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 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?

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Stock Option Course

Sign up for my free 10-email course here:

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And learn what the Founders aren't telling you about your stock options

77 Questions

Ready to hire A-player salespeople? Our free guide is your secret weapon, packed with 77 sales interview questions to help you crush the competition and build a powerhouse team.

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Hiring Bundle

Learn in one hour what took me 28 years to master. The Sales Leader’s Interviewing & Hiring Bundle (19 guides, templates, and 10 powerful lessons) helps CEOs and Sales Leaders hire top talent with confidence. Only $9.99, instant access. Link 👇🏻

https://www.insidesalesexpert.com/landing-page-hiring-bundle?utm_source=Linkedin&utm_medium=Post&utm_campaign=Hiring_Bundle&utm_id=FirstComment

Book Promo

100 Sensational Stories about Sales Leadership Screw-Ups and Big Wins

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VP of Sales Working Out

How to know in 30 days if your VP of Sales will work out....or not

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Mini-Podcast Series

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Avoid the mistakes that almost cost me my sales leadership career.

New Hire Training & Onboarding (not Pentis)

My free guide:  Best Practices for Onboarding and Training New Sales Teams
 
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It Happened on the Sales Floor

For 100 other sales leadership mistakes I've made, check out my book, It Happened On The Sales Floor: 100 Sensational Stories about Sales Leadership Screw-Ups and Big Wins. Link 👇
 
https://www.insidesalesexpert.com/landing-page-book-it-happened-on-the-sales-floor?utm_source=Linkedin&utm_medium=First_Comment&utm_campaign=Taplio_Boost&utm_id=Taplio_Boost

Model Week

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Mini-Pod

3 raw, 10-min audio lessons from my biggest failures as a sales leader...the kind you’ll never read in a textbook.

Practical. Fast. Real Stories. Real Lessons.

Only $4.99 - instant access, money-back guarantee.

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Podcast Promo

Link to the podcast episode here: https://www.salesnotselling.com/1039468/episodes/18403715-episode-69-selling-to-your-customer-not-you-with-guest-kevin-gaither

Job Seeker Course

Free Trial: The No-BS Job Search Course. 
First 4 lessons are free. No credit card required

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Helping job seekers stop guessing and start getting interviews | Free Trial: The Job Search Course

I received a job offer including a savage non-compete agreement. So I had a lawyer review it and she said: 
 
🦈 "This non-compete has more teeth in it than Jaws. If you really NEED a job, go ahead and sign it. If you don't need a job, don't sign it." (wait there's more) 👇 
 
But when I told the CEO why I was declining his offer, he said: 
 
"This is standard language. You know it's not enforceable." 
 
🤔 When I asked him to remove it, he refused. 
 
So I declined and referred another friend who DID NEED a job and he got the job, signing the non-compete. 
 
🚫 And years later, when he left the company, they sued him. 
 
He spent $60,000 to defend himself and then the company dropped the suit knowing the non-compete was not enforceable. 
 
💩 They sued him just to mess with him AND to send a clear message to their current employees. 
 
This was 2008 and the FTC just banned non-competes in April 2024. 
 
How many other employees have been screwed by these vicious, legal instruments since then? 
 
Have you been screwed over or limited by a non-compete? 
 
If you liked this real story - here's something else that can help you. 
 
Check out my book which is a collection of 100 short, real stories about my mistakes and learnings from 28 years of building sales teams at tech startups. 
 
There's even a free sample to download. 
 
https://lnkd.in/gXftNAaw

Bad Sales Leadership: 
 
• It's my way or the highway 
• My reps aren't hitting goal, their fault 
• Sales is art, not science 
 
Good Sales Leadership: 
 
• Let's figure out the best way together. I'm likely wrong. 
• Sales is a combination of science and art. We should always be measuring and testing. 
• My sales reps aren't hitting goal, that's my fault. How can we improve? 
 
One more thing.... 
 
• My sales reps are hitting goal. That's not on me. They did the work. What a testament to their coachability and skills! How can we get even better?

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 don't care about Dials, Meetings Held or Pipeline Generated, all that matters is reps hitting Quota!" 
 
