Senior: My Summer at Umbrella

As I’m sadly nearing the end of my time at Umbrella and looking forward to my senior year of college, I wanted to write down some of the interesting things I’ve learned this summer.

I originally joined with one personal mission: add as much info as possible to my understanding of what I want to do with my life. The role was for a wear-every-hat gap-filler. And I really liked the team — I could see myself fitting in well with the culture. To be honest, I wasn’t in love with the problem space at the time, but it was new and mildly intriguing.

As the summer went on, however, I ended up becoming rather interested in senior living. Growing old creates problems in basically every part of your life, and most modern tech-enabled companies aren’t designed to work with seniors. I’m increasingly convinced that there are a truly gigantic number of opportunities and interesting problems out there.

Starting with some things about seniors in general:

The financial calculus is harder. Many seniors live on fixed income and have a lot of uncertainty surrounding how long they’ll live and whether or not they’ll have unexpected medical costs. This makes seniors reluctant to spend on anything that’s not necessary.

Word of mouth carries lots of weight. Seniors are very deliberate in evaluating their experience as customers. It can take weeks for seniors to get comfortable enough with a product to recommend it to friends — and they often have a smaller set of people they talk to. These dampen viral coefficients for a nascent single-player company like ours. It’s unknown how strong word of mouth will be for a more advanced senior-focused tech product. On the flip side, careful recommendations often have a higher impact and make friends likely to convert.

Trust and security are huge concerns. A disturbing number of Umbrella’s members have been previously scammed by unethical contractors or even had their bank accounts emptied by fraudsters. Some sales leads aren’t comfortable giving us a credit card number or basic personal info, and for good reason given the level of abuse targeting seniors. Figuring this out across marketing, sales, and product has been an interesting challenge.

Serious attention to detail. There were multiple occasions where I’d talk to a potential customer and say something like “we charge $29/month,” then after talking for another few minutes, I’d reiterate that “Umbrella only costs $30 bucks a month.” Then I’d inevitably be interrupted: “wait, I thought you said $29, not $30?” Inconsistent information over the phone and sloppy landing pages are a big turn-off.

It’s harder to consistently communicate. While most of us are available through text, email, or phone calls, seniors often only use one or two of the three. It can be tough to design a system that works when any given user might require that you use a specific channel.

You can’t take all tech product concepts for granted. Ideas like recurring subscriptions (what if I don’t use it this month?) and on-demand work (so who are these people just showing up?) are alien. Seniors usually don’t keep up with tech news that might familiarize them with companies like Uber or Netflix, so you can’t even rely on common context to build a brand image and value proposition.

Bad design is really really bad. You can’t hide much behavior (linking an address to a map application, for example.) Hamburger menus, swiping, and press-and-hold are out of the question. Animations are probably too confusing as well. Other complex products may be able to get away with those design elements, but not Umbrella. Building a crystal-clear interface that is acceptable to everyone on the seniority-spectrum is hard.

You earn a lot of goodwill, at least as far as tech companies go. Serving seniors is a strong mission that unifies potential partners, customers, and teammates. While still one hell of a challenge, BD/sales/recruiting gets 3% easier. And that can make a huge difference.

Your customers love you more than you thought was possible. One of the best parts of working at Umbrella has been the immediate and significant impact we’ve had on our members. Every week we’d get a call or note saying “I don’t know what I’d do without you,” or “Umbrella is a godsend.” It’s a lot easier to push through an intractable bug in your code when the users are so genuinely grateful for what you’re doing.

You work with lot of fascinating characters. Seniors don’t seem to care what anyone thinks of them. Between the hilarious age-gap moments, borderline-crazy 500+ word emails, and heartbreaking reminders of our own mortality, seniors are by far the most human group of customers I’ve ever served.


Thoughts on the space overall

There are a couple strong tailwinds that make me very bullish on senior-focused startups.

First, seniors are becoming more and more digital. While plenty of our members don’t have email addresses or cell phones, that’s changing — fast. You can easily Google around for trends and stats here. By the time a startup begins to scale up several years from its starting point, this will be much less of an issue. So now is a probably a great time to get rolling.

Second, unique senior-specific UX and sales challenges create a surprisingly solid moat. Think about everything I listed above — I suspect that X but for seniors will be a viable startup idea generator. We already see early hints of this from GoGoGrandparent, the Uber for seniors that went through YC. (They’re double dipping on the idea generators: Uber for X and X for seniors!)

I’m convinced there will be several $1bn+ companies out there focused on senior verticals. One of the running jokes at the office was that an online megachurch would be an insanely profitable business. While that’s not a business we would ever want to build, just remember how successful televangelists are. Add on the scale of the internet, modern phone/tablet distribution, and social-network-like community features and you’ve got something huge.

AARP is investing $40mm in senior-focused companies. I’ve also heard more non-specific but senior-related chatter recently from mainstream VCs. I’m looking forward to seeing how the space develops! Let me know if anything catches your eye.


Shoutout to Sam, Lindsay, Emma, Erin, Samra, Caroline, Megan, Manuela, and David for a summer that went by way too fast! I’ll miss you all ❤