Be better prepared to close deals with Charlie App!

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Charlie App

Jorge: I always love to hear how the founding team met and what were your professional backgrounds?


Aaron: I love answering this question, because it’s a personal victory on the power of learning about someone before you meet them. When we were courting Rob, our CTO, to join the team I spent a ton of time trying to figure out what would make us different that the companies he was considering joining.

I did some research and discovered we loved a lot of the same things (concerts, skiing, etc.) and lined up a concert for us to attend together as a part of the interviewing process. Rob’s previously created multiple successful software companies, so many companies we’re courting him, but I guarantee none of them had an interview like ours. We ended up staying at the show until 4am. I’m pretty sure that’s what closed the deal, but don’t quote me.


What’s amazing to me is now that Charlie is a real thing, we’ve received countless emails from people who have been in similar situations where their Charlie research has helped the stand out, close deals, and get promoted.  It’s come full circle, and it wouldn’t have happened if it weren’t for that crazy interview.


Jorge: What was the inspiration behind launching Charlie App and what were the primary pain points you were solving?


Aaron: When interviewing for a new job I spent a bunch of time before each interview researching the interviewer and company so I’d stand out.  I did the same mundane prep work before every….single…interview.  And eventually I thought, is there anything that could do all this work for me? There wasn’t, so I turned down the job and created Charlie to automate the research process for anyone heading into a big meeting.


Jorge: What is Charlie App and what is the ideal user profile?


Aaron: The world’s most powerful people have assistants who brief them on the people they’re about to meet with… so, why don’t the rest of us?


Charlie ( is the assistant for the rest of us. Before any meeting in your calendar, Charlie compiles one-pagers on the people you meet with so you can walk in prepared to close the deal.


Executives and sales people from companies like Salesforce,, Hubspot, Hootsuite, and more use Charlie every day to save time and make a killer impression on the people they meet with.


Jorge: What are the primary user cases for Charlie App?


Aaron: Right before any big sales call, Charlie emails you a one-pager on the person and company you’re meeting with.  Whether it’s breaking company news, blog post’s they’ve written, the passions you had no clue you shared, Charlie covers all your bases so you can walk in ready.


Jorge: What is the Chicago startup scene like these days and what are a few of your favorite b2b startups in the area?


Aaron: It’s amazing how helpful and “all in this together” the startup scene is in Chicago. For example, when we were building Charlie we didn’t know many sales people in the area, so we cold emailed some of them, and asked if we could watch them research their prospects so we could build something to automate it.  With no hesitation, nearly all of them said yes and had our team over to watch them prepare.  Years later, we’ve now built something that does that process for them and we wouldn’t be where we are today without them and the Chicago community.


Some of my favorite B2B startups in the area are:

  1. Simple Relevance, which helps marketers and salespeople automatically personalize the emails they send. It’s amazing.

  2. SproutSocial, which helps you manage your social presence more efficiently than you could have ever imagined.

  3. SpotHero, this one’s B2B2C, but it finds incredibly cheap parking everywhere and I can’t live without it.


Jorge: What are the top venture capital firms in Chicago today?


Aaron: They all have strengths in different areas. Lightbank is amazing for B2B as it was created by Brad Keywell who has perfected B2B sales with his experience creating 3 public companies.  Chicago Ventures is run by Kevin Willer, who created Google Chicago. He was literally so he know’s what he’s doing too. I’ve also always been impressed with Hyde Park Ventures Partners.  Every time I talk with them they give direct, no nonsense advice, and I love that.


Jorge: How do you believe that sales software will evolve moving forward?


Aaron: Due to the emergence of robust prospecting software, the biggest sales problem is no longer getting in touch with the people you want, but rather standing out from everyone else begging for your prospect’s attention.

Sales people know it too: I read a statistic that the average rep spends a quarter of their day preparing for their sales calls so they can stand out.  That’s a quarter of their day they aren’t able to do what they were hired for: selling.  It’s a big waste of time and that’s where sales technology will evolve.

It’s why we built Charlie, so that you can stand out and still have time to sell.


Jorge: In your opinion, what is the impact that mobile has had on the b2b selling experience?


Aaron: Mobile has made things easier for the sales person to get information, but harder for them to make an impression on the people they meet with.  We’re now selling to the always-distracted-generation who could receive a tweet, text, or notification any time to distract them. That’s why it’s more important than ever to do your research before a call. There’s an ever shrinking window of opportunity to capture someone’s attention, and Charlie allows for you to build instant rapport and impress your prospects.


Jorge: What advice would you give an early stage founder when trying to launch a b2b startup?


Aaron: Sell it before you build it.  When we started Charlie we emailed 30 different people and companies and told them that Charlie was real and asked if they wanted their next 3 most important meetings researched for free.  They said sure, and 24 hours before their meeting we sent them research on the people they were meeting with. What they didn’t know was that Charlie did not yet exist.

We were staying up until 2am and doing all the research by hand.  This process helped because we were able to verify that people wanted Charlie and were willing to pay.  I think the research took us on average a couple hours per meeting, and now we’ve automated all of it with Charlie.

Thankfully we never need to do that all by hand again, that was exhausting.


Jorge: What are the most challenging aspects of starting a software company?


Aaron: Our biggest technology challenge has been integrating into 100,000’s of sources and filtering the research that we find into just the key facts you need to know.  Finding the information was a challenge for us, but nothing like the challenge of summarizing the information into just the key points.

We’ve spent years perfecting that technology, and we’ve had to be really patient during that process, which is a challenge in itself.


Jorge: Does Charlie App integrate into any 3rd party systems or CRMs?


Aaron: We’re currently beta testing Charlie for Salesforce so that, in one click of a button, Charlie can research any prospect in your CRM.  Be on the lookout for it to launch soon!


Jorge: Anything else you’d like to share with our readers about yourself or Charlie App?


Aaron: Thousands of salespeople from companies like Salesforce,, Hubspot, Hootsuite, and more use Charlie everyday.  You can get Charlie at and you’ll walk in to every meeting with intel to make a killer impression.