SAN FRANCISCO -- The field of Fantasy Football is surprisingly akin to a cold sales call. One enters the Snake Draft not completely knowing what the other side is thinking. Except, this is a dodecagon, there are 11 other sides in the case of a stacked Fantasy league. You don't know what their budget is, what their risk tolerance is, or what their broader strategy is for that quarter.

I come in last place nearly every year in Fantasy, and I've made $0 in commissions since starting my new role as Head of Sales. I don't really see a correlation. That doesn't really matter though, because I do share the same strategy in the Bottom of the Funnel as I do when I'm being called a bottom in the group chat.

Never Surrender; Never Show Weakness

The keystone to both my sales approach and Fantasy strats are unadulterated aggression and refusal to play nice.

First and foremost, do not propose nor accept any trades, regardless of how grievous the injury. For example, I drafted Patrick Mahomes this season (the Year of our Lord 2026). After his injury did I made a weak trade hoping to get some third rate receiver just incase he came back and lead the Chiefs to the Superbowl again?

No, I drafted Stafford in the first round. This is my sales strategy. Which it comes to horse trading, make sure you bring a gun. We're here to steal horses, not trade them. We don't Open the Kimono to any Tom, Dick, or Harry.

Don't Meet Them Half Way; Make Them Come To Your House

Our organization doesn't have "Solutions Engineers." We're not here to "help you with your problems." We're here to sell. It is up to you to figure out how to work the product into your use-case. This is a sure-fire way to avoid doing any actual work or analysis. You find need to smell the desperation.

How does this relate to Fantasy Football? Great question. I don't build my lineup based on some supposed Synergy. My D-Line is playing against my Quarter Back? I call that hedging. Someones gotta win, and averages rarely go to zero. My WRs and TEs are on 4 different teams while 3 of them run the ball and my QB is known for the Hail Mary? That's a dynamo. I don't check what they want, I check what I need. And what I need is to get off the shitty ESPN app ASAP.

Forget To Follow Up

What even is a bye-week? You think I circle back offline? I can't even set my lineup consistently. No way in God's green Earth will I schedule a canned email 2 weeks from now to see "where we're at with the proposal." Suck me.

Fin

I have the Head of Sales title at 4 organizations for one reason: I keep getting fired. I have last place in Fantasy because I literally don't understand Football. But, I keep getting hired and I keep spending $50/year to play in my League. Can't say I'm a total failure.

My B2B sales strategy is ripped straight from my Fantasy Football playbook. I come in last every year, and have made $0 in commissions.