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

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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

Certified Clay Expert & Agency owner | I'll help you build a scalable outbound engine that gets meetings booked on autopilot in the next 180 days | Visit Youtube: @growth-today to see how

Growth shouldn’t feel random.

Most of the B2B companies hit the same walls:
Inbound leads that don’t convert

Outbound that burns reps out without results

Partnerships that look good on paper but never drive pipeline

A CRM full of noise instead of reliable data


I’ve seen it across founders, sales leaders, and marketing teams. The problem isn’t effort, it’s the lack of a repeatable, scalable GTM system.
That’s what we build at Growth Today.

Instead of disconnected tools or random campaigns, we design and implement repeatable GTM engines across sales, marketing, and partnerships that…

✅ Enrich and qualify data
✅ Activate inbound leads into real opportunities
✅ Automate outbound prospecting
✅ Keep CRMs clean and reliable
✅ Orchestrate multi-channel campaigns
✅ Make BDR teams more effective or fully replace them
✅ Align marketing + partnerships with sales for compounding growth

Recent wins:

 → Built a clean, automated CRM that doubled conversion rates
 → Launched a content-driven demand gen engine that 3x’d inbound lead quality
 → Systematized partner outreach → pipeline from alliances grew 40% in 6 months

Growth doesn’t come from more outreach or more tools.
It comes from building the right system once and scaling it.
If you’re a B2B founder or revenue leader serious about building predictable pipeline, let’s connect.

Book your call: https://calendly.com/growth-today/intro-meeting

Brigitta Ruha

Efficiency is part of building any company. I get it.

But the problem starts when GTM spend goes down… and revenue expectations go up.

Being disciplined about CAC makes sense. But reducing spend removes the crucial part of building, scaling GTM - all the reach, experimentation, and ultimately - staying visible on the market ✌️

all of which eventually influence the CAC, the efficiency….

Predictable pipeline usually sits on top of a lot of unglamorous work:

- Ongoing testing
- Consistent market presence
- Regular feedback from the team, customers, and prospects

When those inputs shrink because we cut down on costs on revneue team, the impact doesn’t always show up immediately. It shows up a quarter later (fewer deals, thinner pipelines, longer sales cycles, etc)

Revenue rarely grows when the effort behind it shrinks. Reducing costs can absolutely work

but only if the system itself is improved, not just scaled back

P.S. How do you balance cost discipline with maintaining momentum?

Co-Founder@Growth Today | We Build Repeatable GTM Engines Across Sales, Marketing & Partnerships 🚀

Before you spin up another outbound campaign this quarter, please:

Do not start by writing new copy.

You’ll end up polishing something that was never the real issue. I promise you.

It’s completely normal to see outbound look like this:

• Emails going out every day
• Activity numbers looking healthy
• A few replies trickling in
• But pipeline still questionable

Some weeks look promising. Others not.

If you’re about to reset outbound (or you’ve been tweaking campaigns but nothing really moved the needle), here’s a simple 7-day reset we use:

Day 1 – Fix the list
Day 2 – Fix deliverability
Day 3 – Fix the offer
Day 4 – Fix the CTA
Day 5 – Fix personalization
Day 6 – Fix sequencing
Day 7 – Fix measurement

(my design team put together this image)

Track these automatically:

Inbox rate (did your email land in the inbox?)
Reply rate + positive reply rate (was your message relevant to them?
Meetings per 1,000 sends (was your follow up timely enough to book them?)

Yes, you want more meetings. But consistency usually comes from fine-tuning the fundamentals

& outbound has a LOT of those levers so first, take a look all these levers.

if i were you: I’d update the offer first!

How can I be SO irresistibly helpful to my prospect?

→provide that value in the email : ) & that can be anything from an audit to checklist to a designer bad

hit the 🔔 on my profile if you want more actionable, no fluff, BS tips like this

best decision in 2025: stopped trying to sound like everyone else.

"Cold emails are all the same."... I lost count of the times I heard someone say this.

not because outbound is broken. 😄

but because everyone is writing from the same invisible rulebook:

- sound professional
- follow the template
- don't say too much
- don't say too little either

I did that too.

signal-based hooks. the 3W frameworks. "best practice" sequences.

results:

- decent reply rates
- sometimes w low energy conversations
- leads that never really felt aligned to how we work/what we're selling

the shift happened when I stopped optimizing for perfect and started writing in my actual voice:

👉 my story, how I'm different + radical transparency

suddenly, copywriting felt SOO much easier.

