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7 Questions on Leadership with Greg Caldwell

Name: Greg Caldwell

Title: Chief Marketing Officer

Organisation: Packsize

As Packsize's Chief Marketing Officer, I have over 20 years of experience in leading marketing, sales, product, and communications teams while creating innovative campaigns for cutting-edge companies in diverse sectors. Packsize provides custom, right-sized packaging solutions that reduce waste, cost, and environmental impact for businesses.

My core competencies include using marketing analytics to adapt to consumer behavior, creating effective ways of reaching targeted audiences, and maintaining a strong customer focus. I also leverage customer insights, value-based positioning, and new digital demand/lead generation approaches, such as e-commerce and other customer engagement models. I am a trusted C-suite advisor providing strategic counsel and guidance on optimal marketing models, marketing investments, and business strategies. I make quick decisions while assessing the overall business impact and adjusting to meet the evolving objectives. My mission is to deliver impactful sales, marketing, and product/solutions that align with the vision and values of Packsize and create a positive difference for our customers, partners, and the planet.

Before Packsize, Greg held varying leadership roles in sales, marketing, product, and communications at companies such as Nano Dimension, 3D Systems, Microsoft, Sun Microsystems, HP, Compaq, and Dell.

Thank you to the 2,000 leaders who’ve generously done the 7 Questions on Leadership!

I hope Greg's answers will encourage you in your leadership journey. Enjoy!


Jonno White

1. What have you found most challenging as a leader?

A few things come to mind, but this certainly isn't an exhaustive list. I'll start by listing work-life balance. As you continue up the ranks, especially in global companies, you have a large employee base spread across many regions and time zones. It can be challenging to be available and accessible to your team, but also be intentional and mindful of your family. I've always said, when I'm no longer at a company, they will fill my role as soon as they can possibly find a qualified candidate... business moves forward. When it comes to family, if you're not being intentional and present in those crucial moments, you'll look back one day and realize you missed some extremely important times that you'll never be able to capture again. My family always has and will come first.

Second, I would say budgeting for next year. Sales, marketing, communications, product management... some teams/roles can be 100% connected to revenue and the bottom line. Others of those roles don't align as easily, and it's harder to prove ROI. As I've progressed through my career, I've always made it a point to make sure that all of my teams set very clear goals and expectations and that we all take on the companies financial performance as part of our yearly KPI's. If you can demonstrate the impact that your team's efforts are having in delivering the company's financial results, it makes it easier when it comes time to request budget and headcount.

Thirdly, managing uncertainty. The business environment constantly changes, and leaders must navigate uncertainty and unpredictability. This includes dealing with economic fluctuations, market shifts, and unexpected events like the COVID-19 pandemic.

Lastly, motivating teams to have a sense of urgency and accountability. Effective leadership involves motivating and managing a diverse group of individuals. This can be challenging, as people have different personalities, motivations, and work styles. Keeping teams engaged, productive, and aligned with the company's goals can be a significant challenge, and you have to be purposeful and intentional.

2. How did you become a leader? Can you please briefly tell the story?

I grew up as an athlete, playing baseball and football, and eventually played baseball collegiately, so leadership was ingrained in me from a very young age. I can't tell you how frequently I draw upon my days as an athlete within the business realm. There are so many great leadership lessons in sports that apply throughout your life, whether business or personal. Things like: teamwork, goal setting, discipline, accountability, leading by example, communication, resilience, adaptability, embracing diversity, preparation and strategy, handling pressure, accountability, celebrating successes, and learning from failures.

In our society today we've transitioned to a place where "no one loses." That's not reality and certainly not in business. I've learned far more from my failures than my successes, and I think good leadership realistically allows for failure and uses that failure to push you and your teams to grow and improve.

3. How do you structure your work days from waking up to going to sleep?

Packsize is headquartered in Salt Lake City, UT and I'm based in Cleveland, OH, so there's a two-hour time difference. I'm not the greatest morning person. I'm more of a night owl. So I start my day around 7:30 ET and use the first couple of hours before our employees at HQ come online to work through email, strategy, planning, referencing data to track progress against goals, etc. I'm then usually tied up in meetings with customers, partners, fellow employees, etc. from 9am ET to about 5pm ET. I break and have dinner with my family and spend a few hours with my kids before their bed time, and then will log back online for 2-3 hours after they've gone to bed.

4. What's a recent leadership lesson you've learned for the first time or been reminded of?

Trust is absolutely critical when you're trying to drive lots of change as a leader. I've driven a lot of change throughout my career, and each time I'm trying to drive change I remind myself that there are a handful of things that are required for success:

1. Clear goal setting or vision for the final outcome.

2. Communication of expectations and a roadmap is necessary to bring your employees along the journey

3. Creative inclusion conditions that enable your employees to thrive.

4. Urgency - if teams don't see positive progress quickly, it becomes very easy for them to start to question the changes.

5. Accountability - you must create KPIs that align to success and then hold your teams accountable to driving those results.

5. What's one book that has had a profound impact on your leadership so far? Can you please briefly tell the story of how that book impacted your leadership?

The bible. I am a servant leader who cares about employees at the human level first and foremost. All people have personal lives and must balance all sorts of heartache, pain, challenges, finances, marriages, divorce, kids, and more. So on a personal level, I want to invest myself in them and their success and progress. I try to listen and understand them so that I can better know what they need from me, and how I can move positively move them forward to their benefit.

At the business level, I want to lead by example. I want to make the jobs of my employees as easy as possible, so I clear roadblocks, manage up, celebrate successes, and push those successful employees to the front to receive the credit they're due. I also love to invest in the employees who aren't performing well enough and try to serve as a mentor or role model for what they too can become. I want to serve my people.

6. If you could only give one piece of advice to a young leader, what would you say to them?

Be yourself, and be real. As a younger employee I can recall being a bit intimidated by senior leadership and I eventually got to a point where I realized that the good leaders actually wanted feedback that went counter to how they viewed things. It enabled them to consider different aspects of the decision being made. Don't be afraid to have an opposing view from that of senior leadership. We're all human and NO ONE has all of the right answers.

7. What is one meaningful story that comes to mind from your time as a leader, so far?

It's really about people and building a chemistry that will enable success. In all of my leadership positions, I've generally brought employees along with me to my new roles. Those employees that you have great chemistry with, that you've invested in, that understand your vision and strategies, and how to successfully execute those things are critical. I've never once been successful without others contributing to that success. People make the difference so ALWAYS invest in your people.

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