Nick Worswick serves as an Advisor at Oak HC/FT. Nick served as Global CRO of Checkout.com, where he built out the North American team. During his tenure, the company grew revenue by 400% and raised $1B in capital. Prior to Checkout, he spent 4 years at WeWork as Chief Sales Officer. WeWork revenue exceeded $3B in Nick’s financial years at the company. Prior to WeWork, Nick spent 4 years on the executive team of GrubHub helping the company through its merger with Seamless and their subsequent IPO. Prior to GrubHub, he grew GTM and revenue teams at Bullhorn (acquired by Vista Equity Partners), IntraLinks (NYSE: IL), and Priceline. Nick started his career at KPMG.
Nick currently serves as the President of Retailer Go-To-Market at Upside, a two-sided marketplace providing cashback to consumers on everyday purchases and driving over $1B in incremental sales to merchant partners.
I fell in love with sales while working for a retail stock broker in Ithaca, New York. I was a 20-year-old junior at Cornell. On my first day, he handed me a stack of index cards. Each card contained information about a family that lived in the area. It was my job to get him meetings. My first week, I got one meeting; it was hard. But gradually I learned how to tailor my message and how to provide valuable insights that led to meetings. I was hooked.
Over the next two decades, I got the chance to scale some incredible go-to-market teams at a few of the best companies in the world. A lot of that goes back to Ithaca, because calling all of those families helped me understand the most important thing in winning customers: What makes someone want to have a conversation?
I have built revenue teams for over 25 years. What satisfies me most is providing the right frameworks for founders, teams, and customers to grow their businesses and their careers - fast. When done correctly, the art and science of scaling revenue teams delivers great outcomes for all three parties, and those outcomes are always measurable.
While each company is different, there are clear repeatable steps you can take to maximize your odds of unlocking sales growth. You need to hire, train, and mobilize teams for sales, marketing, and customer success. Those teams need to be going after the right prospects, with the right messaging, at the right time. Once you land your customer, you need to be launching a robust "Day 2" motion to ensure that customer not only stays with you, but becomes an advocate for your business. And you must always be able to step back and examine the difference between your current and future TAM.