May 10, 2017

Lead(H)er: Holly Chessman, VP of Marketing at Glance Networks

“When my college guidance counselor found out I spent four years studying writing, I remember she said, ‘You’re never going to find a career. Why didn’t you major in something more practical?’”

“The funny thing is, writing has been the core of my career,” Holly Chessman the VP of Marketing at Glance Networks said with a laugh. “I’m one of the few people who actually uses their college degrees on a regular basis.”

Holly grew up the middle child of five siblings in New Hampshire. Her parents taught her the best way to go about life was to figure out what she liked to do and then make a career out of it.

As a child, she loved singing, acting and all things creative. When she got accepted to the University of Michigan, she decided to follow her passion and double major in creative writing and communications.

After college, Holly decided to do some exploring before starting her career.

“I worked in Alaska for about six months or so. It was a lot of fun and had nothing to do with what I wanted to do. I just thought, ‘Alaska sounds cool and I just graduated from college, so why not?’”

After Alaska, Holly decided to explore Israel. Although she initially planned for a short trip, she ended up living in Israel for about four-and-a-half years. Once she realized she was staying, she started looking for a job.

Holly Chessman at Speed Networking Event“At that time, there were a lot of tech companies in Israel but not much call for people who did marketing. However, there was a lot of need for technical writers so I started my career doing tech writing at a company called New Dimension Software, which was later purchased by BMC Software.”

When they were purchased by BMC, a marketing position opened up. Although Holly liked technical writing, it wasn’t where she was looking to stay so she jumped on the new opportunity.

“Technical writing gave me a good background for understanding how products work. It was really my first introduction into the high tech world. But as a creative, I was super happy to move out of that and into more abstract work.”

Holly stayed at BMC for a few years as their Senior Marketing Writer. When she returned to the US, they asked her to work in their California office where most of their marketing team was based.

“They told me if I wanted to move to California, I could stay in the marketing team. If I wanted to live in Boston, I could go back to the tech writing. I didn’t want to go back to tech writing so I started looking for something else.”

Holly found a small startup called and worked as their Senior Marketing Writer for a while before they were purchased by Ariba. After they were bought, everyone working for was laid off and Holly was on the job hunt once again.

“I ended up being a Senior Marketing Writer at MatrixOne, which was later purchased by Dassault Systems. You can see a trend here; almost every company I’ve worked at has been purchased by another larger company. I worked for MatrixOne for a few years and I went straight from there to working for Guardium, which was later purchased by IBM.”

During her time at Guardium, Holly started doing more than just writing. She expanded into coding websites, working with PR companies, helping with pitches, working with vendors and collaborating with designers.

“Only ten people worked there when I first arrived, so I was the entire marketing team. If we needed something, I had to go do it, which was a great experience for me. It made me think about what marketing meant beyond writing.“

After Guardium, Holly went on to Davies Murphy Group, an integrated public relations, marketing and strategy company. Assisting larger organizations, Holly liked the diversity of working with a wide variety of companies and helping them fill gaps wherever it was needed.

“The Davies Murphy Group inspired me to create my own consulting company, which I’ve continued on and off over the years. I called it ‘Holly Chessman Marketing’ - a super original name. It was a good time for me to leave my full-time job and start my own consulting group because I was having a lot of babies at the time. I have four kids, three of which I had in rapid fire succession around that time and I had a lot going on.”   

Through her consulting work, Holly found her next job working at Empirix. She ended up doing so much work for them, they eventually decided to bring her on full-time.

“While I was at Empirix, I had an opportunity to grow and stretch. My manager at the time was really great. If there were ever any areas that I wanted to explore, he’d let me go ahead and do it,” Holly smiled.

Her experience at Empirix made her realized how much marketing was changing. It was no longer just print ads, brick and mortar style websites, data sheets and white papers. Social media, ebooks and infographics were on the rise and marketers were starting to reach out to a higher level audience.

“Marketing was now about blogging and bringing people in. It was about showing yourself as a thought leader, not just through a publication you had to use your PR company to get into. It was about publications like Medium or Linkedin where you could just start writing without having to get approval. That was a great eye opener for me and it also refreshed my interest in marketing.”

After about three years, Holly left Empirix and went back to her consulting company. This time around, she was inundated with requests.

