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 👇
 
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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:

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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

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

A candidate reneged on us recently. While we were gutted, I told him, "You're not burning a bridge." Even though I was disappointed, I meant it. How you handle these situations is super important. Both as an employer and a candidate.
 
We were all excited for this candidate to join us. He already started onboarding. He even came to our holiday party. But a counter offer came that was too good for him financially.
 
He realized the only reason he was leaving was money, and he wanted to see it through.
 
When I called him, he called himself an a**hole. But I told him, "You're not an a**hole at all. You're doing the thing you think is right for you and your family. That's not wrong."
 
I told him that if he changes his mind in 6 months, he can come back, and we'd welcome him with open arms.
 
There's a version of this conversation where I could have gone the other way and let my frustration out. But then I'd have thrown away a relationship with someone who handled a hard situation with more grace than most people.
 
These are the moments that go into the ether of how people view you and your company. And at the end of the day, candidates should not feel sh*tty about their decisions. 
 
Keeping the conversation open is the right thing to do. For you. For them. And for the business.

Matt Stinson💫

Starbridge went from 5 AEs to 14 in 2 months. I expected growing pains. Instead, we iterate faster than we ever have. What changed?
 
I stopped being the central leadership cog.
 
As a CRO, you're probably the most expensive bottleneck on your sales floor. But if you hire right, you don't need to be the only person coaching.
 
Before, we had 1 or 2 people on the team saying, "Here's how we do things."
 
Now there are 14 people asking, "Have you thought about this?"
 
These are winners. But they're collaborative winners that want to help. It's like the "rising tide lifts all boats" idea - and that tide compounds fast.
 
It's amazing having 14 people with incredible experiences and backgrounds... and the chutzpah to bring the "have you thought about this" question up in week one.
 
When a rep surfaces something broken, we don't sit on it. We change, we adapt, and the cycle from loss to winning again shortens.
 
When you hold an impossibly high bar on hiring, you create a different kind of organization. And it changes everything about how quickly everyone gets better.
 
I used to think the CRO's job was to set the standard. Now I think the job is to build a team that doesn't need you to.

“ Starbridge is the platform that I wish I had for the last decade,” said Bobby Offterdinger, Founder of TAM to Target.
 
Same here. Partnering with experienced public sector revenue leaders like Bobby is a joy because I know exactly how painful life before Starbridge was for him.
 
I had a chance to sit down with Bobby and his team recently to discuss how they’re successfully leveraging Starbridge.
 
TAM to Target helps businesses selling into finite markets be more purposeful with their prospecting, build pipeline, and book meetings - working almost exclusively with K12, Higher Ed, and public sector sellers.
 
Before Starbridge, data was difficult to trust, research ate up days, and horizontal tools only provided surface-level answers.
 
Now, TAM to Target can implement Starbridge for their clients as a full end-to-end platform that powers their GTM motion:
→ 5x more valid contact data
→ 2.5x more meetings booked
→ 10+ hours saved on research
 
“Starbridge is a one-stop shop for everything that you need to build a modern, go-to-market motion in the public sector,” said Bobby.
 
Huge thanks to Bobby and his team at TAM to Target for taking the time to chat with me. You can check out the full case study here → https://lnkd.in/ejW6s-pT

I watched one of Nicole's Gong calls from a year ago last week.
 
I expected it to feel like a time capsule. Our product is completely different now. We've shipped a ton. The platform is so much better than it was twelve months ago.
 
But the messaging? Almost identical.
 
That caught me off guard. I figured everything would have shifted — new features, new positioning, new talk track. Nope. The way Nicole described the problem we solve a year ago is eerily close to how we describe it today.
 
And honestly, I think that's one of the best signals a startup can get.
 
It means you got the problem right.
 
Products change constantly. Features ship, UIs get rebuilt, integrations get added. That stuff is supposed to evolve — and it should. But the problem your customer actually has? That moves slowly. Sometimes it doesn't move at all.
 
The problem Starbridge solves is the same one it solved a year ago: there is a ton of really valuable information trapped in places that are nearly impossible to access. Budget documents buried within a link within a link within a link. 300-page PDFs full of procurement data that nobody has the patience to dig through. Contact information that traditional providers simply don't have.
 
That information exists. It's just locked away behind layers of bureaucracy and bad UX. And the reps who need it to build pipeline don't have the time or the tools to go excavate it on their own.
 
We've gotten way better at surfacing it. The product today would blow away what we had a year ago. But the reason someone picks up the phone and talks to us?
 
That's been true from day 0. And we're just continuing to drive on that.

We’re booking 400 meetings a month with a team of 5 SDRs.
 
To do this 2-3 years ago, I probably would’ve said to hire an army of 23-year-olds and let them cook…
 
But now, things are a bit (completely) different.
 
A lot of SaaS companies rely on the Predictable Revenue bible: an inputs-driven approach of more reps = predictable conversion rate = meetings booked.
 
But the way our revenue team is structured has nothing to do with this, and we’re still getting results.
 
The quick breakdown of how we do it at Starbridge:
 
We centralized everything repeatable - list building, messaging, outbound sending - through a GTM engineering function. That team owns the infrastructure where nothing goes out without it running through them first.
 
