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’m 55. I've had 3 successful exits in my sales leadership career & never have to take a W2 job again if I don't want one but... 
 
 ...I still don’t know what the hell I’m doing most of the time. 🤪 
 
Just a reminder that the people you may look up to, so-called "influencers," are still figuring it out. 
 
Life is the trip, there is no destination. 
 
If this resonated with you, you might like my book which is a collection of sales leadership stories of me screwing up and figuring stuff out. 
 
🆓 There's even a free sample to download. 
 
https://lnkd.in/gXftNAaw

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Stock Option Course

Sign up for my free 10-email course here:

https://www.insidesalesexpert.com/landing-page-email-course-on-employee-stock-options?utm_source=Linkedin&utm_medium=First_Comment&utm_campaign=AutoPlug&utm_id=AutoPlug

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.

https://www.insidesalesexpert.com/interview-questions-to-ask-salespeople?utm_source=Linkedin&utm_medium=Comment_Plug&utm_campaign=77_Questions

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

https://www.insidesalesexpert.com/landing-page-book-it-happened-on-the-sales-floor?utm_source=Linkedin&utm_medium=First_Comment&utm_id=First_Comment

VP of Sales Working Out

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

https://www.insidesalesexpert.com/will-the-vp-of-sales-work-out?utm_source=Linkedin&utm_medium=First_Comment&utm_campaign=First_Comment&utm_id=First_Comment

Mini-Podcast Series

Buy the $4.99 mini-podcast series here:

https://www.insidesalesexpert.com/offers/7P4geryA/checkout?utm_source=Linkedin&utm_medium=Text&utm_campaign=First_Comment&utm_id=First_Comment

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
 
https://www.insidesalesexpert.com/playbook-for-onboarding-new-salespeople?utm_source=Linkedin&utm_medium=First_Comment&utm_campaign=Taplio_Boost&utm_id=Taplio_Boost

https://www.insidesalesexpert.com/offers/z8LkYKe4?utm_source=Linkedin&utm_medium=first_comment&utm_campaign=Hiring_Bundle&utm_id=Hiring_Bundle

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

Great sales leaders intentionally manage their weeks. Check out my free guide, How Great Sales Managers Model Their Week, to see how they do it:

https://www.insidesalesexpert.com/model-week-for-sales-managers?utm_source=Linkedin&utm_medium=First_Comment&utm_campaign=Taplio_Boost&utm_id=Taplio_Boost

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.

https://www.insidesalesexpert.com/offers/7P4geryA?utm_source=Linkedin&utm_medium=Post&utm_campaign=FirstComment&utm_id=FirstComment

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 Playbook. 
First 4 lessons are free. No credit card required

https://www.insidesalesexpert.com/landing-page-no-bs-job-seeker-toolkit-free-trial?utm_source=Linkedin&utm_medium=FirstComment

Helping job seekers stop guessing and start getting interviews | Free Trial: The No-BS Job Search Playbook

Old school: Always Be Closing

New school: Always Be Helping

#PeopleHelpingPeople

This is the way

"Let's have this sales candidate do a demo presentation for us at the end of the interview"

Another galactically ridiculous step sales leaders put sales candidate through during the sales interview.

Here's 3 reasons why it's ridiculous for a sales candidate to do a demonstration during an interview:

1. Limited time: Interviews are typically limited in time and may not provide sufficient opportunity for the candidate to fully demonstrate their skills.

2. Lack of context: It may be difficult for the candidate to effectively demonstrate their skills without access to the necessary tools, resources, and information that they would normally have in a sales situation.

3. Unfair expectations: Asking a candidate to demonstrate their skills in a simulated sales situation may not be an accurate reflection of their abilities and may set unrealistic expectations.

Overall, it may be more effective to assess a sales candidate's skills through a combination of resume review, behavioral interviewing, and role-playing exercises rather than expecting them to perform a demonstration during the interview. 

