Ten Career Lessons from the Last Ten Years

Happy New Year! As we enter 2020, I can’t help but think back at my professional journey over the last decade and take stock of what happened. Ten years is a long time in the span of a career. For me, the last decade has been transformative in many ways as I’ve made several career moves and transitioned from middle manager to an executive. Here are some of the key lessons I’ve learned along the way. 

1. If you don’t define yourself, someone else will

At the start of the decade, I was in my mid-thirties and still had a “Marketing Manager” title. I had a good job but was looking for the opportunity to get to the next level. My goal has always been to be the top marketing executive in an organization. I didn’t see a path forward in my current job, so I decided to look outside the company. Unfortunately, I was told I couldn’t get that VP job because I had a “Manager” title. Despite the fact that I was leading a large team, controlling a multi-million-dollar budget and had a lot of C-Level facetime, people outside the company just saw “Manager” on my resume and didn’t even give me a chance. After having multiple recruiters say, “they like your experience but won’t talk to you with that title”, I knew I had to do something different. I realized that I was doing a poor job defining myself. I was letting other people define me. From that point on I started to pay a lot more attention to my “personal brand”. I needed to reposition myself for the position that I wanted. I spent time writing blogs and speaking at industry events so I could really show people what I’m capable of beyond the title on my resume. The more content I created, the more exposure I received and the more calls I started to get from recruiters. Very soon, I did land that VP title I was looking for. A few years later I became a CMO. And it was all because I did the work to define myself so others wouldn’t just define me based on the title on my resume. You can watch a video of my presentation about this subject below.

2. Your success will have less to do with you and more to do with the people around you

Ten years ago I was more of a doer and an individual contributor. As I’ve moved up to management positions, I’ve learned the importance of building a great team to support me. No matter how smart you are, how good your education is, how hard you are willing to work, if you don’t have the right people alongside you, you will struggle. Earlier in my career I made a bad hire and had a few low performers on my team. Rather than doing the hard thing and making a change, I just compensated by doing their work for them and filling in the gaps. That was a bad strategy and not sustainable over the long term. Once I finally decided to make some necessary changes with the team, moving out the wrong people and bringing in the right people, good things started to happen. In the end, if you have the right team, there’s really nothing you can’t accomplish. Check out the ParkMobile Team below (I'm in the Elvis costume).

3. Find the quick wins

I’ve had four different jobs at four different companies over the past 10 years. That’s a lot of change. I’ve found that when I start a new job, one of the best things I can do is get some quick wins on the board. That doesn’t mean neglecting some of the bigger strategic projects that will require long-term planning. But, to gain credibility in the organization and with your peers, you have to start showing results right away. Too many times I’ve see the “strategic marketing leader” start a new role and embark on a big initiative that will take more than a year to implement. It’s not that it’s the wrong thing to do. In most cases, it’s probably the exact right thing to do, but if it takes too long and you can’t show tangible results along the way, you risk losing the confidence of key people in the company. I remember a CEO once asking me about one of my peers in the marketing department, who had launched an ambitious project that was sucking up a lot of time and resources, saying to me, “What has he been doing the last few months?” That’s not a good sign. My advice is that when you start a job, find a few things you can get done fast and knock them out. It could be new collateral, updated trade show booth design, some refreshed digital ads, updated copy on the website, etc. Get them done fast to show that you know what you’re doing and build the credibility you will need to take on those bigger projects down the road. You can read my blog post about a “Quick Win Strategy” here.

4. If your foundation is weak, your marketing will be weak

Many times, when I’ve joined a new company, I’ve found a lot of the basics are missing. The messaging is inconsistent. There are no clear brand guidelines. The website isn’t optimized for search. The collateral is three years old. There is no reporting or data to track results. In marketing, there are tons of shiny objects out there, but the most important thing you need to do as a marketing leader is focus on getting the basics right. Without a strong foundation it’s hard to build a successful marketing program. So, before you go buying the latest MarTech tool or experimenting with some AI based ad platform, make sure you start with the basics.

