Jeff Perkins has spent his career in motion.
He started in New York agencies, moved client-side, stepped into startup life, and then helped scale businesses through major growth phases. At ParkMobile, he helped drive the company from 8 million users to 50 million. At Soundstripe, he is now leading a platform built for global creators and brands. That kind of path gives you pattern recognition. It also gives you scars.
One of the clearest insights from my conversation with Jeff was not about marketing. It was not about product. It was not even about AI.
It was about letting go.
Jeff said, “I think what has been very hard for me as I’ve scaled up as a CEO is really letting go of some of those things and having the trust in the team that they’re going to execute at a very high level.”
That is the CEO lesson more people should talk about.
Scrappy Wins Early. Specialists Win Later.
Early-stage companies need utility players.
You need people who can do five jobs badly in the morning and two jobs well by the afternoon. You need people who are comfortable building the plane while flying it. That is how startups survive.
But Jeff made a critical distinction. There comes a point when that same model stops working.
At some stage, the company no longer needs generalists everywhere. It needs real operators in key seats. It needs people who already know the playbook. Not because the early team failed. Because the company changed.
Jeff put it plainly. Sometimes those early utility players “just don’t know the playbook.” They have not seen the movie before. They are not bad people. They are just not the right people for the next chapter.
That is a hard sentence for founders and CEOs to accept, especially when they built the company shoulder to shoulder with those people.
But it is true.
The Team You Need Will Change
Jeff said one of the biggest scaling insights he learned was the importance of bringing in the right people at the right moment.
- Not eventually.
- Not when it feels comfortable.
- Not when the gap is impossible to ignore.
At the right moment.
He described what happens when you get that timing right. You bring in the right expert in go-to-market, brand, or digital growth, and suddenly the company does not just improve. It jumps.
That is where the hockey stick shows up.
This is what many CEOs miss. Growth at scale rarely comes from effort alone. It comes from replacing improvisation with experience in the places that matter most.
Why CEOs Hold On Too Long
I asked Jeff about the CEO’s own scaling journey, and his answer was the one I hear often, but not always this clearly.
In the early days, the CEO is usually the head of sales, head of marketing, chief evangelist, and often the most visible voice of the company. You go to the prospect meetings. You run the demos. You talk to the press. You do the conference circuit. You make it happen because there is no one else.
Then the company grows.
And that is where the real challenge starts.
Jeff said, “You have to really figure out, when’s that time when you have to kind of say, all right, I’m not going to go to prospect meetings anymore. I’m not going to spend this many hours a week doing demos or talking to the press because I have a really capable team that’s able to do that for me.”
That is the tension.
- You know how to do it.
- You may even be the best person to do it.
- But if you keep doing it, the company cannot scale.
The Cost Of Not Letting Go
When CEOs do not let go, one of two things usually happens.
First, they become the bottleneck. Every meaningful decision, meeting, pitch, or customer interaction flows through them. That slows the company down.
Second, they keep doing work that made them valuable at one stage, but that no longer makes them useful at the next stage.
That is a dangerous trap because it feels productive.
- It is productive.
- It is also limiting.
Jeff understands that your job changes as the company grows. The work is no longer proving that you can do everything. The work is proving that the company can perform without you doing everything.
Hiring Changes Everything
Jeff also said something that every CEO should hear at least once a quarter.
“You’re only going to be as good as the people around you.”
That sounds obvious. It is not obvious in practice.
He talked about walking into companies and realizing within a month that he had almost all the wrong people on the team. He also admitted something most leaders know but do not always say out loud. It is hard to make those calls because often those people are good people. You may even like them. They just are not the right fit for where the business is going.
That is the call.
And when you get the right person in the seat, the feeling is immediate.
- You stop carrying that function in your head.
- You stop compensating for a gap.
- You stop spending time where you should not be spending time.
That is one of the biggest forms of relief a CEO can create for themselves.
AI Should Take Care Of The Menial
Jeff had one of the cleanest lines on AI I have heard in a while.
“AI really helps us take care of the menial so we can focus on the meaningful.”
That is the right frame.
Internally, he sees AI as a force multiplier across the company. Not a gimmick. Not a buzzword. A practical way to remove low-value repetition and increase speed.
He gave a great example using a podcast workflow. Ten years ago, producing a webinar or podcast meant clunky software, manual transcription, manual editing, manual clipping, manual captioning, manual blog creation, and weeks of work. Now, much of that happens almost instantly.
That is not hype. That is operational leverage.
It means your team spends less time grinding through repetitive tasks and more time on judgment, strategy, and creativity.
That is what AI should do inside a company.
AI In The Product Has To Be Useful, Not Cute
At Soundstripe, Jeff sees AI through two lenses.
The first is product discovery. One of the biggest pain points for creators is not the lack of music. It is finding the right track fast enough. The library is huge. The clock is ticking. The project has a tone, but the user cannot always articulate it perfectly.
So Soundstripe built AI into search and curation.
You can upload a video. The system analyzes it and helps match the music to the feel of that video. Or you can describe the project in natural language and work with what Jeff called an “AI music supervisor” that narrows a giant catalog down to the right shortlist.
That is smart product design. It uses AI to reduce friction and improve outcomes.
The second lens is strategic. Jeff was clear that Soundstripe’s edge is not just AI. It is the combination of AI with a deep understanding of its catalog, music licensing, and how commercial creators actually work.
That matters.
Anyone can generate a song.
- Not everyone can safely license music for commercial use.
- Not everyone can guarantee the rights.
- Not everyone can combine human-made music, clear ownership, and AI-powered discovery.
That is where the moat sits.
The Deeper CEO Lesson
What Jeff is really describing is not a story about music.
It is a story about maturity.
- You start by being the person who can do almost everything.
- You grow by becoming the person who stops needing to do almost everything.
- You scale by building a team that can do those things better than you can.
And then you use tools like AI not to replace your best people, but to free them up to do their best work.
That is the shift.
What I Want You To Take From This
If you are a CEO growing through that awkward middle phase, where the company still needs your energy but can no longer depend on your direct involvement in everything, here is what I would take from Jeff’s example:
Hire for the next chapter
Do not build your leadership team around loyalty to the last phase. Build it around what the company needs next.
Let go before it feels comfortable
If you wait until you feel completely safe, you waited too long.
Use AI where it removes drag
The best AI use cases are often operational. Eliminate repetition. Increase speed. Protect human judgment.
Stay close, but stop carrying everything
You do not need to disappear from the business. But you do need to stop being the one holding up its forward motion.
I Coach CEOs
If you are in that transition point right now, where the company is asking for a different version of you than the one that got it here, that is exactly the work I do with CEOs.
I help CEOs figure out:
- what to let go of
- where they are still the bottleneck
- which team gaps are really delegation problems in disguise
- how to build a leadership bench that can carry the next stage of growth
- how to use AI inside the company without losing what makes the company valuable
I am Glenn Gow. I coach CEOs. If you are trying to grow the company without staying trapped in every function, reach out. We can work through what you need to stop doing, what you need to keep doing, and how to build a team that earns your trust.
Listen to the full episode of The Scaling CEO here.
