up begging them to BE urgent later.

And that’s not your job as a sales leader.

Lesson I’ve learned from tons of my own hiring mistakes?

Hire the people who already show Urgency. You can't train that.

For most sales leaders, you're not just in it for the titles and the money.

Heck, if you were in it for the money, might as well be an IC and not have to deal with all the BS of being a sales leader.

No, you're in it because you can really make a positive and indelible mark one someone's life for decades to come.

Go do that.

PS: he took a chance working for me too...

You don’t “own part of the company” when you join a pre-IPO tech startup and get stock options.

You own a promise.

And most promises never cash out....like 90% chance your stock options will be worth NOTHING.

To make matters worse, Founders rarely explain your stock options to you.

And most employees never read the fine print either and/or self-educate, that's on them. They just sign and cross their fingers. Stupid.

Stock options in that sexy new AI startup sound like magic. The next big rocketship in flight. The HUGE potential payday.

Of course, it's a story we all want to believe but it rarely happens and if it does, it's rarely material.

I've been at 8 startups. 3 have had liquidity events, but that means that 5 did not have liquidity events.

So from experience, here’s what actually happens:

The valuation is inflated.
The vesting schedule is brutal.
The exit timeline? You think they're going to tell YOU?

Liquidity? Don’t hold your breath. If you're lucky you have a 1 in 6 chance of a liquidity event and even then, it won't be helicopter money like you think it should be.

Oh and here's one you'll learn the hard way...

You still owe taxes...even if your shares end up being worthless.

And if you have vested stock options but leave before some sort of liquidity event...God help you....

You’ve got 90 days to buy them or lose everything.

So should you ever join a startup just for the equity?

In my experience and in my opinion, never.

Equity is a lottery ticket. It's the icing on the cake.

Your cash comp is critical. If you can’t live on the cash, don’t gamble on the stock option upside because the chances of it happening are slim to none.

And if the Founders can’t back up the value of the options with a real, competitive TOTAL offer, to me, that’s a red flag.

Join for the mission.
Join for the team.
Join because you love the work (because you'll be working your ASS off, no quiet quitting)

But don’t join because someone promised you 0.03% and told you it’ll be “worth billions one day.”

That's just a trick. Don't be a fool.

Learning lessons: if you're going to work at pre-IPO tech startups, you had better learn about Employee Stock Options so that you can assess if you're getting a good deal or not and manage them properly.

Which is why I created a FREE course on Employee Stock Options, How They Work. I took all my learnings and dumbed it down so even a 3-year old can understand it.

Check the link in the first comment to sign up for the free course.

I hired a stay-at-home mom / photographer with no B2B tech sales experience and I should have seen what happened next.

She CRUSHED IT!

We were interviewing for another large hiring class and at that time, I was really involved in the hiring process.

All hands on deck at another startup!

And I was tasked with interviewing this woman who was a single-parent, stay-at-home mom, side-gig photographer.

She hadn't been in sales for 12 years as she was focused on raising her kids. And even then, the "sales role" she had wasn't even B2B sales.

I thought: "Why did this person make it through to the in-person interview?"

But she crushed her interview! 

You see we were interviewing for behavioral characteristics like Coachability, Organization, Competitiveness, Need for Achievement, Optimism and not experience and she had lots of recent stories that demonstrated that she possessed those characteristics.

I made sure we hired her and I'm glad we did. She made President's Club several times!

💡 Learning Lesson: Especially for sales roles at startups, interview mostly for behavioral characteristics that you CAN NOT teach above experience. You'll find diamonds in the rough that others, who are only interviewing for experience, won't find. It will be your competitive advantage. 

Trust me.

What do you think? Does this apply to all sales roles? Even Enterprise?

But if you really want to start hiring A-player salespeople, check out my Interviewing and Hiring Bundle in the the first comment.

99 out of 100 salespeople have common sense. But most policies and rules aren’t written for them.

They’re written for the 1 who either
1) is too stupid even have common sense
or
2) is just smart enough to exploit the gray area.

