The Captain Doesn’t Rig Bait
What offshore fishing taught me about the leadership it takes to scale a revenue team
I’ll be upfront: I’m not a fisherman.
My boyfriend is. He fishes with a team that won the South Carolina Governor’s Cup Billfishing Series and the Georgetown tournament last year. Right now they’re sitting second in the series. I mentioned that to the captain once, a little proud of it, and he didn’t even pause.
“Second place is just the first loser.”
I’ve spent a lot of hours on that boat. Mostly keeping everyone hydrated, staying out of the way, and watching. What I actually do for a living is go-to-market strategy. I work with companies trying to grow revenue and get past the points where most of them stall out. And the more time I spend on that boat, the more I keep landing on the same thought: this is what good revenue leadership looks like. The real version of it.
What I see from the cockpit
When you’re not the one fishing, you see everything. You’re not locked onto a reel or a line, so you watch the whole boat. How the captain runs it, how the mate and the angler talk to each other, how they make calls in real time when the conditions turn.
First thing I noticed, before anyone put a line in the water, was how clean the boat was. Spotless. Every rod racked in order, nothing piled in the corners, nothing where it shouldn’t be. And it’s not for looks. A clean boat is a fast boat. When a fish is on and you’ve got seconds, nobody’s tripping over gear or hunting for a tool that should’ve been in its spot. Nobody decides to get organized in the moment; it’s just the standard. They don’t wait for the chaos to show up and then manage it. They get rid of the conditions for chaos before the day starts.
Second thing was how in sync they are. No confusion about who does what. A fish is caught and nobody gawks at it. Nobody stops to celebrate before the work’s done. The fish gets released, fast and clean, and before it’s even cleared the water the mate already has a fresh rod rigged and in the angler’s hands. The boat never stops fishing.
And under all of it there’s a captain who hates to lose. Not in a way that makes everyone miserable. In a way that pulls everyone up. That kind of energy is contagious. It makes the whole team sharper.
I’ve been on enough boats and inside enough companies to know I wasn’t just watching good fishing. I was watching what leadership looks like when scaling. And what keeps nagging at me is that most companies are missing nearly all of it.
The $10M trap
Getting a company to $10M ARR is a real accomplishment. It means you found a market, built something people will pay for, and figured out enough of the sales motion to make revenue repeat. Most companies never get there.
It’s also where a lot of them stall. The instinct at $10M is to floor it. Hire more reps, run more campaigns, open more channels. And that instinct is usually the exact thing that keeps you from reaching $50M.
It’s not that people aren’t working hard. They’re still fishing the way they did when they were just trying to survive, covering as much water as they can and hoping something bites. Hustle and broad coverage got you to $10M. Precision gets you to $50M. Knowing where the fish are before you ever leave the dock.
In offshore fishing they call that pre-fishing. Watching this team do it has changed how I think about the first 90 days of any revenue engagement.
Pre-fish or lose
The day or two before a tournament starts, the team is already on the water. Running the grounds, testing baits, reading the conditions, logging coordinates. They’re not guessing. The captain is up at night with satellite charts, tracking sea surface temps and currents, working out where the Gulf Stream pushed warm water closer to the shelf, then going out the next day to see if it holds up. By the time lines go in on tournament day, they have a theory about where the fish will be, and it’s built on the charts and on what they saw with their own eyes.
And the charts only get him part of the way. The rest is instinct, the kind you only build from years of reading these exact waters. The data points him somewhere; his gut tells him whether to trust it, and when to ignore it and run the other direction. That combination, the homework and the instinct, is the whole thing. Neither one wins on its own.
That’s pre-fishing. And it might be the most underrated thing in fishing and in revenue both.
The CRO who joins a $10M company and immediately starts hiring reps, rolling out a new methodology, and running plays has made the classic mistake. They skipped the pre-fish. They left the dock without reading the water.
The first 90 days in a new revenue role should be almost all diagnostic. What does the ICP actually look like, versus what the company thinks it looks like? Which segments close fastest and bring the best lifetime value? Which channels are working, and which ones are quietly burning budget? Where is the team losing deals it should be winning, and why?
That’s your pre-fish. It’s the work that tells you where to put capital, which markets to chase, which plays to run. Skip it and you’re running blind right when it matters most. The companies that scale fastest from $10M to $50M are almost always led by someone who did that diagnostic work before they spent a dollar deploying anything.
The captain, the mate, and the angler
This team doesn’t win because they have the fastest boat or the priciest gear. They win because every person on board knows exactly what their job is and does it with a precision that only comes from trust, repetition, and no confusion about who owns what.
The captain reads the water and makes the call. Where to run, when to move, when to sit still. He’s on the bridge watching the horizon and the sonar, marking fish and thinking two steps ahead, not down in the cockpit rigging baits. His job is strategy. The second he comes down to do someone else’s job, the boat loses the one person steering it.