I got way more responses (I actually had to pause the sequence during our GT offsite in ✨ Bali ✨ because the team couldn't keep up with replies)

because I played a little bit differently. in my own way. ✨

turns out, a lot of “outbound hate” is just fear.

(because telling other people how to do it is always easier than doing it 😉)

Fear of standing out.
Fear of sounding different.
Fear of being rejected as yourself.

Cold email copy doesn’t need more tricks.

It needs more honesty. and YOU.

What helped me:

1️⃣ I write to my favorite prospect: I picture one person who could be my ideal client, writing email copy in the same words and tone of voice as I'd talk to them.

2️⃣ I say what I actually believe about what we can and can't do: we're not good for everybody. We also cannot help everybody, & I try to be super transparent about what is realistic or not.

if it resonates and expectations are set right, engaging people who share the same mindset is totally worth it.

(plus I don't need to deal with unrealistic "10X my sales overnight" situations, which anyone who ever achieved anything in sales or marketing would know is BS)

3️⃣ I use AI to amplify my thinking: what to say, how to reach out, when to follow up (although, thanks to HubSpot, lemlist, and our fancy Make automations, I couldn't realistically forget anyway…)

so I'll never be "cold email guru number 3847".

⬇️ ⬇️ ⬇️ my team at Growth Today also tries to be as authentic with our customers' copies as we can be.

We're big fans of using ChatGPT to translate product bullshit into something tangible, short and sweet, while keeping the best practices from the space that we believe in. ✨

but sometimes, you just gotta play the game a bit differently…

would love to hear how you describe your cold email copy/different methods you use right now. ;)

Co-Founder @Growth Today | We Build Repeatable GTM Engines Across Sales, Marketing & Partnerships 🚀

We've ALL made every GTM mistake in the book

I’m sure you noticed it is never about the tech itself 

it's getting people actually to use them 

And we learned this the hard way… 

→ change management matters more than the system itself 
→ not everything needs to be automated 
→ bad data is way more expensive than you think 
→ outbound without relevance is just noise 
→ partnerships need as much system as the sales team (this team is often swept under the rug)

.. a few tips that can go a long way 👐

DM me if your team needs some expert guidance, hands-on execution

5 THINGS WE WISH WE KNEW

Woah, this is happening right now.

Clay is officially here in London 🎡 !

I remember 2023 when I first spoke to Varun Anand.

I felt !! FINALLY !! a tool built for growth.

for Growth teams.

for high-growth companies

Who are all SOO keen to use the data, but what if more business ppl could use it instead of just relying on techy guys from sales engineering backgrounds?

Suuuupperr excited to be here at Clay’s EU/London office and Europe.

& grab some ☕ with Jani Vrancsik Tyler Swanson, Ziqi Deng, Juan Ravagli, and Michael Vitak

We’ve been experimenting with AI in our GTM systems recently 👀

There are 3 different scenarios when you want to build autonomous systems:

chat w ChatGPT or Claude (e.g.: threads)
autonomous workflow (i.e Hubspot or agentic workflow)
ai agent that executes something very specific end-to-end

Let’s say you want to schedule a quarterly check-in with a client.

The first version looks something like this:

1. Assistive setup

So you open the CRM. Check your calendar. Ask ChatGPT to draft the email. Edit a line or two. Send it. AI helped you write it.

2. Automation-based

Now the system does most of it. After 90 days, the workflow runs. It checks the calendar. Writes the draft. Sends the email. Simple. Less work for the team. But it still follows a script. If something unusual happens, it doesn’t adapt. Your ops team needs to debug and fix it.

3. Autonomous Agents

Instead of telling the system, “Send the email.” You just provide the overall goal: “Alert if a customer stopped leveraging the product.”

It watches how the client is using the product using the data from your Snowflake/AWS database. Notices when something looks off. Sends a follow-up to prevent churn. Flags the account for potential churn if the Account is customer Success managed. Provides a summary for the CSM to prepare the conversation. Now the system isn’t just completing a task. It’s working toward an outcome.

& that’s a very different thing!

im gonna share our agentic agents as well, we build internally across sales and marketing ✌️
Where are you experimenting right now? 👇

I was thinking about this over coffee this morning ☕

Most GTM teams don’t struggle with ideas anymore.

The playbooks exist.

Targeting logic is solid.

Sequencing frameworks are mapped out nicely.

