It’s hard to know what to build. If you’re lucky enough to find a good problem, you’re still a long way from your first customer and even longer from success.

We’ve noticed a few things. Peer feedback is effective. Leaderboards are effective. Seeing swaths of people from around the world present ideas is fascinating, per our hackathon last month. We’ve also seen repeatedly that first-time-founders, despite heaps of talent and ambition, are bad at selecting the right problems.

In the absence of the NBA and March Madness, we’re attempting another kind of sporting event. One which, if successful, could generate founders who reshape industries.

It’s called the Pioneer Challenge. Our first installment begins today. The goal: Build a Better Zendesk.

Zendesk 2.0

We’ve spoken with a number of large enterprise companies, their collective valuation over $50B. They all agree: Zendesk is bad. Due for massive improvements, but still the best option.

This is where you come in. Large customers are ready for someone to build a better version of this product, and we’ve brought them to your door for weekly feedback.

At this point, you might be wondering concretely, how to improve on Zendesk. What are the features you should be building? The good news is that there are a very large number of customer support reps around the world, which affords you a huge userbase to talk to. We recommend you take the first week to find and call support reps from around the world and ask them what's broken.

Here are a few things that have come up in our calls:

  • Better integration between Zendesk and Salesforce, with “high-value customer” alerts, Rapportive-like context within the CRM. Quick escalation for any support case opened by a top customer.
  • Better reporting on live sentiment and analytics. Give the customer success leader a live heartbeat for how people are feeling about the product based on their reactions.
  • Make the responses feel like Gmail emails, not Re: CASE 1123232 We’ll Be With You Shortly.
  • Make the interface screaming fast.
  • Natively integrate TextExpander.
  • Robust customer authentication: partial match by email, customer name, etc.
  • Event routing: Alert your ops team based on certain keywords.
  • PII removal from support tickets with audit and logging.
  • Keyboard shortcuts.

These ideas are just suggestions. Don't blindly build a product based on them. Spend some time talking to users, asking them about their problems, and build a product around it.

The Challenge

Today: Register by making a post on Frontier. Your first task is the hardest: pick a name for this project. Introduce yourself in the post, and make sure to include links to any past projects you've built. There is a template there waiting for you at the top.

Sunday (May 17th): Final submission deadline.

Monday (May 18th): We’ll invite all registered participants to an audio-only Zoom call. This will be a chance for you to meet other participants, and maybe find a co-founder.

Friday (May 22th) 5pm PT: Submit a prototype (or a 30s Loom video) walking us through your progress. Show us your research, wireframes, prototype, a product beta, any progress you’ve made. Zendesk customers are everywhere - seek them out and source their needs. Vote on others, see what the rest of the world is building.

Weekly Format

  • Friday: Submit your weekly demo to Frontier. (You can submit it any day you like, and the earlier you submit, the more upvote attention you might get.)
  • Saturday: We'll show the top demos to our customers and we'll ask them which is their favorite.
  • Sunday: We'll announce their top picks. The participating teams will get cut in half every week.


  • The winning team will be incorporated into a company, along with a $10,000 investment for 5% of the company.
  • We'll refer you to the five customers that have been rating your progress. We can't promise anything, but we're optimistic this should smooth the process to closing a sale.


  • If you refer the winning team to us, we'll grant you 0.5% equity in the company. You'll need them to register with a unique link you can generate for yourself here.
  • There might be extreme circumstances where we can't grant you the equity (depending on the country you're in, for example). We'll attempt to exhaust all reasonable legal options to make good on this.


Can I submit more than one update a week?

Yes. We'll take your latest update at the end of the week.

Do I need co-founders?

No! You can get started alone. Our introductory audio-only call might be a fun way to meet others in a low-key fashion, if you'd like.

Who decides who makes the cut?

The team at Pioneer and our customers. Each week, we'll take the top posts on Frontier (as voted on by the audience) and send them to our customers for review. We will be heavily biased on what the customers like – their approval means you're on track to building something interesting.

If I win, am I guaranteed a sale?

No, but we think you're significantly more likely to close given you've been "pitching" the customers for over a month.

I've already been working on this for years, can I apply?

Sure! Anyone is welcome.

I'm already in the Pioneer Tournament, how does this interact with winning the normal tournament?

Dual victory conditions is a bit of a non-goal. We recommend that you either (a) continue in the normal tournament, working on anything you'd like or (b) completely shift to trying this challenge. Doing both simultaneously would be hard.

Who are the customers?

These companies are large, and as such don't lend their logos easily for publicity. We're going to keep them anonymous for the length of this challenge, and offer warm introductions to the winner.

What's the timeline?

First submission deadline is May 22nd. The winning team will be announced the week of June 22nd.