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

*Annual* Performance Reviews should be eliminated for salespeople. Here's 2 reasons why: 
 
- They get "reviewed" monthly or quarterly depending on their quota cycle. "Did you exceed quota or fall below quota?" That's one form of clear, objective performance review and 
 
- They should be getting WEEKLY coaching from their sales manager with fresh, relevant reviews/coaching that point out where they're strong and their areas for improvement. 
 
I eliminated Annual Performance Reviews for my salespeople at my 550 person sales org. 
 
Win-win for everybody involved. 
 
Why wait until the end of the year to review your salespeople?

Here's the good news about being bullied in elementary and high school. I developed thick skin. I was weird then and I'm weird now.

Doing things differently and being weird got me punished back then. But I couldn't stop being weird. And only the truly weird work at start ups.

it's easy to take a job at BigCo. Nobody will judge you for that.

But going to a no name company that has a high chance of failure. Oh there were plenty of people who likely snickered behind my back.

But the thick skin I developed after being bullied for 10 years allowed me to continue on.

Now the joke's on them.

And now, I look back on all of the screw ups in my career and thank heavens that I had the guts to do the cringy stuff that LED ME TO SUCCESS.

Heck, I even wrote a whole cringy book about my screw-ups and failures.

The link is in the first comment.

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

If you think Inside Sales people are "less than" outside salespeople you are dead wrong. 
 
If you think the inside sales reps are the red-headed stepchildren of the sales team, you had better wake up. 
 
First, aren't we really ALL in Inside Sales these days? I mean, who is really spending 100% of their time on the road? When was the last time you walked into an office with an order and walked out with a signature? Yeah, never. 
 
Second, inside sales is one of the fastest-growing areas of the sales organization. Statistics suggest that one of the largest growth levers of inside sales is the opportunity it presents a company to be a “first responder”. 
 
✅ An outside sales call costs $308, an inside sales call costs $50 (PointClear) 
 
✅ 37% of high-growth companies use inside sales as primary sales strategy (vs. 27% for field sales, 23% for internet sales, 8% for channel sales) (Pacific Crest) 
 
✅ Outside Sales Reps Now Spend 89% More Time Selling Remotely Than in 2013. 
 
✅ Inside sales are said to be growing 15x faster than outside sales. (SalesLoft) 
 
✅ Three-fourths of buyers prefer not to meet sales agents face-to-face. (SalesLoft) 
 
✅ Ten inside sales representatives are hired for every one outside sales rep. (SalesLoft) 
 
So the next time you think the inside sales team is the baby sales team and the grown ups are on the Outside Sales/Enterprise Sales team, watch out. 
 
We're coming for you.

I saw sales reps get promoted, earn bigger comp & title & a bigger quota only to get fired when they fail to hit this new quota. 
 
But that is a colossal mistake & it tells me that the sales leader failed to have 2 dead-simple components in their performance management plan. 
 
1️⃣ Clearly documented and objective promotion path 
 
This is obvious. If the rep hits X% to goal X times over X period, they get a promotion. NO qualitative garbage! 
 
2️⃣ Clearly documented and objective demotion path. 
 
This is less obvious and I've rarely seen it. If the rep FAILS to hit X% to goal X times over X period, they get a demotion. 
 
What does this result in: 
✅ A bias-free promotion path. Just the numbers please. 
 
✅ A DEmotion path for reps who get promoted but can't cut it. 
 
✅ A bias-free path to termination (you can only get demoted so far) 
 
I never understood why sales leaders would promote a rep, see that rep struggle in the new higher position and then just fire them if they failed to hit that new, higher quota. 
 
🍼 It's like throwing the baby out with the bath water.

They told me to follow the rules. But then they went and hired their buddy.

I spent weeks tweaking my resume like some crazed lunatic.

Is it 1 page or 2? 
What size font?
Should it be an Objective or a Summary?
I even asked several friends to "review my resume."
WTF did they know?

But then I learned some half-baked "internal referral" waltzed into the job with a limp handshake and a slick smile.

That's when I knew:

The whole hiring process is basically rigged.

It’s not about performance.
It's not about the best resume.
It’s about proximity and safety.

