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:

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

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

77 Questions

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

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

Hiring Bundle

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

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

Book Promo

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

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

VP of Sales Working Out

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

https://www.insidesalesexpert.com/will-the-vp-of-sales-work-out?utm_source=Google&utm_medium=FirstComment

Mini-Podcast Series

Buy the $4.99 mini-podcast series here:

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

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

It Happened on the Sales Floor

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

Model Week

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

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

Mini-Pod

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

Practical. Fast. Real Stories. Real Lessons.

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

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

Podcast Promo

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

Job Seeker Course

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

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

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

Helen Yu

CEO @Tigon Advisory Corp. | Host of CXO Spice | Board Director |Top 50 Women in Tech | AI, Cybersecurity, FinTech, Insurance, Industry40, Growth Acceleration

I'm passionate about human-AI amplification rather than replacement.



As the founder & CEO of Tigon Advisory, I help tech companies multiply growth through responsible AI, cybersecurity, IoT, supply chain, and CX strategies. Offering CXO-as-a-service in digital transformation, risk management, GTM, and thought leadership. Clients include NVIDIA, Salesforce, Microsoft, Cisco and innovative startups in Cybersecurity, SaaS, Fintech, etc. Also serve as board director and VC advisor on ethical tech and governance. 



Credentials include cybersecurity certification from MIT Sloan, MBA from Loyola University Chicago, WSJ/Amazon bestselling author ("Ascend Your Start-Up"), keynote speaker, and host of CXO Spice podcast where I explore leadership in emerging tech.



On LinkedIn, my daily posts (300+ in 2025, 136k+ reactions, 38k+ comments) share practical insights on ethical AI scaling, voice agents, bias mitigation, and building trust in human-AI teams.



I'm passionate about mentoring the next generation, especially women and underrepresented leaders in tech.

If you're shaping responsible AI strategies, navigating cyber risks in AI, or debating amplification vs. automation, let's connect. Comment below, share your take, or reach out. Excited to amplify together.



#ResponsibleAI #HumanAI #AIEthics #Cybersecurity #DigitalTransformation

Director Board of Directors

CEC is a security service integrator with focus markets in manufacturing, healthcare, SLED and Corporate Campus.  Customers with complicated organizations and physical plants rely on CEC as extensions of their teams in making strategic investment and management decisions related to their technology and infrastructure. I serve as Culture and Compensation Committee Chair. 

What would the world look like if we truly accelerated action for women?

Right now, full gender parity won't arrive until 2158 according to the World Economic Forum.

That’s 132 years away.

We have the power to move that date forward.

In this special #IWD2026 newsletter edition, I reflect on the progress we’ve made, highlight the women who inspire me, and share actions we can take to accelerate change.

Inside you’ll find:
✅ Highlights from a powerful Women in Technology panel at the Acumatica Summit
✅ Books and podcasts that expand perspective
✅ Simple actions anyone can take to move the needle

Over the past year, I’ve been incredibly fortunate to learn from many inspiring women leaders across technology, financial services, manufacturing and communications.

Now I want to hear from you 👇
Tag one woman who inspired you and tell us why.

Let's amplify women’s voices together. 
Happy International Women’s Day 🌸

#IWD2026 #AccelerateAction #WomenInLeadership #GenderEquity

To stay current with the latest trends in #Technology and #Innovation,
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Bridging Responsible AI Innovation | Advisor to Tech Leaders | Host, CXO Spice | Human-AI Amplification Advocate

Every March 8th, the world pauses to honor the achievements, resilience, and brilliance of women. But this year’s theme, Accelerate Action, reminds us

Open article: Accelerating Change: Celebrating Women and the Work Still Ahead by Helen Yu • 4 min read

Accelerating Change: Celebrating Women and the Work Still Ahead

What lights you up about the work you do?

For me, it's this.
Fresh off Conga Connect in Orlando and straight into Enterprise Connect in Vegas, I hosted "Hot Takes & Cold Drinks" with two women who are redefining what leadership looks like in communications and technology.
⭐️ Millicent McIntyre, MSOB — 2026 Spotlight Award Winner, Senior Director, Buyer Services IAA
⭐️ Lori Wodrich — 2025 Winner & this year's judge, Senior Systems Engineer Amerisure Insurance

What resonated with me most was HOW they got there.
🔥Millie started in a contact center after cosmetology school.
No title. No roadmap.
She became the person everyone came to through curiosity, consistency, and caring deeply about people.
"Culture is the foundation of everything we do."
She meant every word.

