PEN Profile: Sam Jacobs

We established the Primary Expert Network - a select group of NYC Tech’s leading operators and functional experts - to help us support our portfolio companies through the inevitable challenges of the startup lifecycle. We believe that most operational support is best delivered by peers who are fighting similar battles, not by VCs who are three steps removed from where the rubber meets the road. The PEN is such an impressive bunch that we created the PEN Profile Series to introduce them to the community at large, and to provide insights into how these influencers think and lead today’s most exciting startups.  


Sam Jacobs is a strategic sales and business development leader with an extensive history delivering high growth for early-stage, venture-backed SaaS companies, including Gerson Lehrman Group and Axial. In his current role as SVP of Sales and Marketing at Livestream, Sam is responsible for the company’s Platform Products business, overseeing all sales, marketing and success functions for Livestream's 10,000+ subscription customers. An inspiring leader with a passion for continuous learning, we are thrilled to have Sam as an active and contributing member of the Primary Expert Network.

@samfjacobs | @Livestream | Livestream is hiring!

Hometown: My parents were both in the foreign service - my mom is currently the Special Advisor for Children’s Issues to Secretary Kerry, a role originally started under Secretary Clinton, handling all of our international adoption treaties. My father is a lobbyist specializing in the Middle East. I grew up all over - India, Israel and El Salvador - but home base was always in the DC suburbs.  

What brought me to New York: I went to UVA, and then came to New York initially to work in finance. I followed my passion for music and left for a few years to start a record label in Charlottesville, VA, (unsuccessfully, unfortunately) but returned in 2003 to jump into the tech scene.

Why I love the NYC tech scene right now: I love the heterogeneity of New York. It’s a concentration of the best talent from a lot of different industries. I also love being a part of the movement to help make New York a center of excellence for tech. We haven’t quite arrived, and we’re all working on this project together, cobbling together our own advisory and networking groups. With each successive wave of companies and investment, we deepen our collective expertise and knowledge. 

Favorite business meal/drinks location: My go-to is breakfast at Cafe Cluny, and I never say no to the avocado toast.  You should add the poached egg on top, get a side of bacon, and have whatever their special juice of the day is. If you need help, email me, and we can go together.

Hidden talent: After running a record label (The Annex Group) from 2000-2004, I decided I wanted to be on stage. I started writing songs in 2004 and over time put a few different musical projects together. Recorded music appeals to the same sensibility inside me as building companies; it’s fundamentally about working with a group of people and taking something from an idea to reality. I’ve put out a lot of music and been the founder and lead singer/songwriter in two bands: The Flying Change and Lipstik.

Biggest challenge I've overcome at Livestream: Taking a more traditionally B2C business and moving it up market. Part of that involves raising prices, but what it’s really about is sales team segmentation, enhancing and improving processes, investing in content marketing to demonstrate thought leadership, and designing a go-to-market strategy with prices that reflect the value we give our customers. We already work with so many amazing customers - Fidelity, Salesforce, the NYSE, Thomson Reuters - but we haven’t had a go-to-market strategy or pricing strategy that accurately reflects the value we provide. So our current challenge is making sure we continue to serve organizations of all shapes and sizes, and ensuring that we have the products, services and a strategy that is suitable for all of them.

Business apps you can’t live without: LinkedIn gets mixed reviews in the tech community but I am a huge fan of Jeff Weiner and, from where I sit, they serve an important purpose, especially for non-founders. I am excited for the Microsoft merger and for what those two companies will be able to accomplish together.

What I’m best at: I’m known for communicating to large groups and inspiring teams. I believe the key to truly inspiring a team is through transparency and authentic communication. People want access to information, to know what’s going on and in which direction they’re headed. And if you can help them win in their role, they’ll be even more excited. I think it’s OK to be human and admit that you have shortcomings, versus trying to project an aura of invincibility all the time.  

Thing that drives me craziest: I always want to want to work with passionate, energetic people trying to do big things. I tend to get frustrated by people who are not as passionate about what they’re doing. And a lot of the time it, if my people aren’t motivated or inspired, I have to take a look at my own behavior as a leader and figure out where I can improve my own messaging and communication. 

Proudest accomplishment: Personally, my biggest achievement was running my first marathon in 2014 - the result and culmination of many years of training. Professionally, I’m proud of my overall career trajectory. It’s not a particular moment, per se, but I’m a big believer in daily discipline, and the accomplishment is being able to stick to this routine over years and years, and realizing that it’s a life’s work that leads to success. For me, that's been close to eight years at GLG, helping them get to north of $300M in revenue, almost five  years at Axial helping lead that company through triple-digit growth and three financings, and now Livestream, as just the next step in this amazing New York journey I’m on.

My first job: Mother Nature’s Cafe, an organic food store in McLean, Va.   The name was deeply ironic - the place was filled with roaches.  I was adamant that none of my friends or family should ever eat there.

How I keep stress at bay: My religion is running and exercise. And I try to meditate for 10 minutes each morning with Headspace

My key mentor: Jonathan Glick, founder of a number of different companies, most recently including Sulia. I originally worked with Jonathan at Gerson Lehrman Group. He’s a great friend, colleague and mentor, and he’s my go-to for career advice and questions about technology. He’s one of those folks that is incredibly far-seeing and he’s a polymath.  You can have a conversation with him about Bruce Springsteen, the Civil War, politics, aliens, and the future of mankind all in the space of a single evening (and a few bottles of wine).

Other than mine, NYC tech company I most admire: Bloomberg.  A lot of people don’t really think of Bloomberg when they think of tech, but it’s almost certainly the most successful cash-generating New York operating company that’s been started in the last 30 or 40 years.  Mayor Mike took it from a simple platform for getting bond prices and scaled it up to a global behemoth. It’s the ultimate SaaS platform. I respect how much they’ve continued to invest in new areas, I respect how they’ve executed at huge scale, and I respect their adherence to true value-based pricing.