The hiring manager and our friends in HR aren't looking for genius.

They’re looking for someone who is safe, won’t screw up and is vouched for by somebody else.
(Bonus points if Susan in Accounting already thinks you're cool)

So I stopped playing the stupid game we think we were taught to play.
No more "one-click" applying through job boards.
No more overthinking the importance of that marketing vehicle we call a resume.

I started learning how to build the only thing that actually moves the needle...the network on the inside.

Real conversations with real people there.
The kind who go, “Hey, you should meet this person,”
and suddenly your name's in a hiring manager's inbox BEFORE the role is even public.

That’s the backdoor.
It’s not a hack. It's not cheating.
It’s the only door that matters.

If you think it's unfair. You're right. It is. But that's the game you're playing whether you like it or not.

Your resume is just a cute little marketing vehicle that you have to have.
But if you do it right, it's merely a receipt stapled to a decision that was already made.

So yeah...follow the rules if you want.
Polish the hell out of your cute little resume.
Pray to the ATS algorithm gods.

Just realize that everyone who gets in walks through the back door, name already on the clipboard.

Keep knocking on the front door if you want. Just know no one's listening.

Or choose to learn how the game works so you can take advantage of it.

Build a relationship with people on the inside.
Skip the line.

Or stay stuck waiting in one where you never even get to see the inside.

🟢 Of course, job seekers really suck at this part and have no idea how to do this. Intuitively they know they need to do it, but they never do.

But it's not their fault. Our education system let them down once again and never taught job seekers how to job search let alone network.

But that's why I created the 𝗧𝗵𝗲 𝗡𝗼-𝗕𝗦 𝗝𝗼𝗯 𝗦𝗲𝗮𝗿𝗰𝗵 𝗣𝗹𝗮𝘆𝗯𝗼𝗼𝗸.

I give you exact steps to follow to network your way into that first interview with scripts and templates so you know exactly what to say and what to write.

The link is in the first comment 👇

One of my reps was shooting herself in the foot with her own stupid hangups. Of course, it was all MY fault.

I've learned that sometimes salespeople hesitate to sell the higher-priced option because they wouldn’t buy it themselves.

That thought feels harmless. It’s not.

I talked about this recently after coaching a formerly B-player rep who kept talking herself out of bigger, enterprise deals. Not because the product lacked value. Because she couldn’t see the value from the buyer’s perspective.

Once I coached her on the ROI the customer gets, everything changed. She closed bigger deals, got promoted, make President's Club. Not kidding.

But this isn’t a salesperson problem. It’s a leadership problem. It was my problem. I screwed up.

If sales leaders don’t teach how to think in outcomes, sellers default to their own wallet instead of the customer’s business goals.

I unpack this exact moment, step by step, on a short podcast episode I recorded recently. It’s 16 minutes. No B$. Just a real thought-provoking story (as usual) for sales leaders. 🎧

The link to the short, 16 minute podcast hosted by Stacy Garrett is in the first comment.

VP of Marketing for 💡 Creative 💡 Swag Provider

I've made this mistake and so have you. This is the #1 mistake new sales managers make:

Tolerating Underperformers 📉

I once had a rep on a PIP who worked just hard enough to get off the PIP but then asked me for a promotion. I couldn’t believe it. 🙄

Improving doesn’t mean they’re now a top performer. Effort matters. Improvement matters. But output matters more. 

Too often, new sales leaders unintentionally lower their standards instead of making hard calls. Some reps will improve, but not enough to meet your minimum standards.

😡 And they end up taking more of your time while delivering less than others. 

You don’t have to lower expectations, and you don’t have to give up on them either. Here are two tactics I’ve used to keep standards high: 

1️⃣ Have them self-assess

Ask them to rate their performance in key areas. Then compare their ratings with yours. If they can’t, don't or won't see the gaps, no coaching will work until they do. 

2️⃣ Prioritize your team over individuals

Your time is limited—spending it equally isn’t wise. Ask yourself:

- Would a rockstar rep struggle in the same role? 
- Knowing what you know now, would you rehire them? 