🔥Lori's defining moment was A hackathon.
Surrounded by engineers far more technical than her, she almost changed her answer to fit in.
She didn't.
She held her ground. Shared her reasoning. And the entire panel shifted to her choice.
That's confidence backed by data.

Lori's Three S's I'm taking with me:
✅ Speak Up
✅ Say Yes — to growth, not every task
✅ Share Results

And here is Millie's closing wisdom:
Don't try to be like every other leader.
Be authentically, unapologetically YOU.

These are two women who didn't wait for a title to lead.
They showed up. Over-delivered. Built trust.
And the title eventually followed.

My biggest takeaway: Leadership is earned, not assigned.
Here is my personal hot take:
Sometimes you need to put down your to-do list and focus on your to-be list.
Who do you want to BE? Let that guide everything else.

Thank you, Millie and Lori, for being so open, so real, and so generous with your stories. You reminded all of us of what's possible. 🙌

And a heartfelt thank you to Erica Marois and Cheryl Kahan-Radhuber at Informa and Enterprise Connect for creating this space for women in communications. This is exactly the kind of platform our community needs. 💜

▶️ Watch the full 15-minute conversation below!

#EnterpriseConnect #WomenInTech #Leadership #EC2026 #Communications 

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What did I learn from the OECD - OCDE Responsible AI Due Diligence Guidance?

Responsible AI is shifting from principles to accountability; clarifying who is responsible, at what point, and across the value chain.

👉 The real shift is from “Do we use AI responsibly?” to “Can we prove it — continuously?”

AI governance is becoming a core business capability rather than a compliance exercise.

I’ve broken down the insights that stood out to me me most in the carousel including where responsibility escalates, when scrutiny should be deeper, and why disengagement is sometimes the responsible choice.

Let me know what stood out to you 👇

#ResponsibleAI #AIGovernance #RiskManagement #BoardDirectors #CEOs

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CEO of Tigon Advisory Corp. | Host of CXO Spice | Board Director |Top 50 Women in Tech | AI, Cybersecurity, FinTech, Insurance, Industry40, Growth Acceleration

5 Key Learnings from OECD Responsible AI Due Diligence

Are you modernizing your systems fast and wondering if you’re doing it securely?

In this short CXO Spice trailer, John Picinich and I touch on the real tension leaders are facing right now; moving quickly to innovate while making sure security, risk, and trust don’t fall behind. It’s a conversation about what works in the real world.

This builds on the themes from the #CXOSpice newsletter I shared three weeks ago on breaking down data silos in financial services, where we explored why governance, secure data movement, and a strong foundation are essential before layering on automation and AI.

I had the chance to host John Picinich at Progress Software to unpack:
✅ Where most organizations misjudge modernization risk
✅ How security teams can become enablers, not blockers
✅ What “secure by design” looks like in practice

🎥 Watch the full episode here: https://lnkd.in/gPq8B8Tg

And stay tuned. I’ll be hosting Progress Software’ Chief AI Officer Ed Keisling on agent orchestration soon.

#FinancialServices #AI #Agents

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What the #WomenInTech stage taught me at Acumatica Summit?

Have you ever walked into a room and felt momentum happening in real time?
Speaking at Acumatica Summit this year was one of those moments.

I left thinking less about the stage and more about the people. Leaders choosing courage over comfort. Learning out loud. Lifting each other higher.

A few lessons that stayed with me
✨ Confidence starts with the story we tell ourselves
✨ Preparation creates clarity when pressure rises
✨ Leadership means sending the ladder down

I shared a few deeper reflections in my latest newsletter. Check out the full story: https://lnkd.in/e2Ad_BXf

What is one lesson that has changed how you show up this year?

#WomenInTech #Leadership #Technology #Innovation

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A FIRST TIMER’S PERSPECTIVE I didn’t know what to expect walking into my first Acumatica Summit. I knew the event was significant, and I felt honored 

Open article: What the Women in Tech Stage at Acumatica Summit Taught Me? by Helen Yu • 7 min read

What the Women in Tech Stage at Acumatica Summit Taught Me?

What does success look like twelve months in if you go all in on a frictionless Commerce Chain?

I asked Lisa Martin, CRO of Conga during our interview at Conga Connect.
Her answer was precise.

Deal velocity accelerates. Deal volume grows. Revenue leakage stops hiding in quarterly post-mortems.

