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July 16, 2019

Lead(H)er: Terry Ladisheff, Chief Revenue Officer at Loadsmart

Like many startup veterans, Terry Ladisheff considers herself a builder. But for her, it’s not enough to create something new⁠—she prefers a bit of pressure while she works. 

“The thing I love about the building stage is laying a strong foundation to help a company scale through really rapid growth” said Ladisheff, the Chief Revenue Officer at Loadsmart. “After things are a bit more established, I find the work a little less energizing. 

Though Ladisheff has held many roles throughout her career, from operations manager to vice president to chief operating officer, she has constantly sought out companies in the midst of dramatic growth. 

Ladisheff began her career in consulting before progressing into a sales operations role at Monster.com, where she discovered a passion for both operations and high-growth companies. After nearly three years there, Ladisheff moved to Yahoo!, leading sales operations and financial planning as a business operations manager. 

“At that point, I had been playing a hub-of-the-wheel, operations-type role at those companies, and I found that I really enjoyed it,” she said. “I was helping build skilled teams in a rapid-growth environment and wanted to continue doing that.” 

In 2007, Ladisheff began a five-year run at LogMeIn, beginning as the Director of Sales Operations and adding a position as the Vice President for User Services and Operations to her responsibilities. There, she helped establish sales operations functions and lead the global user services division, a new experience that she welcomed. 

“I try to continue learning, expanding my scope, and mastering different skills,” Ladisheff said. 

When LogMeIn shifted from building mode to the maintenance stage, Ladisheff knew it was time to find another construction project. She became the Chief Operating Officer at GearsCRM, a Salesforce implementation platform, and led the company’s best practice internal operations, talent acquisition, and other internal functions. 

“When I left that role, I was focused on finding another expansion-stage, rapid-growth company that would give me the opportunity to transform a market,” Ladisheff said. 

She found Loadsmart, a logistics platform, and began the next phase of her career as the company’s Chief Revenue Officer in September 2018. In that role, Ladisheff is working on building and scaling the company’s sales organization. She oversees the sales team’s go-to-market efforts, sales operations, marketing, and the integrations team, which focuses on pre-sales support and integration implementation for new clients. 

Cultivating a strong, cohesive team has always been a priority for Ladisheff, who has mentored participants in the MassChallenge program for the last year. 

“I find solving the hard problems that allow you to scale efficiently over the long term with a high-caliber team to be so fun and energizing,” Ladisheff said. 

Looking forward, Ladisheff is committed to continue building, learning, and mentoring both within Loadsmart’s offices and beyond. 

“My work has always been about solving interesting, hard problems and pulling together effective teams that work well together, so I foresee continuing to do that over the long term,” Ladisheff said. 


Quick Q(uestions) and A(dvice) 

What do you enjoy doing in your free time? 

My free time is all about family. I have a six-year-old and an eight-year-old, and we have a puppy as well. Free time is all about spending time with them and my husband. 

What are some of your strategies for managing stress? 

I tend to stay pretty even-keeled. I prioritize⁠—I think that’s probably my key strategy. I also try to keep things in perspective. If I’m really stressed, it’s always refreshing to take a walk and a deep breath. 

How many cups of coffee do you drink in a day? 

I’m a tea drinker, so I have one or two cups a day and switch between decaf and regular. 

What do you consider one of your greatest accomplishments up to this point? 

I would definitely say building high-performance teams, and Loadsmart has been a great example of that. It’s really humbling to work with such a fabulous group of people, and I think I’ve been able to pull together an amazing team here. Having a role in bringing a group together like that is really fun. 

How does where you are right now compare to where you saw yourself 10 years ago?

Ten years ago, I was running sales operations at LogMeIn, and I was about to take a little bit of a tangent opportunity for a couple of years to run the global user service and tech support team there, which was very new for me. Looking back from then to now, I’ve done what I expected to do, which is to try lots of different opportunities. Another big difference is that I didn’t have kids⁠—throwing them into the mix is a big difference, but nothing could be more rewarding. 

What’s your advice for recent college graduates? 

Be confident in your voice and in the contribution you can make. At the end of the day, it’s about assessing the business problems in front of you and being confident in your ability to take them on, and then sharing that. If you work hard and keep perspective, you have an opportunity to set your sights on something that you really want to do and go after it. 


Samantha Costanzo Carleton is a Contributor to VentureFizz. You can follow her on Twitter @smcstnz.

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