If the answers are no, and you've put in the effort to coach the rep, you need to replace the rep.

If you don't make the move, someone else will make the move for you and likely replace YOU because you're lowering standards on your team not raising them.

Job seekers aren't going to like what I have to say...but it's about time somebody stopped coddling them and told them the truth 👇

#ToughLove

Unpopular Opinion: KO your SKO!

6 reasons why I recommend you DON'T do your Sales Kick-Off in the coming months

Most of you are probably right in the middle Sales Kick-Off (SKO) season.

STOP. Don't do it. Kill it. Here's 6 reasons why:

❌ Expensive! The average cost per SKO attendee is between $2,500-$5,000. If you did ANY layoffs this year, don't even think of wasting this kind of money. How many people could you have saved if you didn't spend #SKO money?

❌ Don't fool yourself, SKOs aren't motivational. Salespeople don't come out of the SKO with any long-term improvement in their motivation. Maybe their tolerance to booze may go up but not their motivation.

❌ It's a company distraction. You're likely pulling in people from other departments to do presentations and participate. That's wasted resources again. Also, why don't we have an Engineering Kick Off or an Accounts Receivable Kick Off. Why is there just a SALES Kick Off?

❌ Usually Product/Feature dump. Your Product team will put a great deck together and talk AT the crowd for an hour or so. Save it for a nice email that people can read at home.

❌ Content Retention: Attendees will forget an average of 90% of what they have learned in a very short time. You're going to spend a bunch of money and then people forget 90% of it in a week or so?

❌ Oh, you're going to do it remotely? Good luck. Time for your attendees to catch up on episodes of Severance while they stare into ANOTHER Zoom meeting or a fun little breakout room in Zoom to "collaborate."

💡 Learning Lesson: Ditch your SKO in favor of longer term, practical and structured training with an assessment plan supported by a strong coaching culture.

People who have worked with me know that I've KO'd the SKO at past companies. Do you have the guts to do it?

Be honest, what percentage of your SKO do you find really valuable over the long term?

Learning that SKOs are a big pain in the butt is just one of 100s of mistakes and learning lessons in my sales leadership career.

I document 100 of them in my book, It Happened on the Sales Floor.

The link is in the first comment.

Especially this time of year when new comp plans and quotas are being rolled out, many sales leaders seem to be deathly afraid of losing their high-performing salespeople.

And they should take it seriously. Make sure you do the right things when rolling out those new comp plans and quotas.

But don't think for a split second that IF you DO lose your #1 salesperson due to the changes that you're making that your entire sales team will collapse as a result.

That's just the threat.

The reality is that it never happens. I've been in sales and sales leadership for over 30 years and I've never heard of situation where a sales team or a company fails completely when the #1 salesperson leaves.

Make no mistake about it, there is a dip. Some bigger than others.

But if you think that dip is going to be extremely severe when you lose your #1 salesperson, then that should be a huge sign to you as a sales leader or CEO.

👉 If you think that your sales team or company will collapse if you lose 1 or 2 high performing salespeople, then you have single points of failure that you need to shore up.

Develop the systems and processes (hiring, onboarding, training, coaching, performance management) that hedge against losing 1 or 2 high performing salesepeople.

If you don't, you'll feel like your #1 salesperson has a lot of control over you and that's not an environment that's conducive for you to make great decisions that's in the best interest of the company.

If you think hiring based solely on sales experience guarantees top performers, you are dead wrong. 👎 
 
Everybody knows that hiring solely based on experience is a fatally flawed strategy but I continue to see this mistake again and again. 
 
And I know why: It feels like it would be a no-brainer to hire the "proven" salesperson rather than the less experienced salesperson. 
 
But don't fall into the trap of overvaluing experience and undervaluing potential. Ever met a seasoned professional stuck in old ways, stubbornly rejecting change? 
 
Or the "experienced" salesperson who won't lift a finger outside of their job description? 
 