The weak point is the execution and/or strategy layer.

Most stacks today are deeply connected: CRM, enrichment, ads, content systems, sales tools.

Everything talks to everything. But connected doesn’t mean autonomous.

Someone still has to write an email
Someone still has to decide when a workflow should run.
Someone still has to follow up and follow through.

That’s where things get fragile.

I’ve been testing FlashLabs SuperAgent recently because I wanted to see what happens when that decision layer is automated.

What works here isn’t that it writes emails. (Plenty of tools do that.)

It monitors public and social signals, understands curiosity vs. buying intent, and then triggers predefined GTM playbooks 👀

Which means:

– detecting early evaluation signals
– launching the right outreach sequence
– generating landing pages or ad variants
– updating CRM fields
– preparing follow-ups using meeting intelligence

End-to-end. Without someone babysitting the workflow. (or the team)

& it won’t be 100% pixel perfect

But it does get the job 80% of the time

which is AWESOME

Because if you do 80% best version out of yourself/system

You can buy back SOO much time

With consistency, which will give you a * huge * compounding result over time

This is like the early versions of an autonomous GTM layer.

Still experimenting with it. ✌️

But if you’re a GTM leader thinking about how execution scales

…not just how strategy looks on slides, FlashLabs SuperAgent is worth checking

Link pinned in the comment 👇

random question ☕️

When was the last time you actually trusted EVERY (or any?) field in your CRM? 😅

Not in theory.

But like… truly trusted it.

When you go to the CRM, you start to notice these small things piling upppp 👀

- Titles slightly outdated.
- Mobile numbers missing.
- Company names that don't even exist anymore (rebranded, acquired)

& that’s enough friction to slow things down. 

So instead of planning another BIG CRM sprint, we connected prospeo.io to auto-enrich all companies and contacts directly inside the CRM.

Now, when a new contact comes in:

- Default fields get filled out
- Email address is verified through multiple providers
- Details are refreshed when the person gets promoted, moves to a new employer

(Automatically.)

we still review things occasionally

we still care about governance (LeanData is great for auto-de-duping companies/contact btw!)

but we’re not exporting CSVs back and forth anymore. 🙃

It’s just… CLEANER + EASIER + MORE MANAGEABLE by default.

& saves a lot of time w/o second-guessing the data all the time.

CC’ing Matthew Putnam you can reach out to him in DM directly if you need more 👀

I ran my first outbound campaign 6 years ago. Drove 75 demos/mo for 2 E-Commerce SaaS as their growth leader, and then my cold email agency from 0 to $2M+ ARR. Here are 7 things I wish I knew before starting:

(1) Truly nail down your lead list

Sending your outreach messages to the right person matters more than anything else:

→ Precisely figure out what problem you're solving.
→ Find companies struggling with this problem.
→ Identify relevant individuals in these orgs.

(2) Give as much value as you can

You’re stepping into someone’s inbox uninvited.
& the fastest way to earn attention is to be USEFUL.

Give give give > ask

A simple approach:

→ Identify their problem
→ Share one practical solution for free
→ Do this as many times as you can on all channels where you are.

(Think through: why are you reading this LinkedIn post, right? EXACTLY!)

(3) Pick only one prospect and write for him/her

Many people try to write for 500k+ people.
Start with one instead.

Pick one prospect you’d genuinely want to work with.
& write as if they’re the only person receiving that email.

Then do the opposite:

→ Find 20 similar personas
→ Find similarities in their challenges, org size/org challenges
→ Then automate all these at a bigger scale

(4) Take care of the deliverability

Good deliverability doesn't guarantee your campaigns will succeed. But...

Bad deliverability guarantees your campaigns will fail.

Make sure to...

→ Send a few emails per mailbox (< 20 per day)
→ Set up MX, DMARK, SPF, DKIM records.
→ Disable open tracking.
→ Warm up mailboxes (bare minimum 14 days)
→ Weekly run inbox placement tests
→ Daily run domain blacklists checks

(5) Take the extra mile!! 

Any GTM channel is somewhat hard to crack. The same goes for cold email.

Make sure to go above and beyond when reaching out to your prospects:

→ Look at triggers, signals, current events, org. charts.

→ Reference insights from the job descriptions.

→ Don't stop at 1-2 email variations. At Growth Today, we frontload 8 variations

(6) Complement cold email with other GTM channels

Cold email is my favorite channel because it's cheaper to get started, and you can find what works a lot faster than with any other channel.

