15 outbound plays I'm using today if you want them you can download here:

Enhanced Games but it's the Finance bros on cocaine and cold brew vs Tech Sales guys upper-decking a Zyn with a Vyvanse chaser

Heaven is a twilight round on a pure golf course

PSA - be smart out there

at a FinTech conference this week sitting in the lobby with a CEO I've known for a while a rep walks up. introduces himself. firm handshake, decent opener, name of a company I actually recognized. then i looked down. floppy blue allbirds. they clearly have been treading conference carpet for four months straight I watched the CEOs face shift in real time. eyes drifted past the rep's shoulder. nodding too much. already gone the rep kept talking. mentioned a customer the ceo would care about. didn't matter. handed over a business card. CEO took it like it was a parking ticket walked back over to me. "what was that guy's company again?" get taken seriously. wear the Gucci loafers

here's what I've realized about changing jobs: every company has problems. don't like your boss? easy fix don't like your comp plan? negotiable company not growing? harder to fix you're not escaping problems. you're choosing which ones you want to deal with

Cold outreach methods ranked: Tier 1 (>30% success): - intent signals - website visits, downloads etc. - old opportunities you re-target - warm intros or referrals Tier 2 (high effort, high reward): - cold calling with research - handwritten notes small gift - personalized videos Tier 3 (volume plays): - LinkedIn connection requests - commenting on peoples posts - mass email

our company's been pushing for more cross-departmental collaboration this year one of the early wins: our VP of sales started taking CS reps out to lunch. just one-on-ones. building bridges it's working. we've had more CS people raise their hand to move into sales in the last quarter than ever before the head of HR sat down with him last week. wanted to bottle it. roll it out to other departments. he told her "honestly it's nothing. I'm just getting to know them on a personal level." what he didn't mention is what he takes them to lunch in his car Ferrari (leased) every CS rep walked back to their desk thinking the same thing so this is what it looks like to be paid for what you're worth five more applied to open AE roles this week the head of HR is now writing a deck about "the power of one-on-ones" just lease the car - go into debt if you have to

Sales team characters: - The culture carrier: jokes in Slack, keeps morale up during shit months. Averages 80% quota attainment but nobody cares because everyone loves them - The golden boy: takes the long lunch. minimum dials every day. loves shooting the shit with management somehow hits quota by every month - The CRM/AI wizard: has 8 tabs tracking pipeline, win rates, and commission down to the dollar. Always knows exactly where they stand and incredible at prospecting - The grinder: first on calls, last to log off. Process driven, coachable and never complains. Takes longer to ramp but eventually crushes. You want them on your team - The process guy: has opinions on every tool, workflow, and sequence. "We should be using X instead of Y." Belongs in RevOps but somehow carries a quota - The sandbagger: sits at 80% by November then drops 5 deals in December. Somehow always makes President's Club - Recently single: only joins all-hands to check out the new hire slide deck. "Who's that new SDR?" NEVER misses a work happy hour.

once interviewed a guy about his weaknesses and he looked me dead in the eye and said “Mondays” still regret not hiring him

“Hi! yes, this is a cold call” “trust me, I don’t like my job either” “mhhhhmm, OK” “Yep, I’ll go f**k myself. Have a good one”

got a follow-up email this morning. subject: "circling back." delete

Sales tools actually worth paying for Tier 1 (non-negotiable): - Salesforce/HubSpot - LinkedIn Sales Navigator - ZoomInfo Tier 2 (high ROI if you use them): - Gong/Chorus for call recording - Outreach/Salesloft for sequences - Nooks/auto dialer Tier 3 (nice to have): - Crossbeam for partner overlap - Clearbit for enrichment Tier 4 (overpriced for what you get): - Most "AI SDR" tools - Generic email verification tools - LinkedIn DM chrome extensions What'd I miss?

my company recently hired a VP Sales Exec team was concerned with: - can they move deals forward? - can they accurately forecast? - can they develop the team? we missed one KEY question: "who are 2-3 people you'll bring with you here?" if a candidate can't answer that question- you're about to pay ~$100K in recruiter fees to build their team if they rattle off names immediately- you get access to their entire network if leaders can't recruit, they can't build and if they can't build....what are you hiring them for?

sat through a demo this week. rep joins the call right on time. dialed in. clean background, nice headset. good sign. opens with "look the last thing I want to do is waste your time - so let's dive in" classic. immediately likable. we're 15 minutes into discovery. asking about our process, our team, our timeline. solid questions. nothing crazy. then he reaches up to scratch his nose. Rolex. as soon as I saw that I knew this guy had closed real deals. probably crushed his number three years running. instant credibility. his questions started hitting different after that mentioned offhand he used to sell at salesforce. of course he did. told my team i liked him. never looked at the product. this is why discovery training is dead. just buy the watch

are we in a golden era for sales in the AI age? watching this got me thinking: AI made building cheap and easy. a 2-person team with Claude ships what 12 used to and when everyone can build, the product stops being the moat - distribution is distribution = your ability to actually get the product in front of buyers and convert brand. sales motions. partner channels. existing customers. the newsletter list you’ve been building for 4 years a competitor can copy your product in a month. those things are earned which is why companies with real demand are pouring AI savings into GTM salesforce. anthropic. databricks. snowflake… they don’t need more engineers. they need more closers enterprise reps, complex deal owners, partnership people - roles AI can’t fake (yet) the SDR seat that defined the last decade? hot seat transactional SMB sales? level up or get left behind i’ve been a startup guy my whole career - this is the first time i’m seriously looking at larger companies make hay while the sun is shining

Have a call with a prospect today at 4:00. The worst meeting times ranked: S tier: - 11pm anything (only end of quarter/year) - 4pm Friday before a long weekend A tier: - 4pm Friday afternoons - 12pm anyway (they eat lunch on mute) B tier: - 7am Monday (you lie about being a morning person) - 9am Monday sharp

Remote teammates “connecting” after 3 margaritas at the company happy hour

After a decade of grinding out sales, a few of my AE friends are craving something more. They want deeper relationships. Less 'close and move on' So they consider Account Management. The problem - that usually means giving up the financial upside that drew them to sales in the first place. Enter Partnerships. A perfect middle for people that can do Biz Dev. You get: - the relationship depth of AM - commission upside like sales - a network that compounds If you're an AE with the the flexibility & time to build a channel, do it. If not, you might like partnerships.