And that ONE person ruins it for everyone else.

It always sounds like this:

“Well I didn’t know I wasn’t supposed to do that...”

Or worse:

“Nobody TOLD me I couldn’t do that...”

Give me a frickin' break. 🙄

This is why we get 14-paragraph HR policies.
This is why companies build a handbook thicker than a Bible.
Not to guide the 99...
No, to make it stupid-simple clear to the 1.

Because when left alone, the 1 becomes a problem child.

They test boundaries.
Twist intent.
Weaponize ambiguity.
Then play the innocent card when caught.

I once had this clever salesperson who was allowed to work from home but when I learned she wasn't working her leads/accounts, HR and I met with her the next day she was in the office

😡 But she claimed she didn't know the different between "Working from Home" and "Out of the Office."

She played stupid because I hadn't made the difference crystal clear IN writing.

And that’s when leaders start writing policies to cover every angle.

Which restricts freedom for everyone else.

So now, instead of trusting the 99, we start managing to the 1.
Instead of enabling high performance, we’re policing edge cases.
Which sucks.

Every leader knows who their 1 problem child is.
And every minute they avoid dealing with their BS
Is another minute you're asking for trouble.

Want to be untouchable at work?

Stop playing the loyal employee game and start building a war chest.

Here are 3 money rules that saved my sanity when I still had a boss:

1️⃣ Six months of cash in the bank. If you can’t disappear for half a year, you’re not free.
2️⃣ Track every expense. Live way below your means. If your lifestyle’s eating your freedom, you’re doing it wrong.
3️⃣ Build a side gig. Something that generates a little bit of something something at first.

You do those 3 things and you'll breathe a sigh of relief.

You stop saying yes to stupid meetings.
You stop nodding along when a new commission plan comes out that you don't like.
You stop fearing layoffs, reorgs, or your CEO's mood swings.

Because now YOU hold the power.

And with ZIRP (Zero Interest Rate Policy) dead and Wall Street breathing down every CFO’s neck, companies are being forced to run real businesses the right way:

🔒 Profitable
🔧 Efficient
📈 Growing

So ask yourself: are YOU running your life like a real Profitable, Efficient, Growing business?

✅ Profitable: Expenses < Income. No excuses.
✅ Efficient: Cut dumb spending. Stack cash. Invest cash.
✅ Growing: Build other income streams. Anything. Something. Learning something new.

If your whole identity is tied to your job, you’re screwed the second it turns on you (not if...when).

Don’t wait.

Because the next round of cuts is already being planned and the people with options won’t beg, won’t cry, and won’t blink.

They’ll just leave and move on.

I've been laid off or fired 3 times in my career and my advice above has saved my bacon every time. And I've quit 2 high paying jobs quickly, with no job in sight when I knew it wasn't going to work out for the long haul.

Takeaway: If you're living paycheck to paycheck, you've let your employer take control over your life. Build the war chest that lets you walk the hell away on your terms.

I once hired a woman who crushed quota but had NEVER played a single sport in her life.

No soccer. No basketball. No volleyball.
But yoga? Oh, she dominated yoga.

She was a “front of the class” type. The kind who could hold poses others fell out of after 10 seconds.

But here’s the kicker.

While the rest of the class focused on breathing and balance...
She was peeking out of the side of her eye to see who was falling down.

She didn’t just want to master the pose just for inner peace.
She wanted to kick the other students asses and win.

But that’s when it hit me.

We keep throwing around this idea of hiring “sales athletes.”

We say bullshit things like:

"Find people who played D1"
"Look for team sports backgrounds"
"Only hire competitive athletes"

But it’s lazy logic.

Competitive doesn’t always look like cleats and sweat.

This woman was one of the fiercest reps I’ve ever hired.
Not because of her athletic background.
But because she had the Drive most reps don’t.

She was calm on the outside.
Cutthroat on the inside.

And she didn’t need a scoreboard to tap into it.

I've seen ex-athletes coast and non-athletes outgrind everyone.
The difference?
Real competitiveness is internal.