But it works even better with other channels.

→ Run ads to the same people you're cold emailing. warm them up! ♨️

→ Make great, authentic, and genuinely useful content and use email and LinkedIn to distribute it

→ Use cold emails to distribute valuable lead magnets.

(7) Don’t just use technology, leverage it to SYSTEMIZE

→ Have a look at growthtoday.co/sales-tools (or my fav one: our blog posts that include copy-pastable email templates)

→ Do a few tests manually to see what is the most interesting angle on the market to pitch your prospects.

→ Before hiring more people, ask: “Could I achieve the same with technology?”

→ Before doing more, ask: “Could I build a repeatable, scalable SOP or system instead of me doing this again and again?”

7 TIPS TO GENERATE MEETINGS WITH COLD EMAIL

“I think we’re losing more deals to bad data than bad messaging.”

If that is true,

I can feel you!

The usual process of getting good and accurate data somewhat requires this:

- One tool to find them.
- Another to verify.
- Another tool to find more because the previous ones didn’t find enough
- Export. Upload. Repeat.

It works, but unnecessary very tedious.

& never really knew which source actually found the valid email.

This is what I like most about BetterContact:

Instead of: “Let’s try provider A first…”

1- its email waterfall runs automatically
2-  through 20+ providers 
3- at scale, through the API (through Clay, or your CRM, AWS/DB) so you don’t need to import/exports

If one doesn’t return a valid email → it moves to the next. If it fails verification → it keeps going. Until it finds something actually usable. & you’re only charged IF the email address is actually found and valid.

If you’d like to save time on using 5+ different tools with 3 CSVs whenever you need an email, def try out BetterContact. ✌️

It’ll save you SO MUCH time.

p.s. how are you running enrichment right now?

4 things I did because I trusted my gut (not the people around me)

1-Started building programmatic prospecting in 2020 (way before Clay was cool)

No one understood why I'd struggle with no-code tools and Python when you could "just hire BDRs

After doing it full-time at a company and through consulting, when Clay popped up on my feed, I felt like I could create something different to help more people succeed with outbound.

Way easier than before, BUT leveraging all the experience I gained over the years.

2- Posted frequently on LinkedIn when everyone said it takes forever to see results

By the end of year 1, I was consistently building a pipeline from inbound, which eventually led to building Growth Today (and still keeps us going when the market gets tough).

Now I have CSM, GTM engineers, a team who assist me with content, and with sales, and freelancers helping me build what we believe in every day.

3- Let custom RevOps projects go

The team closed a few deals with enterprise customers.

On paper, it's awesome: no churn, high expansion, upfront payment…

But in the end, it didn't fit our ICP or the service we wanted to build at the time.

Letting go of some customers is hard, but necessary in the long run, depending on what route you choose to build your company.

4- Hired people who didn't have the skills yet, but had the potential

I always get DMs, and sometimes I make exceptions.

There was one person I almost fired in her 2nd week. I told her upfront: if we're both not getting value, it's hard to bring positive outcomes, and none of us will enjoy this work relationship.

I was candid, she was too. She mentioned she should leave herself if she won't hit my expectations.

She did it.

A-players are important, but sometimes your gut tells you to take exceptions.

Eventually, some people float to the top, and some just can't get you to the destination.

What about you?

What are the things you did because you knew better?

what we changed to fix their outbound

One thing I love about outbound is how quickly the truth shows itself.

If the system is off, the results will drag. If the system is right, everything clicks.... even if nothing else changes.

Last week we worked with a services company whose outbound “felt flat.”

But once we dug in, the problem wasn’t just list or the copy
…it was that their system was fighting against them.

Here’s exactly what we changed:

1️⃣ We stopped selling the service at scale only a few people respond to

They have 3 services.

All great.
But one is a terrible conversation starter.

Cold prospects don’t wake up thinking:

“Wow I really hope someone offers me a 40-page report today.”

Their prospects literally respond ~2× better to the other 2 services, but outbound wasn’t aligned to that.

So we repositioned around their two strongest conversation starters

2️⃣ We fixed the invisible killer → deliverability

Their audience = mid-market + enterprise.

Enterprise = Microsoft.

Microsoft = “I will evaluate your entire family tree before letting your email through.” 😅

So yep… we’re have a different mix Google + Microsoft inboxes and all these inboxes are purchased to multiple resellers, so we can continously monitor which ones are performing the best and use the data from our inbox placement tests to make adjustments to keep hitting the inbox.

