Undercover Boss: Lessons from Working Inside 5 Companies After Selling My Startup
This essay is for CEOs and founders running companies with 50 to 50,000 employees who feel things slowing down, alignment destabilizing, or truth getting filtered before it reaches them. Why 50 employees? Because focus breaks as companies scale past 50 employees, even in the AI era.
After working anonymously inside five companies, here is what surprised me most:
• Employees always know more than leaders think
• CEOs unintentionally create massive hidden work
• Founder-led sales scales further than founder-led product
• Culture mismatch breaks teams faster than bad strategy
• Most growth problems are alignment problems, not effort problems
Introduction
Very few people go from being the CEO of a high flying startup to an anonymous employee at a larger company. I am one of those. With my CEO vision (it's like xray vision but much less creepy) activated, I got a whole new insight into how companies work, what they do right, what they do wrong, but from the view of an employee. It was invaluable experience that most CEOs wish they could have (there is literally a show called Undercover Boss for a reason). So I'm going to share some of my learnings over a series of articles that should help CEOs diagnose, fix, and scale.
Why Employees Don’t Speak Up to CEOs (Even in Transparent Cultures)
Some of the companies I worked at truly had trusting and transparent cultures where employees felt very comfortable voicing their opinions. However, even there, I found that employees held back. They held back because they were unsure, because they feared for their jobs, because they were uncomfortable with confrontation..They held back for a myriad of reasons. As a CEO, never operate under the assumption that your employees are telling you everything. When I was a CEO, people went along with my ideas. I thought I was good at convincing people of things. When I was an employee, I struggled hard. It turns out the title did a lot of the convincing. Never assume your ideas are perfect because you get no push back.
Why CEOs Hire Versions of Themselves (And Compound Their Weaknesses)
You know the famous saying, "you marry one of your parents"? Well, first thing to be aware of, CEOs often hire themselves. Take a look at your functional leadership. I'd bet that each of them biggest quality aligns with one of your biggest quality. We often joke that Product Managers are CEOs trying to clone themselves.
Here's the upside of that approach. You are attempting to clone your best qualities. If you are creative, then your VP of Sales is creative.
This is a cliche, but make sure your first 5 hires have the attributes you want the whole company to have. If you are creating a new business line, or changing functional leadership, same premise.
However, I've often seen it with a downside. You end up compounding your biggest flaws. For example, are you someone who hates conflict? I bet your VP of Product hates conflict too. I bet their Product Managers (who have stayed the longest) hate conflict too.
Action Items
1. Know thyself. Know what you are good at, know what you are bad it.
2. Hire for your weaknesses. Make sure the people you hire (who will hire others) do the same thing.
Why a Single CEO Comment Can Create Weeks of Wasted Work
CEOs underweight the impact of their words (and the benefit of focus). Parachuting in does a lot of damage. I've done it myself many times. Particularly in the product team and in the sales team. Product team because there are always little details that can be fixed. Sales team because I'm the one who first sold that product. It wouldn't exist without me!
Me: "Why are you upset?"
Other Director: "Because I know I'm going to have to spend the next three days creating a process that we are going to throw out 2 weeks later."
Another Director: "And then the CEO came in and boom, three weeks of work gone, now we got busy work to show we heard for the next month before we can get back to the normal plan."
One of these was from a company that was 100 people, the other that was above 10,000. It happens at every size company. CEOs don't often know that an oft hand comment in a meeting can cause weeks of work. I certainly didn't know it. But as an employee I saw it cause a mad dash where everything was dropped. Not the best thing, but sometimes necessary. However, you can only do it a few times a year.
When you do it more frequently, the effect is mass demoralization. People know they are doing wasted work. They never do their best because they are all but certain that the work will be thrown out. It causes the creation of processes because employees don't want to do the work, thus processes must be created to ensure it gets done. Then employees get more demoralized because they have unnecessary processes. It is a vicious cycle.
Action Items
1. Know the impact of your words
2. Don't change focus every week
3. If you do change focus, explain why, very clearly
4. If you have don't on the focus, keep them to yourself or a small cadre until they are ready for show time
Product-Led vs Sales-Led Companies: Why the Mismatch Breaks Teams
Are you Product led? Are you Sales led? Are you Customer Happiness led? I've seen all of these things. And I imagine all of them can work. The most important thing is to know what you are as a company, then adjust accordingly. Say you are Product led. Actually Product Led, not masquerading. Then you want to hire Product Managers who are creative, good at 0-1, and master consensus builders. If you are Sales Led, you want your Product Managers to be masters at project management, translating sales speak to Product speak (shameless plug for Arkweaver), and are good at communicating with sales.