Tell me you've never successfully scaled a sales team past 8-12 reps without telling me that you've never successfully scaled a sales team past 8-12 reps. 
 
I've made the mistake of saying this too early in my sales leadership career. 
 
I've also was convinced of this lie when I led an Enterprise Sales team. 
 
The fact is that you can't manage outputs, you can only manage inputs. 
 
With transactional/SMB/Inside Sales, reps must be held accountable for consistent talk time, conversations held, meetings held, and pipeline generated otherwise your outputs will be haphazard. 
 
With complex sales/Enterprise Sales, reps should also be held to Activities, Meetings and Pipeline. ESPECIALLY with expensive Enterprise reps and long sales cycles, if they're not being held accountable for pipeline generation, you're wasting company money. 
 
I know this from experience and screwing this up and then having to deal with the pain of change management.

You can skip your team lunches and "drinks with the sales leader." Here's a stupid-simple way to improve salesperson loyalty on your team. 
 
✅ As a sales leader, you can create loyalty by PROACTIVELY advocating for your deserving salespeople to get a raise, more stock options or a promotion. 
 
🎉 There's no better feeling one of your direct reports will have when you can surprise them with a raise, more stock options or a promotion. This goes way further to create loyalty than SPIFS or team lunches. 
 
Everybody knows that we live in an era where 'job hopping' is a common trend. Many believe that to get a significant raise or promotion, switching jobs is the only option. So, if you're proactive in advocating raises or stock options for your salespeople, you're not only demonstrating that you value their contribution but also showing that there's room for growth within your team. 
 
But remember, every action has an equal and opposite reaction. Advocate wisely, you don't want to create an environment where people expect a raise or promotions every few months. The goal is not to feed entitlement but to nurture commitment, devotion, and a strong work ethic on your team for those who truly deserve it. 
 
So take action today. Look at your team, identify the real go-getters, the silent performers and ask yourself, 'Who deserves a raise or more stock options?' Then, take action! 
 
For other tips on Sales Leadership, check out any one of my 10 free guides here: 
 
If you found this post useful - you might like one of my free sales leadership guides 
 
Get them here: https://lnkd.in/geVRveuC

2 days until the President's Club trip, contracts signed, $500k sent, some reps en route but I abruptly cancelled the trip. 
 
I was so torn. We made so many commitments already & I was going to have to explain my decision to our TOP reps. 
 
😖 This decision was going to be neither easy nor popular. 
 
At that time, there were no travel restrictions but we felt the risks with COVID were too high to continue. 
 
As leaders, we've all been there: 
 
• Tough decisions where you're being pulled in several directions 
• People you disagree with might be pissed 
• Explaining an unpopular decision to the masses 
 
At the end of the day, we cancelled the President's Club trip because it was the right thing to do. 
 
💡 Sales Leadership Learning Lesson: Do what you think is right regardless of the commitments you've already made and how many people you'll piss off. 
 
You'll rarely go wrong.

The contract is signed…but the bank account is still empty. Did the salesperson earn their commission payment?

Hot take: a signed contract means nothing if the cash never shows up.

I have seen teams celebrate deals that never turned into cash collected.

High fives and drinks on Friday. 

Silence 90 days later when invoices age and finance is calling the sales leader to find out where the payment is...

So here is the question I always ask sales leaders.

Did we actually win the deal, or did we just have a nice, fancy signature on a worthless piece of paper?

👉 I believe salespeople should get paid when the customer pays. Not when the ink dries.

This isn't about punishment or "turning our salespeople into collections agents."

Please, I've heard this all before.

What you need is alignment to the proper incentives.

A business that doesn't cash flow, dies.

It's just that simple and responsible sales leaders (and salespeople) should know this.

If your rep DOES become a collection agent, that's awful. That means you're a poor leader.

That is a broken system.

Great companies build tight processes between sales, finance, and ops.

✅ Clean, correct invoices the first time.
✅ Clear payment terms.
✅ Fast follow up.
✅ The rep owns the quality of the deal.
✅ The company owns the collection engine.

When both sides do their job, everyone wins.

