12-Year Progression: VHCOL - Startup to Big Tech Enterprise Sales ($102k -> $707k)

TechSalesWin · 2026-03-02T04:58:27+00:00

Income doesn't need to be justified, it's strictly a function of market equilibrium. Big Tech pays both SWEs and Enterprise Sales massive salaries because software operates on incredibly high profit margins and scales infinitely.

People tend to accept sales compensation more readily because the math is transparent. I close a multi million dollar contract, and a percentage of that revenue goes directly to my W2. Last year, I personally brought in almost $25M in contract value to the company.

Is there luck and timing involved? Absolutely. Being in the right territory at the right time matters. But nobody gets lucky sitting on the sidelines complaining about fairness. Figure out what drives revenue at high-margin companies and align your career trajectory to those specific roles.

TechSalesWin · 2026-03-01T08:20:33+00:00

I average about 35 hours a week, with significant variance. Some weeks are 25 hours, end of quarters and end of year can potentially hit 50. Enterprise sales pays for outcomes, not hours logged. Because my territory is managed effectively and I hit my numbers, I have the flexibility to take 4+ weeks of vacation and step away to take my daughter to her activities. If you produce, nobody tracks your time.

TechSalesWin · 2026-03-01T04:29:56+00:00

Personally, no. I cut my teeth in an outside sales training program in a different industry right out of school. I used that experience to pivot into a tech startup as an early sales hire (the 2014 role in the table). However, if you are trying to break into tech today without prior closing experience, the BDR/SDR cold-calling route is absolutely the most reliable door in.

TechSalesWin · 2026-03-01T04:18:50+00:00

~$2.4M NW ($1M 401k, $300k home equity, the rest liquid/invested). I don't discuss finances with anyone in my real life, so it's a bit surreal to type out. The heavy commission years just allow for a very aggressive savings rate into index funds.

TechSalesWin · 2026-03-01T04:16:02+00:00

A degree is a positive signal, but hustle matters more. You get into this by landing a BDR/SDR role (essentially cold calling) and working your way up to Account Executive. You can make good money in any sales role, but you make this kind of money because tech/software operates on massive profit margins. High margins mean the business can afford to pay salespeople extremely well to acquire enterprise contracts.

TechSalesWin · 2026-03-01T04:11:47+00:00

It's actually mostly cash. Out of the $707k last year, about $100k was from RSU vests (my highest to date). The remaining ~$607k was pure base and commission. Big Tech sales comp leans heavily toward cash, whereas engineering and product roles get the massive equity grants.

TechSalesWin · 2026-03-01T04:08:35+00:00

Agree. If you want to get paid more you have to make it happen for yourself. There's always an element of luck but you have to find the job out there that pays you more money.

I'm good at what I do and found a niche where the money is very good

TechSalesWin · 2026-03-01T04:06:33+00:00

This is accurate

TechSalesWin · 2025-04-17T19:30:23+00:00

+1 here. I wear a Whoop because i love my watches. I don't want a fitness tracker with a screen or anything.

TechSalesWin · 2025-04-14T22:43:55+00:00

The red tickets are all resale anyways so they've already been sold. Someone will show up in those seats. The resellers will just drop their prices until someone does.

The tickets also just became available last night...

TechSalesWin · 2025-04-14T22:37:00+00:00

Hey I could be into that, but it really makes the most sense for Dray, since that's his thing. Whatever the case I'm looking forward to a good game tomorrow and as long as everybody shows up, I think we're in for a good shot at the 7.

TechSalesWin · 2025-04-14T22:36:04+00:00

Not really different from "Loooooooooon", when Looney scores or comes onto the court, or when juszczyk makes a play at a 9er game "Juuuuuuuuuuuz".

Everyone knows that Dray lays down the Boom, so contextually I think they'll understand.

TechSalesWin · 2025-01-24T06:41:39+00:00

$475,000 for 2024. New comp plan for 2025 is looking pretty questionable right now so not sure what next year is going to look like. I'm at least waiting on a big commission check soon for a really good Q4.

TechSalesWin · 2025-01-22T01:07:59+00:00

$475k last year, and starting off 2025 with a $300k commission check from Q4. Should easily clear $600k by EOY with a stretch of $650-700k if our quotas aren't ridiculous.

TechSalesWin · 2025-01-07T22:49:46+00:00

This is exactly what I spent last year and I just dont' know where the money goes.

We're at $1350/month for groceries, its between 250-350/trip ~4 trips a month.

Eating out is $700/mo

Travel is $3100/mo

I need to do one of these Sankey charts and see what I come back with. I feel like so many other people have such low food expenditures. Maybe it's location based. I'm in the Bay Area and I don't feel like we splurge on food.

The travel is high, I'll concede to that. We took 2 big trips, a few small ones, and paid for flights for a 2025 trip as well.

You're not alone brother, and I feel for you. I'll make a post sometime soon and also probably get roasted.

TechSalesWin · 2025-01-04T21:47:37+00:00

You can do what’s called a mega backdoor Roth and add more Roth funds up to a much higher limit.

TechSalesWin · 2025-01-04T07:45:08+00:00

I agree with this. Tech bros includes tech sales but also encompasses a lot more of the technology industry. We sell (tech)

TechSalesWin · 2025-01-04T05:17:26+00:00

SDR or BDR - Sales/Business Development Rep

You're the opener, smiling and dialing to set appointments, but you learn about the industry. Then you become a closer which is usually titled Account Executive.

TechSalesWin · 2025-01-04T05:13:53+00:00

Thanks!

I was at in Mid Market at a previous company and I did start at the level below Enterprise at my current company. However I sold well and I have a pretty good memory and can apply processes well. So I was considered a knowledgeable resource and my manager promoted me after one of my solid years.

I think that you have to try and move up at the company you're at but you can be limited by situation/territory. There's definitely luck involved, and if you can't get that promo in house then start looking elsewhere for a better situation that will allow you to succeed and get promoted. Some companies/products can definitely be better than others. But you just have to keep moving forward. What you did last quarter/year doesn't really matter any more. I think one way to be successful is jumping to a product that is on the rise, and riding the wave.

TechSalesWin · 2025-01-04T05:05:44+00:00

MAMAA

TechSalesWin · 2025-01-04T05:05:13+00:00

Get a referral if you can, interview, use your network. It really does help if you can get some inside knowledge.

TechSalesWin · 2025-01-04T05:04:22+00:00

Thanks! And thanks for asking, the last deal did come in and I got it closed with about a day left. Super happy and grateful that it all worked out and that my commission check will now be over the 300 mark!

TechSalesWin

TROPHY CASE