The best salespeople I’ve hired?
They don’t always talk the most.
But they are driven to win.

🔥 Lesson: Stop filtering your pipeline for sports. Start filtering for characteristics that you can't teach.

Leave room to be surprised. That’s where the killers hide.

But if you really want to start hiring A-player salespeople, check out my Interviewing and Hiring Bundle in the the first comment.

Every sales leader must HIRE for the "mindset" that they want. But don't be a fool.

You can teach skills, but mindset? That’s a whole different game.

I’ve learned this the hard way.

Every team has a few reps who need coaching.
That’s normal. It’s part of the job.
But when you're expected to be a therapist?
Something’s broken.

Truth is...
You can’t rewire someone who doesn’t WANT to change.
Mindset shifts don’t happen on Slack channels and daily standups and ice cream socials.

No, they happen when someone is open, humble, and ready.

And most people aren’t.

So yes, when you want to effect a big mindshift change on your sales team, roll it out!

Raise the bar. Give the training and coaching to those that are ready to change.

✅ But hedge your bets too.
Start HIRING people who already think the way you need your team to think.

Because trying to coach a salesperson into hunger, ownership, urgency, positivity or resilience...when they don’t even value those things?

Screw that. That’s a fool’s errand.

Mindset is not a module in onboarding.
It’s the foundation people walk in with.
Or they don’t.

And if they don’t?
You’ll spend a lot of time dragging instead of leading.

Lesson I’ve learned?
Train for skills
But when it comes to mindset, hire it.

You'll have a higher probability of success, in my experience.

PS: if you want to improve your changes of making a great salesperson hire, check out my Hiring and Interviewing Bundle in the first comment.

Google asked for my college transcript but I instantly knew I wasn’t getting the job.

They wanted to know my GPA. I gave it to them: 2.685 from UC Davis, class of '94 (If you want to see a screenshot of my transcript, ask me in the comments).

That was the first, and only, time in my 30-year career anyone asked for my grades.

Not when I became a VP. Not when I became a CSO. Not when I ran a 550 person sales team.

I’ve hired hundreds of salespeople (maybe 1000s). I’ve never once checked their GPAs from High School or College.

Why do we act like grades predict success ESPECIALLY in sales?

In my experience, they don’t. Drive does. Integrity does. Grit, effort, continual learning, coachability, taking action...that’s what matters.

Would a 4.0 have changed my career? Maybe I get that job at Google. But I wouldn't trade where I’ve ended up for anything.

💡 Here’s my advice to founders and sales leaders: stop overvaluing academic stats when hiring.

They don’t measure the things that actually help you win.

👀 Look for Drive, Need for Achievement, Competitiveness, Coachability, Continual Learning, Hunger, A bias for action, Self-accountability.

Those are the signals that really matter.

And you won't find those on some dumb transcript. 🎓

PS: If you want to start hiring like a real pro, check out my Hiring Bundle in the first comment.

Every sales hiring manager says the same thing: "We want to hire driven salespeople."

Cool. But what exactly does that mean?

Because in my experience, "driven" isn't on a resume. You can't really see "driven" on a resume. So here's the real question:

🤷♀️ Can you teach a salesperson to be driven?

Short answer: In my experience, with adults, no.

Drive isn't taught. It's uncovered. You find out if they have it already or not.

🟢 You can coach skills.
🟢 You can develop technique.
🟢 You can build confidence.
🟢 But drive? That comes from inside.

It's baked in. It's who someone is when no one's watching.

You want driven? Look for people who:

-Take action even when not being told to act
-Laugh at rejection and move on
-Ask for feedback before you offer it....and then IMMEDIATELY put that feedback into action
-Work their butts off without having to be whipped
-Go the extra mile without being told

You don't teach adults this. Drive is a character trait. It's WHO they are already!

If someone doesn't need the push, they'll probably go further than anyone you constantly have to motivate.

✅ The best reps I ever hired didn’t talk about how driven they were. They showed it.

