Annamarie Madaczky on Remote Career Development

Posted by SkillSetz Team on Jan 19, 2022 8:57:32 AM

This interview was conducted by David Liu and was originally published by Authority Magazine

As part of our series "How To Advance and Enhance Your Career When You Are Working Remotely", I had the pleasure of interviewing Annamarie Madaczky.

2022-AM03Annamarie is the Senior Vice President of Platform Operations for SkillSetz, a market-leading Talent Procurement Platform built for today’s modern enterprise. Annamarie is an award-winning Technology and Design leader with more than 15 years of progressive professional experience working on B2C and B2B enterprise software development and implementation projects for clients ranging from SMB customers to Fortune 100 enterprises. Annamarie was part of the founding team at SkillSetz and today leads all Platform Operations, which includes the product development, user experience (u/x), and global design teams.

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Career development is the ongoing process of choosing, improving, developing, and advancing your career. This involves learning, making decisions, collaboration with others, and knowing yourself well enough to continuously assess your strengths and weaknesses. This can be challenging enough when you work in an office, but what if you work remotely? How does remote work affect your career development? How do you nurture and advance your career when you are working from home? How can you help your employees to do this? 


Thank you so much for doing this with us! Before we dig in, our readers would love to get to know you a bit better.  What is your "backstory"? 

I have always been a creative person for as long as I can remember, so it came as no surprise in college when I found myself gravitating towards a career in Digital Design. It was one of those things that came naturally to me and it never felt like work when I was focused on designing things. I knew that is how I wanted to make a living. Shortly after graduating, I was fortunate enough to land a job with one of the largest Marketing agencies in the midwest that served a lot of blue-chip clients. The hours were terrible and it was a cut-throat business, but I had a lot of fun, I learned a lot, and I gained a lot of experience that I still lean on today.

Roughly five years later, I was recruited to lead the Design Team at a B2B Enterprise SaaS start-up in the Supply Chain industry. The experience really opened my eyes to what is possible with software development because I was now being asked to support both software development as well as marketing design work. I found myself embedded with highly experienced software developers and systems integrators working on B2B software implementations for the likes of McDonald's, Kimberly Clark, Disney, Caterpillar among many other amazing companies. It was a great experience for me and I was able to build a really strong professional network during that period that really helped elevate my career.

A little more than three years ago, the CEO of SkillSetz, Matt McCarrick, called me up and told me about this idea that he had. He asked me if I wanted to help him build an amazing software company based on the belief that every human being is great at something. Everything about it felt so right, so I jumped at the opportunity and I have never looked back.


Can you share the most interesting story that happened to you since you started your career?

If I think about my career trajectory, I would have to say that the most interesting thing to happen to me also happens to be the worst professional experience of my life. I am referring to the day I got let go from a job that I loved at a company that I was fully dedicated to. I’m only able to call it “interesting” now in hindsight because I know what happened afterward. At the time, the more appropriate word was “devastating”.  

I was in utter disbelief. I was all-in for this company. I would come in early. I often stayed late. I was absolutely crushing it from a work product standpoint. There was literally nothing I wouldn't do to help the company and our customers succeed. None of that mattered when the sales team had a few slow quarters and the venture capitalists wanted their pound of flesh. It is only when tested that loyalty can truly be measured.

As rough as it was, it taught me something extremely important about myself that I didn’t otherwise know. I was a lot tougher and a lot more talented than I had given myself credit for. Yes I was freaked out, but I was a single mom with two little ones counting on me for everything. It was more important for me to model the right behavior for my kids by showing them how I was pushing through fear, standing my ground, believing in myself, and embracing change.  

It was like a switch was flipped inside me. I no longer needed a company or a logo to validate my worth and value.  Never again would I dedicate my talents to an employer or a customer who was unworthy of me. Never again would I give someone that much control over my happiness and the happiness of my kids. I can honestly say that horrible experience - and the way that I processed it - ended up being perhaps the most significant inflection point in my entire career. Everything about my professional life got so much better after that.


Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I am a creative person and I pride myself on always giving my best and highest quality work to my clients and colleagues. I can do many things, but sometimes clients ask for the impossible. 

Like the time that I was working on an adpiece for a new client. He was super-enthusiastic, very involved in every step of the process. He would call up individual members of the team to get sneak peeks at things we were working on, and had almost no regard for the review process we had established in our onboarding meeting. But he was a new client and I wanted to make sure he was satisfied. One day, he came into the office to talk about the ongoing engagement. He approached me in the coffee room and asked to see the adpiece I had been working on. Eager to please, I went back to my desk and printed it out. I handed it to him and waited for his praise. He said nothing. He just sat there staring at it. I began preparing myself mentally for a complete dress-down in the seconds it took him to take it all in. Then his only comment, and by the way he was MAD, was “Why did you waste all this time writing the ad copy in Italian?” 