I have lived both models.
✒️ I have been paid on signature.
💰 I have been paid on cash.

The difference in mindset is pretty huge.

When the rep is paid on cash, there's other teams that have to be held accountable to make it all work...and that's how it should be.

My lesson is simple.

"Revenue" is just an accounting term. "Bookings" look good on a dashboard someplace.

Your deal is not real until cash hits the bank.

If your comp plan rewards anything earlier, you're already mis-aligned to what makes businesses survive and thrive.

Fix it.

Should sales reps get paid when the deal is signed...or only when the customer actually pays the company?

If you could give your SDR team only ONE enablement resource (that's not a trainer) to make them 1% better every day... what is it?

I’m not looking for “read more books” or “use AI.”

I want specifics.

Exact book titles.
Exact podcasts.
Exact YouTube/TikTok/Instagram channels.
Exact software tools.

If you say AI, tell me the tool + the workflow.
If you say YouTube, tell me the channel.

My goal: build a short, sharp list of resources that actually move SDR performance and make them better, short of hiring a full-blown "SDR Trainer."

What’s the ONE that changed the game for you or your team?

Wanna hear my dead-simple way of measuring my salesperson hiring success rate? 
 
It's going to blow you away. Are you ready for it? 
 
After 6 months of hiring someone, ask yourself: 
 
"Knowing what I know now, would I hire that person again?"
 
Then document the result. Yes or no. It's just that simple.
 
Then optimize your hiring process based on what you learn. 

If you're consistently "yes" 80% of the time over many, many hires, you're in world class territory.

If you're at or below 50%, you're making expensive mistakes that are going to catch up to you if you don't fix it.
 
Not complicated and still most sales leaders are too lazy to do even this much right? 
 
PS: If you want to dramatically improve your chances of making an A-player sales hire, download my Sales Leader's Interviewing and Hiring Bundle for only $9.99.

Learn in one hour what took me 28 years to master. The Sales Leader’s Interviewing & Hiring Bundle (19 guides, templates, and 10 powerful lessons) helps CEOs and Sales Leaders hire top talent with confidence.

https://lnkd.in/gDDmYsJH

8 super annoying things your salespeople do when they're *playing the victim* 
 
Nobody ever writes success stories about people who *play the victim* but it can be hard for sales leaders to identify when their salespeople are doing it. 
 
Here's some to watch out for: 
 
• Blaming others for situations and circumstances 
• Assuming other people cannot be trusted 
• Believing that one does not have control over one's own situation 
• Refusing to take responsibility or accountability for one's role in a situation 
• Becoming defensive 
• Claiming things are "rigged" against them 
• Claiming "Everyone else agrees with me" 
• Making excuses 
 
What are some of the other telltale signs of your salespeople playing the victim?

So you've given your rep the training and you know they know what to do but they're just not doing it and basically resisting your coaching, what do you do?

So basically the rep is saying to you with their actions (and maybe even their words):

"My way is the best way and I'm not going to take your coaching, thank you very much."

My approach?

They have a very short leash. 

1/ If they're NOT producing the results AND they've gone through the training and know what's expected of them but they resist the coaching...OUT.

2/ But if they're producing the results and have figured out a different, better way of doing it, I'm going to look to see if there's something we can learn from them and replicate it.

Our training and coaching can ALWAYS be improved and sales leaders need to be humber enough to admit this.

But if a rep has been trained and is flat-out resisting your coaching and not producing results....well....

Ain't nobody got time for that.

I learned many of these lessons the hard way and those mistakes have made me successful. I write about 100 of these screw-ups in my book, It Happened on the Sales Floor.

Get a free sample in the link in the first comment below. 👇

How do you handle a rep who resists your coaching?

Over the last 4 years, I've read 100+ articles on remote work. 

Truth is, there are 6 indisputable downsides we can all agree upon that most sales leaders don't know how to solve for.

