Jack Gashi is VP of Sales at Avoca, an AI-native platform bringing automation to home service businesses.

At Avoca, Jack is building the sales organization from scratch as the company scales AI-driven voice and scheduling technology across industries.

Before Avoca, Jack spent several years at Cheq, a high-growth cybersecurity startup, where he learned what it actually takes to build durable GTM teams.

Prior to that, he worked in ad sales at Foursquare during the company’s peak growth years, and even earlier in his career Jack cut his teeth in classic boiler-room sales at Yext, making hundreds of cold calls a day selling into home services.

Through experience across SMB, mid-market, and enterprise sales, Jack knows what it actually takes to build a sales org that works.

His philosophy is rep-first and unapologetic: sales is coin-operated, built on trust, and keeps the lights on.

He’s a proud Jersey guy, a former Fyre Festival attendee (lol), and the first to admit that the best sales conversations still happen face-to-face.

The "trough of disillusionment" applies to sales careers, not just technology. Jack adapted the Gartner hype cycle to map the sales career arc: early excitement as an SDR, a malaise in your mid-to-late 20s when you've done 1,000 demos and wonder if this is really it, then a fork in the road where some people stagnate and others break through into enterprise sales. The job gets way more interesting, more consultative, and the money follows.

Stop romanticizing work. Borrowing from Scott Galloway, Jack pushes his team to stop looking for passion in their day job. The swimmer who swam competitively in college? Stopped loving it when it became their job. Sales is how you extract value from the economy. Find your pleasures elsewhere and you'll actually enjoy the work more.

You can smell whether a founder likes salespeople. It's binary. Some founders can't stop talking about wanting to pay reps a ton of money. Others treat sales as a necessary evil. Jack's litmus test when evaluating Avoca: the co-founder couldn't stop bragging about his reps who were crushing it. That energy tells you everything.

Losing a top rep is a $2M hole that nobody treats like one. If a rep doing $2M in ARR leaves, it's a revenue hole plus a six-month replacement cycle. Odds of finding someone equally good? Maybe 1 in 10. Top reps should be treated like golden geese: aggressively promoted, handsomely paid, fawned over.

The best reps are coin operated, and that's a good thing. Jack pushes back on the LinkedIn crowd who say reps should "live off their base and invest the rest." Half your income is commission. If you don't care about money, he doesn't want to hire you. The job is structurally coin operated. Pretending otherwise is just virtue signaling.

Sales is art, not science, and the art guys are under pressure. Jack argues the trust meter has only gone up. Sequencing and automation promised that the right five-step email would make sales rain from the ceiling. It worked for a couple years when people didn't know what was happening, then quickly died. Every time a fad dies, you come back to Sarah or Chad at the steak dinner gaining your trust.

"All roads lead back to steak dinners." Every company wants to be PLG, but even the most product-led companies eventually end up with an army of enterprise reps. The question is whether you get there enthusiastically or reluctantly, and the best founders are the ones saying "I want to pay a sales rep $1 million this year."

Automation made human touch more valuable, not less. Jack walked by his AE's desk and found him hunched over hand-writing 100 letters with his SDR. His reaction: "I fucking love that." Do what doesn't scale. Sniper shots over buckshot. 20 deeply personal emails beat 500 automated ones, especially when your hit rate is already high.

If you don't know the answer, just say so. The worst thing a rep can do on a call is stammer through a two-minute tangent when they don't know something. The best move: "I actually don't know the answer to that. I'll get back to you tomorrow." That honesty builds trust. The opposite destroys it instantly.

Build the culture you wished you had as a rep. Jack's whole thing: sales cultures are too often fear-driven, with a guillotine hanging over everyone. Reps already start at zero every month, they don't need more of that. His approach at Avoca is accountability with encouragement, never yelling, always in the foxhole together. It puts a ton of pressure on hiring well, but when it works, the vibe is electric.

(00:00) - Why fear-driven sales cultures fail (and what actually builds trust)

(03:29) Lessons from Fyre Festival: why the outside story often lies

(06:03) Jack’s entry into sales: recession-era hiring and boiler-room reps

(07:14) 150 cold calls a day at Yext and learning how to really sell

(09:28) How tech sales talent has changed over the last decade

(10:19) Why Ivy League grads are now choosing sales on purpose

(11:18) Sales vs consulting, banking, and law: quality of life math

(15:03) The “trough of disillusionment” in a sales career

(18:19) Stop romanticizing work

(21:26) Why sales morale is the beating heart of a company

(23:09) How to tell if a founder actually respects sales

(24:40) The real cost of losing a top rep

(26:11) “All roads lead back to steak dinners” and the limits of PLG

(29:00) Why sales is ultimately a trust transfer, not a script

(45:06) Why great AEs treat job hunting like a sales cycle

(29:00) Why sales is ultimately a trust transfer, not a script

(31:02) Why sequencing, automation, and “perfect emails” keep failing

(33:04) Why product knowledge builds more trust than charm

(36:31) When to leave a good job — and why Jack chose Avoca

(40:54) Why bad sales hires are more expensive than founders realize

(44:15) How elite AEs evaluate roles when data doesn’t exist

(45:06) Why great AEs treat job hunting like a sales cycle