They were always coachable.
They were always learning.
They continued to persist.

And when I asked where that came from?

It was never training. Never books. Never ME.

👉 It was always internal.

If you’re a hiring manager, stop asking outright if someone is driven.

Start asking them to tell you stories about how they persisted or worked theri butts off or went above and beyond or took initiative or incorporated feedback.

And if you're a rep trying to break out?

Don’t wait to be taught. Start proving it, daily.

Drive shows up in behaviors and real stories, not just words.

Founders, CEOs, Sales Leaders: What's your favorite question to ask to determine if you have a Driven salesperson on your hands?

PS: if you want to step up your Interviewing Skills and make better Sales Hires, check out my hiring bundle in the first comment.

When the CEO gives you massive goals for next year, don’t say:
❌ “We can’t hit that number.”

Say this instead:

✅ “Under what conditions could we hit that number?”

That one sentence changes everything and sends a pretty killer signal to the CEO...

It signals problem-solving instead of resistance.
It opens a door instead of slamming it shut.
And it shows you’re thinking like an owner, not a victim being handed unreachable goals.

I’ve been on both sides of this conversation.
The leader who says “this is impossible.”
And the one who asks, “what would make it possible?”

One shuts down conversations with their closed mindset.

The other starts a great conversation with their growth mindset.

CEOs don’t set easy goals. No. We all know they're crazy AF.

They expect you to test the limits of what's possible

But if you come back with a "now way we're gonna hit that" instead conditions that could exist that will help you hit that goal, the CEO is gonna be giving you the side-eye.

And then they start networking with other sales leaders.

Reframing the conversation with “under what conditions...”
makes you the person who can be reasoned with,
not the person who needs to be replaced.

It shows you’re solution-oriented, not just looking for easy street.

Lesson I’ve learned?
As the VP of Sales, you had better not be the "yes-person" and just agree to everything.
You BETTER challenge your CEO with diverse and divergent opinions.

But if you're gonna just say "there's no way we can hit those goals," instead of saying "under what conditions CAN we hit those goals," why are you even there?

Especially at a pre-IPO tech startup.

PS: if you want to quickly know if your VP of Sales is gonna make it or not, check out my free guide in the first comment.

"I can tell in one conversation if I'm going to hire someone."

Then why do only 30%-50% of your sales hires actually work out?

You can hire better if you stop thinking....

👎 I know what to look for in a sales hire but I haven't written it down

👎 I can hire successfully but I've never read a book on interviewing before.

👎 I'll ask them to "sell me this pen" and that's a good way to assess a salesperson (I saw it in the Wolf of Wall Street movie so it must be credible)

👎 Why would I measure my hiring success rate?

👎 "Do you hate to lose or do you love to win?" is one of my favorite interview questions.

Hiring successfully is a methodical process.

According to TopGrading, "The average mis-hire rate for companies ... is approximately 70% (if you want the source, ask me in the comments)

These aren't the only myths sales leaders believe when hiring salespeople.

But if you really want to start hiring A-player salespeople, check out my Hiring and Interviewing Bundle in the the first comment.

I had this one VP of Sales I worked for tell me to hire salespeople with a "sales personality." Here's what they meant by that:

Hire salespeople that are loud, extroverted and gregarious.

But I learned over time that if you're hiring "loud, extroverted and gregarious" salespeople, you're doing it wrong.

In fact, one time I hired this rep who the quietest salesperson on the sales floor but was also the #1 salesperson.

I could barely hear what this dude was saying to me during the interview. His answers were very brief. Yet his answers were solid and he knew his numbers and his track record of success was demonstrable.

Thankfully several people on the team referred him to me and told me to hire him. But he still went through my difficult interview process. No free rides here.

And I kept thinking 

"salespeople are usually more gregarious"

"salespeople are usually more talkative"

But instead of giving in to the stereotypes we lay on salespeople, I stuck to my hiring benchmark and hired him.

