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