When And How To Move on From Silicon Valley Startup Senior Role?
December 1, 2017 7:11 AM   Subscribe

After three years working for a San Francisco tech startup, I am considering looking for new opportunities. I am interested in input on what Silicon Valley software technical manager or senior-level manager/developer hybrid career paths might look like, what general opportunities and pitfalls I should consider, as well as advice on how to navigate the particulars of my situation.

I started out as an individual contributor software engineer and "leveled up" to VP of engineering. The startup is small (< 30 people), about 5 years old, not a household name. There is a great deal I enjoy and appreciate about the company, the team, and my work there. I like my coworkers, my compensation and work/life balance are good, and I get interesting problems to work on. I could ride this out for as long as it goes. Unfortunately, our product has so far failed to find a niche in the market and I am not confident in the directions we are currently pursuing. There are some possibly fatal culture and process problems with the company that are beyond my power to resolve. I also have some skill-building/career-growth goals specifically around hiring, team building, and product scaling that I won't get much traction on here.

We might get acquired for some of our technology (in which case I guess I could make a bit of money on my equity) or we might just fizzle out after another year or so.

The status quo is comfortable for me. However, I'm concerned about possible stagnation, burning out on pivots/hail marys/silver bullet initiatives, and missing the chance for further professional growth. I might be close to maxing out how much value I can get from this role and I want to position myself well for the next 10 or so years of professional life.

Things I'm curious/concerned about:
  1. If this company fizzles while I am still there what are the career implications for me? It won't be embarassing on the level of Juicero but I will still be associated with the management team of a failed company. I also don't want it to look like I am job-hopping or not committed.
  2. My executive-level title is fancy, but it's in the context of a small startup. I can use it to tell a good career progression story. I also wonder if it is a liability in some ways. Maybe people will assume I am too expensive/pointy-haired/high maintenance?
  3. In practice I split my time between research/planning/analysis, talking with customers, hands-on development and related work, and managerial tasks. I am pretty happy with that balance. As a developer I have a a couple of currently uncommon and desirable skills. However, I know for certain that I do not want to be a full-time individual contributor software developer. I am probably not interested in a principal architect path. I'm also not certain that I want to give up hands-on development entirely. How can I (and should I) continue to maintain this balance? What are some potential career progression scenarios?
  4. Any general guidance on what company size and stage to target?
  5. I am female. I am gay, unmarried/no kids, comfortable in majority-male environments, but still female. Sexist bullsh*t is well-known to be endemic in the tech industry and I have definitely experienced some. I've been fortunate to avoid really toxic frathouse cultures and active harassment. There's also the general sexist bias that women professionals deal with like having to repeatedly prove competency from scratch while the competency of men is assumed. I've had to work past some of this at my current company, but at least I've successfully proven and established myself here. Are there ways I can bypass the "prove it again" dance if I move to a new company? How can I continue to screen out teams and companies where sexism will be a greater than usual problem?
  6. I am also (a bit) over 35, possibly getting past my tech industry sell-by date. Do I need to start being concerned about this?
  7. I have over 10 years of experience but never seriously pursued a job at a prestigious/big name tech company (Google, Amazon, etc.) or unicorn startup. Is that something I should actively consider at this point? Even if it meant stepping back to an individual contributor role?
  8. After spending several years outside of a tech industry hub I'd like to remain in the Bay Area, both for career potential and because I have family here.
posted by anonymous to Work & Money (5 answers total) 6 users marked this as a favorite
Most unicorns/fast growing startups enter a phase where they realize they hired a lot of early career engineers very quickly, but those engineers are either too junior or uninterested in stepping into managerial roles. At the point that the existing managers/team leads have too many reports, they often become interested in hiring hands-on team leads or managers - someone who will pass a technical interview but has management experience. When it’s well thought-out, the onboarding path is you as an IC at the company for 3-6 with a transition into managing a team at that point. If the company keeps growing, your team keeps growing. If you have the energy/interest in doing the high-growth company thing, it could be a great fit for the other interests you outlined.

