How to discover WHAT product features Build

Making a great tax data collection experience. Imagine having 200 contractors... Taxes are due in 20 days. You are missing 170 forms.

We had a problem…

Not a direct problem for us (Routable), but being the payment facilitator with a growing client-base, manually producing data for clients was becoming unsustainable.

Clients were spending cumulative days and, in many cases, weeks collecting their contractor’s tax information.

Those in charge of collecting tax information from contractors (usually, finance / accounting team members) were exhausted from manually entering data. 

Maxwell, my partner product designer, and I were interviewing clients of all sizes- small business to mid-market, asking questions about their end-of-the-year process for issuing 1099s… And, it was sounding brutal. 

How were our clients collecting the forms? Everything from texting business owners for their W9 forms, to email, to random external portals, to snail mail…
Then, they’d take that data and manually enter PII (Personal Identifiable Information) into databases that issue those 1099s.
It was time for a change…

Background – How W9s & 1099’s work

In order to really understand this story, I’ll back up a bit and explain why this process evens matters.

If you pay someone over $600 for a service, generally you are required by the IRS to issue them a 1099.¹
The 1099 is a tax form that typically is mailed (or emailed if the other side has stated they will take electronic communication) to both the contractor and IRS.

In order to complete a 1099 you need a couple things:
1) A W9 (domestic contractor) or W8 / W8-BEN-E (International / international entity) 2) How much you paid them (depending on the type of 1099, you may need further breakdowns / more information)

So, the best practice is before you pay any one a dime, you send them a W9 to complete. You may not need to file a 1099 after the end of the year, but at least you’ll have that W9 form in the event you do need to declare how much you paid them.

Here’s an interesting part few know - Signatures on W9s are not necessary in all cases.²
That said, something I learned previously when creating a startup that generated legal forms for users³ — We don’t want to be seen as interpreting the law for users (acting as attorneys / CPAs when we are not, even if we were / have team members who are, it’s best to avoid that responsibility⁴).

With that in mind, even though signatures weren’t technically required for most cases, rolling out digitally certified e-signatures was the conservative move here… Add another line item to the scope list.

One other thing to note here, is psychologically, clients liked having a completed W9 form with signature. You don’t even need to send those W9’s to the IRS, but if the client wants it and is running around trying to get them completed, then that’s one more reason.

Back to the product

The paragraph above you may have read, or perhaps you skimmed, was exactly what had to be re-explained to every person on the Product / Engineering team and in the company that didn’t directly speak with clients.

Now came the heavy lifting… The actual product work…

Here’s how we approached the problem…

Steps to launch something users want

1. 😶‍🌫️ Hypothesize the problem - This problem you’re working on started somewhere… I say hypothesize because I started with an idea of the problem, but had some fixes once we got to #2.

2. 🎙 Interview clients- You probably know everything about your user-- but do it anyway just to prove to yourself you are in fact the king-pin, the queen bee, of your target audience. (I’ll get into this in another post.) To be honest, I did not want to do this. I wanted data. At some companies, getting data is as easy as firing up Google Analytics and looking at page views / bounces. At other companies, data is locked up with the data scientists or worse, there is no data tracking, or maybe the views / clicks are so small, there isn’t a lot of statistical significance. In that case, it’s even more paramount that you talk to people who you intend to build for. Or, AT LEAST, the Support team who probably has heard an ear-full about problems.
   👉 Note: Invite / include your Product Designer if applicable. Product Designers should be there with you, in fact, they may have better questions than you! Just as an Engineer knows the technical difficulties, a designer will have ideas they' may want to ask about / you want them to be 100% in the know so they can make a great design with you.

3. Check out competitors and similar products - You wouldn’t want to start selling something without trying all the competition… Chances are your users mentioned this, or you can just search online and see who’s competing with your company on SEO.

4. 📊Analyze the Data - This was trickier, we had only #1 to go on. In previous companies I had loads of data. So much data, data heaven. Data hell. Here there was none of that. So, when lacking, find another way to get what you need to help guide your decisions.

5. Fix your Product Spec (aka Product Document / Product Brief) - Now that you can speak to the problems and wants of your users you can continue on your product brief without sounding like an idiot, or being corrected when you pitch your brilliant idea to the CEO who ALSO sells the product (kudos to ALL startup CEOs who actively get out there and pitch their own products. I highly respect that… There’s nothing more deflating / exciting than a rejection or a sale.)