💡 Adaptability and Continual Learning outweighs Experience in tech sales. What was successful five years ago might be obsolete today. 
 
👉 Bet on potential. Find the eager learners. Their experience might be less, but their hunger to learn and adapt is priceless. 
 
Redefine 'experience', invest in potential, and you'll find hiring success like I have. 
 
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

I don't know about you but I don't think I stepped foot into the career center in College and I couldn't even tell you we had a career center in High School.

But I can tell you that I learned Spanish in High School and now I'm really good at ordering a beer in Mexico and then asking where the restroom is.

Great success!

👉 In reality, especially after having two kids go through high school and college, I've come to the conclusion that the so called career centers at our schools are useless, if they even exist.

Our education system fails us. The main point of school is to teach you HOW to think. But the secondary point is the promise that if you go to school, work real hard and get decent grades, you'll get a good job.

That couldn't be further from the truth.

I read somewhere that unemployment for college-educated 20-somethings is around 9%.

9%! That's insane...and it's unacceptable.

But it's not their fault. Our education system failed them. Nobody ever taught them how to search for job the right way.

Instead they open-mouth breathe and one-click apply to hundreds of jobs they like while intuitively knowing that they're not going to hear anything back and they won't get that job.

But there IS a better way. It's just that nobody ever taught you.

That's why I created my No-BS Job Search Playbook.

-After nearly 30 years as a hiring manager
-After owning my own recruiting business until I sold it in 2018
-After working at the job board, ZipRecruiter for 8 years
-After coaching countless people to teach them how to get their job

I decided to create a no-fluff job search course.

Here's where you're going:

In less than 10 days, I’m going to help you master the entire job seeking process, position yourself properly to get the interviews you want and quickly find your dream job (and avoid landing in a crappy job) for less than a few orders from DoorDash

And you can get a free trial of my course too. No credit card required. If you don't like what you try, don't pay for the rest.

The link is in the first comment.

“We went in a different direction.” That’s the default rejection email (if you even send one) but there's no feedback to the candidate about how to get better...

Cold. Vague. Useless.

I've sent those myself. Hiring managers, we need to do better.

Every candidate you reject still needs help. Especially the good ones. The ones some liked, others didn't and almost made it to the final round.

And guess what? They remember you. They remember how you made them feel when you kicked them to the curb.

Some of you want to help and give feedback to help them get better but either you can't, won't or HR won't let you.

I get it. I've been there. It's tricky.

But maybe you can do better than merely throwing rejected candidates back into the job market with nothing but a bruised ego and a B$ boilerplate email.

Here’s what you can do instead:

Send them this.

I built a job search course that breaks down how hiring actually works and then shows them:

→ How to network
→ How to write cold outreach
→ What to say in interviews
→ How to negotiate offer letters like a pro

It’s simple. It’s fast. It’s free to get started.

And it shows candidates exactly how to improve for next time...without you needing to lift a finger. Win win.

If you rejected that candidate but still respected their time and talent, this is how you show it.

I’m not asking you to be a coach (your HR team might slap your wrist). I’m asking you to be a better human.

You have a boatload of power as a hiring manager.
How you use it matters.

👀 The link to the No BS Job Seeker Course is in the first comment.

Accounts you assign to your sales reps work are yours. 
 
👉 you decide who works the Accounts and Leads 
 
👉 you decide if you want to reassign the Accounts or Leads to more capable reps. 
 
Your sales reps don't "own" the Accounts, they rent them. 
 
As a sales leader, it's wise to set expectations around that so your reps don't feel entitled to Accounts & Leads you assign to them in perpetuity. 
 
I've made that mistake before and learned my lesson. 
 
If you'd like to read about a few more of my mistakes and learning lessons, check out a free sample of my book here: 
 
https://lnkd.in/gVrxP73k

Experience <> (Expertise, Success & Drive)

Experience just means you've done it for some defined period of time but not necessarily well.

I got fooled by hiring "experienced" Enterprise Sales reps who couldn't close their way out of a paper bag.

