Harris Osserman

Harris Osserman

I'm the Founder & CEO at Talk Hiring. We're building a realistic mock interviewing tool with instant feedback that's fully automated. I was formerly a Senior Software Engineer at x.ai, an AI meeting scheduling tool, and graduated from Duke with degrees in ECE & CS.

I enjoy watching the dumbest comedies, pushing the limits of what you can air fry, and biking uphill more than downhill. If you want to contact me, my email is harris DOT osserman AT gmail DOT com

I don't, by any means, think that I know what I'm doing when building companies, but I think that I have a lot of experience to share!

MailBadger: A Postmortem

At the start of junior year at Duke, I was working on a startup called MailBadger with my friend, Kirill Klimuk. Essentially, MailBadger was a two-fold enterprise software solution. It helped companies automatically follow-up with their clients, and it displayed these results in a simple, user-friendly interface organized by client or by reminder. MailBadger was going to solve the problem of requiring employees to remind themselves to follow-up with their clients. Instead of reminding themselves to remind others, employees would simply set a reminder with MailBadger for their clients, and MailBadger would send an email reminder at the specified date and time.

We were interested in helping accountants that handle taxes. Many accountants that we talked to echoed the organizational challenges of being an accountant. During tax season, it is very time-intensive to make sure that all of an accountant’s clients have sent the accountant all of the legal forms that the accountant needs to do the taxes. What often happens is that a secretary will keep a huge Excel document with client names on one axis and documents required on the other axis. Then, the secretary will mark off which clients have submitted which documents. When clients do not submit documents in a timely manner, the secretary has to constantly follow up until the client has sent all of the required documents.

Kirill and I saw accounting as a huge opportunity to digitize the receipt of documents and automate the following up with clients to send required documents. However, we realized very quickly that CPAs are slow to change, are not particularly skilled with technology, and value the personal connections that they have with their clients. Many accountants are Excel power users, and do not like using products that are not tied into Excel. Additionally, because many accounting firms are run by multiple partners, it can be difficult to get all of the partners to agree on a new technology product to implement throughout the company. Finally, many clients stay with accountants because of the personal connection that the clients have with their accountants. Some accountants saw MailBadger as a product that would make communication less personal, and could translate into lost clients at an accounting firm.

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