MeMail me if you want more info about what that can look like.
posted by asphericalcow at 8:20 AM on December 1, 2017

1. Startups fizzle, so no worries, but you want options and offers before the doors shut. As a VP you should be able to review the books and see when you run out of money. Make sure that your exit is in place the month before. It helps to schedule a buyout in advance of the money running out. You can influence this as a VP
2. To be blunt, being a VP at a startup doesn't carry much weight.
3. Sounds like a TPM role in a bigger company
4. The company should be as big, rich, and successful as possible.
5. Bigger/older companies tend to have a more mature HR policy to keep lid on BS. "With certain noticeable exceptions". How to find the exceptions is largely magic. Good luck.
6. A bit. I'm a decade older and have not yet hit the wall. The valley is different from the rest of the market due to demand so ageism is a thing, but perhaps not a deadly thing. You should be looking for jobs that pay enough to bankroll an early retirement
7. The prestigious companies are where the money is, where the good HR teams are, and where you can make the contacts that you need. They look good on your resume. I would start studying. I would not work for the 'Zon unless you had a clear exit strategy with a 1.5 year horizon.
8. Yep, for techies the valley is the place to be.
posted by pdoege at 10:38 AM on December 1, 2017

What are some potential career progression scenarios?

I'd suggest having a look at The Manager's Path. Fournier lays out a bunch of different progression paths.

To the extent you're willing to stay in management, your age is less likely to be a liability. IME ageism is a bigger deal for IC roles; it's also self-filtering, because the companies more likely to have ageism problems don't tend to put a premium on management, so you're less likely to come across them in your search.

As far as screening out teams and companies where sexism is an issue, the best way I've found has been to check the "about us" page of any company I've been talking to. If they have more dudes wearing blue shirts than women on the page (or more dogs than women, etc.), they're probably not going to be a place you'll want to work.

Oh, and I wouldn't worry about the company fizzling reflecting poorly on you (unless you've been personally responsible for its fizzling, which it doesn't sound like you have been). IME everyone in the industry understands that that's just how it goes sometimes.
posted by asterix at 12:54 PM on December 1, 2017

I'm in basically your same demographic and was in an eerily similar situation a year ago. I've since moved on to a full-time IC role at a larger company, which has been a weird transition but is turning out reasonably OK. MeMail me if you're interested in more anecdata about my experience.
posted by introcosm at 7:04 PM on December 1, 2017

1. Lots of startup companies fizzle, but it'll be important to highlight what your successes have been, how have you navigated challenges, what's been the impact. The fact that the company hasn't found product-market fit isn't uncommon, but at this stage (5 years) you are right to start proactively looking for other opportunities.
2. On paper, what would stand out is that this is your first leadership role. You'll likely compete with people with much more management experience, not to mention companies typically look for leaders who have a set of diverse experiences, so you'll need to recognize that you need to make yourself stand out from the competition in that regard. Since you're a technical leader, I would suggest cultivating an in-demand technology skill (eg machine learning, AI, cloud technology, etc) to position yourself well.
3. Look for mid-sized start-up companies (100 - 500 ppl) - these companies will give you the opportunity to still wear multiple hats. Frankly, you'd probably be an attractive candidate for those folks as well.
4. See #3. You might need to compromise and be OK with Director/Senior Director titles in your job search. I would suggest, given the new leadership experience, that's a reasonable tradeoff as long as you join a company with a stellar team and technology.
5. Seek out companies that have explicitly called out unconscious bias or sexist behavior. Use your network to do informal culture checks. Check LinkedIn to see what how many senior or mid-level leaders have women.
6. I don't think so. You are a unicorn, really, as a female engineering manager. Some companies actually seek that out.
7. What I mentioned in #2 may be a challenge, but if you can pass the engineering interviews, you may be able to find a team lead role. Silicon Valley has a diverse number of attractive companies, so I wouldn't limit a search to just the big unicorns or behemoths. Memail me if you want some suggestions and some insight on what these companies look for.
8. For technical roles, SV is hands-down the best place to build your career. You have lots of earning potential and career development options, so do a lot of networking, do some good research, and make the most of it!
posted by hampanda at 7:33 PM on December 1, 2017

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