Director at PayPal vs VP at unknown startup

Square Switchitup
Aug 15, 2018 26 Comments

9YOE
Non-eng, non-product

TC @ Square: $1M+ (Joined at IPO), L7/Director level

Sick of my boss and no other team has an immediate need for my skills as it’s fairly niche. I’m leaving to take time off regardless.

Two offers:
1) Director at PayPal, priority area for the company, high visibility.

Annual TC:
—————
$225K Base
25% Bonus
$150K RSU annually
$100K Signing Bonus
I heard they do 50% RSU refreshers annually.

High potential for future growth given importance of role. Very aligned and great rapport with VP.

2) VP at unknown startup. I’m confident it will either IPO or get acquired within 2yrs given the recent C level hires they’ve done, but it’s a very old business that recently got its shit together, somewhat. Reporting to the CEO.

Annual TC:
—————
$225K Base
25% Bonus
??? Options
$25K Signing Bonus
Vague promises of generous options grants annually.

Reasonable outcomes would mean Annual TC of 650-750K, highest projected outcome is TC of 1.5-2M if all the stars align and my acceleration triggers kick in.

There is a downside scenario where the company continues to stay private after 2yrs, in which case my annual TC stays around 285 (base and bonus)

I know a bunch of people at PayPal, and it’s comfortable work IMO. The VP role is a step up in title but they need a lot of work in everything including culture. The people are definitely not top tier, and I’m not super passionate about the field they’re in, but the mandate of the role is very interesting.

What would you do?

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TOP 26 Comments
  • Uber YugeTC
    Wait around for a better startup gig. Doing a startup gig if you're not passionate about it will make you miserable. At this point all you're getting is the VP title.
    Aug 15, 2018 2
    • Square Switchitup
      OP
      I don’t want to burn too much cash, and I have a family and giant mortgage to support, so I’m eager to plan out my next move. I will continue to search, but let’s say these are the two roles available.
      Aug 15, 2018
    • Uber YugeTC
      Then I'd go with PayPal and spend a year or two looking around for the perfect startup opportunity
      Aug 15, 2018
  • PayPal Yolo0
    Looks like you are ~30 years old. Most of the Directors and above at PP are 40+. So, keep that also in mind!
    Aug 15, 2018 1
    • Lero Labs / Mktg
      lyVd32

      Lero Labs Mktg

      BIO
      Marketing
      lyVd32more
      This is a good point. If most of the directors are in their 40s, they may not appreciate that OP got to a director level without “paying his dues“. He may just be shut out and face a lot of political battles.
      Aug 15, 2018
  • Proofpoint / Other gaaandu
    Neither. Keep looking. If you aren't sure, it's not worth going.
    Aug 15, 2018 0
  • HP DLCr75
    If you have a good cushion, I’d go for the startup gig. If it works, you’re a step up to VP somewhere more stable afterwards. If it works REALLY well, you’re a CEO candidate not in a distant future.

    On hindsight, PayPal will give you some leeway to build into a VP career without startup concerns.

    Bottom line for me: Startup to fast track career; PayPal to live the humdrum life.
    Aug 15, 2018 1
    • Square Switchitup
      OP
      I do have a good cushion, even after my eye watering tax bill! Fair points.
      Aug 15, 2018
  • Lyft 2hia5b
    Director at paypal is professionally nothing, it does not require a profession, nor knowledge, nor talent, you just have to be "high up" somewhere. directors fired from PayPal in the 20% HR cut are still unemployed.
    It's a good retirement job if you're a good politician and can navigate and manage up.
    Aug 15, 2018 0
  • Lero Labs / Mktg
    lyVd32

    Lero Labs Mktg

    BIO
    Marketing
    lyVd32more
    I would say take the VP role. You will automatically get access to the VC network and if things don’t work out, they’ll find you a VP role elsewhere. It’s all about who you know in the Valley.
    Aug 15, 2018 2
    • Square Switchitup
      OP
      VC angle is interesting. I’ve heard that before but never worked in a true startup so I have to guess. The board exposure will open up future opps?
      Aug 15, 2018
    • Lero Labs / Mktg
      lyVd32

      Lero Labs Mktg

      BIO
      Marketing
      lyVd32more
      Yes it will. Especially if you meet with them on a regular basis to talk about your product strategy, which you definitely will because it’s a start up. Even if things don’t end up working out between you and the CEO, the board members will see your intelligence and bring you into another start up instead
      Aug 15, 2018
  • PayPal ucgr74
    As a Director at PayPal, I'd say go for it. Esp if you're going to be in San Jose and working on a high visibility initiative. If long term you want to go startup, wait for the right one - it doesn't look like you're super enthu about the one you're considering.
    Aug 15, 2018 0
  • Microsoft KyJeLlY
    Seems like your heart is at PayPal but the money is at Start-up
    Aug 15, 2018 1
    • Square Switchitup
      OP
      I think so, and I’m trying to justify it as if I can either get promoted to a Sr Dir role within 2yrs if I’m coming in on the higher end of the scale, or if the initiative they’re hiring me for is successful, then I have an incredible amount of cachet in my narrow specialization, which can lead to a future VP role.
      Aug 15, 2018
  • Microsoft CiPt68
    Follow your passion
    Aug 15, 2018 1
    • Square Switchitup
      OP
      They’re both interesting in their own regard. I think the core business of PayPal is more interesting but the roles themselves are equally cool.
      Aug 15, 2018
  • Apple / Eng JobsHand
    Take PayPal. Like you mentioned if the company doesn’t IPO in the next 2 years then you could be taking a major hit on comp.
    Aug 15, 2018 0
  • Intuit Kite24563
    Non engineering and Non product ?
    R u going to join their risk team ?
    Sep 21, 2018 2
    • Intuit Kite24563
      Which product ? I can give more insights
      Sep 21, 2018
    • Square Guc
      Made the decision to go for the VP role. Thanks for the offer though!
      Sep 23, 2018
  • Intuit Porky
    Op here as well . I ended up going to PayPal
    Nov 18, 2018 1
    • Square Chachasl
      Op would never have considered Intuit as an option 😂
      Nov 18, 2018
  • Wells Fargo qUyB01
    What did you eventually end up taking? Sounds like it was a decent hit to TC regardless so what prompted your final decision?
    Nov 18, 2018 1
    • Square Chachasl
      Op here. I ended up going with the startup for higher upside and more agency over the direction of my team and adjacent teams. Some changes happened recently and I’m effectively a GM now. That would never have occurred at the Dir level.
      Nov 18, 2018
  • Zillow Group ENOENT
    What skills you have?
    Sep 24, 2018 0