Author Archives: DaveGreenberger

How we cracked the Mid-Market sales playbook at Foursquare – 10 Pro-Tips

Over the past 8 months or so, I’ve taken one of my top Local sellers to build out our Mid-Market team here at Foursquare. At Foursquare we define the Local sales team as selling to small businesses with 1-50 physical locations (Joe’s Pub, Sally’s Coffee House*). We define our Mid-Market team as targeting companies with 50-500 locations, focusing on $15k-50k deal sizes (a Footlocker, Applebees, Louis Vuitton for example*). Our Enterprise team focuses on helping the largest brands and merchants leverage the power of Foursquare (Heineken, Volvo, Macy’s etc*).


Upon creating this new team we imagined that Mid-Market would be a very different playbook than our Local, high-transactional sell. We also quickly found that the sell is decidedly different than the Enterprise playbook, which focuses largely on selling through top media agencies. In this “mid-level” sale you’re selling mostly client-direct, although the use of smaller agencies is an often occurrence. You’re talking to Cheif Marketing Officers (CMOs), but there’s often multiple stakeholders involved. Your job is to ‘wow’, but unlike an enterprise client there’s no travel & expense budget; in fact you’re doing most interactions over the phone. It’s a nuanced sale that’s quite a beast of it’s own.


After banging our heads against the wall for about 8 months, with many, many  fails, we’re starting to find a playbook that works. We’re focused on being persistent, but helpful. Differentiating by adding value to every single person we’re in contact with. Allowing personality to take a forefront, and not forgetting our powerfully assertive Local sales skills.

As we’re starting to find the playbook and beginning to expand this team, Jack Gashi, our Mid-Market seller put together some thoughts and tips for those that might be moving into this Mid-Market sale. His advice was so well put, that I asked if he might guest post on this blog. He obliged.

Jack was one of my first hires at my last company, Felix, and was the first person I brought over with me to Foursquare. He’s fantastic.

Thoughts below:


Uncle Jack’s Top 10 Mid-Market Pro-Tips

Most of this is stuff that I wish I knew a while ago, and some of it I was told ahead of time. But, like most things in my life, I had to bang my head into the wall and spill the milk before I learned to not play ball in the house. You can follow that same path, or you can take my word for it.


1. Organization is everything
This goes for anything from your Google calendar (treat it like Scripture) to Salesforce - if you cut corners now, it’s going to come back to bite you later, big time. I know everyone is foaming at the mouth to sign a big deal ASAP, but move methodically. Don’t drag your feet, but definitely don’t rush. 


2. Prospect the right clients, and learn to say no
You’ll start to learn who is a good prospect and who isn’t, and that’s really important. I definitely wasted some time going after people who didn’t make sense. The big key here is that when you first talk to someone – the “discovery call” as Dave and I refer to it – you need to ask a lot of questions. Where do they spend money? Who are they trying to reach? What has and hasn’t been successful for them in the past?


Similarly, learning to say “no” is a big step. You’ll have someone dying to throw $25k at you, but their whole goal is to get people to download their app – something we aren’t good at. Say yes and sure, you might get $25k (or half, before they pull the plug) and an unsatisfied customer who will never work with us again AND badmouth us. Say “no”, and not only have you avoided that situation, you’ve also been honest and upfront with their best interest in mind, at the expensive of losing the deal for yourself. This is a surprisingly refreshing trait in a salesperson. Now that person can go back to his team and figure out a way to use Foursquare that makes sense. Yes, that actually happens.


3. Reach out high
I had to learn this the hard way. You want to shoot high – CMO’s, C-level execs – and if they kick you down to the right person, great. At least they know you exist. I did the opposite when I started: I was reaching out to “Social Media Managers”. I quickly learned they can’t do everything, and worked my way up – digital marketing managers, digital marketing directors, and now finally I’m going for the big fish. If you have a product that is truly helpful to the CMO, be confident. Work from the top down.


4. Act the part
To piggyback (#startuplingo) on the 3rd point – you’re not talking to Vinny from the block anymore. When you reach out to a CMO, act like you’ve been there before, and you belong. You’re here to help them with an amazing product. Don’t act like a stiff – personality is extremely important – but be professional.