Of all the things he could have been giving me feedback on, he was questioning the COPY, and I wasn’t even in charge of that. I was the designer! But I kept my cool, took it back from him, and suddenly realized his confusion. The actual copy wasn’t even in there. I’d used standard lorem ipsum placeholders to keep the design part of the project on track while the copy was being finalized. It probably took me 10 minutes to explain what lorem ipsum was, and when he finally let it go, he told me to just send the final proofs to his Gmail account because he didn’t have email. I smiled and promised I would, without explaining to him that Gmail is email because that wouldn’t have helped the situation at all. 

I learned a lot from that experience - like the importance of having and adhering to a complete project plan, managing expectations by sharing context with clients, not to mention when and how to correct an important client. 


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

Life is a mirror and will reflect back to the thinker what he thinks into it. (Ernest Holmes)

It’s entirely too easy to get comfortable with negative thinking, but I’ve learned that whatever energy I put out there comes back to me. Negative or positive - it always comes back. So I choose whenever possible to emit positive energy. As a result, I’ve discovered I’m more capable of doing helpful, creative things when I share positivity with the world. I believe that we are all magnetic and that we attract what we put out there. That’s why I surround myself with positive, hopeful, open people whenever possible because that is what I want to be mirrored back to me. 


What advice would you give to other business leaders to help their employees thrive and avoid burnout?

Burnout is a huge issue for employees and employers alike. My two best pieces of advice for employers are (1) to encourage work/life balance and (2) to work on communication across all fronts. 

Employers can reduce employee stress by showing that they understand their team members have lives beyond the workplace. They can help them with setting and maintaining boundaries. We are all too connected - why not advise employees against checking their emails or pings after hours? They might check anyway but by making it clear that this is not an expectation of the company culture,  that goes a long way towards making sure employees are ready to dig in and work hard when that is really needed. Streamlining the workflow is also critical. When employees have visibility into what their colleagues are working on, they understand where their own contributions fit into the grand scheme. It’s both motivating and exciting. I’ve seen it drive success, especially when a team is distributed or working from home. I also believe that leaders need to offer workers the flexibility and trust to work their own best schedule. Technology allows us to coordinate tasks, timelines, and priorities better than ever before.* published some research earlier this year that I found really interesting. It highlighted the challenges of remote work and burnout, which was exacerbated by the Covid 19 pandemic. It’s clear from that report that flexibility and boundary-setting are key determinants of successful healthy workplaces.

I cannot stress how important communication is for a distributed workforce. It’s important to think about not only WHAT is being shared but also HOW it is being shared. Email or phone? Zoom meeting or Slack huddle? Leaders should evaluate what they are trying to communicate before choosing the method for communicating. They should also make sure that their teams know when and how to choose a communication tool. Having crystal-clear communication guidelines that all parties can understand makes the workflow more easily all the way around. And remember, people may not be coming to the office every day, but very few of us would choose to work on an island all by ourselves. By scheduling regular check-ins, talking about work and about life helps ensure that teams are on top of the priorities set and gives leaders insights into any roadblocks they could run into. It’s just good business sense to manage an internal communication strategy as carefully as the external one. 



Ok, let’s jump to the core of our interview. Working remotely can be very different than working with a team that is in front of you. This provides great opportunities but it can also create unique challenges. To begin, can you articulate for our readers a few of the main benefits and opportunities of working remotely?

The benefits of working remotely are huge for both employers and workers. 

  1. Flexible schedule. Start times/end times vary with the ebb and flow of the home schedule. This is great for natural early birds or night owls, and for people with families to manage. 
  2. Zero commute time. Can we all agree that rush hour traffic is just the worst? It also saves money on gas and tolls, not to mention walking through the kitchen to get a cup of coffee versus heading to a drive-thru!
  3. No office distractions (or water cooler drama) to navigate or supervisors lurking over the shoulder. That kind of trust is critical in today’s remote work environment. 
  4. It’s easier to make calls when privacy isn’t an issue. No conference room? No problem. Just pick up the phone and dial.  

And…. if I’m being completely honest here, being able to wear pajama bottoms absolutely belongs on this list!


Can you articulate for our readers what the five main challenges are regarding working remotely? 

While productivity can flourish in a remote working environment, obviously it is not without its challenges for the team leader or any member of that team.

