Onboard.io enables companies to automate, organize & manage their customer onboarding and implementation processes

After spending about a decade building Ambassador Software, it was acquired in October 2018. I spent a few months assisting with the transition and in January 2019 I found myself without anything to do.

I knew that I wouldn’t be able to sit still for long. I hadn’t spent any time at Ambassador dreaming about a new company (or new ideas) — I just didn’t think that was right. However, as I reflected on the way we built Ambassador and the challenges we faced — there was an obvious opportunity to build something we desperately needed.

Despite having only ~45–50…


10 Principles to Control Your Finances Before They Control You

Be Controlled OR Take Control (photo credit)

The year was 2006, I was nearly 6 figures in debt (with a negative net worth). I was a 2L in Chicago, hated the idea of being an attorney and quickly approaching my 30s. I wasn’t sure what I was qualified doing after law school and I felt trapped.

Little did I know that a housing bubble was forming and was about to pop (in 2008) which would unleash a global financial crisis…

Let me back up a bit, and explain how I got here. I grew up in an upper middle class family outside of Detroit, Michigan — my…


After nearly a decade of thinking about Ambassador 24/7, I have worked my last official day with the diplomats. It is incredibly bittersweet. I am so grateful and honored to have worked alongside such great people — it is something that I am worried will not be easily replicated in my life.

One of the challenges of a founder is celebrating the victories. Perhaps it’s due to the fact that we know a new (and more difficult) challenge awaits — either way, I am so incredibly proud of this team and what we accomplished. I cannot say it enough. Building…


Leadership perspective from a founding CEO

Nearly everyone strives to become a ‘leader’. It’s natural. We’re told at a young age that it’s important to lead. Leaders are the heroes of books and movies — they overcome insurmountable obstacles and face challenges head-on. These fictional leaders are always the biggest, strongest and fastest, however, in real life anyone can emerge a leader. This is especially true in business.

This post creates a framework for those looking to step up and lead. Use this as a guide to grow into the leader you’ve always wanted to become. It’s possible, I promise


A holiday gift guide for the tech enthusiast in your life

Last year I wrote a holiday gift guide for the entrepreneur (or tech-guy) in your life. The premise is that these gifts are for people who appreciate quality items and are particularly excited to find new, relevant brands who make great stuff!

Enjoy!

Cool stuff:

Beats Studio3 Wireless (Wireless headphones, $349.95)

Quite possibly my best purchase of the year. For those who don’t know, I sold my company and this was a total impulse purchase at an airport store. I love Beats and have been eyeing wireless headphones to pair with my 2nd favorite travel necessity, my iPad Pro (see last year).


I’m deeply honored and humbled to share some exciting news….

Ambassador has been acquired by West Corporation!


In almost every industry, referrals are the gold standard of customer acquisition. Research has repeatedly shown that referred leads close faster, buy more, and stay longer — all with significantly less effort and at a much lower CPA than non-referred prospects. A University of Pennsylvania study[1] found that referred customers are more loyal and profitable — by a 16% margin — than their non-referred counterparts.

What’s not to like about that?

Truth is, most of us inherently understand the value of referrals. When we make a big purchase, we seek out reviews or ping our networks for recommendations. In fact…


Relationship marketing is not a tool, but a strategy. It’s a way of looking at the relationship your brand has with customers, fans, and followers that parallels any other type of marketing tactic. Numerous studies show that referred customers convert at a higher rate, buy more, and hang around longer. In fact, across industries, 82% of Americans seek recommendations from friends and family when considering a purchase[1].

So in an era where most marketers and business leaders inherently understand the value of a high quality relationships, how can brands leverage these connections to drive revenue?

Well, let’s start with what…


Trying to find a gift for the entrepreneur who has everything? I can help. I’ve been called extremely hard to buy for — I’m particular and when I find something I like, I get more of them.

So I put this list together to share some of my favorite things. I’ve broken them down into 3 categories: stuff, books & clothes. I guarantee the entrepreneur in your life will appreciate any of these items this holiday season!

Cool stuff:

DeLonghi Magnifica S

Okay, we’re starting BIG. This magnificent espresso machine is what they call a “fully automatic” one, meaning that it grinds…


One of my favorite parts of running a startup is seeing the growth and development of our Diplomats (the endearing term for our team at Ambassador). It’s incredibly fulfilling to watch people come in with little (or no) experience and become high-performing leaders inside and outside of the office.

From an employee perspective, much of the allure of joining a startup is upward mobility. You enter as an individual contributor and — if you crush it long enough — may find yourself with a seat at the table. It’s no small feat to move from an individual contributor to a…

Jeff Epstein

Founder of @onboardio (http://onboard.io), a B2B SaaS to streamline onboarding for every customer. prev: founded, built, & sold @Ambassador

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