5. Don’t forget what you’ve learned
A lot of this is different, but a lot of the Local sale is applicable. Persistence comes to mind – don’t be afraid to keep following up (respectfully, with the appropriate wait times) until you get an answer. These guys are extremely busy and will miss a lot or not have time to respond; don’t take that as a “no”.


6. Make yourself memorable
I consider myself a likable guy, and this was still super difficult for me. Being able to come across as memorable and likable over an e-mail is not easy. I have the same problem with dating apps – I never get any responses. Try your best to not be corny. Be genuine – be yourself. Dave put it this way once to me: “Do you ever put that many exclamation points in an e-mail to your friends or family? No – it’s not you. So don’t do it.”
There’s a zillion salespeople who send an email with a “Hey there, Don! How about them Yankees? So, about Q3…” feel to it. Be different.


7. Do your HW
Dusting off one of Dave’s favorite phrases here, but it’s true. For example: before a call, check a guy’s twitter account. See what he likes; what comments he’s made about the industry. Don’t be awkward; the worst thing you can do is say “Hey Bob! I saw you love the Giants – I saw Eli Manning in Hoboken!” Be smart, maybe keep it all in your back pocket. The point is to arm yourself with as much information in your “utility belt” as possible, like Batman. People appreciate you going the extra mile and it’s always useful to know what interests your audience.


8. Remember – Work is Work, to Everyone
This was a big learning for me. When you have a call with, say, a Digital Marketing Director, recognize that he’s at work. Making the call NOT boring is step 1; making his job easier is even better. The easiest way to make him hang up and say “F*** that” is to add to his To-Do List. You’re here to make him look good – you’re going to handle almost everything, and in the end, make his company money and make his boss think he’s a genius. Take that approach.


9. Leverage our clients
We’re lucky, our Enterprise team has done great work over the years; learn to use it. I was reaching out to a client, and mentioned we had worked with a few of their competitors before. The fact that we have them on our client list piqued interest, and now we’re discussing a proposal. Don’t be afraid to use your wins appropriately.


10. Ask for help
I generally hate asking for help (unless I need a 48 hour loan in Vegas) but I’ve learned its necessary. There’s great people everywhere. Keep a good network. Our Brand Partners are all studs; they’ve been doing it a while and they know the ropes. Lucky for us, great people are usually very willing to help. If you run into a situation, chances are you know someone who has seen it 50 times (whether inside the company or out). Be respectful of their time, but if you ask for 15 minutes, or take someone out for coffee, or shoot an e-mail, you can get some great information and help.


Thanks to Jack for the great advice. Jack’s new blog about random musings as a 26 year old in NYC can be found at / @dailyrandomcom.
We’d love to hear your tips and tricks for building value with larger clients.


* Does not neccessarily represent actual Foursquare customers

Building the Sales Machine with Bryan Rutcofsky – VP of Sales SMB & Certified Partnerships – Yext

My good friends Eric Friedman, Evan Bartlett & I put on a sales event here in NYC which we call Building the Sales Machine.

These events are open to anyone who is building the sales and revenue machine at a startup and wants to hear from others in their position, meet like minded people, and solve real problems.

Our next event is happening in January and this time we are happy to welcome Bryan Rutcofsky from Yext.

Bryan has a close spot in my heart as my first direct boss, mentor and great friend. We call him the Godfather and for good reason. His sales playbook is one that many of us are using in the NYC tech scene.  Bryan was employee #1 on the sales side at Yext and has helped build it into the enterprise it is today. We are going to spend time talking about selling to SMBs and partners relevant to their business.



As with other events the format is:

1/3 Networking and coming up with questions for Bryan
1/3 Eric Friedman and Bryan talking about what has worked, tactics for the audience, and answering Q&A
1/3 Back to networking with others in the crowd and with our guest


Unlike other events, the purpose is to meet others who are experiencing your same challenges by inviting sales leaders and their teams.  If you are interested in a non traditional format focussed on getting you real takeaways and an interview focussed on tactics vs. backstory then please come out to our event.

Our goal is to make sure this is time well spent and you walk away from the time with real actionable insights and things to try.

Checkout our previous event with Steli Efti from Close.IO



Huge thanks to my co-hosts Eric Friedman and Evan Bartlett as well as to Foursquare for the space!