5. If the sales team isn’t successful, you are not successful 

In many of the companies I’ve worked at, the Sales team is on its own island. Many sales reps don’t work in the corporate office. The team has its own culture. At the end of the day, though, Sales is the critical function when it comes to the success or failure of a company. If you’re not selling, you’re not growing. One of the interesting dynamics I’ve seen in organizations is the disconnect between the Sales team and the Marketing team. Both sides seem to think that the other side just “doesn’t get it”. As a marketing leader, you have to recognize that you are not successful if the sales team is not successful. So, you have to do everything you can to build that relationship. Listen to the sellers, spend time in the field and deliver programs that will help your Sales team crush their quota. When Sales and Marketing are aligned, great things can happen for the company. You can read my blog post about Sales and Marketing alignment here.

6. Manage your stress with exercise 

Stress will be a constant factor in your career. There is always going to be pressure. I don’t think I’ve ever met an executive who was totally laid back and stress free. One way to manage the stress is to exercise. In the most stressful times in my career, working out has kept me sane. I remember one particularly tough time many years ago when I was having significant issues with my boss. It was a toxic situation. I would go into the office and my blood would be boiling before I even got to my desk in the morning. My outlet was pouring myself into a workout. I would sweat out the stress. After a good workout, I’d always feel better. It has helped me get through the toughest times in my career. Today, I make time for exercise at least 4 to 5 times a week. I truly believe it makes me better at my job. So, the next time the stress is getting to you, hit the gym, go for a run, or come race me on the Peloton (“BaldGuy” is my leaderboard name). You can read my blog post about how exercise can help your career here. And check out the time lapse video of me doing a Peloton ride below!

7. If the culture of your organization requires you to change who you are, you’re working for the wrong company

At one point in my career, I looked around my company and realized I wasn’t really a good fit. That’s a tough thing to recognize and takes a lot of self-awareness. The more time I worked there, the more I realized I just didn’t belong. People talked about all the executives as “[Company Name] Guys”, meaning they all fit a certain mold. I just wasn’t like them. But I wanted to be an executive in this company so I tried to change who I was to fit the mold. It didn’t work. In the end, I decided to leave and find a place where I’d be a better fit. It was the best decision I could have made. Working in a place where you feel like you can’t be yourself can be debilitating. On the flip side, being at a company where you’re the perfect fit will make work more fun than you ever thought it could be. You can read this blog post to learn more about finding a company that’s the right fit for you.

8.        Be real

As a CMO, I get asked to speak at a lot of events and do podcast interviews. One thing I always try to do is show people the real me. I’m not perfect. Not even close. I’ve made a ton of mistakes in my career. But failing has always helped me get better at my job. Being vulnerable by talking about your failures in front of a group of people isn’t comfortable or easy. It can be a bit embarrassing and even painful at times, but I love when people come up to me after my session and tell me that my talk really resonated with them. Hopefully people out there can learn from things I got wrong. That brings me a lot of satisfaction.

9. Define your core values, then live them

In my last two companies, QASymphony and ParkMobile, we didn’t have defined core values when I started. So, I led the exercise with the executive teams to develop our core values. I believe having strong core values is critical to having a strong foundation as a company. These values help define who you are as an organization. They determine who gets hired, who gets fired, who gets promoted, etc. Once we defined our core values, we put them on the walls of the office as a constant reminder of who we are and what we stand for. We even established the annual “Core Values Awards” to recognize the team members who truly embody each core value. It’s a critical part of the way we operate and make decisions. Recently, I was interviewing a candidate for a position on my team who said that one of the reasons she wanted to work for ParkMobile was that she identified with our core values. That really made me happy, and the candidate ended up getting the job and is doing great. You can watch this video to learn more about ParkMobile’s core values.

10. Network your ass off

Over the past 10 years, I’ve spent a lot of time building and maintaining my professional network. I try to make time every week for lunches, coffees and drinks with people in my network. There are huge benefits to this. First, having peers to talk with helps me bounce ideas off smart people and learn what works for them. It’s a great way to learn what others are doing and bring some of those concepts to my work. Second, it’s helped me in my career moves. I was referred to the last two companies I joined by someone in my network. Third, it’s been great for hiring. In my current role at ParkMobile, I’ve sourced almost the entire team through either my network or the networks of other people on the team. The result is that we’ve hired some great people and we’ve saved a ton of money in recruiter fees (no offense to my recruiter friends). I believe that if you have a strong network, you will have a strong career. So, it you’re thinking about your New Year’s resolutions for 2020, make networking part of it.

Those were my ten lessons from the last 10 years. What are some of your lessons? Let me know in the comments below.