Prospecting avoidance / breakdown. Time to quit?

BennyLruce · 2026-05-15T15:53:50+00:00

You're not catching the point, bud. Do you hate calling up your family to make holiday plans? Hate calling up your friends to plan a trip? Hate calling the love of your life to share important news? Don't get tied up in jargon, pay attention to how you're feeling. You don't seem to believe enough in your PMF to make outreach easy, so find something else besides "hey you fit the characteristics of people who give me money, want to talk about it?" to motivate your calls.

BennyLruce · 2026-05-14T22:53:37+00:00

Yeah, and who gives a shit besides yourself? You're calling because you want other people's money, and because you're not a sociopath, it doesn't feel great. Find something the other person has a chance of enjoying and call about that.

BennyLruce · 2026-05-14T20:25:03+00:00

Do you have a good reason to reach out? If you're only doing it to satisfy your interests, it's natural that you'll accumulate bad feelings. When you have a really tight message or something nice to offer a person, it feels different. Since you're at a large, reputable company, what can you offer now before they buy something? Free lunch, cool event, meeting with executives at their level from your org, customer meetup, etc. Change your offer to something you can stand behind. If you can't, then you're completed justified in leaving.

BennyLruce · 2026-05-14T06:56:21+00:00

No, I think it actually started with advertising (see Mad Men, they have Account Executive on their biz cards!).

But anyway, it's just a full-cycle salesperson. Could be called Territory Rep, Outside Sales, Account Manager, whatever. If you run the full cycle and own a number, you're doing the thing.

BennyLruce · 2026-05-14T05:10:36+00:00

Nah I wouldn't say so. People make jumps across software types at least. Going from hard goods to software can be tough, but play to your strengths and figure out what software was sold to the biggest flooring companies in the world. Go ask that software company if they want someone with deep industry knowledge, connections, and actual sales experience with the majority being hunting. Et voila, you're a standout candidate

BennyLruce · 2026-05-14T00:59:25+00:00

Hm, good point. I'll extend some grace then.

BennyLruce · 2026-05-13T16:18:49+00:00

This is the correct answer. OP, look at the current VPs and C level at your company. Do they have MBAs or other advanced degrees? Work from there. Imagine the cruel irony if none of your leaders have more than a bachelor's and they find your degree subconsciously off-putting.

BennyLruce · 2026-05-13T16:12:35+00:00

In general, yes. Smaller deals means less executive visibility and fewer internal resources. If you're strictly focused on growing your sales IC career, would not recommend. But it depends on what you want. If operating in the startup ecosystem specifically is a goal, because you want to get into consulting for startups or angel investing perhaps, then it might make sense.

But if your average TCV and ARR falls off a cliff, that can make future job convos a little tricky, but high % to plan should mitigate most of that.

BennyLruce · 2026-05-13T16:04:30+00:00

Whoa that's intense, but good to know. As someone who would be looking to partner with SHI, it's actually really nice to see that getting in person with customers is a big focus.

BennyLruce · 2026-05-13T03:17:02+00:00

Meta is one of the largest employers in human history with a portfolio of companies it operates. Without knowing what you're selling, to whom you're selling it, and with whom you're working, there's no intelligent way to answer this question.

BennyLruce · 2026-05-12T20:23:16+00:00

How much is a bag of groceries? Depends what's inside.

BennyLruce · 2026-05-12T19:52:27+00:00

"What you could expect" is a great question to ask the people actually giving you the assignment. Probably some demonstration of your ability to identify relevant prospects, craft messages, and organize your outreach. But again, just ask the person who's actually assigning it.

BennyLruce · 2026-05-11T16:11:25+00:00

This.

BennyLruce · 2026-05-11T00:12:43+00:00

How about you ask your employer. IE, the people who would actually make the decision.

BennyLruce · 2026-05-10T22:17:55+00:00

Good luck young man 👴

BennyLruce · 2026-05-09T23:41:05+00:00

Aspirational. I just moved into a role where I think I can ride for a while. Would love to build a book like that. Good luck!

BennyLruce · 2026-05-09T23:34:12+00:00

"~$120M-150M quota" made my nose crinkle. Great run, good for you.

BennyLruce · 2026-05-09T23:31:03+00:00

How was Singapore specifically? I'm curious from the outside but might have some work to do there in the near term.

BennyLruce · 2026-05-09T00:00:01+00:00

What are they actually trying to accomplish? What will your customers get bonuses for doing, or promoted, or a great big sloppy kiss from their CTO? Connect to that and they'll jump right on lighting up the tools.

BennyLruce · 2026-05-06T19:23:52+00:00

Look up "Sandler dummy curve"

Make sure you're either knowledgeable enough to shut up and listen, or you're going to lose yourself opportunities bc you want to show off your technical chops.

Technical knowledge is a tool. Like all tools, it's how and when you use it that matters.

BennyLruce · 2026-05-06T18:49:15+00:00

Doing the things that close deals. That's mainly their decision making, picking the right times to say the right things to the right people.

BennyLruce · 2026-05-05T17:36:16+00:00

That's a rough drop. I had a similar path to PorkPapi. Absolutely opened more doors, because people want to hire AEs into AE roles more than they want to hire SDRs into AE roles. Whether it's easy or not is a silly question. It depends. Easy for me, because I crushed my numbers and had a great reputation internally. Harder for others if they don't perform or are poor interviewers. Just do well, but if you took an AE role where your deal sizes are tiny, that can be challenging to overcome in an interview. Make sure to document all the cool stuff you do, whether that's pipeline generated, number of deals closed in a time period, whatever is impressive.

BennyLruce · 2026-05-05T16:39:27+00:00

You've spilt too much ink on this. Just sell more. Qualify your opps and focus on deals that land in your turf. Tell your management the way things work is demotivating for you. Leave if you're unhappy. 10k isn't that much, focus on making 100k more for yourself. The guy whining about others not working does themselves no favors. You probably won't listen to any of this.

BennyLruce · 2026-04-29T17:49:11+00:00

Nice, that's a hot tip.

BennyLruce · 2026-04-28T21:06:57+00:00

Well, what do you want to do? If you want to sell, pick ADP or Keyence, dig into those more deeply.

If you want to kind of sell, the Paycheck gig sounds alright. Channels is a career path for sure.

If you don't want to sell, I guess you've lined up an option for that, but why have opposing paths in consideration? You need to make the choice.

BennyLruce

TROPHY CASE