How Gina Ryan is building a world-class Sales Development Team

Motive
Life at Motive
Published in
4 min readJul 7, 2020

Since starting with KeepTruckin in May 2018, Gina Ryan has been a driving force behind pushing innovation, diversity, and fostering relationships at KeepTruckin. It was no surprise when she was promoted to Head of Upper Sales Development.

Her knowledge of the transportation industry remains one of the top reasons that fleets have decided to sign with KeepTruckin. Under her guidance, her teams routinely achieve 100% of their quota targets. She has successfully restructured the way her sales team thinks about the transportation industry, particularly with fleet technology. She did this through extensive research on the industry and market and presented the data to the team to indicate how the industry needs technology and how the market has been responding. Drawing on 15+ years of sales experience, Gina has been able to build relationships with each and every individual on her team and enable them to be their highest performing selves.

A recent recipient of the Women in Trucking Top Women to Watch in Transportation, Gina is a true champion of diversity. Her team is currently the top-performing team in their segment, and it is clear that the diversity of the team is a major driver of their success. Gina is a key advocate of bringing more women in the transportation industry and helping them succeed in their careers. In the Women@KT Employee Resource Group at KeepTruckin, she helps to not only recruit, but to also mentor, sponsor, and advocate for women’s careers in a male-dominated industry.

Gina Ryan (far right) with members of her team.

We sat down with Gina to discuss her recent promotion to Head of Upper Sales Development and what her team will look like as she builds out the new Sales Development Representative organization.

You were recently promoted to lead the Sales Development Representative (SDR) org for KeepTruckin. Can you tell me what makes our SDR team different from others you’ve worked within the past?

Overall I’d say this group is special mainly because of their sourcing power. Historically they have sourced over 65% of all net new logos and that is entirely driven by their outbound efforts. On top of being responsible for new customer acquisition, they are also the ones that win back customers that have left KeepTruckin. There’s a high level of ownership on our team- this group is the driving force behind the right conversations and engaging the right people. They make discovery calls, book demos, and provide super helpful content that sparks interest for potential customers.

Spirit Week at KeepTruckin’s Nashville office

What does career growth look like for your team?

This is the highest moving group within the company. We typically require someone in their role for a year before moving into the Account Executive role but there are a number of micro promotions that you can receive within that first year (SDR 1 to SDR 2 to SDR 3 and so on). One thing that I always tell people is how broad your options are from this role. SDR has a wide level of options in terms of career options. You’re not stuck in cold calling — you work cross-functionally with Customer Service and Customer Success so your options are wider moving forward than other teams. If you want to be a part of revenue growth and a pivotal player in this company — SDR is a great place to start.

Why is now a good time to join?

While we are in an unprecedented time, we are fortunate to serve a customer base that is keeping our world running even during COVID-19. This time has really proved our ability to persevere in overcoming challenges, adapt quickly, break down obstacles, and push forward.

Leading these teams and what excites me the most about this role and organization, is the immediate impact we have on our Mid-Market and Enterprise segments’ overall success and acquisition of New Logo business resulting in increased revenue for KeepTruckin.

Gina and the SDR team at the TedX Women Nashville event

Anything else you want us to know?

I’m a very vocal advocate of Diversity and Inclusion. In addition to my own experience, there is so much public data that proves that diverse teams make better decisions, are more innovative, and more profitable. Hiring and promoting more women and minorities in the sales organization is something we’re all focused on and will continue to be for the foreseeable future. I am personally dedicated and invested in helping each individual in our Upper Sales Development organization with their personal and professional brand development, and getting them to the next level of their career.

Interested in joining Gina’s team? Learn more here.

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