As the decade wraps up, it’s fun to go back and look at the journey you’ve been on.  Here is mine.  

I’m in sales mode for James Pellizzi & Co.  We want to double in size in 2020, so if you need help with any type of marketing or automation work, you might consider glancing through this article, as it will give you more than just a few taglines of how the leader of a potential partner/company of yours views marketing & business.  

Baby faced and ready to make an impression!

2010:
I was working at IEWC as a Marketing Coordinator, making a name for myself in marketing.  I had been out of college for two years and loved my job.  I took on a major branding initiative and was eager to make social media work in a B2B environment.  I couldn’t wait to get into work everyday.

2011:
In my eagerness, I began taking on anything and everything.  I became more of a Marketing Generalist, eager to please everyone.  For all the wins I was racking up, I also began to start losing.  I started to realize that human nature is to focus on mistakes.  I could do 9 out of 10 things right, but people focused most on the one thing I failed at (It didn’t help that I usually bombed in dramatic fashion).  My failures started to prevent me from capitalizing on my successes and I was frustrated stuff I thought didn’t matter overshadowed major wins.  I became somewhat disgruntled and occasionally took the long way into work.   

2012:
I had a new boss and shared with him my frustrations. The fact that he was willing to sit down and meet me halfway on things has always meant a lot. He acknowledged my ability to get things done, but helped me understand that I needed to walk alongside people first. I was running too far ahead of everyone. As a result, I was put on a team responsible for implementing Salesforce CRM, an initiative that failed in the past.  I couldn’t get enough of the marketing & sales processes and began traveling around the United States.  I lived in an airplane seat for a year but found myself loving every minute of it. 

One of the groups after a training session.

At its core, the project was a people & change management initiative.  I mostly just told people everything would be okay on a regular basis and to give things a chance… and it taught me that getting started is often times better than being perfect.  Starting is the hardest part and I found I excelled there.  This year/initiative will always be a fond memory.

2013:
At the start of the year, I was promoted to Channel Manager and the CRM project moved to it’s second phase, which was a roll-out around the world. I was rewarded for my good work with more responsibility. We no longer were using the Consulting firm as a crutch. I would be responsible for training and administration all on my own. I was more than up to the task and traveled to Canada, Mexico, Brazil, Europe and China.  I’m not sure I’ll ever do another 17 hour flight to China again…but I’ll never forgot how much my travel companions looked out for me on all these travels.

The feeling you’d get when the wheels would touch back down in Milwaukee, whether across the US or the world…Mission Accomplished. I loved it.

2014:
With the CRM project over, I began to wonder what was coming next.  I had been turned down by all the major advertising agencies in Milwaukee, but upon some advice from my Dad thought I might have what it takes to make it in consulting.  I applied to all the major players and got an interview with Accenture!  I got the job and more than doubled my salary overnight.  Instead of working on CRM implementations, I was re-assigned to Emerging Technologies and began working with Marketing Automation platforms, specifically Eloqua and Marketing Cloud.   I remember during the orientation & training, everyone was posturing & talking about how great they were.  I thought to myself, “I’m going to eat these people alive…”


At one of the many training sessions Accenture puts on for it’s employees.

My client at Accenture was a major business retailer in Chicago.  I’d be up before 7 am, and drive from Milwaukee to an outside suburb every morning for 90 minutes.  I’d get home around 9 pm every night.  Sounds arduous, but my project manager and team took excellent care of me and I continue to incorporate many of the things she taught me in our current offerings.  The things we were doing were unbelievable.  Most of my work was focused on platform integrations, e-mail marketing and scoring models.  This was one of the only times in my career where no one tried to slow me down and I was once again hooked.  I couldn’t wait to get in and push the platform to new limits.  I’m very grateful for this opportunity and I still talk to a few people, although to be honest it seems like a different time & world…

2015:
My ego got the best of me.  I had been promoted at Accenture twice and seemed to be on the fast track to success.  Yet that didn’t stop me from taking a job as a VP of Marketing Automation (I really liked having that title) at an agency in Milwaukee, WI towards the end of the year.  In part, it was me proving to myself I could make it in the agency world, but it was for all the wrong reasons.  Even still, I was beaming with excitement as the year came to a close. The sky was the limit and we were going to conquer the market place!

James Pellizzi
My shiny new VP mugshot



2016:
I don’t have anything bad to say about the agency I was working for, but I learned the meaning of, “Too many cooks in the kitchen,” first hand during this year.  We were among the first Pardot partners and what I felt was working, I poured all my effort into.  Slowly, but surely our client list was growing and I was sending regular updates to everyone to make sure I wasn’t operating on my own. Even still, my vision at times came into conflict with the other leaders and eventually sapped my energy.  I’m still not sure if I was right or wrong to feel this way, as it wasn’t my company and I really wasn’t treated badly.  