SDRs come in on top of that, but only for the high-touch stuff that requires a human in the loop and doesn’t scale yet (i.e. cold calls, gifting, LinkedIn).
 
It’s been working really well (🙏🏻), and we’re not the only ones doing this. Sat down with Bobby CEO of TAM to Target recently, and his team is also using the new “doing more with less” playbook.
 
Check out our full chat below if the old playbook isn’t working for you either.

Education and government sales teams generally invest in 10-20 conferences a year. You often get the list. You don't often get the contact information. Teams shouldn't have to live with that data gap.
 
Booking meetings ahead of conferences is the only way to actually run an effective conference strategy. But if you don't get a list with contact info, you have to go mining for it by patching together sources of data.
 
It's frustrating. But it's also avoidable.
 
With Starbridge, you can enrich that list with verified contact info - emails, phone numbers, and any other attribute you need to drive flow to your booth - in an instant.
 
Conference ROI starts with showing up ready to close. And with our database, you also have access to 2,800+ upcoming gov and edu conferences, ready for GTM teams.
 
If you're heading to a conference soon and want to see how this works, let's talk.

This cold call was so bad, I had to turn it into a LinkedIn post. If this rep used Starbridge, he'd never have such an awful cold call script.
 
Look, I get it. Outbound is hard. But this is the result of 0 research.
 
If you're selling to government and education, you can't afford these mistakes. Every bad touch erodes trust you can't get back.
 
Here's what actually works:
→ Knowing who you're targeting and why 
→ Understanding org structure before you reach out 
→ Having a real reason to believe they're in market
 
With Starbridge, you're not guessing. You know which districts just bought from competitors, which universities have budget for your category, and which contacts actually own the decision.
 
And you'll never send an email to the CRO about hiring backend engineers.

A lone wolf sales rep at 140% of quota will still destroy your team. After interviewing 100s of AEs, here's the 3-question screen I use to catch lone wolves before the offer goes out.
 
Question 1: How do they talk about failure?
Listen for external attribution.
 
"My leader wasn't good."
"The product-market fit wasn't there."
"The territory was bad."
 
That signals a "Me vs. Them" belief system. That belief system doesn't go away when they join your team. As you're asking general questions about their experience, pay attention: Are they drawing a stark contrast between themselves and the company, their leadership, their peers?
 
That chip on the shoulder, that animus toward every organization they've been a part of - that's the tell.
 
Question 2: What did their peers think of them?
This is the question I've started asking references on every call: "What did their fellow peers think of [person]?"
 
You'll hear 1 of 2 things: "People were jealous of them." Or: "Everyone loved them. They'd help other reps, people followed them, super collaborative."
 
One of those builds teams. The other burns them.
 
Question 3: Can they explain their own process?
When someone says they were at 140% of goal, I ask: "What were you doing that other AEs weren't?"
 
Most people really struggle with that question. Lone wolves, especially. They win, and they win... but they can't document their system, their process, or what specifically they did at any level.
 
If you can't reflect on your own process, you can't change it. And if you don't even know what you're doing, that's the starting point you're building on.
--
 
We coach a lot here at Starbridge. We invest real time in making our people better. A lone wolf doesn't want that. They're running their own process, in their own world, and they'll resist every attempt to change it.

How to spot lone wolves in sales

Episode 1 of Deal Diaries is live! 🎙️
 
In our first podcast episode, Nicole Baldassarre💫 and I reflect on our crazy first year at Starbridge and the dynamics of building a sales org from 0 to 1.
 
We also compare our personal selling styles, workshop the future of AI in sales, and I try to decipher which Gong quotes are Nicole’s.
 
We’ve already recorded Episode 2. It’ll be dropping next week. 👀
 
And Episode 3... we might have a surprise guest. Stay tuned.
 
Watch the first episode! https://lnkd.in/eic58mAA

I've sat in on thousands of discovery calls in my career. There's no excuse to come to a first call without a POV anymore. Here are 4 openers that actually land in the first 30 seconds:
 
1. "I see you've been at [company] for X months. What's it been like? What's been going on so far?"
 
Look at the tenure of the person you're working with. New leaders are in motion. They're building context, proving themselves, trying to figure out what's broken. That question gives them permission to tell you everything.
 
2. "I was super excited when I saw this pop up on my calendar. We work with X and Y and have had great success with them. Do you know their business well?"
 
Look up and see if you share similar logos. If they know the logo, you're not a cold call anymore.
 
3. "I see you're connected to Joe. I'm guessing you worked with him at X. When's the last time you caught up with them?"
 
People buy from people. A shared reference changes the temperature of the room instantly.
 
4. "Hey! I see you've been CRO for 3 months, and it looks like you raised an A round pretty recently. I could imagine you're thinking about how to scale the team and onboard reps quickly. Does that resonate? What's been top of mind for you?"
 
Synthesize everything into a POV (the 301 version). This is the one that separates good reps from great ones. You're not asking discovery questions yet, but you are showing them you already did the work.
 
--
 
Share this with your team before their next discovery call!

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