If you’re building an ambitious sales team or hope to in the future & this would be a useful event for you Register Today

Why it’s helpful to tell your story

Telling a story is always a powerful way to drive home a point. The more specific the better.

When I’m speaking to a client I always find it’s helpful to use a pointed story to state my case. This week we were talking to Julie, the marketing manager of a fast-casual dining chain here in the city (think Umami Burger, Shake Shack, etc). She liked the idea of what Foursquare had to offer, but just told me, “everyone knows about us, we don’t do any advertising,”. My usual response here might be, “I totally feel what you’re saying, Julie. I’ve had lots of my customers tell me this is exact same thing during our initial call, what they found was they’ve had great success, etc.”

This time I decided to take my explanation to the next step.

“I totally feel what you’re saying, Julie. Many of my customers have felt the same way. Just this week I was talking to Raul Kranz from Bar A**, down the street from you. Do you know him?

When Raul signed up with me a year ago he had the exact same concerns. As you might know, Bar A is one of the hottest bars in Williamsburg. In fact, Raul tells me that he’s lucky enough to constantly be written up in tourist and travel magazines, he’s also regularly featured on NY Mag and Thrillest-type lists as a ‘must go’. The place gets very steady traffic, so he never thinks about advertising, especially if it’s something that he would have to pay for.

After chatting, I was able to help Raul discover some interesting insights about his audience via Foursquare and convinced him to give it a try. He was as skeptical as they come, but liked that promoting yourself on Foursquare is very native experience. Since there’s no contract and no commitment, if it didn’t make him money, he found he could always shut it off.

Raul is now one of my best customers. He’s found that even adding a few new customers a week to his bar, though not a life altering change, has steadily made him a great amount of money. He tells me that his average customers spends about $25 / night at the bar. And his customers usually came back, conservatively, around once per month. So far Raul has yielded over a 1700% return on his investment. I have a dozen others right in the area seeing similar results.

Now, I can’t promise that you’ll see results that great, but what I can say is if you ever feel that it’s not a great decision for you, you can always feel comfortable knowing that you can walk away at any time. So, I always suggest at this point if you think it’s even a decent idea to try it out for yourself and see if it’s worthwhile. Does that sound reasonable? ”


I found that it was so much more powerful to actually tell the story and have something Julie could relate to. Apparently, she thought so too.

In general, as a buyer there’s so many different messages coming at you to ‘buy this’, ‘try that’ and find ‘guaranteed success here’, it’s just hard to make sense of the mess. Hearing another person’s story, and the safety of their journey can help you feel more comfortable and think about the conversation logically, rather than with a defensive, skeptical mindset.


Learning on the job

A few members of my team and I recently took Andrew Linderman’s short General Assembly class titled Storytelling for Entrepreneurs: learning how to utilize storytelling techniques in business settings.” It was fantastically insightful and really helped us to flesh out the idea of including specificity in our stories to create a more relatable and digestible point.

We learned that the key to a great story is having an identifiable main character, a relatable challenge or conflict, and overcoming that challenge. In Andrew’s words:

  • Every story must have a beginning, middle and end.
    • Beginning: Character, Setting, Problem.
    • Middle: Stakes, Conflict, Tension.
    • End: Crisis, Climax, Consequences.

We don’t always quite get there with our asides, but having the foundational knowledge helps the anecdotes come to life. We also learned that specificity generates relate-ability in storytelling. I find this makes a huge difference. Often just telling our own story, as reps, have been helpful for our prospects to here.

“I was selling bonds to hedgefunds for Credit Suisse before coming to Foursquare. I was always drawn to the start-up scene and knew these guys were working on something special. Foursquare’s one of the largest startups in New York City and I knew that they had super smart people working here.

To combine that with the mission of helping people find great businesses around them and to keep unique quirky neighborhoods alive is just so great. Now I have the easiest job in the world because I get to sell a product that actually helps small businesses thrive. I’m lucky to be here.”

I often hear things like this on our floor, now. That level of specificity is just so much more powerful than “I love working here and you’re going to love the product, trust me.”

Thanks to Andrew for helping us learn to explain ourselves in a more engaging way and help our customers. I’m finding it applicable for all kinds of life’s scenarios.

