Pizza delivery. Event planning. Bill splitting. We see many of these at Pioneer. I call them “incombustible ideas”. Founders relentlessly try to ignite them, but they just don’t light up. I don’t blame the firebrands. Solving anecdotal problems is a good instinct in most situations. But it can also lead founding teams down a stray path, spending years working on a company in a dog market.

There's a bit of a meta-issue at play. People who want to start startups aren’t exposed to enough of the right frustrations. Sure, it’s slightly annoying to split a bill with friends. But the frustration is small. The market difficult to monetize. It’s really annoying to use Google Groups in a large organization. And that’s very easy to monetize. I doubt most humans know this “secret”.

Our hope with this post is to enlighten the hacker-class to some of the small-but-big problems that large enterprises face. Any of these projects could turn into a $200M+ startup within one year if executed properly. Pick one, start working on it, and get in touch with us!

1. Better Zendesk

Zendesk is a $9B public company. The product is good, not great. The company has few moats. If you built a Roadster to their Corolla, you might win a few deals quickly. Something that was fast, responsive, undercut on price and gave leadership a sense of control.

Small startups find Zendesk uncomfortably expensive. Larger businesses are looking for something with better reporting. This is an important problem, because it makes executives unhappy. It’s one thing if the customer service rep finds the Zendesk UI slow. They aren’t the buyer of the software, so that doesn’t matter much. If you’re making the executive unhappy ( “are we getting better or worse at support?”), you’re at risk of losing customers. Make something managers want. Here are some specific issues you’d want to fix:

  • No built-in support for account context (which every company needs).
  • No support for authenticating customers (which every company needs to do).
  • Doesn’t interoperate with G Suite and other communication tools.
  • Janky subject line prefixes like [CASE 34984311111].
  • Doesn’t interoperate properly with the rest of email (CCs etc.).
  • Has been breached twice.

2. Better Google Groups

Every company has internal email lists. Managing them through the Google Admin UI is terrible. Build something better here, one that allows for *-prefix rules, has a nice internal viewer interface, etc.


Every company runs reference checks as part of a hiring process. Some references are provided by the candidate. The best are often unsolicited. A friend, or a friend-of-friend. These are often more useful than the interview. Backchannel references are tricky: you don’t want to call people at Foo’s current company because they haven’t told them they’re leaving. Even once you find people from a past company or position, you’ll need to somehow incentivize them to be honest (non-monetary rewards work best).

Figure this out and you’ll find yourself establishing the next LinkedIn.

4. Better Personality Models

The Big Five Aspects Scale is considered the cutting-edge of personality models, yet like much of social sciences it’s on the backbone of self-report surveys. I doubt a Google Form is the best we can do. We need something better. Something that durably captures differences in human personality. Instead of measuring using self-report surveys, look at emissions: the messaging, music, movies, browsing history, that people create, and cluster based on that. You might not know the labels of the clusters (“openness”, “conscientiousness”), but you’ll at least know who is similar to who. Monetizing this should be relatively easy. (We certainly have a few ideas ourselves we’d be happy to share).

5. Org Chart As a Service

Like a scene from an FBI movie, every good sales team has a cork board of people within the organization they’re selling to. The golden dataset everyone wants is the org chart. Who reports to whom. Who is new. Who has been at the company for a while. Find a way to get this data and sell it to companies. I suspect you’ll have many takers.

Find all the images on the web that look like charts/graphs. Convert those pixels into data. Let users search the entire Internet’s store of graphs, both by name and shape (“what are Things that are trending up?”). Like a Tesla Roadster, this product wouldn’t have billions of users, but you could charge the elite few quite a bit for using it.

Every founder goes through an identical process: downloading Microsoft Word, changing variables in a legal template, opening it in Preview, attaching their signature, and sending it over to the counterparty. Automate this process. Offer templates for common documents (company formation, SAFEs, etc). In time, you might become the store-of-record for company documents.

Pioneer Sales Booster

Success in the enterprise is equal parts software and sales. Getting 3 landmark deals can catalyze a feedback loop that turns a small project into the next Oracle. In addition to funding, Pioneer will try to help you get these for any of the ideas above. We can’t guarantee anything (you’ll have to make a good product, of course!), but we’ve got customers lined up for the right thing. Mention this post in your application when you apply.