He quickly went on to become our #1 salesperson in no time at all. And I never heard him on the phones and yet he was always on the phones. LOL

Learning Lesson: Don't listen to the stereotypes that you think you have about great salespeople. Create and stick to your hiring benchmark, put the person through the full interview process without premature judgement and look at the whole picture of the candidate.

What are some other salesperson stereotypes us hiring managers should look to avoid applying when hiring salespeople?

But if you really want to start hiring A-player salespeople, check out my Interviewing and Hiring Bundle in the the first comment.

#Sales #Leadership #startups #InsideSales #ExperienceNotOpinions"

I once had to sit in front of HR and explain why I was trying to fire a rep who missed quota six months in a row...

…and HR wouldn’t let me.

Why? Because I made one of the most rookie mistakes a sales leader can make.

And the lesson I learned that day changed the way I lead forever.

Every CEO and Sales Leader thinks they’re clear with expectations.
I thought I was too.
Until HR proved I wasn’t.

I go deeper into this painful (but valuable) story, and two others, in my new Mini-Pod Series: “Sales Leadership Mistakes You Can’t Afford to Make.”

🎧 It’s $4.99 and might save you from a $499,000 mistake someday.
👉 Listen today.

The link is in the first comment

Craig Wasilchak

Entrepreneurs'​ Organization

As a Growth Expert for the Entrepreneurs' Organization (EO), this role focuses on driving significant global growth by supporting EO leadership and chapters in achieving their objectives. Extensive expertise in digital business development, marketing strategy, and scaling is utilized to provide guidance, mentorship, and support to EO chapter leadership and members.

Responsibilities include analyzing chapter growth performance, identifying new growth opportunities, sharing EO growth best practices, and co-developing strategic plans and solutions that align with EO's mission of fostering entrepreneurial success. Emphasis is placed on creating a collaborative LinkedIn learning environment where entrepreneurs can tackle growth challenges, exchange ideas, and implement strategies that propel their EO chapters and businesses forward.

This approach not only enhances individual and chapter success but also contributes to EO’s overarching goal of empowering entrepreneurs worldwide to unlock their full potential and drive meaningful impact.

Entrepreneurs' Organization Growth Expert

The Entrepreneurs' Organization (EO) is a non-profit organization dedicated to helping entrepreneurs achieve their full potential in business and personal life through life-enhancing connections, shared experiences, and collaborative learning. Joining this member-led group of over 19,000 global entrepreneurs was undoubtedly one of the best decisions I’ve ever made.

In one sentence, EO is truly life-changing. As an entrepreneur and EO volunteer, I support other entrepreneurs in discovering the value of EO and understanding what it takes to qualify for and join local and global EO chapters.

Entrepreneurs' Organization Membership Chair

The Entrepreneurs' Organization (EO) is a member-led group comprising over 19,000 global entrepreneurs, each averaging revenues of $4 million. The Organization's members have a combined annual sales volume of over 72 Billion dollars. The Strategic Alliance Partner (SAP) Chair's purpose and passion lie in engaging existing and prospective Strategic Alliance Partners through a network of more than 19,000 global and local entrepreneurs. The Entrepreneurs' Organization represents a community of like-minded exclusive individuals that rank among the top 4% of successful entrepreneurs worldwide. EO fosters an environment where Strategic Alliance Partners can meet and form friendships and business relationships with high-value, successful entrepreneurs.

Entrepreneurs' Organization Strategic Alliance Partner (SAP) Chair

Imagine an organization that helps you achieve your full potential in your business and personal life through life-enhancing connections, shared experiences, and collaborative learning. The Entrepreneurs’ Organization (EO) helps entrepreneurs achieve their full potential in their business and personal lives.  

EO is a high-quality support network of 19,000+ like-minded leaders across 80 countries. We help entrepreneurs achieve their full potential through the power of life-enhancing connections, shared experiences, and collaborative learning.

EO has been helping entrepreneurs achieve transformational growth since 1987. Our member network is committed to learning and helping each other succeed. Gain access to the world’s top experts. Grow beyond your personal limits. Make breakthroughs as you redefine and realize your goals in life and in business.