And that's MY mistake not theirs.

I got duped.

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

Often, salespeople interview better FOR the job than actually doing the job. 
 
Said another way: 
 
 
🤡 don't be fooled by the gregarious, good looking salesperson who dresses nicely and has shined their shoes. 
 
They've gotten really good at GETTING sales jobs but often fail to sell.

PS: If you avoid getting tricked by this and 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

I’ve hired over 1000 people.
Unfortunately, I’ve rejected even more.

Most job seekers don’t fail because they aren’t qualified.
They fail because they don’t understand how to 𝙖𝙘𝙩𝙪𝙖𝙡𝙡𝙮 conduct their job search from beginning to end.

And I've helped countless others for years and years learn how to do their job search the right way...the way that nobody ever taught them before.

So to help the tons of others that are struggling with their job search...

I built 𝗧𝗵𝗲 𝗡𝗼-𝗕𝗦 𝗝𝗼𝗯 𝗦𝗲𝗮𝗿𝗰𝗵 𝗣𝗹𝗮𝘆𝗯𝗼𝗼𝗸.

It walks you through the entire job search...from positioning yourself to interviewing to negotiating the offer...using the exact words hiring managers listen for.

🟢 First 4 lessons are free.🟢

If you’re tired of guessing,
If you're tired of struggling,
If you're tired of the black hole...here’s the system.

The link is in the first comment

Currently building Starbridge, the GTM Intelligence Platform for businesses selling to government & education. We help our partners leverage industry-specific buying signals - such as strategic plans, board meeting notes, budgets, grants, competitor contract expiration dates, and more - to build a tailored, outbound strategy that drives pipeline.

Before Starbridge, I led sales at Parchment on a journey to $100M in ARR selling to K12 districts, Higher Ed, and state governments before being acquired by Instructure. While at Parchment, I lived the challenge of selling to government and education entities. With the proliferation of spray-and-pray outbound, that challenge has only gotten harder.

I’m helping build Starbridge to simplify selling to government and education. We’re making it easier for businesses to access public contracts and compete on the merits of the product. Our goal? To catalyze a new era of public-private partnerships that change the world for the better.

Matt Stinson

10 AEs, $1M booked in 30 days, and systems that operate like a company 3X our age. We ended last year on an incredible streak. Here are top wins and lessons from Starbridge's biggest month to date.
 
3 Wins:
1.) We booked $1M in a month for the first time in company history. We're now in the top 0.1% of companies historically when it comes to revenue growth at our stage.
 
2.) We've gone from 5 to 10 AEs. Dan, Sam, Nicole, then added McKay, Zac. Now, we've added Bobby, Paige, Steven, Simone, and Patrick. They're all incredible people with energy and contributing from day one.
 
3.) Our systems structure is maturing well beyond our real age. Big shout-out to Jordan, our COO, for spearheading this transformation.
 
3 Learnings:
1.) Never compromise on hiring
After meeting with hundreds of people, I've learned never hire someone unless the team has absolute conviction that we would be at a loss if we didn't bring this person into the org. Maintaining a .1% talent bar is the highest leverage activity I can help support as a leader in the business. 
 
2.) Reframe fear to optimism
I often operate from a position of fear mitigation, playing not to lose. I always think about what will go wrong versus what if all of these things are going right? Justin challenged me to bring my most aggressive, optimistic view and ladder back into what we need to accomplish that. All I can say is, Game On.
 
3.) The power of customer on-sites
We should continue hosting in-person events with customers. The feedback was incredible from our holiday party and our mini-onsite, with people saying how invested they feel in us. People have hours to give you in person versus virtual meetings where they're off and on.
 
To end up where we are and have booked a $1M month at this stage is unfathomable. It's an incredible testament to the product, market fit, and the problem we're solving for our customers.
 
2026 will be the year of Bridge Builders... and I can't wait to meet more of you.

Matt Stinson💫

A comment on my "80 hours a week grind" post stopped me cold.
 
