What commercial leaders really ask behind closed doors
Inside the messy realities of sports partnerships, straight from real operators.
I’m Niru, and each week I tackle reader questions about commercial strategy, partnerships, comms and growth in the sports and entertainment industry. Send me your questions, and in return, I’ll humbly offer actionable, real-talk advice.
Hey there!
A few months back, I started with this idea of reaching out to commercial leads across sport and entertainment.
The goal was simple: I wanted to get underneath the surface. Figure out what’s actually causing friction in partnerships. The kind of challenges that never make it into the press release, the analyst notes, or the conference panel.
The stories that came back were far from glossy. Most weren’t even about the size of deals. They were about all the things that happen after the deal is signed.
People shared the headaches that keep them up at night. I listened, took notes, and tried to make sense of the real themes bubbling under the surface.
Here’s what I’ve been hearing, over and over, in these first conversations:
Nobody agrees on what “success” means.
Ask three different people about a deal. Brand, rights holder, agency, and you’ll hear three definitions of what a “win” looks like.
Some say brand awareness. Others want sales, engagement, or a new audience. Teams set KPIs but rarely align on why they matter.
This lack of shared meaning? It’s the source of endless confusion. Commercial teams chase one result while the board wants another. Brands launch a campaign, but months later, they can’t say if it actually moved the needle.
Alignment gets lip service, but most partnerships start and end with a few slides, not a clear plan.
Reporting is a mess, nobody trusts the numbers.
Let’s talk about measurement.
Again and again, I’ve heard the same frustration: Teams invest millions, then try to measure outcomes with tools that haven’t changed since 2012.
Some still track everything on Excel. Others use a patchwork of dashboards. People mention software names, but admit they barely use them for more than ticking boxes at reporting time.
When it’s time to show impact, boards get reports full of vanity metrics. There’s pressure to prove ROI, but the data is scattered, or worse, shaped to fit what someone wants to see.
It’s not a tech problem, it’s a trust problem.
Ownership gets blurry once the contract is signed.
Before the deal, everyone is clear on roles.
Afterwards, responsibility slips.
Brands wonder who’s steering the partnership day-to-day. Properties assume the brand will push activations. Agencies step in or sometimes out without much warning.
Commercial leaders shared how much time gets lost chasing answers to simple questions:
Who is updating the activation calendar?
Who is following up with the creative team?
Who owns the next step when the campaign stalls?
Nobody wants to drop the ball, but everyone’s juggling.
The result? Delays, mixed messages, and missed opportunities.
The tension is felt on every side, but rarely spoken out loud.
Most pain points are personal. Few people talk about them publicly.
There’s a lot of advice in the industry about launching partnerships. Far less is known about what to do when things get complicated.
Every leader I’ve spoken to—Dean in Singapore, Brett in agency and SaaS land, Diego with his global experience, Daniela with her experience at Inter Miami—has their own version of the same story.
No one wants to be the first to say, “This is broken.”
But the minute someone does, others nod in agreement.
These conversations remind me how much we need more honesty in this industry. Not just ideas, but real stories and real questions.
A big thank-you to the experts this week
Dean Martin (Blend Group, Ex. Sport Five), Daniela Gallardo (NextGen FC, Ex. Inter Miami Concacaf), Diego Jimenez (EMW Global), Brett Zallek (Stream Hatchet, Ex. BlinkFire Analytics)
Your turn: What’s the #1 thing you’re struggling with?
If you’ve made it this far, you probably have your own headaches, frustrations, or unanswered questions.
Reply to this email. Tell me what keeps you up at night.
Send me your questions and in return, I’ll humbly offer actionable real-talk advice.
Next time, we’re digging into the real art of sponsorship measurement and why most teams are still getting it wrong.
If you want the deep dive, make sure you’re subscribed to the paid issue.
See you at the table.
— Niru
P.S. If you’re running partnerships or leading a commercial team, and your LinkedIn presence feels like another mess that never gets cleaned up, I can help.
I work directly with leaders across sport and entertainment to turn the chaos of your day-to-day work into sharp, credible content that gets attention (and trust) from the people you want to reach.
If you want to see what this looks like for your own brand or role, just hit reply or message me with “co-writing”. I’ll share how I help other commercial leaders get clear, credible, and seen.
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