Entrepreneurs' Organization Global Member

Visionary Entrepreneur | Podcast Guest & Keynote Speaker

I share real stories and lessons from building successful businesses as a founder, CEO, and leader. My talks focus on the realities of entrepreneurship—the wins, the losses, and everything in between.

I like to speak about:
✅ The power of vulnerability in leadership
✅ Building and scaling businesses
✅ How you have the ability to change the world
✅ Creating a legacy through entrepreneurship
✅ Entrepreneurial lessons that drive growth
✅ How Entrepreneurs' Organization (EO) shaped my journey

My mission is to inspire and equip entrepreneurs and leaders with practical strategies and mindset shifts they can apply immediately. Whether on stage or behind the mic, I believe real stories have the power to spark real change.

Founding Member

JW Management Company

Family-owned & operated Commercial Property Management & Leasing in Dallas Fort Worth.  
ARLINGTON TEXAS PROPERTY LOCATION: The 10 acre Westgate Business Park is adjacent to Arlington's Entertainment & Restaurant District. The Comercial Busines Park is located 1 walking block East of "Globe Life Park", Globe Life Field, & "Texas Live" with many superb restaurants. In addition, the property is only 3 blocks from the "Dallas Cowboys AT&T Stadium" & "Six Flags over Texas". The building space for lease consist of Office, Retail, Flex-Space, including Commercial Warehouse & Industrial buildings

DALLAS TEXAS PROPERTY LOCATION: The 4 acre 1625 Mockingbird Business Park is on Mockinbird in the Love Field Corridor, Stemmons Corridor area (Between I-35 and Love Field Airport).
The building space for lease consist of Office, Retail, Flex-Space, including Commercial Warehouse & Industrial buildings

Chief Executive Officer

TOP ELITE - Esteemed Member

Top Elite is an invitation-only esteemed group of dedicated business leaders fostering personal growth worldwide. And the best part? It's free to join once you're verified! Our mission is crystal clear: to equip individuals with the skills and resources they need to thrive. We invite you to be part of our journey!

About Top Elite:

Top Elite stands independently as the preferred community for Top Elite Members, an exclusive group recognized for their commitment to personal and business growth. Our mission is to empower individuals, enabling them to become influencers in their own lives. We achieve this through our free membership program, equipping participants with the tools to become influential in their chosen fields and connect effortlessly with key decision-makers.

Free Membership for Qualified Industry Experts:

Peer Support: Boost your social media posts with support from fellow Top Elite Members, leveraging social media advantages.

Efficient Networking Tools: Access tools that enable you to seek support from other Top Elite Members within seconds.

Member List: Enhance your LinkedIn visibility by utilizing instant connectivity with up to 50 of your industry's like-minded most active Top Elite Members. Approval for multiple Member List access is available based on your community performance.

Amplify Engagement: Multiply your LinkedIn engagement potential by 100X by being a Top Elite Member.

Prestigious Title: Earn the esteemed title of 'Top Elite Member.' Once approved for free membership, post that you are a Top Elite Expert in your industry on your LinkedIn profile under the Experience section as a member of the select group. The "Top Elite" Company Logo will appear on your LinkedIn Profile Page.

Top Elite Member Company Posting Feature: Seize the opportunity to be featured in the Top Elite Company Page.

Personalized Top Elite Influencer Training: One-on-one influencer training is available upon request.

Crushing B2B Digital Strategies

The team at Crushing B2B specializes in partnering with business groups seeking expert guidance in developing a LinkedIn-focused marketing and branding strategy aimed at attracting high-quality prospects. Their services are exclusively available to financially stable business teams, with a prerequisite of having annual sales exceeding $2,500,000.

As a lifelong serial entrepreneur and systems strategist, Craig Wasilchak understands business as well as wealth creation. He has walked a mile in your shoes and has implemented the Crushing B2B system within his own companies as well as many other successful companies.

