Isn't the answer to "will the customer get better service" a definitive "yes"? I mean, obviously it depends on the UX of said security feature(s), but generally speaking, more secure == better. Right?

Not necessarily, lets say its just "security debt." Start with something like "we built this system with MD5 passwords in the user rows of a database that includes a bunch of other information" And 10 years go by and you (the guy who worries about security) realizes that hey, rainbow tables can be really really big these days, perhaps MD5 isn't the answer anymore.

So you go to the annual planning meeting and you pitch to the execs ,,, We want to take 5 engineers to first fix the password encryption we are using, second to update all the databases, third to build and test a system that makes swapping out the encryption method of passwords easier and less disruptive in the future, and finally updating the build system to do some sort of regression test on passwords to insure we aren't creating new services with weak algorithms.

The person after you pitches ... we'd like to take 5 engineers to build an algorithm to identify viral videos on the web and then put them into an iframe on our properties, thus increasing the length of time someone spends on our web pages which early A/B testing with some hand picked videos suggests increases revenue per page by .5%.

They give the 5 engineers to the kitten project it makes for more revenue.

A year goes by, the security guy pitches and the second pitch is "Our videos are doing great but we have discovered that people really hate that it takes three clicks to change their preferences on page layout. We want the 5 engineers to tweak the portal pages to make customization easier and we'll add a frictionless ad portal where they can just click on a product that appears and it will order it for them."

The updated portal gets the 5 engineers.

Now they are at a due diligence meeting with a potential suitor who discovers that millions of passwords were breached and later compromised because for years they knew they were using an insecure way of storing them but had not done anything about it. This materially affects what they consider the 'value' of the company to be.

The challenge is that if the security guy is really good the customers don't "see" anything, just their password is better protected than it was, and future projects start with strong password management systems. So from the people visiting the web property "nothing" changes. From the executive planning group's perspective they have spent 5 precious head count on a feature that they will have no way of "reporting" its success either in their own resumes or to their bosses. Kittens and better click through? Easy to measure and report and you can point at dollars in the bank as the benefit.

Not really. Passwords are a pain in the ass - and every new complication adds bugs. Things were a hell of a lot easier when you could just put something up and not worry about security.

That said, the alternatives are much worse than the price of security.

It's great if the higher up executives / managers starts valuing security, and are more open to the idea of reallocating more company resources (employee time) accordingly.

How will this pragmatically trickle down to middle managers and their subordinates? With politics and personal incentive that are potentially unaligned with the company's long term interests (not having a data breach), will more resources actually be spent on security?

The return on investment of information security is not obvious / tangible, especially on a quarterly basis. Data breaches are "black swan" events, rarely occurring but with disproportionate consequences when they do occur. It's harder to quantitatively track progress, or lack thereof, of investment into security.

People can (over) claim the amount of time reallocated to security. These claims would be hard to falsify. Teams who are behind on other deadlines can blame time being reallocated to information security. Managers can use the purported reallocated time to spend on feature work, or whatever it is that makes them look objectively better for promotion.

I admit I'm being a bit cynical. I think company culture would help mitigate these issues. Executives valuing information security, even if it's just words rather than policy, nurtures such a culture.

From the top down, executives need to communicate that it is a company priority. Even better if they can make it a cultural thing, instead of an afterthought. A lot of the time, engineers just don't know best security practices or in the case of web development, common exploits[0].

For middle management and below, if upper management doesn't care about security, despite the "look at Yahoo" argument, then you'll find no leverage there for security funding. If they care at all, then managers and individual contributors can argue for security to stand out and accelerate their career. Yahoo's security troubles brighten the spotlight on the need for security funding at companies for training, audits, and setting aside time to do retroactive security work. It's not a silver bullet, but it helps.

[0] OWASP has a lot of great web security resources. Here is their top 10 list from 2013, https://www.owasp.org/index.php/OWASP_Top_Ten_Cheat_Sheet

I believe the cost to Target was quantifiably roughly US $300 million.

Some people say it materially affected their brand value but outside of the costly downtime during the holiday sales period I am not certain it affected their brand much if at all.

Don't quantify security. Just do it.

If people ask, just doing my day job'

edit: care to explain the downvotes?

I didn't down vote but lots of devs don't have that sweet luxury to not be held accountable for what they're working on in quantitative business terms.

Nor access to all the code for the entire backend.

Sometimes it's better to ask forgiveness afterwards than to ask for permission beforehand.

A strong security posture is not a perfect security posture. It seems likely that someone will invest in security, get hacked anyway in a really sophisticated way, and feel that they wasted all that money.

BitSight provides a service that quantifies the security of a company based on publicly visible data. Even now it is being used for underwriting insurance and for evaluating alternative partners.

So basically people who grab a company's data can extort the execs instead of trying to sell the data to third partied

Yes, but would be tough, since how could you guarantee you deleted the data you stole