Most organizations look at discounting retrospectively. A scattergram tells you where you bled. Commerce Chain stops the bleeding.

A connected Commerce Chain changes the equation. You see where margin is slipping in the moment. You catch at-risk customers before renewal. You act on upsell signals the data was always telling you.

And when agentic AI matures inside that chain, it executes the insight.
Faster deals. Protected margin. Smarter renewals.

👉 Read the full story in CXO Spice Newsletter 
👉 Watch the conversation: https://lnkd.in/gpdCFhkS

#CommerceChain #CRO #CongaConnect #CongaPartner

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“It’s not growth at all costs anymore. It’s growth, but profitable growth , and the thing getting inspected is how easy we are to do business with.” —

Open article: Commerce Chain Is the Revenue Operating System Your Business Has Been Missing by Helen Yu • 5 min read

Commerce Chain Is the Revenue Operating System Your Business Has Been Missing

What does every business leader need to understand about the agentic era?

Here are 5 things I took away from Jensen Huang’s keynote at NVIDIA GTC:

1️⃣ Tokens are the new oil
Jensen redefined what a data center is.
Data centers are no longer places where we store files.
They are factories producing tokens.
Power goes in.
Data goes in.
Intelligence comes out.
Every watt of power you have is either generating revenue or wasting it.
The next metric CEOs may start tracking alongside EBITDA: tokens per watt.

2️⃣ The inference inflection
For years AI was a training story about who had the biggest models and the most parameters.
That era is over.
AI now must think, reason, and act in real time.
That requires inference at massive scale.
Compute demand has grown roughly 1,000,000× in two years.
That’s not hype.
That’s infrastructure reality.

3️⃣ Every SaaS company will become an AaaS company
Just as every company eventually needed:
• an HTTP strategy
• a cloud strategy
• a Kubernetes strategy
Every company now needs an agent strategy.
The question is no longer if.
It’s how fast.

4️⃣ The security model just changed
Agentic systems can:
• access sensitive data
• execute code
• communicate externally
Jensen said that out loud. Slowly.
Let that sink in.
The opportunity is enormous.
So is the risk.
In the agentic era, security and governance are the foundation.
The companies that get this right will win.

5️⃣ Synthetic data will unlock robotics
Real-world data will never be sufficient to train robots for every scenario.
Simulation closes the gap.
Synthetic data allows robots to learn faster than the real world can generate experience.
The GPT moment for autonomous systems may already be happening.
BYD, Hyundai, Nissan, and Geely just joined the platform, representing 18M vehicles per year.

The closing scene of the keynote said everything.
Robots and humans sitting around a campfire in a forest.
Playing music together.
The caption:
“The future’s here. Won’t you come and see.”
Not a warning.
An invitation.

Two stops worth making on the show floor today:
✅ Cisco Booth #1421 - The agentic era needs a secure foundation. I’ll be interviewing Kevin Wollenweber, SVP & GM of Data Center at Cisco, on what Secure AI Factory means at enterprise scale.
✅ Elastic Booth #3200 - Jensen said 90% of the world’s data is unstructured and largely inaccessible. Elastic is building the retrieval layer to unlock it. Don’t miss their sessions on eliminating the data bottleneck and how NVIDIA itself is using it.

The token factory is only as powerful as its security, networking, and data retrieval layers.

That’s the story continuing on the show floor.

#NVIDIAGTC #NVIDIAPartner #CiscoPartner

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What Boards and Security Leaders Must Know about AI-Driven Threats?

Last week, I hosted Mike Riemer, Field CISO at Ivanti on a webinar secure by design: prevent weaponized AI attacks with Kernel security strategies.

Mike put the stakes in sharp focus from the start:

Threat actors can reverse engineer a patch and weaponize it within 72 hours.
In some cases, attacks begin within 90 seconds of code being published.

Let that sink in.

This is not a technology problem you can delegate to your CISO.
It is a governance issue, and boards have a fiduciary duty to act.

In my latest newsletter, I cover:

✅ Why traditional perimeter defenses are failing
✅ What Secure by Design means  and how to hold vendors accountable
✅ Why kernel-level security is the new line of defense
✅ The questions every board and audit committee must be asking now

Knowledge without action leaves your organization exposed.

As AI-driven threats accelerate, kernel-level security has become the new line of defense.

Are you ready for it?

