David Greenberger, Director of Merchant Sales, Foursquare

David Greenberger, Director of Merchant Sales, Foursquare

David Greenberger is the Director of Merchant Sales at Foursquare. He has experience building and scaling high intensity SMB sales teams in the local, ad-tech space for companies such Yext and Felix. Find more insights from David at his sales blog, DavidGreenberger.nyc, and follow him on Twitter.

How does the sales process for Mid-Market Sales at Foursquare differ from Local Sales?

[David] At Foursquare our Merchant Sales team is made up of a Local and Mid-Market team. We define Local sales as 1-50 physical location merchants with the focus on unique “mom+pop” restaurants, bars and retail stores. Our Mid-Market team covers the larger end merchants, the Applebees, Finish Line, Louis Vuitton’s of the world.

The larger, more enterprise, Mid-Market sale is a decidedly different playbook than our high-transactional Local sale. Local is a high-action numbers game. You’re going to need to make 100-150 calls just to get 6 conversations on the day, wading through bartenders, and cashiers and gatekeepers until you can get to a busy owner. When you get them on the phone you need to close it right then and there. We find in Local that the likelihood of closing the sale drops by 45% after the first call with a decision maker, and the half-life decreases dramatically for the next 72 hours.

The skills that make you effective in Local are different; you need to be extremely engaging, relatable, and know how to get to a decision quickly. Most importantly, being willing and able to wade through the frustratingly endless sea of cold calls, gatekeepers, and “partners” to get to your decision, without losing your charisma, is a skill all on it’s own – relentlessness and persistence. This is quite a special skill-set and a great training ground for anyone looking to cut their teeth in the sales profession. Those that have lasted 8+ months on the Local teams I’ve been a part of have become some of the best all around sellers in the city right now.

In the larger, more complex Merchant sale, the keys to success change. This sell involves calling on Chief Marketing Officers and then navigating through 5-10 different stakeholders in order to strike a deal. In this role the salesperson plays much more of a “quarterback”-type role, rather than strictly being a closer. Your job is to differentiate yourself, educate your prospects, and then manage the process through to the close. The pitch is only 20% of the game – getting a verbal “yes” is just the tip of the iceberg. Keeping everyone on the same page, managing all the different stakeholders involved in the decision process, and coordinating assets towards a deadline are entirely different set of skills. It takes a lot of patience, organization and coordination.

While cold calling requires much better “hand-to-hand” combat skills, if you will, the larger sale requires more strategically placed strikes.


What are some simple tests sales teams can implement to become more efficient?

Sales is a numbers game. We all know that. A good salesperson is testing everything he does. That’s the beauty of the day and age we live in: data is everywhere and everything is trackable. Your whole life should be A/B tests – everything from the voicemails you leave, to the pitches you give, to the GIF’s you include in your “Happy 3-month Anniversary” e-mails. Testing should not be broad sweeping changes; it should be minute alterations compounding on each other.

I wrote a blog post, Start Selling like an Engineer, that speaks to the effect A/B tests can have on your process.

Starting this whole process of “A/B testing” can seem intimidating. Stop right there! You don’t have to build some complex, elaborate process overnight. Start small, one step at a time. Just send your usual emails, and with 50% of them change up the subject line that you use. Track the results on sticky note at your desk – now you’re A/B testing. Just get started! As the saying goes, “The best time to plant a tree is 20 years ago, the second best time is today.”


What is one of the biggest mistakes that you commonly see in sales?

Failing to be yourself is the thing I see so sorely missing from people trying to sell to me. Typically, a person goes into sales because they are fun, engaging and like talking to other people. Social butterflies. Suddenly, as soon as they get on a sales call, they become a professional robot feeling the need to spit back all kinds of buzz words – everything is an “optimization” or a “efficient costs savings.” No one talks that way!

The most important thing to remember: the person across the table is at a job too. They likely don’t want to hear about your product’s “cost saving optimization” monologue any more than you want to say it. Make it easy and fun for your buyer. Be a person, be relatable, tell a story that the gal on the the other side can identify with and understand, and they might even enjoy the sales process. You might too! If they’re enjoying their time with you it’s a lot easier to make a decision to want to work with you moving forward.


When is a drip campaign the sales team’s responsibility vs. the marketing team’s responsibility?

Keeping your prospects and clients engaged is everyone’s responsibility. For both salespeople and marketers, your job is to build a relationship with your prospects, hopefully leading to a fruitful one where money is exchanged ;-).

In sales, this conversation is generally on more of a one-to-one basis, where marketing typically works on the one-to-many scale.

At Foursquare we like to keep our prospects involved in what’s happening with their venue page, what’s going on in their industry and any other helpful way we can add value. Again, our goal as company is to help make our clients’ and future clients’ lives a little bit better. That might mean educating them, helping them make money, or just adding some fun to their lives. It’s important that we’re staying top-of-mind and actually adding as much value as possible.

My sales people generally have formulas they follow to ensure they’re checking in with prospective clients in a good cadence. At times we’ll give updates on things that are happening with their account; other times, we’ll update on newest trends at pizza places in Brooklyn that they might find relevant. Still other times we’ll reach out to tell them about something affecting the Local, Social or Mobile industry. We want to help arm our clients to be as successful as possible in their business.