A woman shared her experience growing up as the daughter of a Microsoft employee in the 80s and 90s. It was a time when everyone bought into the mission of “changing the world.”
 
Her mother loved the work. But that devotion often meant choosing the mission over being home.
 
Now, as an adult, the daughter doesn’t celebrate that dedication. She grieves the moments she never got to share with her mother.
 
That really struck me hard.
 
Am I trying to have my cake and eat it too? Can you be a really successful executive at a fast-growing company that demands a lot of you, AND be a really great, present dad?
 
I learned work ethic from my own dad. He was a contractor who came home every day with a broken back and bloody knuckles. I have negative feelings about him missing Saturday games. But I also learned a ton from watching him grind.
 
Unequivocally, being a present dad matters way more to me. But professional success makes that possible - flexibility, financial freedom, and the ability to show my kids that hard work is important and doesn't come easy.
 
I don't know too many people I look up to as role models who are doing both well.
 
I just finished reading Bob Iger's "Ride of a Lifetime." Midway through, he casually mentions getting separated from his wife.
 
Of course he did. He was working 75-80 hours a week at ABC, then Disney.
 
The people who reach the highest levels made very clear choices. They went almost 100% in on career or family.
 
Just be realistic with yourself about what you can and can't do. Because there are sacrifices to make on both sides.
 
What I'm learning is that there will be some things I might miss as a dad that I'll never get back. And there will be things I won't be able to do as a leader. I just have to figure out what those things are.
 
There are no easy answers here. But pretending you can do it all at 100% without making hard choices is dishonest to yourself, your family, and your team.

Every comp plan has this clause: "Management reserves the right to make modifications as they see fit." NEVER ever use it.
 
CROs need to stop any nitpicky argument battles over compensation deals. It’s so penny-wise and pound-foolish.
 
I recently interviewed 3 or 4 AEs who said, "Yeah, I didn’t get paid. It was the first chink in the armor."
 
And I’ve heard so many other stories of reps not getting paid their full commission because it was "too big of a deal."
 
Sure, adjusting the payout may save $100,000 or $200,000 right now. But it burns leadership credibility with your AEs.
 
So while that clause is in there, build the comp plan so that there’s always alignment between incentives.
 
I know people are worried about efficiency and growth at all costs. But pay your sales reps what you told them you'd pay.
 
Even if it's a massive check...pay them the massive check.

Behavioral questions when interviewing salespeople are stupid.
 
I've interviewed 100+ sales reps in my career. Most of the questions that get asked during an interview add very little value to the actual evaluation of that candidate.
 
Sales reps are all good actors to some degree. They are so good at knowing the test and giving you the answers you want to hear. 
 
In my experience, the number one predictor of success for any candidate is whether someone you know or trust has said that this person is elite at what they do. 
 
That's why at Starbridge, we really prioritize references...especially references the candidate didn’t hand-pick.
 
If I can't find people who are ravenous fans of this candidate, I don't hire them.

I used to swear by upfront contracts. Sure, the Sandler Method worked great in 2010. But it's 2026. Now I think they need to be retired.
 
You know the drill. You begin a discovery meeting with a very prescribed structure: Set the agenda, confirm the time, confirm mutual potential outcomes, then bring up your biggest concern.
 
The idea was to get the prospect to psychologically buy upfront. If there's a fit, then schedule a next step. But I think it's gotten so overused over the last decade that it feels like a relic.
 
So much has shifted. Buyers come to meetings having done way more homework and research. They're prepared and know what they want to explore.
 
What bothers me about it now is that it feels like I'm doing something to deceive you. I'm making you commit even though we haven't even talked yet. And I asked for the meeting.
 
It's very transparent when tactics are being used. Especially when you're selling to salespeople who know the playbook. It just doesn't make sense anymore.
 
Look, there are still good elements. Confirming you've got a hard stop at the 30-minute mark, making sure you understand their calendar, overall framing of the call - that's just being professional and respecting their time.
 
But the psychological manipulation at the core of it? That needs to go.
 
I know a lot of people will have different takes on this. So I'd be open to hearing why I'm wrong.