I can recommend following Andrew’s Blog The Story Source to pick up on more tips and tricks for telling great stories.


**Names have been changed to protect the innocent :-)

Sell Like An Engineer

One of the helpful things about working with super smart engineers is that we get to see how they approach and solve problems. What I’ve learned from my time in tech is that great products are built on small 1% gains, compounding on each other over time.

These days there are so many data points to track and scale in sales, we salespeople can take this same approach to build great efficiencies. Here’s an example of an email that went out to our team earlier this week that inspired me:

“We just finished 3 more opinionator / tip compose experiments.  All 3 beat their respective control groups and are now on for all users.  They ran for 10 days as 50-50 experiments for Foursquare users (> 100k users enrolled in each)


Opinion Points Lift, US Users1

experiment % lift
experiment 1 3.12%
experiment 2 1.90%
experiment 3 73%

-engineer ”



Emails like these are sent around Foursquare multiple times / day, and as a salesperson it’s easy to ignore and write off as just a bunch of weird numbers.

If you take a minute to think about it though, we salespeople can do the same thing.

The product teams are doing small experiments with lots of people, to get statistically significant data, and driving really small (1-3%) gains. These small little 1% gains make all the difference in the world over time, especially as you begin to compound them on other 1-2% changes. Eventually, you’re dealing with a much more efficient system.


How can we apply the same strategy?
To put that in perspective for us salespeople: that means if you did an experiment with your email reach out, sent them to 100 people and got just 1 extra person, out of 100, to engage, that would be a win. That’s something that you can build on.

The only way to really make sure that you’re gaining 1% wins is to be organized and diligent in your tests. This is hard for a salesperson. I know. But it’s not impossible. And if you can achieve little 1% wins, week over week you can see big gains.


The numbers
1% gain on an email test of a 100 people this week = 1 extra email response this week.
Continuing that same email for the rest of the year = 12 extra responses in a quarter
Another experiment the next week that yields 1% on top of that = 1 extra email response the next week. -> 11 extra responses for the rest of that quarter.
Now have 23 more email responses in a quarter.
Continuing that trend with a new experiment each week is 78 extra responses in a quarter.

That’s a lot of prospects to talk to.

Now imagine if you send those emails to 200 people/week rather than just 100. Imagine if you can get 2% gains with any of your experiments, or 12%.

Very quickly this can all work in your favor, for doing the same amount of work. It just takes a little bit of organization.


Becoming more efficient in your messaging doesn’t only help you by getting better numbers with less work. If you have a great product to sell, you’re also helping your future customers. Prospects are hammered with so many annoying messages that they can’t help but characterize you with everyone else and write off unengaging messages. (How many of us are navigating through annoying sales / marketing emails every morning when we wake up?)

If your message is efficient and engaging, AND you have a great product to tell about, getting a more engaging message through saves your customers time and money as well.

We use the CRM,, which helps us track open and response rates on our emails. Using different email templates, it makes these experiments all incredibly easy.

So, we’re going to start taking some inspiration from our friends across the office. Smart stuff.


The Power of Repetition


The 5×5 sales method seems to be the ‘hot thing’ out in sales marketing trends. Generally, this refers to sales people becoming mini marketers, creating drip campaigns for their prospects. This is a method that I’ve always been driving with my sales team.

Why? Because life.

You know the drill. You don’t lose weight from eating a salad once. You’re not getting fit by going to the gym twice. Real results require repetition.


Once is Never Enough

In my line of work, helping small business owners find online advertising solutions, you need to play the #’s. It takes about five calls with a business before you even reach a decision maker (usually an owner or general manager). Until that point, you’re usually leaving messages with a receptionist, bartender, voicemail etc. This means if you just call the business 1 time and leave your number with the receptionist, there’s an extremely low chance the owner is actually going to call you back.

Why? Maybe the message was never actually taken, Barb fooled you and did the “air write-down”. Or maybe Barb did actually write down the message but forgot to give it to the owner. Maybe she wrote it down and gave it to him but he never saw. Maybe she wrote it down, and gave it to him, AND he saw it but didn’t understand the need. Maybe he understood and didn’t care. Maybe Barb wrote down the message and gave it to him, and he saw it, and understood it, and cared, and actually wanted to speak to you, but had 10 other things going on and forgot, and then lost the message with your number on it. As you see, if you’re putting your hope in that 1 call to Bob’s Auto Emporium doing the trick, you’re going to have a pretty long week.

