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“To create a fantastic work culture be transparent about the company’s goals and where it is going.” with Jeff Dickerson and Chaya Weiner

Be transparent about the company’s goals and where it is going. Talking honestly about the company’s goals means everyone can share the vision, and then you’re far more likely to achieve those goals. Getting everyone “rowing in the same direction” will help a company make faster progress, but I’m also a big believer in shared […]


Be transparent about the company’s goals and where it is going. Talking honestly about the company’s goals means everyone can share the vision, and then you’re far more likely to achieve those goals. Getting everyone “rowing in the same direction” will help a company make faster progress, but I’m also a big believer in shared values. It’s easy to lose sight of the horizon when you’re heads down making widgets in a factory all day. Knowing those widgets are finding their way into systems that safeguard your neighbors might imbue that work with greater purpose.

I had the pleasure of interviewing Jeff Dickerson, the CEO of DaySmart — the leading provider of business management software driving small business growth. Jeff is a six-time executive with more than 25 years of experience in the software solutions space. Prior to his work with DaySmart, he led successful leadership positions in the cloud, automation and sales industries.


Can you tell us a story about what brought you to this specific career path?

Well, as many coaches told me over the years, I was never going to make it in the NBA. Sales always seemed like a natural fit for me. It may sound hokey, but I’ve always had a passion for people. If we end up sitting next to each other on a flight, by the end of that journey, I’ll know most everything about you. I enjoy building rapport with a prospective customer, probing for root causes and finding a way to present value that addresses real pain. I have had to sell things I didn’t believe in, and that’s no fun, but solving business problems is fun. Winning is fun.

Ultimately, you cannot grow a business — any business — without sales. So, while salespeople sometimes get a bad rap and are seen as something between really annoying and downright predatory, building a successful sales career is all about balancing persistence and patience, learning to deal with rejection, overcome objections and believing in your own abilities. These are lessons that will not just make you a better seller, but a better, more resilient person.

Can you share the most interesting story that happened to you since you began leading your company?

The most interesting part of the job has definitely been how a change of venue changed our people and our atmosphere. When I arrived, the office was a large space, not unlike a warehouse. A handful of large rooms had been built out, and each had 4–6 employees in them. Some of these rooms kept their doors shut to reduce noise or regulate temperature. The result was an environment where most of the team was segmented and, in some cases, isolated. We are fortunate enough to be very well-capitalized and moving the entire office was a possibility, although the inherent disruption couldn’t be overlooked. Moving means big expenses and potentially longer commutes; it could force key employees to look for jobs closer to home and we could experience downtime moving phone and computer systems. There were a lot of reasons to just stay put and focus on product development and customer satisfaction. I mean, who cares where we sit?

Part of me just couldn’t let it go, though. If we moved 20 miles south, we could situate ourselves in the middle of a tech and startup hotbed that would make recruiting top quality candidates easier. Plus, a new space would give us a chance at a fresh start. Looking back, it exceeded my expectations. While the move didn’t work for everyone, the majority of our employees embraced the chance of scenery. And now, a year and a half later, our open concept space (there are only two offices for 80 employees) has dramatically increased inter-departmental interaction across the company. The change of venue led to a change of attitude that I didn’t anticipate and that really can’t be quantified. While the majority of the people are the same, the atmosphere is completely different- and much better than it was before.

Are you working on any exciting projects now? How do you think that will help people?

We just released a new service for our customers that helps them to bolster and manage their reputations online. With online reviews playing an ever larger role in search results and consumer decision making, they’ve grown beyond simply being a social media phenomenon. Online reviews can make or break a brand, especially a small business. We have been working for the last year to design, integrate and deploy a system that was powerful enough to make a difference and simple enough to use easily. Soliciting reviews, monitoring reviews, responding to reviews — all are integral components to making the most of your online potential, and it’s really gratifying to deliver something that was both easy to use and worth using.

According to this study cited in Forbes, more than half of the US workforce is unhappy. Why do you think that number is so high?

Wow, that’s a real surprise to me. But, there are lots of pressures on the modern worker, as AI and offshoring encroach on any number of job functions, and the fact that work/life balance is just plain gone for most of us. Phones on the night table mean email at all hours; Slack, G-chat, Asana, Trello — whatever the mechanism, work doesn’t stop when you leave work. It wasn’t always that way, and I don’t think “always on” is healthy.

I do believe that the generational shift in workforce likely plays into this, as well. I’m not convinced that older line managers fully understand how to manage millennial workers, and I’m equally unconvinced that some of these younger workers don’t come into the office expecting to receive more than they earn. I’m pretty old school, and when I “came up,” I didn’t expect (let alone demand) to have all of these perks. There were a few places I worked where I was glad (and sometimes surprised) that the check cleared every other week. Free breakfast? Foosball? Nap rooms? We didn’t even dream such things were possible, now they’ve become table stakes, especially in tech.

