Transitioning Careers in a Remote World

Interview by Lisa Cohn, PHR

As a Remote Work Strategist at the Ignite Career Center of Jewish Community Services, I am fascinated by remote work trends, onboarding and mentoring processes, successful career transitions, and challenge and success stories. Recently I had the opportunity to interview a high-level financial professional who has been in the industry for over 20 years. Going from Managing Director of Finance at a mortgage lending company to Manager of Sales Finance at an innovative specialty food and snack company, he was able to navigate a successful remote career transition, while also gaining personal and career insight throughout the process. Here’s what he had to say about his experience. 

Give us an overview of your current role and company. 

I started to work remotely this past May at a specialty meats/snack company headquartered in Seattle. In my role, I support and manage the Sales Finance Department, handling $400 million in sales. I’m responsible for profit & loss income statements, annual promotional trade planning, customer and product financial forecasting, and trade financial support for customers’ requests for proposals. 

How did you feel about your remote job search process? How was it different than before? 

I actually enjoyed this job search process more than I expected. I thought it was neat that I was able to ramp up my career even in my mid 50s and was shocked how many companies responded to me favorably online! I spent more time than normal getting my resume crafted, as I felt that this was the way to really show employers where I could add value to their businesses. I worked closely with a family member who is a career coach and certified resume writer, and she showed me how to leverage job sites and add key words/terms to my resume to grab the attention of employers.  

What was your experience transitioning from a large to small company?   

My past financial and management experience working at one of the world’s largest food and beverage companies and at another Fortune 500 company and growing leader gave me opportunities to work with staff, vendors, and management at all levels. I’ve noticed that working at a small company brings benefits like getting to know my team better as we work more closely together and working directly with the CEO (instead of a more rigid chain of command in the past). Both have strengthened my relationship building and taught me to be more patient overall, as I want to nurture these relationships. I’ve also enjoyed that there aren’t issues related to backstabbing or corporate abuse in this smaller company environment.  

Do you enjoy working in a totally remote role? Are you finding that there are challenges? 

I don’t mind working remotely and appreciate not having the commute. I’m saving money by eating at home, not paying for parking, and avoiding wear and tear on my car. I enjoy the aspect of being able to manage my own schedule from home and having fewer interruptions. I do wish that I got out a bit more! Sometimes the boundaries are blurred with home/work when working remotely. But that is how the world is revolving right now and we just have to adapt! I’m learning to set a routine and make sure that I get out for at least an hour a day for some fresh air. I’m also still getting used to my evening meetings/phone calls, but that’s expected when you work remotely and have customers and teams in different areas. 

Describe your remote onboarding process for your new job. 

It was very different than my last job’s process. I’m used to having a strict checklist related to colleague/vendor/management introductions, formal meetings, and assignments, and this was the opposite. It was more informal and I initially felt like a deer in headlights! There weren’t many social opportunities to meet colleagues, so I needed to be resourceful and make it happen for myself. Luckily, I was able to utilize Microsoft Teams to find individual and team documents and schedules, leave notes, and meet colleagues.  

What advice would you give to someone in their 50s seeking a job in today’s job market? 

It’s never too late to change your career! Stay relevant and current, be on top of any trends and standard operating procedures in your industry/field, and write down your career goals. Keep up with the most current technology needed for the job you want to show that you can keep up with your younger competition. Do your homework before any interviews! Research the company, including their website, social media presence, financial reports, etc. so that you are prepared! Also, find out what their competitor’s advantage is and be able to explain what experience you can bring that someone who is “green” may take years to learn.  


This professional’s inspirational journey demonstrates that everyone can take their career into their own hands if they heed these five tips: 

  1. Write down your career goals and figure out what makes you happy  
  2. Take risks and go out of your comfort zone 
  3. Realize that age is just a number and doesn’t dictate your career path 
  4. Stay up to speed on current industry technology and software 
  5. Stay positive and patient throughout your career journey, even when things are tough 

Ready to make your own remote career change? Contact Ignite to get started today! 

Lisa Cohn, PHR is a Remote Work Strategist at the Ignite Career Center of JCS

Whether you are new to the job market or a seasoned professional, the Ignite Career Center, a program of Jewish Community Services, can help you go further and get there faster. Our highly experienced Career Coaches provide individuals of all backgrounds and abilities with the customized services and tools they need to stand out from the competition. To learn more, visit ignitecareercenter.com or call 410-466-9200.

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