The age old marketing adage says that a person needs to see a message seven times in order to internalize it. Seven times JUST to pay attention. We shouldn’t treat sales, or any important life task, any differently. So on our sales team we don’t. I don’t assume that because I called a business once and never heard back, that my prospect wasn’t interested. I assume that she is running a successful business and is quite busy. I also know that no one has time for something that doesn’t work, but I know my product does work. So I give my future customers the chance. I remind him.

(If I want to reach a potential customer with a great opportunity this week that I know is going to better his business, I make sure that he actually gets the message. And more importantly, that he understands what the opportunity involves, so that he can make the educated decision to take the opportunity or pass.)



The 5×5 Approach

1x – The Opportunity

I’ve learned that I, myself, work this way. I get sales calls and emails all the time these days. Most of which I don’t have time for. Everyone is coming to me with the same basic lines, “Hey Dave, I work with company A + B and wanted to see if our X and Y can help drive your bottom line, when’s a good time to speak?”. Typically, I think that most salesmen and most products out there are no good, so I almost never respond.


2x – Push to Top of Inbox

The better sales people will follow-up a day or so later: “Hey Dave, just wanted to push this to the top of your inbox…”. Rarely will I respond here, either.


3x – Add Value

Even better sales people will follow up again in a few more days with something of value to me – NOT just asking for a sale or conversation, but proving how they can add value to me. For example, recently an email tracking company was reaching out to try to win business from my team. A value-added email might go,  “Dave- did you know that after analyzing x thousand email subject lines we found that the simple subject line ‘too busy or not interested’ got a 30% better response rate than the average subject line. I thought that might be a useful tip for you to try. Hope we can talk soon. – Jim”.

Well, now you’ve piqued my interest. We’ve already been through the first two contacts, so I’ve likely ignored your outreach twice now… but it’s finally starting to register a bit. Also, you’ve just added some value to my day. Now I feel a little bit better about you, and a bit better about your company. I’m still not going to respond to your email. I don’t have time to “talk to some salesman about nonsense”, but I might do a quick google search to see what your company’s all about.


4x – “Too Busy or Not Interested?”

Fourth email. Subject: “Too busy or not interested?…” Yup, you guessed it, he uses the same subject that he told me works. And guess what? I feel it. He just wants a yes or no, and I feel like I owe him that. But, both he and the product actually seem pretty interesting. I don’t want to lose out on the opportunity and he seems a bit better than the other 100 salesmen coming to me. I might give an “I’m sorry Jim, I’ve been swamped. Can you send over the details?” Alright! Jim’s got a win now. At least we’ve got a ballgame.


5x  “Breakup”

If there is no response from the fourth email, a smart salesman will send the ‘Breakup email’. “I just wanted to let you know we’ve filled this opportunity. I’ll continue to keep you in mind as new things come up. Cheers, Jim.” This is a great way to say: Hey Dave, remember when I was telling you we had a good opportunity, but time was limited. Well, that was true and you missed out. Fear of loss is psychologically the biggest driving factor towards making decisions for most humans. This last email gives credibility to your other 5 urgent reach-outs and allows you to cultivate your leads. Next time when you go back to him with another opportunity, he may not wait until the 5th reach out to get the wheels turning.

On my team, we’ll additionally work calls in between the email contacts. If I want to reach a potential customer with a great opportunity, this week, that I know is going to help their business, then I’ll make sure I can reach them. I make sure that understands the opportunity so that he can make the educated decision to take the opportunity or pass.



Pete and Repeat…

This repetition method doesn’t just apply to sales. I am NOT a guy who likes to do the same thing over and over. I like new challenges and new adventures; tackle one problem and then on to the next. Unfortunately, that’s not the best way to teach. With my own team, if I teach them a new strategy or give them a new idea every week and don’t ever revisit, it’s bound to get lost in the shuffle. Trust me, I’ve learned this the hard way. If I want a message to sink in I’ll hit the concept, (you’ve guessed it), five or more times. (Pro tip: I’ve found Boomerang by Baydin to be an extremely helpful gmail tool for this, allowing you to chose to push sent messages back into the top of your email if no action taken.)