President CEO

Do you have a LoopNet account you utilize for advertising your Single or Multi-tenant properties? Crushing B2B teaches Commercial Real Estate teams and business owners how to fully use LoopNet and exponentially generate more leads from your ads.  Do your current ads receive over 30,000 views in the last 90 days? 

LoopNet holds the key to generating Commercial Real Estate Leads. Businesses must understand how to build a multi-tiered digital brand that can be measured through lead generation. Simply placing a LoopNet ad and trusting the account rep to update your ad with industry best practices is a great way Not to get your share of LEADS.  LoopNet account reps are not SEO experts, so you get what you pay for... minimal leads. Ask us how we can help your company Maximize the number of leads your Commercial Real Estate properties generate monthly.

SEO and social media digital platforms are here to stay. Knowing how to properly utilize SEO within your LoopNet property profiles gives you a competitive advantage. Contact Craig Wasilchak to learn about improved ways to retain and grow your tenant customer base.

LoopNet Commercial Real Estate Lead Generation Strategist

Do you have a Crexi account you utilize for advertising your Single or Multi-tenant properties? CB2B teaches Commercial Real Estate teams and business owners how to fully use Crexi and exponentially generate more leads from your ads.  Do your current ads receive over 30,000 views in the last 90 days? 

Crexi holds the key to generating Commercial Real Estate Leads. Businesses must understand how to build a multi-tiered digital brand that can be measured through lead generation. Simply placing a Crexi ad and trusting the account rep to update your ad with industry best practices is a great way Not to get your share of LEADS. Crexi account reps are not SEO experts, so you get what you pay for... minimal leads. Ask us how we can help your company Maximize the number of leads your Commercial Real Estate properties generate monthly.

SEO and social media digital platforms are here to stay. Knowing how to properly utilize SEO within your LoopNet property profiles gives you a competitive advantage. Contact Craig Wasilchak to learn about improved ways to retain and grow your tenant customer base.

Crexi Commercial Real Estate Lead Generation Strategist

Entrepreneurs' Organization (EO) Fort Worth

The Entrepreneurs' Organization is for entrepreneurs only, with annual sales of over $1,000,000. The organization is a dynamic, global network of over 18,000+ business owners in 58 countries. It was founded in 1987 by a group of young entrepreneurs, Verne Harnish, Kevin Harrington, Ted Leonsis, and Michael Dell to name a few. EO is the catalyst that enables entrepreneurs to learn and grow from each other, leading to greater business success and enriched personal life.

Global Impact of the Entrepreneur's Organization:
 
• 19,000+ Global Membership
• 3,200,000+ Global number of workers EO Members Employ
• Most influential community of entrepreneurs in the world
• EO is a non-profit, and volunteer member-led organization.
• Benefits of being an EO Member  - Global Website: www.eonetwork.org

Fort Worth Entrepreneurs' Organization, Chapter Member

Travel Vacation Tips

Have you ever planned out your dream vacation only to learn it was not the dream vacation you envisioned? Knowing where to start when planning your dream trip can be challenging. Follow Travel Vacation Tips to find the best vacation tips and locations for your next vacation.

Alternative Business Automation Solutions

Sold in 2019 after 27 success years in business. Alternative Business Automation Solutions (ABAS) Acquired by Complete Mailing Partners.

ABAS specialize in workflow automation/optimization in the office environment. ABAS provides the automation equipment and software to streamline a business and reduce a company's overhead.

ABAS is a dealer for FP Mailing Systems, Secap (Pitney Bowes), Epson, Okidata, Konica Minolta, Kyocera, NextShip, Formax, Satori Software, and others.  We sell and service Pitney Bowes, FP and Neopost mailing machines and postage meters.  Along the way, ABAS has received countless service accolades and captured multiple sales awards from their manufacturers and customers.  ABAS strives to be our customer’s most trusted solution provider.  We rent and lease our mailing and MFP products to our customers utilizing fixed term agreements that are flexible.  We fit the right machine for the right customer.

Our employees are an integral part of the process.  We work as a team to find new ideas and methods to recycle and improve the way we do business.  We all pitch in to help out other team members whenever the need arises.