3️⃣ We replaced the “quick chat?” CTA with value

Their CTA used to be a meeting request. (in a soft way which is GOOD).

But (especially in the agency space), you’re likely selling something that is “easy” to execute, so the barrier to entry is low.

So we introduced CTAs that give something instead of ask for something:

- campaign ideas
- roundtable theme maps
- insight drops
- quick audits

Concrete example if you’re running an ad agency:

→ “I have analyzed your ads published in the last 90 days. Can I send over a quick audit to decrease the CPL?”

→ “Would you be open to exploring how we can help you decrease the CPL on your Meta ads?”

GIVE → GIVE → GIVE → before you ASK.

4️⃣ We added intent + timing signals instead of guessing

Before: outbound went out in usual prospecting campaigns
Now: outreach triggers when something meaningful happens.

Signals we added:

→ new senior hires
→ hiring for marketing roles
→ aggressive ad spends
→ thought leadership indicators
→ content activity

5️⃣ We refreshed the messaging (just enough)

Not a rewrite — a refresh.

We updated angles based on:

the market’s current priorities
2026 plans
current challenges in their space
This avoids message fatigue

The fun part?

We didn’t change:

❌ the ICP
❌ the TAM
❌ the channel
❌ the core offer
❌ the send volume

Takeaway:

When outbound stops performing, people jump to copy first.

But the real leverage is almost always in:

→ targeting
→ timing
→ positioning
→ offer
→ infrastructure

Once the system is right, the copy suddenly becomes “amazing.”
Even if it’s the same copy you thought was the problem. 😅

Whenever sales slow down, the first instinct is usually:

Automation won’t fix a broken GTM system:

- Wrong ICP.
- Weak market signals.
- No clear value.

Before we automate anything at Growth Today, we run one test. We call it the Manual 30.

(like Forbes U30 but Manual U30 ✌️)

Open a simple sheet. Add 30 accounts you genuinely want to work with. Not random prospects. Not scraped lists. Companies you’d be proud to call clients.

Then go deep.

Layer 1: Buyer signals. Promotions. New mandates. Ad infos, 10-K report, and their initiatives. What they’re consistently talking about. What’s top of mind for them?

Layer 2: Company signals. Hiring insights. Expanding into new markets. Fresh funding. Sales leadership changes.

Layer 3: Thought leadership context Search their name + “podcast.” Search their name + “interview.”

Long-form conversations reveal operational tension people never post about.

Layer 4: Their GTM stack. CRM. Routing. Scheduling flow. Form logic.

Just by looking at their tech stack, you’ll know so much about how they operate and what GTM context their potential challenges are.

Layer 5: Process gaps. Job descriptions. Reviews. Case studies. Tells you what they’re focused on and what they’d like to actively solve

Layer 6: Job posts. Look at the language they use:

If this doesn’t generate real conversations, doing this at scale (by leveraging automation) will just help you fail faster.

& ONE MORE thing most teams underestimate: Speed-to-lead.

The longer they need to wait for your response, the lower your chances of turning that lead into a real conversation — and a booked meeting.

Strike while the iron is hot 🔥

Every GTM system we’ve successfully scaled started with manual validation first.

Not because it’s cute.

Because it works.

How do you validate targeting before turning automation on?

AUTOMATION WON'T FIX A BROKEN GTM SYSTEM 

If your database charges you PER CONTACT 👀 Your ABM motion turns into credit math 🧞 like this:

Want the CEO? pay. 💸

Need RevOps + Marketing too? pay again 💸💸

Want the buying committee? Now you’re doing FINANCE 🪄, not outbound.

You want to use these tools to maximize the coverage on your target accounts & the whole buying committee

So why pay for each individual When you get ALL of THEM?

With saasyDB: 1 credit = you get the whole buying committee 👀👀👀

The whole org, so you can actually multi-thread all relevant exec, functional leaders, operators …whoever influences the deal.

Stuart from saasyDB realized we shouldn’t be multi-threading to require a CFO’s approval to have access to the prospects at the target accounts we want to talk to ✌️

if you’re targeting SaaS = use SassyDB alone or on top of your existing tech stack

p.s. Does your enrichment provider force you to optimize for CONTACTS… or ACCOUNTS? or you can get both? 👀

I just * literally * watched AI build my workout plan in real-time!!