The marketing team then should be responsible for overlaying a broader content strategy. Emails like: “4 tips for improving your venue page” “Clients we love this week” “Foursquare Success stories” “How Joe’s Restaurant used Foursquare feedback to alter his menu and increase sales”

Everyone should be keeping in touch with potential clients, sales should be personal while marketing tells a broader story.


What is the most important question you can ask on a discovery call?

“What do you want to get out of this relationship?”

Understanding what “success” is for your client is the most important way to start your relationship. It tells you how to approach the entire process. My job, as a salesperson, is to make my client happy. How can I do that if I don’t know what drives their happiness? If you don’t ask, you’re guessing.

Are they a CMO/co-founder that cares solely about driving bottom line, or do they care more about brand recognition right now? Are they a mid-level marketing director that just doesn’t want to lose their job, or are they a ladder-climbing star that wants to take risks, find the next “big thing” and blow their boss away?” Each scenario requires a different touch.

For the “bottom-line founder,” I know I need to get down to business. Someone more brand-driven will require a more exploratory and creative conversation. For the person that just wants to keep his job, it’s important to convey that this is a safe, no-brainer choice that lots of their competitors are already successful with. The old ‘nobody get’s fired for choosing IBM’ logic.

Understanding what the client actually wants allows you to “begin with the end in mind” and drive towards both of your goals.

Far too often I see conversations go way too far, sometimes even after the buying process, before realizing that buyer and seller intentions were not on the same page. It always ends in a lot of bad feelings and frustration from all parties. Best to avoid that from step one.


What are some natural ways salespeople can make themselves more memorable?

Lose the jargon. Lose the graphs. Tell stories. Be yourself.

“Use the Force, Luke.”


You’ve worked in sales for a while now. What keeps you excited about being in this business?

I’ve always wanted 3 things from my career, and until recently I thought the only way to get them was to eventually own a business.

I want:

  1. Flexibility – Control when I work, who I work with, where I work, etc.

-> I’ve learned a good salesman never goes hungry. I know if I can continue to sharpen my sales skills, I’ll be able to find good work wherever I want.

  1. Equity – The ability to reap benefits of the work I put in. I work hard, I want to be able to see the benefits of that work.

-> Commission is a beautiful thing!

  1. To help people – We weren’t put on this earth to simply party as much as humanly possible. As a society we should always be trying to get better. I truly enjoy learning and I like helping others get ahead.

-> Being a sales leader helps people to get all 3 of these things. The ability to work with employees right out of school has been particularly impactful; you have the chance to put people on the right path for success.

Then, something that I didn’t realize until after I started work is having FUN is important! Your job consumes ~60% of your waking life (much more for some jobs). If you’re not having fun at whatever you’re doing, it’s time to hang it up – that day.

I used to be a big competitive sports guy. It almost seems like sales has replaced that itch for me. I get excited to push through to win the deal, hit a deadline, and help team reach it’s goals. And believe me – we celebrate WELL. Any person on my sales floor will tell you: when you’re doing well, this is the best job you’ll ever have. When you’re doing poorly, it’s absolutely the worst. That always pushes me to do well.

We have a blast on my sales floor. I used to tell people I get paid for being a DJ / adult day camp counselor. As my good friend Adam Liebman says, #optimizeforfun.


What 3 books would you recommend to a newly hired SDR?

Influence by Robert Cialdini – Sales is a psychology game. Robert Cialdini is so easy to read and examines why people react they way they do to many of life’s scenarios. He tackles things from a social sciences perspective.

Secrets to Closing the Sale by Zig Ziglar – The classic sales bible. This is the book that made it all click for me. It’s a bit dated, and Zig can be pretty cheesy, but he tells stories in such a relatable manner that it’s incredibly easy to read, and to pick up on his timeless tricks to help frame your story.

Blink by Malcolm Gladwell – Again, I’m a psychology guy. Most of the sales books out there are quite honestly a bit tacky for my taste. Gladwell tackles social sciences from a really interesting perspective, helping to understand subconscious tendencies and why people make the decisions they do (often without realizing it). Understanding these tendencies can help you avoid unseen landmines and steer things in a direction that is most beneficial for everyone.

What’s the best sales advice you’ve ever received?

People reflect what you project.

If you’re not confident in your product, they’re going to question it. If you’re not confident in yourself, they don’t trust you. If you ask boring questions, guess what? You’ll get boring answers.

Likewise, if you’re engaging, fun, and assertive, they’ll feel that way about you and your product. As a salesperson, like a guy on the dance floor, it’s your job to lead and set the tone. Too crazy and they can’t keep up; too slow and they’re bored; too self-conscious and they’re feeling awkward.

Drive the relationship where you want to go and you’re going to enjoy what you’re doing. When you’re confident and having fun, the rest comes easy.


Find more insights from David at his sales blog, DavidGreenberger.nyc, and follow him on Twitter.

David also runs a quarterly event Building the Sales Machine in New York City for founders or sales leaders looking to give and gain tactical help from peers building teams in the NYC tech space. The event does not have an official website yet, but if you’re interested in joining, contact David directly via Linkedin.