Where you get into trouble is when there is a mismatch. You hire the wrong profile of employee. I've seen the frustration it causes employees. They are being told they are empowered only to have the weight of the organization work in a completely different way. The reality distortion field needs to be used to create the engine, not convince the engine its a chicken.
Action Item
Ask 5 employees across different functional areas and level in the company, what type of company are we?
Why Founder-Led Sales Scales Better Than Founder-Led Product in Enterprise Companies
Raised in the Steve Jobs era that the founder should be in every little detail, this was an eye opening experience for me. In Enterprise companies, Founder led sales scales much better and much further than founder led product. The Product team's challenge is fulfilling many customizations and requirements. It's a detail oriented job that founders are not great at communicating and staying on top of as they bounce around the org. Founder led sales is quite effective as long as you have someone (or AI) to offload the follow-up communications. For example, if you promised a big customer a specific feature, you need a way to communicate that to the team. Otherwise your Account Manager will get on the next call and be in for a rude awakening. I've seen Founder led sales scale to hundreds of employees.
Action Items
1. Keep selling longer than you think
2. Be sure someone is handling the operational details
Why “Work Harder” Is Almost Never the Real Problem
Employees work really fucking hard. Especially at a decent company, which most of you run (or I'm guessing). Even when you aren't in the room, they work hard. In fact, many employees often outwork you.
The solution to most issues your company is facing is not "work harder". Often times CEOs pull that lever because its the only control they have over the company.
Action Item
Keep appreciating your employees.
Why the Second New Product Is So Hard for CEOs (And Why Jumping In Still Works)
At multiple of the companies I worked with, they were faced with the challenge of what to do for a second product. They had killer first products and weren't sure what the second products would be.
The companies that did this best, jumped in. They shipped rapidly. They made concerted bets. They resourced the teams. I didn't always agree, but I admired their fearlessness. You have to put yourself back in the headspace of Day 1 instead of Day 730. It doesn't need to be perfect. It's doesn't need to be a billion dollar product right away. Make bets. Analyze their effect. Get started.
Action Item
Don't fear failure, it's what got you to where you are
Why Culture Fit Matters More Than Strategy as Companies Grow
There was a company I advised that I did not like. Every direction I advised, they went the opposite. Every cultural norm I thought was important, they did the opposite. It was a miserable experience. But you know what? I talked to a dozen of their current and ex-employees recently. They love it. It was the culture for them.
The faster you know thyself as a company, the faster you accept it, the faster you grow. Not every culture is right for everyone. Want to save a lot of time? Only hire those people for whom the culture is right.
Action Item
Know thyself...I believe I've said it before
Why Companies That Undervalue Sales Struggle to Grow
Sales is still thought of as a dirty word in software. It's thought of as a necessary evil. The companies I worked with that did the best, they treated sales people and leadership well. They appreciated the effort and craft. It showed. The rest of the company did the same.
In other companies where sales was a "I mean we have to have a sales team because that's what you do" it showed. Customer voice tended to be undervalued. Top talent left quickly. Growth came in fits and spurts and not from any discernible process.
With AI enabling engineers to build products faster than ever, it's all about selling the product. Companies that value sales people will thrive. Remember, sales is the only role where compensation is tied directly to performance. Imagine if 50% of a Product Manager's cash compensation was tied to feature usage?
Sales people will do what your incentives tell them to do. Make sure you give them the right incentive and be sure to shout them out in the organization. Despite money being a reward, they also want props!
Action Item
Make sure you have an appropriately staffed, resourced, and respected sales team
How Board Meetings Often Create Organizational Whiplash
You exit the board meeting. You open your phone. You text your team 3-4 action items. I've done this time and again. Do not do this.
First, not all board ideas are great. They are parachuting in. Often times they are throwing ideas out there.
Second, this causes a whiplash with your team. Often the ideas are very high level. It causes a lot of downstream work that a CEO doesn't see. It can often seem out of left field. "Hey, can you analyze the veterinary market?"..."Um...sure, but don't we sell phone cases?"
Third, you need some time to digest. See what sticks with you after a board meeting. Give it a day or two. I'd even recommend messaging the board members two days later and asking some version of "would you still stand by that?"
Action Items
1. Wait two days before sharing action items from a board meeting.
2. Double check with board members to see if they stand by their advice.
Conclusion
I got the rare opportunity to be an employee after being a CEO. It gave me a truly unique insight that will make me a better second time CEO. I hope it can help you too. If there is one line to remember it's this: Know thyself and be true to thyself. Everything will follow from there.
After seeing this pattern repeatedly, it became obvious to me that most companies are not suffering from a lack of data. They are practically drowning it. They are suffering from filtered truth, misaligned teams, and slow translation between sales, product, and leadership. That realization is what led me to build Arkweaver.