The same goes for my own goals. Every self help book, religion, sales guide, etc. preaches, in some way, to repeat your goals to yourself over and over again; whether it’s praying, writing them down, visualizations, whatever. With repetition comes understanding. Let me repeat that: with repetition comes understanding. First, things start to sink into your subconscious Then, you’re ready to pay attention to. Finally, you’re ready to “buy” the actions that need to be done to reach those goals.

People are busy. There’s a lot going on this world. If you want to get something done, you need to put in the extra effort to be noticed.

Try this concept once… and then try it again. And maybe a few more times. Have you gotten anything out of it? I’ll check back in a few weeks.



When the sales floor of my first company was just starting to really take off in early 2009, hashtags were not quite hip yet (not sure that they really are now?). I was a manager at the time, with 3 others, in charge of a sales floor of about 30 people. The sales team had grown rapidly since I started there a year earlier.


When I arrived in June of 2008 I was one of 15 people at the company + 6 sales reps on the floor, which quickly narrowed down to 5 after my “best friend” at the company quit 3 weeks into our career. I was selling online pay-per-performance advertising to gyms + healthclub owners who, many times, didn’t quite know how to turn on that “box” in their office, let alone how that new “internet” worked.


Fast forward a few months later, we were a sales team of 30 reps, cold calling into about 20 different verticals; selling to gyms, veterinarians, tv repairmen, auto-glass technicians and all other kinds of small businesses across the country out of a little dance studio in Columbus Circle. We were often selling ideas + services that weren’t quite built yet- a common practice in the startup world known as vaporware, meant to ensure that there was a demand of orders for the product to justify building out. It was likely one of the craziest experiences I’ll ever have. The stream of sales conversations would bounce off the brick and hard-wood floors creating a mesmerizing buzz of “Stay for as long as it’s working for you,” “Don’t take my word for it, it’s free to try”, “Just give me a try Bob, I won’t let you down.” etc.


It was my job, as a newly groomed manager to keep the team motivated, hungry, and provide direction in order to hit our aggressive goals. Many of my new employees were my friends and peers just a month earlier. I was responsible also, to mentor + train up the new reps, mostly coming in with no experience. It was stressful, it was crazy, it was a blast.


All rowing together we’d constantly send out motivating emails and messages on Yammer (our company-wide chat). Often these chats / messages would end with a joking hashtag (#nicejobdave, #moresalesplease, #cansomeonepleasebringmeacokefromthefridgethanks).


I was known for my #hardworkpaysoff tag. I’d use it to encourage people to keep working, striving towards that next dial. I’d use it to celebrate the rep that made his 241st call today, or hit his 5th hour of TalkTime on the phones. Most often I’d use it to call out a win from a rep that took the extra mile in the week or day before, which drove success; “200 calls per day from Adam last week, results in 12 sales this week #hardworkpaysoff”. “Alexa just closed an Autoglass technician from Springfield, IL that took 21 calls to land, BOOM #hardworkpaysoff”. “Laura’s work speaking with Sam Grossman in California to ensure he’s comfortable and happy with the product long after the sale just landed her a 10 location referral, 4 months later #hardworkpaysoff”


As I’ve grown in my career I’ve noticed that this silly montra I made up in order to get my reps to up their game has been a cornerstone in my life and general success.


We all know a successful sales job does not require rocket science. In fact, far from it. It requires, persistence, creativity, and hustle. This is true of most success in the start-up world. It is rarely the “smartest” company that wins the race. It’s those that have the hustle, the drive, and put in the hard work to gain that slight edge and constantly stay alive.


I tend to see this everywhere in the world. It’s rarely the best musicians who you’re hearing on the radio and MTV. It’s not the most talented college receivers that make the biggest splash in the NFL. It’s the ones that hustle, that work; the guys take that extra step the others aren’t taking, that pay off in the end.


I am by no means the best salesperson I know, and I’m rarely the smartest guy in the room. I’ve been lucky enough to have learned with and from some truly incredible people and was reared early to put in the hard work. It’s given me success in my life so far and I’m grateful for it.


Somehow I’ve now been blessed to build out the merchant sales team at one of the the most pivotal start-ups of the time. #hardworkpaysoff