Watch the full conversation with Mike here:
https://lnkd.in/gP4hnwGT

Join us for the upcoming #LinkedInLive where we'll be continuing this critical conversation. Register here: https://lnkd.in/gF8YcTqf

#CyberSecurity #BoardGovernance #KernelSecurity #AIThreats #CISO #RiskManagement #IvantiPartner

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“Threat actors can reverse engineer a patch and weaponize it within 72 hours — and we’ve seen attacks begin within 90 seconds of vulnerable code being

Open article: What Boards and Security Leaders Must Know About AI-Driven Threats and Kernel-Level Defense by Helen Yu • 6 min read

What Boards and Security Leaders Must Know About AI-Driven Threats and Kernel-Level Defense

Why are companies still using 8 platforms to move money?

I just saw a CFO’s finance stack:
Stripe. Wise. Ramp. Mercury. Chargebee.
Plus 3 international bank accounts.
Eight logins. Eight reconciliations.
And they’re still losing 4–6% on every international transaction.

Here’s the hidden tax 👇
You get paid €100K → converted to USD (≈3% gone)
You pay a European supplier → USD back to EUR (≈3% gone)
That’s 6% lost moving the same money in a circle.
On a $10M business? $600K/year.

This is why Airwallex exists.
One platform to:
✅ Accept global payments
✅ Hold 20+ currencies (no forced FX)
✅ Pay suppliers same-day
✅ Issue cards globally (zero FX fees)
✅ Open accounts in minutes
One integration. One dashboard.
Companies doing $10M+ internationally save $400K–$600K/year just by consolidating.

Airwallex just opened their second HQ in San Francisco. They're bringing global-first infrastructure to companies tired of fragmented stacks and hidden fees.

So Why are you still using 8 platforms to move money?

#AirwallexPartner #CFOs

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How do you prepare for the next frontier of transformation?

AI is reshaping how we build, decide, and serve customers; and getting ready means learning, experimenting, and connecting with others who are doing the same.

You’ll find a mix of business leaders and builders at the #MicrosoftAITour. 
People like me, are focused on turning AI ideas into real impact. What I love about this experience is how hands-on it is. You not only hear about the technology, but also get to explore it, build with it, and learn directly from Microsoft engineers and the community. From secure apps to agents and solutions using tools like Foundry and Copilot, you walk away inspired and ready to apply what you’ve learned.

This 20-second clip is a throwback to my favorite moments from the Chicago tour last September 🎥

I’m excited for the upcoming U.S. stops:
📍 Washington, DC on March 10 - Register here 👉 hhttps://lnkd.in/ebyjqCQb
📍 Atlanta on April 29 (I will be there in person)- Register here 👉 https://lnkd.in/ey83fdKc
📍 Houston on May 28 - Register here 👉 https://lnkd.in/eKVZVvE9

If you’re looking to prepare your organization for this frontier transformation, join a tour near you and start turning possibilities into action.

#MicrosoftAITour #FrontierTransformation #AILeadership #MicrosoftAmbassador Microsoft in Business

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When was the last time a support call made you feel heard?

After 2.3 million miles in the air and more support calls than I can count, I've come to believe we've been measuring customer experience all wrong.
We track resolution time. Handle time. CSAT scores. But nobody measures how it felt to be spoken to.

I've been hung up on agents who said all the right things and still left me feeling dismissed. And I've had problems go unresolved by agents who somehow made me feel taken care of anyway. The difference was never the script. It was tone. Pacing. The small human signals that say I hear you before a single solution is offered.

As executives, we've optimized everything we can see on a dashboard. But the felt experience of a conversation, that's been the blind spot.

That's what made me pay attention when I came across ElevenLabs' emotional voice agent. Because it points at something I've believed for years: conversational quality is product quality. And we're finally at the point where AI can deliver it at scale.

The leaders who get ahead of this won't just have faster support. They'll have support that people remember for the right reasons.

See it in action: https://lnkd.in/eDtV-aGs

#VoiceAgent #ConversationalAI #CX #CustomerOperations #ElevenLabsPartner

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How many of your #security alerts matter?

Last quarter, my team reviewed 14,000 alerts. Only eleven led to investigation.
That's not a security program. That's noise with a compliance checkbox on it.

As a Board Director, the question I keep bringing back to leadership is simple: would we catch it before it happens?

Most organizations can't answer that with confidence. Not because they lack tools. But because they're measuring the wrong things. Volume of alerts. Hours logged. Endpoints covered. 

None of it tells you what the board needs to know: where is the human risk, and is it escalating?