I don’t want to come off as blaming the victim here either — many managers do not take the time to get to know what their employees care about and what they hope to achieve, nor do they work to construct personal development plans. How do we get you to where you want to be? Taking the time and effort to overtly invest in people goes a long way toward people feeling valued.

Based on your experience or research, how do you think an unhappy workforce will impact a) company productivity b) company profitability c) and employee health and wellbeing?

Clearly, if your employees aren’t happy, then your company cannot perform as effectively as it could. There have been countless studies done that prove this is true, such as this Social Market Foundation report that found happy employees are up to 20 percent more productive than unhappy employees. But you don’t need a study to tell you this. Hopefully, you’ve had the experience of working on a team, or in a company, where people loved being there, where they loved the people they worked with or where they saw genuine value in the service they were delivering. Enthusiasm is infectious. Likewise, poor attitudes can fester and affect those around them. To combat this, management should focus their energy on promoting the wellbeing of employees, as it pays clear dividends.

Stats aside, from personal experience, I can tell you what a difference it makes when an employee feels truly valued, passionate and happy in their job. When I first came to DaySmart, I made it a point to talk to each employee and figure out what they liked and disliked about the company. For any across the board dislikes, I worked closely with the rest of the management team to find solutions to those issues as quickly as possible. For issues that were raised by a subset of employees, I tried to find solutions for those individuals. Look, at the end of the day, it’s work. It’s not supposed to be a vacation. That said, it is the responsibility of the company to remove impediments, and wherever possible, make it easier and more enjoyable to do the job.

Can you share 5 things that managers and executives should be doing to improve their company work culture? Can you give a personal story or example for each?

1. Dedicate time to get to know your employees on a personal level

I encourage leaders at every level to get beyond their immediate peers and daily colleagues and meet people you might not otherwise. You have to work to create these opportunities — select one employee every two weeks to take to lunch, or stay late and hang out with support staff who may have non-traditional hours. Forging these relationships will unearth valuable insights from which you can benefit. People throughout the organization have closer relationships with partners and customers or have big ideas born from years of doing something. It is your job to identify and evaluate every opportunity for improvement and those insights live inside other people. Plus, I think it’s just good form to really get to know as many people as you can at work.

2. Turn your culture into one that’s more about giving than receiving

This may take some time, but in my experience, employees take greater pride in a company that is present in the community, that participates in local happenings and finds ways to give back. Maybe your company is not in a position to write a check or to muster 20 employees to clean a local park, but I would encourage you to find a way to contribute somehow. The experience should matter to your employees more than relate to your company, so if your employees are “dog people,” maybe find a way to help out at a shelter or bring therapy dogs to a nearby nursing home. The point is to engage and delight your team — not extend your brand.

3. Be transparent about the company’s goals and where it is going

Talking honestly about the company’s goals means everyone can share the vision, and then you’re far more likely to achieve those goals. Getting everyone “rowing in the same direction” will help a company make faster progress, but I’m also a big believer in shared values. It’s easy to lose sight of the horizon when you’re heads down making widgets in a factory all day. Knowing those widgets are finding their way into systems that safeguard your neighbors might imbue that work with greater purpose.

4. Make it a point to publicly recognize hard-working employees on a regular basis

This is an obvious one that I think too many companies fail to do correctly. Doing this effectively requires training managers to keep an eye out for superlative performance at all levels. Too often, it’s the salesperson who closed the biggest deal, or the Business Development exec who brought in our largest partner. What about the support rep who handled the most calls last month? What about the customer service rep who spent hours helping a single client recover their data? Dig deeper within the organization to find high performers at every level.

5. Learn from your mistakes, so that you don’t repeat them

Like everything, this is easier said than done. For me, there is nothing more frustrating than making the same mistake twice because it means it didn’t have to happen — I should have known better. This usually happens when you lose focus. I have also known people over the years who simply refused to recognize when they made mistakes, which pretty much guarantees they’re going to make those mistakes again, since they won’t recognize them when they reoccur. Mindfulness is a big part of this, as is spending time at the end of each day to quietly look back and ruminate on mistakes made that day, by you and others. Focus not on the results of those mistakes, but the steps that led up to them.

It’s very nice to suggest ideas, but it seems like we have to “change the culture regarding work culture”. What can we do as a society to make a broader change in the US work culture?

Our definition of corporate culture has become a little muddy nowadays. Too often people focus on “perks” as the driver behind company culture: bagel Fridays, shuffleboard tournaments, summer outings, dental benefits, etc. While those things are certainly important in ensuring your employees have fun and feel valued, I think the true definition of culture needs to center more on what you give, not what you get.

