Authority Magazine
Published in

Authority Magazine

Remote Career Development: Samantha Reynolds Of Helpside On How To Advance and Enhance Your Career When You Are Working Remotely

An Interview With David Liu

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 be able to continually 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 and away from other colleagues? How can you help your employees do this? To address these questions, we started an interview series called “How To Advance and Enhance Your Career When You Are Working Remotely”. As a part of this interview series, I had the pleasure of interviewing Samantha Reynolds.

Samantha Reynolds began her career at Helpside right out of college. For nearly 15 years, she has worked her way through several departments including sales, customer service, and human resources, to reach her current role as Marketing Manager. Her drive to succeed and valuable relationships at Helpside have allowed her to grow professionally without changing companies.

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 went to college at Washington State University and graduated with a degree in Communications. After graduation, I applied to jobs in my desired field of marketing, advertising, and public relations, but I was unable to find a full-time position. I took a chance on a temporary position at Helpside as a Sales Admin, just to pay the bills until I could find something that aligned with my future goals. As you can see that temporary role turned into a career lasting nearly 15 years so far.

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?

When I first started, my role as a Sales Admin was to support the Sales Manager and the Sales Agents. My first week, the Sales Manager asked me to take a package with some books in it to be shipped back to someone he borrowed them from. He handed me a scrap of paper with a name and an address on it. I didn’t ask who the person was or what the address was, even though I found the address difficult to read. I should have asked a few clarifying questions, but out of fear of looking incompetent, I didn’t. As result, I read the address incorrectly and the package never arrived. We were able to track it down through the store I had attempted to mail it from and get it cleared up, but that moment made me realize that asking a few extra questions can save you a lot of work in the long run, even if you think you may look silly for asking.

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

I recently read the book Greenlights by Matthew McConaughey and one of my favorite quotes from that book is, “Great leaders are not always in front, they also know who to follow.” This has been true in my career. I haven’t followed what most would see as a traditional career path. In fact, some might say that opportunities fell into my lap. I would argue that I surrounded myself with supportive people who helped me be the best leader I could be, even if I wasn’t always in the front.

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

Help employees understand the “why” behind your business. Why was the company started? What impact do you have on customers? What impact do you have on the community? Help employees understand what their hard work actually accomplishes.

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?

I have worked remotely for essentially all my career, When I started at Helpside, I worked in a satellite office where only four of us were located. I have never physically worked in our main office. Overtime, as our company evolved, we moved from four of us in a satellite office to working from home and now, I am the only one working for Helpside in my state. Working remotely has allowed me to live in my hometown and raise my family here instead of moving out of state. As opportunities at the company became available, I had demonstrated my ability to work away from the main office and as a result, I was still allowed to take on new roles and responsibilities even though I did not work in-person in our corporate office. Some of the other main opportunities for me have been:

  • Eliminating my commute saving me more than an hour per day.
  • Flexibility in scheduling, so I can be present as a mom and wife.
  • Influencing remote work policies at the company, since I was wone of the first remote employees.

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

  1. Lack of visibility- Often the saying “out of sight, out of mind” is so true, especially when you are one of only a few remote employees.
  2. Lack of communication- It can be hard to get ahold of people sometimes. You may not know if they’re in the office, in a meeting, or on vacation.
  3. Maintaining personal relationships- You don’t bump into people in the hall. You miss out on that “water cooler” conversation.
  4. Managing conflict- Without the benefit of body language, it may be difficult to recognize and resolve conflict with co-workers

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?

  • Lack of visibility- You have to be willing to raise your hand, to volunteer for projects that help you stay visible. This may mean reaching out to leaders in other departments (with the support of your supervisor) to find out how you can get more involved. Talk to your supervisor about available opportunities regularly, so they know you are still interested in expanding your reach.
  • Lack of communication- Learn how individuals prefer to communicate. Maybe one person responds quickly to a Teams or Slack message while another would prefer you to give them a phone call. Also think about the time of day. Are there times when people are typically in meetings? Avoid reaching out at those times, so you don’t get lost on the “need to reply” list.
  • Maintaining personal relationships- You have to be proactive. Reach out to co-workers, just to chat for a few minutes, Utilize all types of communication (chat, phone, email). Don’t forget about small-talk and pleasantries. I have struggled with this one. I’m one who typically wants to get straight to the point, so I have to be deliberate.
  • Managing conflict- If you do the work of maintaining personal relationships, this becomes much easier. When possible, use video calls for tough conversations, so you can see the other person. This allows you to benefit from body language and voice inflection. Tone is so often lost in written communication. IF you are someone who does better with writing, plan out your conversation before you make your call.

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?

As I mentioned earlier, you have to advocate for yourself. Build relationships with leaders in the organization. Ask about opportunities to participate in projects. I highly recommend scheduling regular one-on-one meetings with your supervisor. Have an agenda and explain what you are working on. Ask your supervisor what else is going on at the company that you should know about. Ask what projects are coming up that you may be able to eb a part of. I personally meet weekly with my supervisor, even though he meets bi-weekly or monthly with his other direct reports. Being remote means that having more regular communication is important. Also, plan an annual (or quarterly) meeting to review your accomplishments for the year and share your goals for the upcoming year. This is an opportunity to demonstrate your value to the organization.

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

Don’t get caught in the trap of feeling like a career path must be linear or follow a traditional path. Look for opportunities to grow that be on the same level in the company hierarchy but will allow you to advance your skills and abilities. Demonstrate leadership even if you aren’t leading people by leading projects.

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. :-)

I hope to inspire people to see that non-traditional career paths can be incredibly valuable. I took a chance on a temporary job, found a company I believe in that also believed in me and found ways to grow with the organization. I encourage people right out of college to find a company they want to work for, not a job they want to have. In the right organization, doors will continue to open for you.

How can our readers further follow your work online?

I am most active professionally on LinkedIn and Twitter

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



In-depth Interviews with Authorities in Business, Pop Culture, Wellness, Social Impact, and Tech. We use interviews to draw out stories that are both empowering and actionable.

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store
David Liu

David is the founder and CEO of Deltapath, a unified communications company that liberates organizations from the barriers of effective communication