The shift I've been advocating for is moving from reactive reporting to predictive intelligence. Not just flagging what already happened, but understanding behavioral patterns early enough to intervene before damage is done.

When I look at what predictive risk scoring is doing now, platforms like Teramind being able to detect behavioral shifts weeks before an incident occurs, that's the kind of intelligence that belongs in a board briefing.

Rule-based systems catch what you anticipated. Behavioral AI catches what you didn't. In insider risk, what you didn't anticipate is almost always what gets you.

Stop counting alerts. Start asking: what does this pattern mean?

#PredictiveIntelligence #Workforce #AIGovernance #TeramindPartner

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What happens when AI stops living in the cloud and starts living in the world?

That's the question at the center of NVIDIA GTC.  That’s the premier global AI conference where developers, researchers, and business leaders come together to explore the next wave of AI innovation.

From physical AI and AI factories to agentic AI and inference, this is where the breakthroughs shaping every industry get unveiled. With 500+ sessions, labs, and workshops, there's no better place to go deep on real-world AI use cases and connect with the people building the future.

Last year's GTC drew 27K in-person attendees and 40M+ keynote views. I can't wait to see what 2026 has in store.

Register now and explore the session catalog: https://nvda.ws/4kfWXS8

#GTC25 #NVIDIAPartner #AI #PhysicalAI #GenerativeAI

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What does a connected, intelligent Commerce Chain look like in action?

At Conga’s 5th Annual Inspire Awards, we celebrated real, measurable business impact with CRO Lisa Martin.

When pricing, quoting, contracting, and revenue operate as one connected system, companies move faster, price smarter, and scale growth.

Here’s what that looked like this year:
✅ Commercial Excellence — IBM
Unified quoting and renewals for 3,000+ sellers and partners worldwide, accelerating deal cycles while improving seller productivity and global customer experience.
 
✅ Future of Commerce — Electronics Digikey
2× market outperformance in 2025 by unifying e-commerce with customer-specific pricing through neural networks and real-time pricing execution.
 
✅ Momentum Leader — Pediatrics Plus
Automated ~50% of monthly billing and reduced DSO from 84 → 54 days.
 
✅ Buyer Experience — Jack Henry 
Eliminated manual pricing errors, unified siloed sales processes, and accelerated time-to-revenue for financial institutions nationwide.
 
✅ Judges’ Choice — Southwest Airlines
Reduced contract creation time to just 5 minutes, delivering enterprise-grade governance with startup speed.
 
✅ Community Champion — Natalie Myers
Amplified peer voices and strengthened knowledge sharing across the entire Conga community.

A connected Commerce Chain unlocks measurable revenue performance across the entire lifecycle.

Stay tuned for my conversation with Conga CRO Lisa Martin with a deeper dive into what the Commerce Chain means for the future of revenue leadership.

#CongaConnect #InspireAwards #CommerceChain #CustomerSuccess #CongaPartner

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What does it take to turn B2B influencer content into qualified pipeline?

I recently had a great conversation with Heather Barnett about this challenge and it’s clear this topic is rising on many B2B leaders’ agendas.

There’s a smarter way to approach it.

The Insight Collective and Custom Influence have put together an ebook that breaks it all down, featuring insights from leading B2B voices.

If you’re focused on making influencer marketing deliver measurable impact, this is worth your time.

https://lnkd.in/epkRekqz

#B2B #Influencer #Marketing 

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When was the last time an AI investment delivered what it promised?

I've sat in enough boardrooms to know that question lands differently depending on who's in the room.

For most enterprises, the pattern is the same; a promising pilot, a growing consulting retainer, and a strategy deck that never quite becomes a production system.

That's the cycle Klika Tech built VELOCITY™ to break.

It's a 16-month, fixed-price program that takes organizations from AI uncertainty to a fully operational, self-sustaining AI capability. One contract. Five structured phases. And your team owns everything they build including the models, the infrastructure and the IP.

Team don't get paid for hours. They get paid for outcomes.

ROI validation begins at Month 8 so you get proof mid-journey
If AI is on your roadmap this year, reach out to see what it looks like in practice.

Drop a “Yes” comment if you want to learn more. 👇

#AI #EnterpriseAI #KlikaTech #VELOCITY #DigitalTransformation

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Ready to launch your #career in #AI in 2026? 

LinkedIn just released its Skills on the Rise 2026 list and the signal is clear: AI is reshaping every role, not just technical ones. 

