Subscribe to Entrepreneur for $5

Why the Leader of FreshDirect Has a 6-Foot-6-Inch, 260-Pound Assistant

Jason Ackerman, the CEO and founder of online grocer FreshDirect, shares his leadership and company culture tips.


In this series, Leader Board, we speak with CEOs, managers, founders and others who lead organizations to learn what makes them tick, what they look for in new hires and even where they eat lunch.


If you want to schedule a meeting with the CEO of FreshDirect, you’ll have to check in with his six-foot-six-inch, 260-pound assistant first. Being the founder and CEO of a major food company is demanding, but with the help of his assistant, who “is not technically a bodyguard [but] can pick me up and carry me over his shoulder with one hand,” Jason Ackerman says he can get his work done.

Related: Why the Entrepreneur Behind iRobot, Which Has Sold More Than 20 Million Robots, Burns Frustrating Documents at the End of Every Year

After a career in banking, Ackerman launched the online grocer, FreshDirect, in 1999. Fast forward 18 years, and the company employs more than 3,000 people. In 2016, the Long Island City, N.Y.-based company secured funding of nearly $189 million, which is more than double the funding of the year prior. As the CEO, Ackerman has made sure he’s continuously growing the company and meeting the needs of investors, employees and customers.

“As a manager, just like as a human, you never stop evolving,” he tells Entrepreneur. From inventing to hiring to building a company culture -- Ackerman’s learned and grown a lot over his nearly two decades at the company. And one of his top priorities has always been his employees. “I believe that people have to enter the company as people, not as job titles,” he shares.

To find out more, we caught up with Ackerman to learn about his leadership techniques and how he’s built a $600 million company.

On the most important leadership traits:

“First of all, clarity of direction. A CEO's main job is to set the ship on the right path and make sure that path is understood and communicated on a daily basis. People can lose their way so it's important to make sure that we are constantly pointed in the right direction.

“Second is team-building [and] assembling the right teams. As the environment and the tasks at hand are changing you have to be constantly evaluating the team and making sure that you've got the right players doing the right activities and that they're working well together. Third is setting the tone. You have to maintain the right attitude through all of the ups and downs [of] the business, and people are constantly looking to the leadership.”

On leadership style:

“It's about going from a builder and an inventor to a leader. And that transition has been happening slowly over the course of [my] 18 years. I know more than anyone collectively about the business, but as time passes that can also be a curse, because two things: One, you don't want people dependent on you. Two, you don't want to micromanage. You've got to build talent. A lot of [my] leadership style has migrated from being the person who makes sure everything is being done properly to the person who is stepping back and thinking about one to three years from now as opposed to how today went. As a manager, just like as a human, you never stop evolving yourself.”

On habits that help him lead:

“I try to think on a consistent framework about what I'm supposed to do. Over time I've developed a series of reminders to myself about perspectives that I need to consciously maintain. Usually Sunday night, as I review my week and prepare for next week, I go through some of those things to make sure that my head is in the leadership role [and] not necessarily in some problem that the business needs to deal with, and whether or not I'm getting too caught up in that vs. pointing in the right direction.”

On challenges:

“This is a very operationally intensive business. We have extraordinarily fast turnarounds in a very fast paced environment -- from order to home in 12 hours or less. So in that environment, the biggest challenge is not getting caught up in the daily intensity of the things. We have to deliver every single day [and] everything’s got to be as perfect as it can. That daily pressure of operating excellence can often take away from your focus in some medium- and long-term work because there's always short-term issues that have to get fixed, so maintaining that balance is hard.”

On the toughest business decision:

“You have to know when you're on the wrong path and when to cut your losses. People get very committed to a path they're on and it becomes deeper [and] more personal. You have to be able to step out of those shoes.

“You could [have] made an important big hire and it turns out that hire [is] the wrong fit, but you put so much effort into that commitment that you stick with it and try to make it better even when you know the right answer is to cut your losses.

“I see that all the time -- people not facing the reality of the situation. Truths are truths, and the faster you recognize them, the faster you deal with things.”

On the most important traits in a new hire:

“Not physically fit, org fit. Over time, we’ve learned that FreshDirect has its own way of existing -- just like human beings have their own personalities. And there are really two types of characteristics you generally look for: one is content and the other one is personality. We have absolutely prioritized cultural fit over content expertise. The really great, talented content with the wrong fit never succeeds. You [have] to know your organization so you know what you're looking for.”

On recognizing employees:

“Recognition has to happen for the small and the little, not only the big. The organization used to often celebrate large wins. It's usually the same group of people who are taking on big responsibilities so it [is] the same group of people who [are] getting thanked. But the real recognition and value to the organization happens when the small things happen that somebody helps them on that they didn't need to do.

“I encourage that recognition happen every day in small little doses. We have a weekly all hands process, and part of that ritual is we have a thank you session so anyone can come up and create a recognition.”

On team-building:

“Trust comes largely from knowing each other more personally. Most of my routines with my team are reoccurring off-sites. I do a several days-long off-site once a year and quarterly off-sites. And there's always a balance in making sure that the team is doing things that [aren't] about work that build personal connections.