At DaySmart, we certainly try to ensure our employees feel appreciated with our perks and benefits offerings, but our culture extends beyond that. When I joined the company, I made sure there was ample opportunity for growth and set to establish a stronger sense of transparency throughout the organization. I established a bi-weekly company-wide meeting, where we talk about what everyone’s working on, how the company is performing, what we have coming up, etc. We also started a “Stars Among Us” initiative to identify and recognize deserving employees at this meeting. Sure, we give them a $150 Amazon gift card for their exemplary effort, but the real goal is to get them to stand up and be recognized by everyone. Not only does this meeting give every individual the chance to feel included and get involved in the success and progress of our company, but I hope it sends a message that we value hard work and that we take the time to recognize those who deliver it.

On the theme of giving rather than receiving, we’ve also established a culture very much focused on philanthropy. This past holiday season, we visited a center in Detroit for homeless veterans and delivered them thousands of dollars worth of new clothes. We also lined up hair stylists to donate their time and give haircuts to the vets living in this home. We did something similar this past summer with a local pet shelter, recruiting local groomers to pretty up the pets in order to encourage adoptions. Employees who want to organize an effort like this are welcome to do so, and while the perks and the benefits are certainly important, culture should really be defined based on what you are able to give back and what makes you proud to work at your company.

How would you describe your leadership or management style? Can you give us a few examples?

As a leader, I am extremely transparent with my team. I’ve always found it important for executives to make the rest of the company feel “in the loop” on company happenings, and while I can’t always share everything, I do strive to ensure everyone is on the same page.

I also always ask open-ended questions of every individual I work with: whether that’s an employee, a customer or a partner. To be a successful leader, it is critical that you get to know the people you work with inside and out. This personal touch is something that can so often be overlooked by executives who are laser-focused on running the business. Spending the time to get to know people and finding out what motivates them is what sets the best managers apart from the pack. It’s something that you just can’t fake, and if you do, people will know.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I have been fortunate enough to have had a couple of mentors that guided me through different stages of my career, but one that does stand out was during my first CEO position at a company called eCredit. On the Board was a gentleman who retired as the CEO of GE Capital Finance, an $80B division of GE, and had taken me under his wing. I described an opportunity that I saw in the market that I wanted to go after. I felt it was the right move at the right time for the company and I seized the opportunity. I soon became disenchanted by the lack of my team’s passion at making this move a success. My mentor said he agreed with the move and complimented me on the detailed work that went into its planning and execution, but then asked how much effort I had spent bringing my management team into the opportunity so that they would feel that they are part of initiative, and not just worker bees carrying out someone else’s idea. He reminded me of the importance of earning “buy in,” and making people feel that they are part of the decision-making process whenever possible. I learned that, despite my title, more people than just myself need to believe in the moves we make as a group.

How have you used your success to bring goodness to the world?

Making the world a better place is more of a mindset than one or two stories. Stories about goodness have a start and a finish, whereas a mindset is a continuation of good. At work, I try to be supportive of initiatives outside of our walls — embrace our team members’ ideas of how we can make a difference in the communities in which we live and work. For me personally, I am continually on the lookout for opportunities to leverage my network to do good, such as encouraging my business contacts to donate used computers to Community Nursing and Hospice, or, as I have for the last eight years, raise money and ride nearly 200 miles in the PanMass Challenge for Dana Farber cancer research. I volunteer to run a basketball program every Saturday morning during the winter for boys and girls in first through third grades for the past 11 years. The trick then is to spread that “good mindset” to friends, family and business associates. I truly believe it is contagious and have seen that first hand.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“Don’t forget where you came from.” I learned this lesson (and many others) from my dad when I was in the early stages of my sales career. It was right after I had gotten promoted for the first time, and he encouraged me to always remember what it was like to be in that entry-level position and to have a sales manager swing by my desk to ask how I was doing or see if they could help me with anything. It’s certainly something that has stuck with me throughout my career, and I always try to check in with each individual employee to ensure they feel supported and valued.

We all start somewhere and we all end up somewhere. Keeping both of these compass points in mind (where you want to go, as well as where you’ve been) should work to keep you grounded and relatable. I’ve heard the expression “it’s not where you start, it’s where you end up” and I get that; your origin should not determine your destination and your potential is determined by your aptitude and your attitude. However, “forgetting where you come from” is an expression often applied to people who have lost touch with the people around them. It’s hard to lead (or even participate) when your team doesn’t respect you because they feel you’re not connected to the journey.

If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be?

I do believe that access to affordable quality healthcare continues to hold too many people back. It is clear that the healthcare system in this country is broken. I am well aware that I’m privileged to have company-subsidized health insurance, which means my family needn’t worry about stratospheric drug costs or having to declare bankruptcy because of a serious diagnosis, but that is certainly the reality for too many Americans. Looking around the world, it is obvious that other nations have figured this out already and it seems absurd we haven’t.

I would love to start a movement that makes healthcare in this country a human right, guaranteed to each of us. I don’t pretend to know how to unwind the mess we have created, and I think that all of the labels (socialized medicine!) and the relationships between lawmakers and lobbyists are limiting our ability to innovate in this space. Unlike a lot of other problems we have as a society, this one is literally costing lives.

Thanks for all the great insights!

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