From Retention Rep to COO: The Case for Staying and Growing
David Adams · September 2025
In August 2011, I joined Venntro Media Group as a retention representative. In August 2024, I left as the Chief Operating Officer. Thirteen years, one company, seven roles.
In a world that celebrates job-hopping, portfolio careers, and the perpetual hunt for the next title bump, staying at one company for over a decade feels almost countercultural. I've had people look at my LinkedIn and ask — gently, carefully — whether I just never had other options.
I did. I stayed because every year the problems got bigger, the responsibility got heavier, and the learning got deeper. And I'm convinced that the depth of experience I built by staying is more valuable than the breadth I would have gained by leaving.
This isn't a universal prescription. Some companies don't offer growth. Some industries reward mobility. But for me, the decision to stay — and the opportunities that came with it — shaped everything I am as an operator. And I think there's a case to be made that more people should consider it.
What retention taught me that nothing else could
My first role was on the phones, talking to customers who wanted to cancel their subscriptions. That's the sharp end of the business. No strategy decks, no quarterly planning, no management layers. Just you, a customer who's unhappy, and a few minutes to understand why and try to change their mind.
Most people see retention as an entry-level role — a stepping stone to something better. It is a stepping stone, but it's also the single best education in customer psychology, value proposition, and product-market fit that exists in any company. Because the people calling to cancel are telling you, in real time, exactly where the product is failing and what they expected that they didn't get.
I learned more about what makes a subscription business work — and what makes it break — in nine months of retention calls than I would have learned in two years of reading reports. That knowledge stayed with me through every subsequent role. When I was CRO making pricing decisions, I could hear the retention calls in my head. When I was COO evaluating product changes, I knew how they'd land with the person on the other end of the phone.
You don't get that from joining as a VP.
The compound effect of institutional knowledge
There's a type of knowledge you can only build by being present for a long time: understanding how the company actually works. Not the org chart — the real dynamics. Who makes decisions and how. Where the bodies are buried. Which systems are fragile and why. Which processes look efficient on paper but are held together by one person's institutional memory.
By year five, I understood the business at a level that no external hire could have matched. I knew the partner relationships — not just the names, but the history. I knew which product decisions had worked and which had failed, and why. I knew the team — their strengths, their limitations, what motivated them, what burned them out.
By year ten, that knowledge was compounding. I could see patterns that repeat across cycles. I could anticipate problems before they became crises because I'd seen the early signs before. I could make faster decisions because I had the full context, not a briefing document.
This is the compound effect that people underestimate when they move every two or three years. You restart the knowledge clock every time. You spend the first six months learning the basics, the next six months building credibility, and then — often — you're already thinking about the next move. The deep, compounding institutional knowledge never has time to develop.
Every role was a different job
One of the reasons the 13 years never felt stale is that I held seven distinct roles, each with fundamentally different responsibilities, challenges, and skills requirements.
Retention representative → Partner account manager → Senior partner account manager → Partner team manager → Head of business development and account management → Chief Revenue Officer → Chief Operating Officer.
Each transition was essentially a new job within the same company. The context was familiar, but the scope, the stakeholders, and the problems were completely different. Going from managing a handful of partner accounts to leading an entire business development function required a totally different skillset. Going from CRO to COO required another leap entirely — from owning revenue to owning the whole machine.
The advantage of making those transitions internally is that you carry your context with you. When I became CRO, I didn't need six months to understand the partner landscape — I'd been managing it for years. When I became COO, I didn't need to learn the revenue model — I'd built it. Each new role let me go deeper faster because the foundational knowledge was already there.
The relationship capital is real
Thirteen years in one industry, at one company, builds a network that's qualitatively different from the kind you build by moving around. The relationships are deeper. They're tested. People have seen you operate in different contexts, at different levels of seniority, under different pressures.
When I left Venntro, I had genuine relationships — not LinkedIn connections, but real relationships — with partners, suppliers, industry peers, and former colleagues across the dating and SaaS world. Those relationships are built on shared history, not shared attendance at a conference.
That capital is enormously valuable as a founder. When I started Lucennio, I wasn't starting from zero. I was starting with a decade of trust built up across an industry. People took my call because they knew me — not because of my title, but because of the history.
The honest downsides
I don't want to romanticise this. There are real costs to staying at one company for 13 years.
Your salary growth is slower than it would be if you moved. External hires almost always command a premium over internal promotions. That's a financial reality, and over 13 years, it adds up.
Your perspective narrows. When you've only seen one company's way of doing things, it's easy to mistake local practices for universal truths. I've had to actively work to broaden my frame of reference since leaving.
And there's a risk of identity fusion — where you become so entwined with the company that you lose sight of who you are outside of it. Leaving after 13 years was a significant personal transition, not just a professional one.
These are real trade-offs, and anyone considering a long tenure should weigh them honestly.
What I'd tell someone early in their career
If you're in a company that gives you room to grow, that promotes from within, and that solves problems you find genuinely interesting — think carefully before you leave for a 15% pay rise and a slightly better title at a company you know nothing about.
The depth of knowledge, the relationship capital, the operational understanding, and the compound credibility you build by staying and growing are assets that are extremely difficult to replicate any other way. They're invisible on a CV but they're the foundation of everything.
My career isn't impressive because I held a COO title. It's impressive — if it is — because I understand a business from the retention call to the board meeting, and everything in between. Because I've sat in every seat. Because I know what breaks at scale and why, not from a case study, but from having been there when it happened.
That's the case for staying and growing. Not blind loyalty. Not inertia. A deliberate bet that depth beats breadth — and that the best operators are the ones who've done the work themselves, at every level, and carried the lessons forward.
David Adams is the Founding Partner of Lucennio Consultancy and Lucennio Property. He spent 13 years at Venntro Media Group, rising from retention representative to Chief Operating Officer.