“At that point in particular, I had made so many connections with people from the different jobs I had worked at, the many social media connections from my time at Empirix and from all the events I had attended. The range of people that I knew was amazing. The first time around, there was a little bit of scrambling. The second time around, I couldn’t even accept all of work that came to me.”

Similar to Empirix, Holly started doing some consulting for Glance Networks and her role grew to the point where they eventually asked her to run their marketing department.

“Glance is wonderful company to work for. There are a lot of women here which is really not something that I’ve seen at other tech companies. Everyone here is smart, motivated, driven and excited about what they do. Everyone here wants to hear input from everyone else. No one cares if you’re a male or a female, if you’re black or you’re white, if you’re short or you’re tall or if you’re green or purple. If you do your work well and if you’re smart, we want you here.”

Rapid Fire Questions

What’s your favorite thing to write about?

I would say I like to write about anything I get passionate about. I write for Forbes about a lot of general marketing topics and concepts that I think are really interesting. I also write for a publication called Maximize Social Business where I write

Holly Chessman at Salesforce Event
At Dreamforce

about really cool pieces of social media. I still write stories for my kids, I make little books for them, which is really fun.

As long as you’re excited about what you’re writing about, writing is really fun. I think the reason I was getting me kind of bored about marketing a few years back was because it was all data sheets and whitepapers. Although that was interesting to a certain extent, I couldn’t get passionate about it because it was very dry and technical, and there with no real story about something. That’s what I like—the story.

Consulting versus working for a company, do you prefer one over the other?

I don’t have a preference. I just like working in a situation where it’s a little bit scary because I’m almost out of my comfort zone and I really have to stretch and grow to take on a big honking challenge. Whether that’s through a company or a consulting group, it doesn’t matter to me, as long as I feel like I’m expanding and learning and I’m doing something where I’m proud at the end.

Where is your favorite place in the Boston area?

My house because that’s where my family is—my husband, my four children and my dog. We live in Bedford. My kids are 5, 7, 9 and 15.

How do you manage stress?

I’ve gotten into meditation. I had a very rough health year last year and I found that meditation helped me get through a lot of it. It’s been helpful in a lot of areas, whether I’m stressed about work or my health or my kids. It’s great to be able to have a way to think about your breath, think about the sounds around you and realize the here and now.

What do you like to do for fun in your free time?

I grew up in a very musical family where we all played multiple instruments. I love to sing, play viola, violin and guitar. I also like hanging out with my kids and I do a lot of reading; I like the science fiction and fantasy stuff, like the Harry Potter books or anything by Neil Gaiman. And I love, love, love Doctor Who, from the old stuff to the episodes just coming out.

Holly Chessman and family at Disney
Holly and her family at Disney

If you had to choose one thing, what would you say is your greatest accomplishment?

My kids. There’s no doubt about that. They are four wonderful, amazing children. Of course I think so because I’m their parent and I hope one would think that way. But, when I go to parent teacher conferences and the teacher tells me they don’t have anything to say to me in terms of improvement because they use my kid as a role model, that makes me super happy. It also makes me realize the things that I’m teaching them consciously or unconsciously are rubbing off in a really good way. I’m super proud of them.  

How many cups of coffee do you drink a day?

I actually don’t drink coffee but I drink a lot of decaffeinated tea. I feel like I have enough scary energy on my own that if I added caffeine to the mix, it could be really frightening and I probably wouldn’t sleep at all at night which would make me even more frightening.

Ten years ago, is this where you would have seen yourself?

Yes and no. I would say ten years ago, I definitely would have seen myself being a VP of marketing or a CMO. But ten years ago, I had no idea how social media would play in all of this. Ten years ago, HubSpot was just beginning and there was no such thing as inbound marketing. The technology is always changing.

What one piece of advice would you give to a recent college graduate?

Always keep a learning mind. When you graduate from college you think, ‘Oh my god I’m making the life decisions for the career I want to take’ but the truth of the matter is, there are not many people who don’t, in some point in their life, either change careers or their career path.

I’ve used my writing all throughout my career, but that doesn’t mean my career hasn’t changed. Starting out as a marketing writer and learning the broader picture, learning how to manage teams and learning how to work in a small fast-paced company where you really have to be aware of other things around you—those are all things I didn’t start out doing or learning or knowing.

Brianne Shelley is a Contributor to VentureFizz and an Account Representative at BlueGrace Logistics.  Follow Brianne on Twitter: @MuddleandMix.

Images courtesy of Holly Chessman.