Here are the fastest-growing skills: Prompt Engineering, RAG, LangChain, Vector Databases, and Model Fine-Tuning along people skills like Stakeholder Management and Leadership Communication. Employers want professionals who can build and lead with AI.

Meanwhile, the U.S. Bureau of Labor Statistics projects 20% growth in computer and information research roles between 2024 and 2034. The opportunity is real.

I've consolidated what I learned from Coursera and U.S. Bureau of Labor and put together a table of 9 high-demand AI roles with required skills, salary ranges, and core responsibilities to help you find your best fit.

Which role excites you most? Drop it in the comments 👇

#SkillsOnTheRise #FutureOfWork #ArtificialIntelligence #TechCareers
#AI #Jobs #MachineLearning #DataScience #WomenInTech

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9 AI Jobs to Consider in 2026

What are the two things that define a world-class data center?

Here's what I learned from Equinix team at last year's NVIDIA GTC 
(watch the 1-minute clip below)
→ Environment - power, space, and cooling
→ Interconnectivity - dense access to public clouds and GPU-as-a-service

Equinix operates 280 data centers across 77 global markets. The London facility Aaron showcased was built with his in mind: 170,000 sq ft, 100% renewable energy, 99.999% availability, and 200+ cloud interconnection points all water-cooled.

Equinix also announced they'll be the first to offer the NVIDIA Instant AI Factory; fully provisioned AI infrastructure powered by DGX GB300 and B300 systems, across 45 global markets.

This year, I'm going deeper on the #sustainability side of all of this.
I look forward to speaking with Christopher Wellise, Global VP of Sustainability at Equinix to talk about what it takes to build and operate AI infrastructure responsibly; from closing the gap between pledges and results, to whether the industry is measuring the right things.

Tune in to our upcoming CXO Spice from #NVIDAGTC. What would YOU ask Chris? Drop it below 👇

To stay current with the latest trends in #Technology and #Innovation,
Subscribe to 👉 #CXOSpiceNewsletter here https://lnkd.in/gy2RJ9xg
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Where are the real conversations about the future of revenue lifecycle happening right now?

At Conga Connect.

Just arrived at the venue and the energy is already building. This quick clip gives a glimpse of the space and a great catch-up with Amy Williams from the Conga team as things get underway.

Looking ahead to a packed agenda for Day 1:
✅ The future of commerce keynote from David Osborne CEO of Conga
✅ Accelerating Innovation across the commerce chain from Rohit Chhabra, CPO
✅ My 1:1 with Lisa Martin, CRO, diving into Commerce Chain
✅ Tonight’s customer panel and awards
✅ And wrapping the evening with the VIP dinner with Conga executives, select customers and fellow analysts Shelly DeMotte Kramer, Roy Atkinson, Eric Kavanagh.

Events like this are where product vision, customer experience, and strategy come together. I’m interested in hearing how organizations are approaching revenue lifecycle transformation and connected commerce.

Let's connect if you're here at Conga Connect. Or follow #CXOSpice to get the latest updates.

#CongaConnect #RevenueLifecycle #CPQ #CommerceChain #Analysts #CongaPartner

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What does responsible AI governance look like when the infrastructure at stake is an entire city?

It's a question that I'm proud to have helped answer along with an exceptional group of experts in collaboration with AI & Partners.

In this whitepaper, Digital Public Services: Governance Challenges in AI-Enabled Smart Cities, we explore how we can build trustworthy, interoperable urban infrastructure as AI becomes central to transport, energy, health, and public administration.

Key takeaways:
✅ Interconnected systems create cascading risks - resilience must be built in by design
✅ Interoperability and open standards are governance tools rather than just technical ones
✅ Privacy-by-design is essential as sensor networks and data fusion expand across cities
✅ The EU AI Act creates real obligations for municipalities deploying high-risk AI

Thank you to my fellow contributors for making this such a rigorous and timely piece of work:
Sean Musch, Michael Charles Borrelli, Dr. Don Liyanage, Dr. Benedikt Kohn, Harvey Castro, Lisa Ventura MBE FCIIS MBCS, Mariia Shcherbakova, Patrick Orsos, Shreyas Karanjkar, Edward Cole, Mitko Karushkov, Vibhav Mithal, FHCA, Mateo Jarrin Cuvi, Michael Boevink, Ina Schöne, Richard Chiumento, and Carolyn Harrison.

If you work in urban policy, AI regulation, or digital public services, this one is for you. 

#SmartCities #AIGovernance #EUAIAct #DigitalTransformation #AI

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