The mate runs the cockpit. He rigs the baits, manages the spread, and always has a fresh rod ready before the angler asks. The angler never waits. When the mate is on his game, the cockpit looks easy, because he saw the chaos coming and handled it before it arrived.
The angler fights the fish. When the reel screams, his only job is to land it. Not to manage the spread, not to second-guess where the captain put the boat. Just land it. The celebration when a fish is released is real, but it’s quick. The mate already has the next rod up, and the lines need to go back in.
When those three get out of alignment, the captain’s in the cockpit, or the mate’s not ready, or the angler’s distracted, you lose fish. Every time.
Now put that on a revenue team trying to go from $10M to $50M.
The CRO is the captain. Read the market, set the strategy, put resources on the best opportunities, change the plan when the data changes. The moment a CRO starts building comp plans, running individual deals, or babysitting CRM hygiene, they’ve left the bridge. And when the captain leaves the bridge, the boat drifts.
Sales ops and enablement is the mate. The job is to have everything ready before the rep needs it: the right sequences, the right content, the right onboarding. When sales ops is underfunded, which it almost always is at $10M, the cockpit is a mess. Reps are rigging their own baits, doing it a little differently every time, and the CRO is burning half their day cleaning up execution instead of reading the water.
The AE is the angler. When a real opportunity is in the pipeline, their only job is to close it. The companies that scale fastest give their AEs the cleanest, most focused job on the team, and they’ve invested in the mate so the angler never has to rig their own baits.
The role nobody talks about: the owner
There’s a fourth role on the boat I haven’t mentioned, and it might matter most.
Here’s the tell. The owners who get in the way are always on the bridge or down in the cockpit, in the captain’s ear, hovering over the spread. The good ones watch from the salon. This owner isn’t second-guessing the spread or asking the captain why they’re running this direction instead of that one. He hired a championship captain and then got out of the way and let him run the team.
That sounds easy. It isn’t.
When you’ve put real money into a boat, the entry fees, the gear, the crew, the urge to weigh in on every decision is completely understandable. It’s his boat. He wants to win as badly as anyone. But he has the discipline to know that the minute he starts overriding the captain, he’s wrecked the exact thing that makes the team work. You can’t hire an expert and then refuse to let them be the expert.
I’ve watched some version of this play out across a lot of the smaller companies I’ve advised. A company hits $10M, brings in a seasoned CRO, and the founder who built the thing from nothing and knows every customer by name can’t help being in every deal. Overriding pricing. Changing the ICP mid-quarter. Running plays that worked two years ago and don’t fit the market anymore. The CRO spends half their energy managing up instead of running the team. The strategy never gets a fair shot. And when results come in slow, the conclusion is that the CRO is the problem, when the real problem is that the captain was never allowed to run the boat.
Hiring a great CRO and then micromanaging them isn’t a growth strategy. It’s an expensive way to stay stuck.
The owner of this boat gets something a lot of CEOs don’t. At this stage your job is to fund the team, hold them to outcomes, and then trust the people you hired to make the calls. That takes more confidence than jumping in does, not less. And it’s one of the clearest signs I’ve seen that a company is actually ready to scale.
Quiet coaching, and a team that compounds
Two more things from this boat that I think get badly overlooked in revenue leadership.
The first is how they handle mistakes. Something goes wrong, and something always goes wrong, and the captain doesn’t let it sit. He deals with it right away, quietly, no drama, and then everybody moves on. No lingering embarrassment, nobody getting chewed out in front of the rest of the crew, no hit to anyone’s confidence. Quick correction, back to work. That kind of coaching is rare, and it’s a real edge. A team that can mess up, get corrected, and keep its momentum is a team that keeps getting better.
The second is what time together does. The longer this crew fishes together, the better they get. Not because the people changed much, but because the system tightened. They anticipate each other. They talk in shorthand. The roles that were clear a year ago are automatic now. You only get that compounding when you keep the right people in the right seats long enough to build real trust.
Revenue teams work the same way. The CRO who’s always reorganizing and reshuffling roles never gets the benefit of it. I’ve learned this one myself, the hard way: every reorg resets the clock. The chemistry you spent a year building is gone, and you’re back to people relearning each other’s moves while the market keeps moving. The leaders who win get the roles right, coach fast and quiet, and keep the team together long enough to build real chemistry. That’s the one who wins the series.
Second place is the first loser
I opened with what the captain said when I congratulated him on sitting in second.
“Second place is just the first loser.”
That’s not bravado. It’s the standard. And it’s the same standard that separates the leaders who get companies to $50M from the ones who stall at $10M and wonder what happened. The winners aren’t satisfied with a good quarter or a healthy-looking pipeline. They’re reading the water the night before. They’ve got the mate rigging baits before sunup. They correct mistakes quietly and move on, because every second the lines aren’t in the water is a second the competition is gaining.
I’m not a fisherman. But I’ve got a great view from the cockpit. And what I see from there looks a lot like the best revenue teams I’ve ever worked with.