Craig Wasilchak has been on the AIMED Board of directors since 1998 and won the AIMED Murray Keating Dealer of the Year award in 2005.  He diligently serves the AIMED Community and gives back to the membership by running the AIMED Affinity program that has brought in just under $500,000.00.   

Our clients include names like Six Flags Over Texas, Brinker International (Chili's), Marriott,  Snelling Personnel, Airbus Helicopter, The City Of Arlington as well as hundreds of other small to enterprise level companies based in the Dallas Fort Worth Area.

Quadient

Quadient (Neopost) has sold Postage Meters and Mailing Equipment through independent Dealers who make up the Authorized Independent Dealership Program.  The Quadient Authorized Independent Dealership Program has provided local independent Dealers across North America the opportunity to sell Quadient equipment & solutions in their communities. As a Quadient Dealer we sold Postage Meters & Mailing Equipment to a wide range of customers in the Dallas Fort Worth Metroplex.  Currently, the Quadient Sales Model only sells direct in the Dallas Fort Worth Metroplex and does not works with Local Dallas Fort Worth Independent Dealers.

Xerox

For more than 20 years Xerox has sold its primary line of office products through independent local businesses who make up the Xerox Authorized Agent Program. Since 1982 the Authorized Agent Program has provided local businesses across North America the opportunity to sell Xerox equipment and solutions in their communities focusing on sales to small and medium-sized businesses. As a Xerox Authorized Sales Agent we sold the industry's leading portfolio of office products to a wide range of customers in the Dallas Fort Worth District

XEROX - Authorized Sales Agent

CEO | LinkedIn Top Voice | Top Entrepreneurship Voice | Top Commercial Real Estate Voice | Top Elite Founding Member | Multi-Tennant CRE | Branding & Social Media Strategist | EO Member |

In today’s digital-first landscape, buyers are more self-reliant than ever—they kick off their research on platforms like Google, where your LinkedIn profile often appears in the top 1-3 results before they even engage with your brand. That first impression is crucial: if your profile isn’t polished, professional, and trust-building, prospects will move on fast. Mastering social selling, digital marketing, and LinkedIn marketing is key to converting interest into engagement.

As a serial entrepreneur who’s built and sold 11 companies, I understand the challenges you face. My journey in developing strategic business models, driving sales growth through digital marketing, and learning from successful entrepreneurs has taught me the value of authenticity and continuous learning.

At Crushing B2B, I’ve created outbound and inbound marketing strategies that generate recurring income and attract high-quality prospects. As a dedicated LinkedIn Growth Expert working exclusively with Entrepreneurs' Organization (EO) Chapters, I build a repeatable inbound lead flow system that guides prospects from your digital presence into your EO Chapter, empowering you to share your valuable experiences with local entrepreneurs. I’m passionate about giving back to the community that fueled my own growth, volunteering my time to help EO thrive.

I also own a thriving multi-tenant CRE business in Dallas-Fort Worth. Leveraging strategic business models and trust-driven marketing, I bring innovative solutions to the CRE market by identifying lucrative opportunities, optimizing property portfolios, and guiding tenants through real estate challenges. By integrating deep industry knowledge with digital insights, I deliver tailored strategies that drive growth and foster lasting relationships.

For entrepreneurs growing or facing challenges, balancing business expansion with a sustainable lifestyle is key—build a solid foundation, nurture your team, and create harmony between your professional and personal lives. Focus on trust-based growth to overcome hurdles and build a lasting legacy.

I regularly share creative social media growth strategies on LinkedIn. Follow me or reach out to schedule a LinkedIn training session for your organization.

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The Battle

Kevin Gaither

Craig Wasilchak

Followers

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Performance ScoreKevin Gaither's LinkedIn Performance

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taplio

The Battle

Kevin Gaither

Craig Wasilchak

Followers

Posts

Engagements

Likes

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Kevin Gaither's LinkedIn Performance

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Performance ScoreKevin Gaither's LinkedIn Performance