How I Used Email Tracking to Help Sell My StartUp

When I was the CEO of my second startup DoctorBase, I discovered the first wave of email tracking tools and they really helped in sales, fundraising and when I ultimately decided to sell the company. These simple Gmail plugins told me when investors, customers and eventually CEOs of potential acquirers were opening my emails. And, as I’ll detail throughout this post, I used it as a platform to get potential acquirers to think about exactly the message we wanted them to focus on, thereby controlling the narrative of our brand (which turns out is hugely important when attracting potential acquirers).

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It was as simple as when a busy investor or executive was opening my email. I would call them (or text them if I had their cell) and it worked because the simple desktop notification that would pop up on my laptop screen told me when my prospect had me on top of mind.

I realize it’s much more acceptable behavior to cold email an investor or executive, then hope schedule a call. But I’ve found that even when this is successful (and it’s not most of the time) you still have to follow up with more scheduled calls and meetings – most deals aren’t closed on one call alone. CEOs and investors are so busy, attempting to cold call them or follow up with them with scheduled meetings is just too routine – and you’re entering their funnel, not creating a funnel of your own for them to enter.

Sending them tracked emails (and happening to be in front of your laptop when they do open) with a cold call, or follow up text or follow up call has worked wonders to bring executives to conversations about our company vision. As some investors like to say, “Timing is everything.” For me, it was about knowing when to call/text.

But I wanted Email tracking to do so much more –

  • I’m mobile a lot, and I didn’t always get all the important desktop notifications on my Macbook. I mean, Tim Cook could be reading my cold email (he wasn’t) and if I was on my iPhone I’d have lost the opportunity for him to selfie with adopt me. And the chance to Dance Dance Revolution together on father-son Sunday Fundays.

  • The other thing about these email tracking tools is that they’re not all that accurate. The 50% of the time they are, they’re golden, but there are a lot of false positives (really, someone opened my happy birthday email 11 times?) and they can’t tell you when your email recipients have forwarded your emails. This can be interesting when sending a VC your deck – don’t you want to know if they’ve forwarded this to other VCs or even your competitors? And what I would’ve really loved was to be able to see which pages VCs paid the most attention to so I could refine my messaging and pitch deck.

  • But the most important thing by far was to be able to get my email recipients to click a link within my email, which sent them to a special page on my website (e.g. “Check out our confidential revenue growth stats here”) because once they did that, my engineers were able to create a script on that page that cookied the executive or investor called a pixel. Meaning that when they went to other properties across the web, they would see my ads on those sites. But not just any ads, ads I had specifically written for them.

I still laugh at loud at how little we spent on our retargeting campaign with a list of less than 50 email addresses, with ads specifically targeted to executives and investors. It must’ve been the greatest ROI in retargeting history (maybe). For example, my ads towards our customers (who were doctors) would say something like “Be a 5 Star Doctor Online!” and were expensive at scale, but towards our 50 target executives our ads said, “How One BootStrapped StartUp is Beating HealthXXXX” (a famously overfunded startup who had raised 30x more money). We spent a few hundred bucks on our retargeting campaigns in total. 

  • In order for this strategy to work, you must know both the work and personal email addresses of the investor or executive, which can easily be found (mine included) on many Chrome-based email guesser plugins.

Having investors and executives see your vision in both their personal online experiences as well as your voice is much more powerful than voice alone.  Also, think about it from the purchaser or investor’s perspectives – they’re getting inundated with offers and are surrounded by opinions they trust. As a hobby angel investor and advisor to VC-backed startups, I see how many deals fall apart behind the scenes without the founders even knowing about it because someone else is controlling the backchannel conversations about your company.

In our case, we had numerous competitors with similar feature sets but our advantage was that we had unique components of our company that made it a better purchase candidate than our competitors. We couldn’t message that in general ads, but to our investors and potential acquirers, it allowed me to keep everyone on message – my message.

So after I sold DoctorBase to the leading digital health company in our space in a mostly cash deal, I went to work with my core engineering team to build the ultimate Email Tracking Weapon of Mass Destruction. Or something like that.

We wanted –

To make it super simple to combine 1) more accurate email & attachment tracking using machine learning and 2) the ability to automatically “pixel” your email recipients so they see your affiliate ads online.

Basically, I wanted to take the homegrown scripts we created on top of Gmail to help sell DoctorBase – and make them available as one free(mium) tool.

From code day one we’ve been working on leveraging true machine learning (not algorithms disguised as “A.I.”) to make our email tracking the most accurate on the market. As is designed, JetBridge becomes increasingly more accurate over time about email and attachment tracking, and also tries to gauge how interested your recipients are about your message. Again, it takes time for JetBridge to get smarter, but that’s how we designed it from the ground up with Dr. Scott Locklin (well known in the machine learning and AI space) and our two technical co-founders Mischa and Adam.

The beta release is out now and while we’re still building more features to come, we’ve priced it to be free for unlimited email tracking, and the premium features like CRM integration are so low it’s affordable by all of our amazing friends in Eastern Europe and South America (not just well-funded startups in San Francisco or London).

Finally, for JetBridge I want a different type of company. We’re not funded by institutional investors so we don’t have pressures to become “yuuge,” and as an employee-owned company we have an international team that treats each other with dignity and respect. We have an amazing female General Manager named Lilly and our product is designed by the fabulous Crystal Lin, and while equity ownership (and female leadership) for employees is a foreign concept in Eastern Europe where our second office is based (Kiev), we’re making it a thing there too.

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The JetBridge team coding it up in San Francisco.

I want to hear all your product bitches and ideas for how to make JetBridge better for your startup or team. Email me at john.kim@jetbridge.com or catch me at any number of Mexican restaurants in San Francisco or bars in Kiev.

You can download JetBridge for Gmail here on the Chrome Store.

 

Bye Bye, Panda

DoctorBase Founders

In 2009 my buddy Mischa and I wanted to make a ding in the healthcare universe. We were both pretty fed up with the status quo for consumer health, and felt like we could build a communications app that made it much easier for doctors and their patients to communicate digitally.

Man, we learned some really harsh lessons about the American healthcare system. Namely, the folks who control our national healthcare policies at the highest levels make Russian mobsters look like pussies.

  • If you work for the Russian or Ukrainian mob, please know that I have the highest respect for your craft – no insult intended.

DoctorBase was also a lesson in competing with better funded competitors by sticking to your passion for building the best damn product and ignoring the VC hype machine. Our closest competitor HealthXXXX had raised 30x more money than we did, but at the time of our acquisition we were a totally employee-controlled company and was doing almost triple their revenues with nominal churn.

healthtap competitors

This took 5 years to build out completely, and by then it was one of the dominant apps in the market with very little funding or marketing. Of course, VCs passed on us because, well HealthXXXX had raised much more money and that meant they were going to win. A very famous VC said he felt that “HealthXXXX is going to run away with the market.”

At the time I sold the company we had about 13,000 doctors communicating electronically with nearly 7 million American patients. We were small, but we were a bad ass gang. I mean, not as bad as Russian mobsters, but still.

You can check out our latest software project for sales & marketing executives: JetBridge – a Free plugin for Gmail to get nearly 40% more responses.