x.ai Pros And How They Do It: Jonathan Lehr of Work-Bench

Name: Jonathan Lehr
Title: Co-founder and Managing Director
Company: Work-Bench
Location: NYC
Twitter handle: @fendien
x.ai boss since: February 24, 2014
Describe yourself in one word: #beastmode
Tell us one fun fact about you!
I’m obsessed with enterprise tech! My goal is to one day have an “enterprise tech decathlon” against Aaron Levie to see who is more hardcore enterprise. I’m the Co-founder and Managing Director of Work-Bench, a New York City based enterprise venture fund and community, and the founder of the NY Enterprise Tech Meetup, where x.ai live demoed back in July 2014. Check out the video of Dennis and Pear here.
What do you enjoy most about your job? Best part?
Hands down the best part of my job is our team. We like to joke that we’re all “enterprise eccentrics” at Work-Bench, but it’s actually true. That passion for our mission and helping grow enterprise technology startups shines through every day in what we do and accomplish.
Worst part?
Before Andrew (at x.ai), it was scheduling meetings.
What type of meetings are you having? How many?
So many. The unique aspect of Work-Bench is that we’re a bridge between leading enterprise startups and forward-thinking Fortune 1000 companies. In a given day I’ll have several startup pitch meetings with my colleague Vipin, meet corporate executives to talk through their IT pain points with my colleague Michael, catch up with fellow VCs, and meet folks from the ecosystem who could make good talent referrals for our portfolio companies.
So figure in a month it’s about 60-75 meetings that Andrew has taken off my plate to schedule!
How do you introduce Andrew to new people?  
Usually I just say my assistant Andrew. Usually people don’t notice that “he” is AI. But when they do, they think it’s so cool and ask me about my experience. Then after I rave about Andrew they ask if I can help them get off the waitlist 😉 Once I was even chasing an investment and got some street cred because the founder loved that I was using such innovative new technology.
Any Pro-Tips you’d recommend to Andrew’s other bosses?
Don’t hold back. Throw every meeting at him, and then forget about it. Beyond eliminating the time it takes to go back and forth scheduling, Andrew is also nice to clear head room so you’re not spinning cycles still thinking about whether that meeting got scheduled. It took me a bit of time to not totally stay on top of every single meeting, but after a while I adjusted and the freedom to focus on other work is refreshing.
This is a benefit that Andrew has over human assistants. Whereas a human can potentially forget to follow-up, Andrew has it in his DNA (or in his case…his code ;p) to follow-up thoroughly, and alert you when the person you’re meeting hasn’t responded so that you can choose how to handle the next step.
What’s your favorite quote?
Something that Dennis and I share in common is a passion for Seinfeld. I watch it daily, and one of my favorite quotes is the following:
Jerry: I wanted to talk to you about Dr. Whatley. I have a suspicion that he’s converted to Judaism just for the jokes.
Priest: And this offends you as a Jewish person.
Jerry: No, it offends me as a comedian.