“A couple of months ago we got a beach house for 10 of us. We go out to the docks, go fishing, go for walks, go to a winery. People [have] a chance to casually talk."

On unique office rituals:

“Every new person in the company gets introduced at an all-hands by their managers, and then rather than saying what their job is they're required to interview them and find out three pieces of personal information that are quirky, interesting and fun. So the first time you meet someone you may learn that [they] used to be a bear wrestler or [they] love to play guitar. I believe that people have to enter the company as people, not as job titles.”

Related: Why This Entrepreneur Who Leads More Than 1,000 Employees Prefers to Eat Lunch Alone

On managing meetings:

“There are lots of different types of meetings, [and] each meeting type [is] handled a little bit differently. There are operating meetings that have a certain cadence to go through [such as] metrics and accountability. There are one-on-one staff meetings where you make sure that you know what the staff needs of you.

“Then there are general meetings, [where] you've got to state upfront the purpose so that everyone knows what we're trying to accomplish, [you’ve] got to be prepared in advance and you've got to end the meeting with a clear set of net actions and mutual commitments.

“One thing I hate is meetings that become conversations where we're just sharing stuff with each other but there's no understanding of what we want out of it and there's no conclusion [in] the end. It drives me batshit crazy.”

On scheduling:

“I have a six-foot-six, 260-pound assistant and he basically blocks everyone from me so that I get my routines managed. Although he is not technically a bodyguard, he can pick me up and carry me over his shoulder with one hand though.

“I work in three segments on my calendar and they're color coded. One are my 'routines' -- a series of touch bases with a series of people that are always on a cadence.

“I have meetings that are requested in other colors and I review [them] to see if I want to accept or reject those. And then I have yellow, which is my block time -- I make sure I have at least half a day twice a week for unscheduled time when I do my walk arounds. I need unplanned time to walk around and talk to as many people I can in the business [to] get a pulse, read people and make sure I understand what's going on across the business.

On office setup:

“We have one large open floorplan with a few offices along one of the walls. [My] office is basically one large conference room for about 10 people and the entire office is open glass. I basically live in a conference room and most of my meetings are held in my office. The glass runs the entire length of [my] office facing all of the open desks so people always know if I'm here or if I’m in a meeting.”

On lunch:

"'Lunch breaks' maybe happen twice a year. I don't get a break in my schedule for that."

On a strong company culture:

“Having one, knowing what it is, living it [and] reinforcing it. Cultural values [do] not happen because you state what they are. They happen by living it. Those things only come about by the daily routines and conversations, and they have to happen from the ground up and not the top down.”

On cultural mistakes:

“In the early days, when we were building our business, we were always trying to trade off things around serving customers vs. being financially profitable. We would ask the service agents [not to] give away too many credits but make sure the customer is always right. What I realized is that when you're trying to set a culture, you have to be externally black and white.

“If someone calls up and says, 'Hey, my jelly broke and there's jelly all over my food.' The agent could say, 'Can you go in your order and tell me which products got destroyed? Or, can you send me a photo? Then we'll see what we're going to credit you on.' And the customer's just pissed at you because [they’ve] got something broken and now [we’re] asking them to validate what's wrong. In the early days, we would pressure [our service agents] not to give away too many credits if the customer's not being honest but still serve them. The message was unclear.

Related: The Success Secrets of the 4-Time Entrepreneur Behind BarkBox, Which Brought in $100 Million in 2016

“When we started saying, ‘Don't worry about the credit system, do right by the customers,’ we made more customers happy. And I think understanding how to manage a culture and making those really strong black and white statements became very powerful.”

On his biggest cultural win:

“We're in the food business. And one of our differentiations is our ability to deliver consistently high quality food. Our food is touched by thousands of people, [but] I actually have less influence on the quality than a line worker or an associate member who's picking the tomatoes for a customer. So the way that [I] manage that is [making] sure that [we’re] very black and white.

“For example, if quality is more important than anything we do, the team associate who is picking for the customer has to be told very clearly that they will never be chastised for throwing something away and that they will only be celebrated for giving good quality. And that can't be unclear. So if people understand [the values] and they're reinforced every day, then they make decisions on their own based upon that standard.”

On his role models:

“Generally speaking, I'm a retail fanatic, so my two favorites are Sam Walton of Walmart and Jim Sinegal of Costco.

“[They] really built from the ground up the culture and the objective of the business and what [they were] trying to be. They were very visible on the floor to all employees and very accessible. You've got guys running huge businesses but they were setting the tone at the troop level every single day.”

On his favorite leadership books:

“I’m a big fan of biographies. Howard Schultz's book has some interesting aspects. When he came back into Starbucks for the second time he realized that the heart of the organization was broken and had to make some tough decisions on how to rebuild at the barista level, not at the top level.”

On where most leaders go wrong:

“The biggest one is speed of decision-making around talent. Everything is about talent. The difference [in] what makes a great leader or an OK leader is the speed at which they act on truth. The faster you do it, the faster you deal with it. You've got to be transparent. If you've got a team leader who you know is wrong for the culture but they're doing good things, [and] you let that sit, it can be very damaging. The best leaders make fast, good decisions.”

Rose Leadem

Written By

Rose Leadem is a freelance writer for