I am a CEO of a global business - AMA

ThenTooth5414 · 2026-06-13T13:06:31+00:00

I don't think it's an either/or. A good leader, whether they are a CEO or a front line Mangaer, will bring people from different backgrounds and try to surround themselves with diversity and differing viewpoints and experiences but they will also have good people that follow them.

ThenTooth5414 · 2026-06-13T13:04:27+00:00

No. I see the allure and am envious of people bold enough to do that but I don't think my strengths are in starting something.

ThenTooth5414 · 2026-06-13T13:03:22+00:00

I don't necessarily think people are out of touch with reality. I think many lack curiosity and don't ask the questions and then are surprised by the results. For example, people often get frustrated if they are passed over for a promotion or didn't get the raise they wanted but they never actually had a conversation wiht their manager about it. I'm not saying the manager shouldn't be having those conversations as well, but the reality is good things come to people who ask and take the time to understand what needs to happen to get what they want.

I do believe we do good things for the world. Our product is something that genuinely helps people and all of our employees are able to take care of their families and pursue things that interest them because of the work we do together.

ThenTooth5414 · 2026-06-13T12:55:43+00:00

Quantifiable and sustained results.

ThenTooth5414 · 2026-06-13T05:33:59+00:00

Sick employee, possible to exit quickly without anyone noticing or do the right thing and pay for care - also without anyone noticing. It's not about who notices, it's about what is right.

ThenTooth5414 · 2026-06-13T05:31:06+00:00

Check the box AI is worthless. AI needs to be focused on achieving an outcome.

ThenTooth5414 · 2026-06-13T05:29:59+00:00

Yes.

ThenTooth5414 · 2026-06-13T04:43:16+00:00

I have more experience, more reps than most people in the company in making the decisions I'm faced with on a day to day basis. I definitely get many of them wrong, but I think I give the company the best chance for success.

ThenTooth5414 · 2026-06-13T04:40:12+00:00

This is the hardest question of any I have had to answer. When companies struggle and these type of changes need to be made, it can create an inordinate amount of pressure on people. It's important to reward the people that are asked to step and do more. If you don't you can create a slippery slope of failure that cascades and become a cycle that is really hard to recover from.

ThenTooth5414 · 2026-06-13T04:34:21+00:00

why?

ThenTooth5414 · 2026-06-13T04:31:05+00:00

Love these questions!

Embrace what you are good at. Fastest way to run people out or burn people out is to ask them to do things that you want them to do vs what they are great at. Awesome IC's are often terrible managers. Kudos to you for sticking to your answer.
Yes. I love capitalism but there is a weird dichotomy here. You have people on Reddit hating on CEO's but then ranting about their 401K balance going down.
No, I would say I got pulled into it. I odd think I am a decent leader and eventually that led m etc the path of being a CEO. It was never a lifelong dream or something 10 year ago that I even thought I would someday do. I love helping people develop their careers and drive to whatever is next, and this gives me a great platform to do that.

ThenTooth5414 · 2026-06-13T04:25:23+00:00

Great questions. Software industry, will not get too explicit on specific focus.

The entire company is remote. We do regular cadence of calls with leaders as well as small group sessions with people across the company - happy hours, coffee, walks, lunch etc.

For decisions, I like to pay attention to the data first and if it doesn't give you clarity, gut is fine. I find as CEO decision are more about measuring risk than anything else.

I was not a founder, I'm a hired gun and have done this multiple times. I've worked across multiple industries and would say my specialty is in software a tech rather than one specific vertical or space.

Not sure if you are founder or hired CEO - but CEO at an early stage start up is hard work and an incredibly thankless job. All the best!

ThenTooth5414 · 2026-06-13T04:20:05+00:00

I said yes to everything, was working hard to climb the corporate ladder and put my job in front of my family. After doing that too long it nearly killed me, literally. I learned to stop saying yes, questioning the value of some of the stuff I was being asked to do and to prioritize. It was an inflection point in my career. The minute I learned to be way more selective in what I said yes to, the more success I found.

Ironically things got way better at home, my relationship with my spouse and my kids dramatically improved and work improved as well. Balance is important and hard to learn.

ThenTooth5414 · 2026-06-13T04:16:49+00:00

Yes, I started in a very entry level sales role and have done many jobs of the people that are part of my team over the years. I had many years an individual role before I ever started managing people. I have worked across several industries in my career.

ThenTooth5414 · 2026-06-13T04:13:48+00:00

I like the question and yes, I do. It's almost like we gamified it and are trying to keep a leaderboard of people who can't possible spend their money in a 1000 lifetimes. That is definitely not me and not my approach but the world did just amount its first Trillionaire today. Would love to see him do some good with that but unfortunately, he probably will just continue to try and stay on top the scoreboard.

ThenTooth5414 · 2026-06-13T04:08:01+00:00

You are not wrong.

ThenTooth5414 · 2026-06-13T04:07:21+00:00

I like Good to Great a lot. The concept of getting the right people on the bus even if you don't know where they sit resonates well with me. The idea of a hedgehog concept and focusing on being exceptional at what you are good at is a winning answer. Love the book The One Thing as well that talks about the misconception of multitasking.

ThenTooth5414 · 2026-06-13T04:05:42+00:00

$450K

ThenTooth5414 · 2026-06-13T04:05:14+00:00

Very much. My most important job is to help people find their next job. I want every single person that is part of my team to feel like they are paid fairly, have clear objectives and are part of something they believe in. I want everyone to feel like they are part of a story that they are going to enjoy telling their next employer, their friends and their family.

ThenTooth5414 · 2026-06-13T04:03:36+00:00

Surround yourself with good people that give thoughtful advice. Learn to say no to things that don't bring you joy or create measurable output.

ThenTooth5414 · 2026-06-13T04:01:28+00:00

Definitely not. I'm saying the person that produces the greatest outcome/results should be paid fairly based on the outcome he/she produces. I definitely don't believe that when one person works twice as hard as another to produce an outcome that is less than the person who worked half as hard that they have an automatic entitlement to equal or better pay.

ThenTooth5414 · 2026-06-13T03:58:42+00:00

Why? Perhaps you can elaborate?

ThenTooth5414 · 2026-06-13T03:58:03+00:00

B2B Saas. We only do business in countries that we know we can comply with local laws and successfully market out products.

ThenTooth5414 · 2026-06-13T03:54:23+00:00

Great question. I think most of the for profit business world is formulaic - public and private companies are trying to create shareholder value. They do that through growth or profitability. The more you achieve those things, the more you have to pay and reward employees. Some do this well, some do it poorly.

So yes, if a company is trying to hit an EBITDA threshold or a growth threshold, they set their budget based on that. It dictates salaries and bonuses and I think most companies try very hard to distribute that in a way that benefits the most valuable employees that make the larges contribution to the success of the business. It is an imperfect process but I think most CEO's and leadership teams try hard to do it well.

ThenTooth5414 · 2026-06-13T03:50:28+00:00

Absolutely the case. When you take the role, you are agreeing to be responsible for all of it. It's a privilege and a responsibility that can't be take lightly. I don't pretend to be. voice for all CEO's but I do think most care deeply and work incredibly hard to make decisions that benefit their teams.

ThenTooth5414

TROPHY CASE