Prompt 1: "I want isolated exercises to form all parts of my glutes." AI responds with: → Exercise selection (cable kickbacks, bridges, abductions) → Sets, reps, rest periods → Why each movement targets specific glute regions

Prompt 2: "Generate this in the app."
(so that I don’t need to add each exercise to my workout plan. sorry im lazy! 😄)

Done.
Workout is live and ready to use.
This is the best AI implementation I've seen in a fitness app.

I’m just SO fascinated by how easy to use AI in every part of our lives
& honestly I can’t wait to see

-AI cold callers to do the phone calls
-AI to prospects target accounts

I’m already using AI to amplify my prospecting processes, content creation, and ideation

& I can’t wait to see what else it can do
The future is SOO exciting!

Some tools with AI (agents) you can test:

FlashLabs’s super agent for list building, prospecting, and follow-ups
Roman Hipp’s crawler AI agent to give you valid data
Carmen from Scripe to write content on LinkedIn
& to make the most out of these tools

Roxana Irimia Lemlist course on how to build a personal brand
Lara Acosta’s course on how to think about content creation on social
Nathan Lippi 🥾 Lippi or 🌪️ Marcos Stu’s Clay bootcamps and courses on GTM engineering/sales prospecting

Clay’s own university
P.S. NOEX Training if you're curious ✌️

A company came to us with a problem: they couldn't fill their sponsorship slots.

They run newsletters for crypto, gaming, and startup audiences.
But their sponsor pipeline was empty.

The issue? Their ideal sponsors (crypto companies, indie game studios, funded startups) didn't exist in Apollo, ZoomInfo, or any database they could buy.

So they asked us: Can you help us find and market us to them?

Here's what we did:

1️⃣ Email Infrastructure:

We bought domains, configured inboxes, and inbox placement tests to adjust sending based on inbox/spam ratio to maintain their health to prospect programmatically at scale.
If emails don't land, nothing else matters.

2️⃣ Custom data for list building

For crypto companies, we identified crypto monitoring directory sites. Built a custom Python script to scrape all of them. Enriched the companies. Found the right contacts.

For game developers, we scraped the Google Play Store's trending games. Used Claygent to reverse-engineer which studios built them. Then pulled decision-makers from those studios.

For startups, we sourced from different directories and databases and ran look-alike modeling to expand the list.

3️⃣ Messaging

Looked at scalable & cost-effective public data points that would either add value, or prove we did our research instead of just saying "hey, nice game."

4️⃣ Execution, Testing, Maintenance

Launched 6 campaigns.

Ran our frameworks to figure out what worked for each vertical in 90 90-day timeframe. Monitored, adjusted, scaled winners, killed losers.

The results over 90 days:

→ 104 interested responses
→ 2.4-5% reply rates depending on vertical/offer
→ 30% of positive response rate
→ $270K+ in qualified pipeline ($3k ACV on average)

The best part? They now have a repeatable system to fill their sponsorship inventory without waiting for inbound.

With proprietary data that their competitors can't access. 👑

If your ICP doesn't exist in standard databases, you're not stuck.
You just have to get creative about where to find them. 💡

We can write Python scripts to scrape niche sites. Or use tools to reverse-engineer company data. Or build enrichment workflows that run on autopilot.✌️

Proof in the pudding below 🍮

Let’s just send more emails.

The CRM that hasn’t been cleaned since 2022:

Ok, jokes aside.

How to GUARANTEE an unpredictable pipeline:

- Send more emails every time numbers dip
- Ignore deliverability because “we’ll fix it later.”
- Hire more SDRs to drive the car before fixing the engine
- Blame messaging before mapping out your service market
- treat your CRM like a storage unit

& how to help build a PREDICTABLE pipeline:

- Validate ICP before scaling volume
- Test messages manually before automating
- Fix routing before adding fuel
- Treat your CRM as a revenue architecture,
- Reference job descriptions, funding, and K-10 reports in your cold emails
- Treat tools as an access to systemize, not just tools

We can’t fix the pipeline if we don’t fix the fundamentals:

- Better reply rates with more conversations held
- Reduced response time
- Scaled outreach without hiring more reps
- turned “meh” campaigns into repeatable systems
- finally trusted their CRM data

& yes, every “let’s just send more emails” moment usually came right before someone opened the CRM and went… y tho.

So next time when sales slow, and the instinct is:

“Let’s just send more emails.”

Remember to take a look at the car engine first,

not just the car itself 🚗

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