2017: 
I went out on my own.  I figured if I could build a practice for someone else, I could build it for myself.  The early months were fueled by my excitement.  I had taken a risk and was determined to make it a reality.  I also realized I took my busy routine for granted and began to feel bits of anxiety as I had been going 100 mph for so long and now I was at an abrupt 0.  Doubts about whether I was actually ready for this began to creep in.  Although, I used them as fuel to get my business up and running, come up with my brand and get some clients.  Strategic Digital Marketing was born and the mission was to help clients get the most out of their Marketing Automation platform.  I also advised them on how to tie together all the digital marketing components using the platform, and picked up new skills in SEO, PPC and Social.  

My primary offering was helping companies get the most out of their Marketing Automation platform and building confidence.

By the end of the year, I had a handful of small, but happy clients…but trouble was on the horizon. I was pursued by a start-up Salesforce shop in Milwaukee and routinely turned down their offers to hire me.  After being bullied into it and promised the world, I decided to give it a go.  I began working for two entrepreneurs who at first seemed to love my high energy and ability to get things done.  I was in charge of Marketing Automation and Marketing Services. I was directed to sell big and was promised resources to do the work would come after the deals were signed. 

2018:
Easily the worst year of my career. The honeymoon period at my new employer didn’t last long. I found myself working around the clock and on weekends, playing whack-a-mole because the Calvary that was promised never came.  The floodgates began to open and we started having lots of disgruntled clients.  I started to feel like a conman because I knew what I was selling couldn’t actually be completed, but leadership didn’t seem to care as long as the bottom line looked good.  I was dealing with familiar problems around taking on too much and being judged on what wasn’t going well. Nevermind the fact that two practices had been launched after multiple failed attempts by these men. It was all terrible and I’ll never forget any of it.

Luckily, I had a vacation planned after everything came to an end.

Reaching a boiling point after communications completely broke down, I left this company in spring of this year.  I felt like I had been punched in the gut.  My credibility in the Salesforce world was shot and I was told I wasn’t a leader and had failed.  They offered me a position as a salesman, which made my blood boil (of course they wanted to keep making money off me).  I swallowed my pride and accepted my fate. I remember sitting on a beach in Alabama with my family afterwards feeling stunned, angry and exhausted.  I also harbored concerns that this was the second time in less than two years I’d exited two start-ups that should have been excellent opportunities. Was I a difficult and ungrateful person? I also wondered if I wouldn’t be the last one to leave the company, and if so, the writing was on the wall and I had been shown first hand all the things a good business leader doesn’t do…quite a silver lining. I knew it would take time to find the answers to both those questions.

At the same time, I knew what I was going to do.  I’d rebuild Strategic Digital Marketing, which had been sitting idle as a back-up plan from the beginning.  This time I was ready and wanted help.  I found an adviser and partnered with other entrepreneurs to offer more than just Automation consultation.  If the night is darkest just before dawn, I felt like early 2018 was that, as by the end of the year, a few previous clients signed back on with me, I had my energy back and I had a local law firm that was willing to take a chance on my digital marketing methodology…

Back in business, ya’ll.

2019: 
Strategic Digital Marketing changed it’s name to James Pellizzi & Company.  I felt strongly that it was my reputation on the line and I wanted to prove to clients and the marketplace that we’d take good care of them and take all of their marketing efforts to the next level, especially ones that had failed in the past.  If we succeeded, I’d reap the rewards.  If we failed, it was on me (and all the more reason not to).  With a team of experts in place, over the course of the year we managed all marketing efforts for 6 clients.  This included aligning the right people, processes and technology as it relates to Marketing including SEO/PPC, Email, Social, Web, Automation, Traditional and CRM.  Everything is done with increased brand exposure, lead generation and customer retention at the top of our minds (and we can help with your story, too).  Our mode of operation? Slow, but sure. Our difference maker? We want to (and will) be around for the long haul.

By the end of the year, we moved into a new office, culled a team of 8 contractors (all experts in their fields) & 2 full time employees, received multiple recognition as a top Marketing firm in Milwaukee and began formalizing some of our business processes…all boot strapped instead of funded by venture capital.  I feel strongly we have something special..and a foundation in place for it to grow.  It’s been an amalgamation of the past 10 years and I’m very proud it.

Devin Grainger joined as an Account Executive in the Fall of 2019.


I wouldn’t change the journey I’ve been on for anything and I feel very fortunate for all the experiences…


My new years resolution?  Introspection has a purpose and has helped me a lot, but I’ve analyzed everything to death.  We’ve got everything we need…including big plans for growth.  That’s where my focus will be.  Here’s to 2020.

P.S. Stay tuned for a website face lift.

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