Here they are (and I'll even cite my sources):

1. Higher Rates of Depression

"Fully remote [is] associated with an increased likelihood of anxiety and depression symptoms compared to in-person work, according to an analysis by the Integrated Benefits Institute"

2. Hard Time Disconnecting from Work

2023 Buffer study found that while 98% of those surveyed wanted to continue some form of remote, 22% reported having difficulty unplugging from work—with 81% checking email outside of work hours.

3. Perception of Lower Productivity

A Stanford report found workers thought productivity was higher at home (~7% higher) while managers thought it was lower (~3.5% lower). Regardless of the reality, you may be 𝙥𝙚𝙧𝙘𝙚𝙞𝙫𝙚𝙙 as being less productive.

4. Increased Chance of Being Laid Off

A recent report from the Society for Human Resource Managers (SHRM) showed that remote workers are 35% more likely to face layoffs than their office-based peers.” Out of office, out of mind.

5. Bias against those not in the office

UC Davis study found that the amount of time you’re 𝙨𝙚𝙚𝙣 in office can affect your boss's perception of you. Not in the office & others are? Some bosses may be intentionally/unintentionally biased against you.

6. Some can't afford a killer home workspace

No research here, just my own experience. Working from the kitchen table sucks. When we went to remote in March 2020, many sales reps just didn't have the right home work space because they couldn't afford it.

Am I opposed to remote/hybrid work? Absolutely not. I think it's the future of work.

But that doesn't mean we've perfected it yet and I think we can agree on these downsides and that we have a lot of work to do to make remote work as great as it could be.

Have any of you seen work environments that have solved for all 6 of these?

This is common and it's a tough one, especially for inexperienced interviewers.

You scheduled the interview and confirmed it. But then the candidate flakes. No call-no show. Now what?

My move: find out if this is a pattern. Is this the first time they've been late or flaked during the interview process?

Did they miss any deadlines or interviews in any previous part of the interview process? You see:

👉 Past performance is a great indication of future behavior.

Yes, missing one time. No problem. Let's reschedule.

But another time? Now that's a pattern.

And sorry, not sorry...the excuse or reason for either miss is not important.

Regardless of the excuse or reason given for the first time missing an interview/deadline, I'll give them a second chance.

Frankly, I don't want to hear the excuse.

But the second time.

1/ I definitely don't care what the excuse or reason is and
2/ The candidate is showing me a pattern of behavior and that won't fly on my team.

💡 Remember, during the interview process, the candidate is showing you their absolute best self. This is the BEST that they will ever be.

So if they're showing a pattern of flakiness during the interview process, you have somebody on your hands that is most likely a flaky person.

And don't fool yourself. You might be making your own excuses for this person thinking that this is likely an anomaly. A rare event.

The chances that's true are low. This is a candidate to avoid.

Hiring is one of the most important skills to learn as a leader. And learning how not to get duped by a flake is part of that.

If you're ready to step up your hiring and interviewing skills, check out my Sales Leader’s Interviewing & Hiring Bundle. The link is in the first comment 👇🏻

I made such a rookie mistake. If you can believe it, I couldn't fire a rep, who missed goal 6 months in a row! 😕 Here's why: 
 
The rep had missed their goal 6 months in a row!! Time to let them go right? So I went to HR to get the paperwork finalized to fire them and she said: 
 
👉 "Does he KNOW that he's not meeting your expectations?" 
 
My word....how could he not? They've missed goal 6 months in a row!!! 
 
💡 My mistake: I never TOLD the team that missing goal consistently was grounds for termination. I didn't have ONE conversation with the rep warning them what would happen. 
 
The learning lesson here is 
 
✅ make sure your reps KNOW in writing what it takes to get fired from their job and 
 
✅ if they fall short of those expectations have frequent, documented conversations with them when they fail to meet your expectations. 
 
I created a simple Sales Leader's Checklist for Terminating a Salesperson. Learn how to fire someone with professionalism, using a smooth and respectful process. 
 
Download it here: 
 
https://lnkd.in/gfhJqHk4

When your sales leaders run to you with problems they've found, here's the power move I learned that's good for all involved. 
 
I like sales leaders who appear like they've thought through a couple of possible solutions and a loose solution before they come running to me and write on Slack "can we chat?" or "got a sec?" 
 
