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Twin Cities Business Journal 2019 Chief Financial Officer (CFO) of the Year—Calabrio’s Jenny Kray

It came as no surprise to me when the Twin Cities Business Journal selected Calabrio’s very own Jenny Kray as a 2019 honoree for its prestigious “CFO of the Year” award. The only thing that bewildered me was why it took so long!

That’s because—in only two years—Jenny has been a driving force behind several massive initiatives that have helped mold Calabrio into the leading workforce optimization (WFO) software company it is today.

Here’s what I mean.

Jenny helped accelerate Calabrio’s hyper-growth mode while rapidly transitioning it to a Software-as-a-Service (SaaS) business model.

As CFO, Jenny (of course) was expected to help Calabrio continue its aggressive growth. The difference? She had to do it while also accelerating Calabrio’s transition to a SaaS business model—a decision with significant repercussions on financial forecasting and reporting, and product and business decisions.

Despite heady challenges, that’s exactly what Jenny did. Under her guidance and watchful eye—and by tapping her extensive SaaS experience—Jenny flawlessly implemented a framework and the many processes Calabrio needed to operate as a scalable and global company. For example, she helped accelerate Calabrio’s transition to a cloud-based software deployment and SaaS-based pricing model; implemented new enterprise resource planning (ERP), human capital management (HCM) and automated reporting applications; and expanded Calabrio’s Salesforce customer relationship management (CRM) implementation to support the automation and scaling of Calabrio business processes.

Jenny also lent her pragmatic viewpoint to Calabrio’s platform integration and buy-versus-build M&A strategies, which helped us more than double our recurring revenue from 2016 to 2019.

Which leads me to my next point…

Jenny helped Calabrio grow strategically through acquisition, and think and behave more globally.

If all of the above accomplishments weren’t enough, Jenny also led the financial aspects of the due diligence and operational integration efforts for two key acquisitions Calabrio made in the last two years: Swedish workforce management software provider Teleopti in 2019 and Vancouver-based contact center business intelligence (BI) software provider Symmetrics in 2017.

The Teleopti acquisition alone immediately grew Calabrio’s headcount by 50 percent—increasing employee count from 400 to 600 in one fell swoop—and significantly expanded Calabrio’s international footprint.

Beyond these two acquisitions, Jenny also helped all of us at Calabrio develop a stronger international mindset in everything we do. For instance, she introduced to Calabrio’s product development team the integration framework eventually used in our first international integration. She also participated in an exclusive program sponsored by the Mayor’s Office of London where she and 14 other finance and technology leaders mentored female Imperial College graduates who now operate their own technology companies.

Jenny’s become a trusted resource, both inside and outside of Calabrio.

Jenny’s interesting perspectives and insights have been shared via articles and videos like “CFO Thought Leader Podcast: The Race for Real-Time Data” and TechDotMN’s “Calabrio CFO Jenny Kray’s Advice on M&A Deals.”

But what Jenny really loves to do is share her expertise with fellow Calabrio team members, students and peers. That’s why she:

  • instituted internship programs at Calabrio and her previous companies to give college students hands-on experience in their respective fields;
  • participates in The Collaborative CFO Workgroup, a forum where top Minnesota finance executives come together to share, learn and problem-solve financial best practices;
  • sponsors Calabrio’s Women in Technology (WIT) group, which provides a variety of activities—such as technology trainings and exercises, fireside chats with female leaders, lunch-and-learns, events for local Girl Scout troops, and offsite visits to WIT seminars and other WIT groups—geared toward advancing women’s role in technology;
  • mentors aspiring business owners on how to run a business;
  • prepares taxes on a pro-bono basis for low-income households;
  • mentors female MBA students at Minnesota’s University of St. Thomas; and
  • acts as an executive sponsor and is heavily involved with Calabrio’s “Bring Your Child to Work” annual event.

Through it all, Jenny maintains perpetual ease, confidence and composure, presenting a seemingly unflappable appearance despite the inevitable chaos that presents itself to someone in her role.

As the top CFO I know, Jenny truly is in a class of her own. Every day I’m thrilled she decided to join Calabrio two years ago. And I can’t wait to see what the next two years bring.

Congratulations, Jenny!

Rebecca Martin
As Chief Marketing Officer at Calabrio, Rebecca is responsible for lead generation and pipeline marketing, content strategy, customer marketing, and corporate communications. An unflappable veteran of Minnesota’s emerging technology industry with nearly 20 years of experience, Rebecca has been entrusted with millions in venture capital and the formidable task of building lead funnels, and differentiating and positioning entrepreneurial brands. Most recently, Rebecca was Director of Integrated Marketing for Code42—a data protection and security company—where she fueled a content-driven lead-gen strategy, customer engagement/advocacy and communications initiatives. Prior, Rebecca held marketing leadership roles at Trissential, Stellent, and Oracle. Rebecca holds a B.A. degree from the University of Wisconsin.
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