Tech Sales Guy

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

I quit my big consulting job to go solo 4 years ago. Here’s an update. Last year we were just shy of $5M in revenue. 74% gross margin. Over 50% EBITDA. Nearly $10M in cumulative bookings all time. 98% CSAT. No website for the first year. Started on Upwork. Built through an aggressive partner channel and by finding overlooked but world-class consultants before anyone else did. My superpower is recruiting. Year 2, we grew 4.5x. Year 3, growth normalized to 74% YoY — the base was just a lot bigger. We came into 2026 and booked $2.4M in Q1 alone — ahead of plan. We hired a VP of Sales in February and we’re targeting 60% growth this year. Lots to execute against, but it’s been an awesome ride so far. I’m not planning to add headcount anytime soon beyond that. The next hires will be AI talent focused on automating work we used to do manually. Every hire has to have an excellent client-facing personality — gone are the days of boring, grumpy, stuffy consultants. If you don’t have a personality, you don’t have a chance. That’s the new reality in professional services. How we deliver today looks nothing like six months ago. That’s because we built our own internal operating system — purpose-built for how we actually work, not how software vendors think we should. We did this inside the privacy tech market, which gives the playbook real depth and repeatability. We’re also considering the next chapter: finding good tech services businesses, acquiring them, and installing our operating model and AI tooling on top. Bootstrapped, profitable, good people — that’s the profile. There are a lot of well-run firms leaving margin and growth on the table because they never built the engine. They can’t quite figure out AI. We did. Now we want to use it.

Last year I got a last minute invite to a partner event in San Francisco. The kind you don't turn down - cocktail reception on a private yacht touring the harbor. Booked everything last minute (classic)…. flight, hotel, rental car. $4500 on the personal card, to be expensed later. Before the event, I grabbed beers with a former colleague near the waterfront. The event started at seven and my plan was to show up 5-10 minutes after. One Kona Big Wave turned into two, then three. We got to the harbor at 7:02. By the time we found the dock, the boat was drifting away from shore moving with the casual confidence of something that was definitely not waiting for us. I watched my $4,500 expense report sink to the bottom of the harbor. Thank god, we weren't the only ones left on the dock. A woman arrived at almost the exact same moment. We started talking... Turned out she was an active prospect my team had been chasing for two months. Invited her to dinner. Great conversation. Justified the expense report. This is not a guide for how to approach customer dinners or happy hours. That's just how these things go sometimes. The actual guide to customer dinners is here:

@TechSalesGuy as someone who is finally getting into a role that requires getting in person w prospects, ie lunches, events, drink, (hopefully golf down the line) - i’m looking forward to reading this one.

@salesxsaas there's definitely a play to be made

@TechSalesGuy Honestly could work well if it’s a targeted lead list & you’re in the GTM space

there's a sneaky new outbound sales play where reps share google docs with prospects to bypass spam filters it works and it's exactly why buyers don't trust salespeople

@tizimmer still have the receipts to back this one up ha

@TechSalesGuy best pipeline stories always sound a little made up

@sammarelich you right only had it to drive south for a golf trip later

@TechSalesGuy The real lesson is that unless you’ve got meetings in the south/ deep east bay, there’s no point getting a rental car in sf

@TheDealMakerGuy literally have the receipts to show it did

@TechSalesGuy Out of all the things that didn't happen, this didn't happen the most

Subscribe if you're interested: techsalesguy.beehiiv.com Post drops around noon

@RooktoRep yesssss

First time in the lab this year. Swing felt great. The road to breaking 80 has begun.

@emiratli_ lol

me: "the deal is tracking well" the AI: "the decision maker hasn't engaged in 7 days, the CRO is a missing stakeholder, and this deal is at high risk to being lost" me: "anyway like I was saying it's tracking well"

@thesuspendedrep correct

You need to ask for permission before sending a lead magnet to a cold audience. Back it up with stats and a relatable customer story. Then make a simple ask. Also worth noting that employees do IT security and OpSec training to specifically not fall for this.

@DavidSchlais same game different name

@TechSalesGuy It’s the calendar invite thing all over again

@GolfnTex how's it working?

@TechSalesGuy We’ve done this for years.

@gtmba_ if you're in sales and trying to land you next gig... doing the job will help you get the job: 1. prospect hiring managers 2. align your skills to problems 3. ask socratic questions 4. give to get 5. follow-up I promise you will land interviews/offers doing this

New episode of the Vibescaling Podcast with Jason Miller, VP of Sales at Unify! His path to VP of Sales is pretty much the ideal playbook for anyone trying to build GTM chops from scratch: Fell into sales → founder-led sales takeover → Monday.com as one of the first 12 US sales hires → scaled through IPO → now building the GTM motion at one of the most interesting signal-based selling platforms in the market. This one is for founders hiring their first sales leaders, VPs building outbound from scratch, and reps trying to figure out what "signal-based selling" actually means in practice. Our key takeaways from the conversation: 1️⃣ Generic signals are table stakes now. Web intent, job changers, champion tracking: everyone's running these plays. The teams pulling away are building “bespoke signals”: job req spikes before a funding round, compliance gaps on a competitor's site, data breach alerts for ICP accounts. That's the last remaining edge. 2️⃣ LinkedIn is a no-fly zone. Some vendors are scraping it anyway. Jason's take: if your clients go back and read their Sales Nav ToS, it already prohibits what they're asking the software to do. The short-term win isn’t worth the long-term liability. 3️⃣ PLG is a cheat code. Until it isn't. When you've got a PLG motion, you're never worried about top of funnel. But the moment you try to build outbound inside a PLG org? It's like asking someone who's been fed from a bottle to go hunt. 4️⃣ Quota attainment without context is just noise. If everyone at a company hit quota, the person at 103% might be your weakest hire. And a great seller stuck in a bad market at 60% might be your best one. Jason's been burned by the shiny number and now he digs into the inputs first. 5️⃣ Never lower the bar because you need to hit plan. Jason learned this one the hard way. One candidate did something incredible in a mock roleplay he had never seen before. He fell in love and let it blur everything else. Two people told him not to hire. He did anyway. Didn't work out. 6️⃣ Cold outbound isn't dead. Untargeted outbound is. There will always be companies that don't show intent signals but should be buying from you. The whole job is to go find them with better messaging, tighter ICP, and more precision than five years ago. 7️⃣ The super rep era is here. Fewer reps. More tools. Higher output. Jason sees teams at 20-30% of their current headcount producing more pipeline than they do today. The reps who figure out AI leverage early are the ones who'll be worth the most. We got a lot out of this one. If you're scaling GTM at an AI-native company or trying to understand where signal-based selling is actually going, worth the full listen. Link in comments 👇

@emptyguitar53 ewww

@TechSalesGuy I mean would it work if customer is on MS Office package

@emiratli_ let's go @emiratli_ the day has come.... x.com/TechSalesGuy/s…

We raised $50M to build the First AI Revenue Agent. It runs New Business, Expansion, and Prospecting to close you more business while you sleep.

@CliftonSellers @legacybuilder @JonaTHildreth you love to see it

This is what success looks like Hired this guy a year ago because he DMed me asking for an opportunity Now he is a top producer @legacybuilder Personal brands for founders >>>>>