But here's the power coaching move when they come to you with a problem they've found: 
 
✅ "Thank you for bringing this to me. Now go back and put a deck together for me that 
 
1. identifies how BIG the problem is, 
2. has 3 possible solutions and 
3. your recommended solution." 
 
This usually results in 3 outcomes: 
1. They don't bother doing the work 
2. They do the work and realize it's not a big enough problem themselves. 
3. They come back to me with a well thought out set of solutions and their recommended solution. 
 
Either of these 3 options are fine by me especially relative to running to me and expecting me to always solve the problem. 
 
What's your go-to way of handling your employees coming to you with problems and expecting you to solve them?

Once again, our US education system has let job seekers down. You spend 10s, even 100s of thousands of dollars for a fancy degree and this is what it gets you:

"Unemployed Americans with four-year college degrees hit a record in January, at 36.6% of those 25 and older, per Bloomberg"

Job seekers are really hurting and they need real help. And honestly, they have no clue how to conduct their job search.

But it's not the job seeker's fault.

Nobody taught them the right way to do it. The system failed them.

We got those fancy degrees from those expensive colleges but these colleges never taught us how to search for jobs, interview and negotiate offer letters!

But that’s why I built the No-BS Job Seeker Course.

19 lessons. Free trial. No CC req'd.

Link in first comment 👇

I used to hire based on gut instinct.
Charisma. Confidence. A great resume.

And more often than not, I paid the price.

But it wasn't my fault, nobody ever taught me how to hire great salespeople with a good repeatable process. As a result...

Some hires did great (actually the number was 30%).
Most flopped (the other 70%).
And the cost? About $400k PER mis-hire.

I realized that making bad hires WAS my fault and they're really expensive.

Let alone having to fire the ones that don't work out.

I felt guilty as hell and it WAS ALL MY FAULT.

So I made a change.
I didn't buy some sort of fancy tool.
I didn't go find "better recruiters who get it."
Just one major shift:

I documented the entire hiring process.

From how we screened resumes...
To the exact questions in every interview...
To a simple scorecard that forced clarity over charm.

Suddenly, hiring wasn't random.
It was consistent.

We knew who to hire.
We knew who to pass on.
And we moved fast...without second-guessing ourselves.

I’m not saying it was perfect.
But our success rate jumped to nearly 80%.

Because we stopped gambling.
And started implementing a repeatable interviewing and hiring process.

Here’s the kicker:
Most founders and sales leaders say they have a process.
But when I ask to see it?
Yeah, nothing. "It's in their head."

You can’t scale what you haven’t written down.
And you definitely can’t improve what’s not measurable & repeatable.

Your next 10 hires will either accelerate your growth…
Or cost you $4million when you screw them up.

Which side are you betting on?

👀 Learning Lesson: If you want to win in sales hiring, stop winging it. Build a clear, written process you can follow every single time. It’s not sexy...but it works.

PS: Hiring salespeople is hard. I know, I’ve screwed it up a ton. 

But that’s why I created the Sales Leader's Interviewing and Hiring Bundle Learn in one hour what took me 28 years to master. The Sales Leader’s Interviewing & Hiring Bundle (19 guides, templates, and 10 powerful lessons) helps CEOs and Sales Leaders hire top talent with confidence. Only $9.99, instant access. 

https://lnkd.in/g-3wryFJ

Insurtech companies need a predictable and scalable sales and marketing engine to hit growth milestones, meet investor expectations, and deliver consistent ROI. 

Standing in their way is the Growth Gap, a barrier fueled by misalignment, fragmented strategies, and uncertainty.

At Flashgrowth, we help Insurtechs overcome the Growth Gap. We identify barriers, design clear strategies, and execute hands-on to accelerate results. 

Insurance is all we focus on, and we have built a reputation as the go-to partner for Insurtech growth.

When the Growth Gap wins, execution stalls, capital dries up, and growth goals are missed. But when you defeat the Growth Gap, growth becomes measurable, scalable, and aligned. 

You gain confidence, focus, and market leadership.

Move from frustrated and reactive to focused and scaling predictably.

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Kevin Gaither

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