"I'm blown away." This is real feedback from Zachary Oxman, VP of US SLED at Abnormal AI, after our kickoff last week.
 
Getting to lead a revenue team that sells a product that elicits feedback like this is incredible.
 
Knowing that our product will enable Zach's team help more schools, universities, and governments protect against cyberattacks is what it is all about.
 
If you want to be blown away, too, drop me a DM.

I'll be honest. Not every company should use Starbridge. But the customers who get the most out of it share the same 3 characteristics.
 
Characteristic #1: They are open to experiment
Not only do our customers run the core plays like most teams, they're also thinking about their business and use cases. Because of this, they're coming up with novel ideas and building them.
 
Characteristic #2: They have real internal ownership (the “Bridge Builder”)
With our top customers, there’s someone in sales leadership or revops who’s a systems thinker. They partner extremely closely with our CSA team to create and effectuate what matters most to their business.
 
Characteristic #3: They actually add value to the market
Our best customers have a product or service that solves a real problem. Someone has to theoretically want what you offer. Then, we can help you get in front of more of those people. 
 
A lot of prospects will come to us and say, "Man, our sales suck." So we ask them, "Tell us why you're different? Why are you winning?" And they can't explain why.
 
If you can’t figure out why someone would want your thing, we’re not going to help you win more.
 
We can't help you create product market fit. But we can help you exploit it.

This used to be my reality: 2-3 promising conversations with a customer, only to find out that their budget is frozen or there's no appetite for innovation. I’d spend hours on the phone or prospecting before learning what I should’ve known day one.
 
Me: "Great discovery call. Awesome demo with stakeholders. Let's talk budget."
Prospect: "Budget's down 15%."
 
Cool. Glad we wasted all this time.
 
With Starbridge, I don’t even start with a call. With our new budget trend data feature, we now rank propensity to spend, so I put them in some other drip campaign right away.
 
We run a thorough analysis up front on whether or not an entity is likely to spend in a given category. I filter my accounts by that data initially, versus finding out about it hours later.
 
This is the kind of insight that significantly influences where I'd be spending my time as a sales rep and where I wouldn't. It's changing how public sector sales teams operate.
 
If you're selling into government or education and want to see how this works, let's talk.

Every revenue leader wants growth coming out of SKO. But actual growth depends on the coaching habits that follow. 
 
While SKO is usually treated like a once-a-year event, the goal of an SKO is to accelerate growth and jumpstart learning.
 
The problem is that most teams expect those outcomes to come from 3 days of sessions that try to wrap together 12 different topics.
 
You might tease out 1 or 2 things. But without a system to reinforce them, the learning fades, and behavior doesn’t really change.
 
The way you accelerate growth and learning is through continuous improvement and feedback.
 
This became painfully obvious when I wasn't physically there on the final day. I could see that people looked confused, but I couldn't grab them afterwards and talk through it.
 
That moment reinforced something I already suspected: The real value of SKO is everything that happens outside the sessions - the getting to know people, connecting with them, and creating energy together.
 
So while we’ve done an okay job of this as a business last year, this year, we’re being much more intentional.
 
Going forward, we’re building off SKO momentum with one-hour weekly coaching calls for the entire revenue team.
 
In these sessions, we’ll do film review, role play, and break things down into very discrete, bite-sized pieces so the team can actually absorb and apply the learnings.
 
In this way, we’re training and building the muscle of expecting feedback, getting that feedback, and integrating it.
 
That shared context and trust are what will allow learning to stick once everyone is back in their day-to-day work.

When you start closing deals with the biggest players in K12, you know something's working.
 
That's why we're so honored that Frontline Education chose Starbridge to fuel their GTM strategy.
 
We're stoked to support Frontline's mission to empower K12 leaders. And we're grateful they're betting on us to help them win more deals.
 
See more of our amazing customer stories on our website. (Link in the comments)

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The Battle

Kevin Gaither

Matt Stinson

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The Battle

Kevin Gaither

Matt Stinson

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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