6. Work with your designer on the initial ideas - Add that to the spec. This could be a whole additional blog post

7. Share the spec with your Engineer BEFORE showing it to others - By doing this in advance, you keep them in the loop and can cut scope before getting the smack down in a stakeholder meeting (or worse, over promising and under delivering.) Ask them to come up with estimates. They won’t want to tell you. It’s not them, it’s the way building a product works. Often times, Engineering doesn’t know how hard / long it will take until they dig into the code / actual tech spec… Which, probably doesn’t exist yet.

8. Get feedback - Ah yes, feedback, everyone’s favorite thing. Get it early and get it now, before you present the grand idea. Pull in people who will have to pitch it, help users with it, and are invested in your idea / impacted by it on another team.

9. Stakeholder meeting / get the green light - Depends on your organization / team’s process, but I’ll leave this one to you.

10. START work

I’ll leave out the details of the important part - Actual development, testing, and launch, but that’s how ideation / discovery operates from a high-level.

What we did to create a great user experience

As far as our process (the product designer and I) and how we devised a solution, we observed trends across industries with tax collection -

• what was awful (PDFs filled out in iframes),

• what was great (no iframes, easy signatures), and

• what we personally liked (layman’s terms like our contractor users would like and mobile-friendly).

We took all that and fused it together, the entire time thinking of how our client’s contractors are likely reaching these forms… Most would be on their mobile phones, in cars, or on slower internet speeds, they don’t have time to poke around an iframe with a PDF.

We then thought about all sorts of edge cases-

• What if they fill it out incorrectly? (Thanks @Support for that, a common support ticket)

• What if the client already has the W9 PDF? (As we discovered in a user interview)

• And… Technical challenges - How will we build e-signatures? In-house or use a third-party? Questions like this were frequent and daily.

The final product…

The final product was a 3 phase initiative — Involving benefits for both the client and their contractors… I won’t spoil the product but I will say it involved:

1. Great user experience for onboarding contractors WITH full W9 tax support

2. Ability to DOWNLOAD W9s easily, by both parties

3. Ability to UPDATE and INVITE contractors to update their tax information

4. BONUS - Ability to download full CSVs at the end of the year with necessary data for 1099s so clients no longer have to manually enter PII. Some clients didn’t even know this was possible! (Why it’s important to ask their pain / process instead of just their ideal solution.)

And those are just a few of the features of the 3 phase initiative.

Wrapping up

I didn’t go into every single detail as that would either bore you to tears or make my previously mentioned spaghetti cold, but I hope this gave you some insight / ideas on how it’s done.

It’s all about thinking about what your client needs and their problems (in our case we had 2 user types - Clients and their contractors). From there, thinking critically about edge cases, removing your assumptions of what you initially thought would work, and devising what the world SHOULD have.

Then, it’s about translating your vision to the team, your designers and engineers want to know, so they can keep that in mind as they work. And don’t just say it once, say it often.

Encourage questions and let your team members and others challenge you.
It’s in those challenges and your openness that something even greater may arise.

You don’t have to be a pushover, but if you’ve built up enough camaraderie, it should be fun or at least, not painstaking, to hear them out. Maybe they can work faster, maybe an idea can be done in parallel, maybe they have an idea that would push your vision to new, great heights.⁵

That’s a part of the formula for how you can launch some great products.

1. Note: There are exceptions and this is just a general rule-of-thumb. I am not a tax professional, nor a CPA, if you’re wondering if you owe people or companies 1099s and/or should have been collecting W9s / W8’s all along, I recommend speaking to a CPA.

2. Many clients think they need it signed, but as per Page 5 on the W9 form, there are only certain cases in which it’s required that it’s "certified with a signature. I’m not a lawyer or CPA, but that is on the actual form instructions.

3. Cofounded a company called EasyTrust, Inc. It was anything but easy to explain to users, “We’re not your legal counsel. We can help you generate legal documents but we can’t tell you what you should do… And, oh yes, if you don’t fill that field out, that could be a total disaster.” We had to solve this in creative ways otherwise we could be construed as giving legal advice. Ironically, even lawyers don’t want to be responsible. That’s why you always hear, “Ask an attorney.” Even from attorneys. In which case, you have to push pretty hard with questions to get any sort of inkling of a recommendation.

4. Why TurboTax is pitching their new $300 more service to get actual CPA help.

5. Without unreasonable scope creep that is