  1. Individual visibility within the organization can suffer. The team can achieve greatness but the individual parts of the whole are often overlooked. That’s one reason why a very transparent workflow and taking time for regular check-ins with team members is so important. 
  2. If people don’t work at it, team culture can shift significantly. The traditional workplace allowed for, and encouraged, teaming and camaraderie. When the entire team is remote, finding bonding opportunities in different ways is important. 
  3. Maintaining a routine that promotes efficiency can also be a big challenge for those who are new to working from home. Household distractions are different from workplace ones but no less distracting. It’s important to establish and maintain a routine that gets the right work done early on, or team members and overall group productivity will certainly suffer. 
  4. Balance. When team members work from home, they never really leave the office. Workdays can easily turn into work nights. That’s why it’s important that leaders promote a remote culture that engages and respects the individual. It’s why I also put hard boundaries around my team’s availability to me and to each other. We all need work/life balance and as a team leader, I think it’s my responsibility to lead by example. 
  5. Mental health and well-being. Workers have struggled with loneliness and isolation when COVID-19 forced so many into remote-working conditions they weren’t prepared for. Some people are just not naturally built for this; others thrive on their own. Understanding how a  team functions best is critical to thriving in spite of these challenges. 


Based on your experience, what can one do to address or redress each of those challenges? Can you give a story or example for each?

In a lot of ways, the answer to each of these comes down to leadership and the overall commitment to making a distributed group of individuals feel like a team. When a leader is transparent - in terms of goals, achievements, and priorities - team members feel valued as individuals. Gone are the days when managing by walking around is effective. I’m not sure it worked particularly well before the pandemic forced certain changes on the typical workplace. But now? Forget it. Leaders have to connect on a deep level, and they have to be willing to put their own struggles out there too. We all need connection. We all need balance. We all need routine. We all need accolades and accountability. I have been happiest in my career when my leadership has been open, honest, and direct with me, and that’s what I strive to give my own teams. I used to think I got lucky when it came to culture, but I now recognize that luck as something of my own making, my own insistence. Leadership sets the tone of culture, but the team embraces it and carries it throughout the organization. It starts at the top but it can’t end there or it simply does not work. 


Let’s talk about Career Development. Can you share a few ideas about how you can nurture and advance your career when you are working from home and away from other colleagues?

The best advice I can give anyone is to keep learning. Take advantage of any and all opportunities that will help expand your skillset and keep you not just relevant but also sought after. Meaningful learning happens in many ways. Take an online course. Attend a conference - virtual or in-person - and listen in on what people are talking about. Spend time reading up on industry news. For me, I make time every day to learn from some of my favorite industry-focused publications, like Creative Bloq, Smashing Magazine (, and UX Design Weekly (

Networking is also super important in one’s career advancement and development. Take advantage of networking events virtual or in person. I ask the people I encounter what they read, where they learn, and who inspires them. Asking someone else, “how do you prioritize learning?” and getting advice from another perspective has really helped me to up-level my own game. And of course social media platforms, like LinkedIn, have been really instrumental to me making new contacts and uncovering trends in the markets we serve but also in seeing who’s moving and shaking and what they are moving and shaking about. 

Last but not least, I think the biggest piece of advice I can give anyone is to consistently perform at a very high level. Because teams are not in the same location, people don’t just naturally see the hustle and the effort. As a result, the work product is the best example of an individual’s talents, experience, and acumen. People judge the output, so the work speaks volumes about the individual and the teams they run. I make sure that my work is beyond reproach so that my reputation matches my career goals. 


Can you share a few ideas about how employers or managers can help their team with career development?

In my experience, putting resources into a team… their development as individuals and business professionals… is actually a great investment in the business. Early in my career, I met a lot of managers who were afraid they’d train people, only to have them leave. And yes that happens. Not everyone stays with an organization for their entire business lives, and that’s a good thing. We all need new ideas, new synergies, new experiences so we all learn and grow. Leaders who invest in their workers consistently get more productivity, engagement, and loyalty. Who doesn’t want that? Yes, it costs money to send team members to conferences or training programs, but what would it cost NOT to make the investment?


You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

If I really could inspire a movement, I guess I’d want to put my energy toward the same things I try to teach my kids. Always leave everything better than how you found it. Be kind. Be considerate. If someone is having a bad day, make a genuine attempt to connect with them. Share a smile. Acknowledge hard work. Do a good deed. Random acts of connection and kindness really can change the world. I believe that. So put good out there, because good is just as contagious as bad can be. There are ripples far beyond what each of us can see. 


How can our readers further follow your work online? 

I plan on spending the rest of my professional life helping businesses and professionals find each other and create economic opportunities for themselves with SkillSetz. That is the only place I want to be and that is where you will always find me. I’m also on LinkedIn!


Thank you for these great insights! We wish you continued success.