SalesTechStar Interview with Cheryl Boeckman, Senior Vice President of Global Sales, Terra Dotta

SalesTechStar Interview with Cheryl Boeckman, Senior Vice President of Global Sales, Terra Dotta

Global sales and marketing teams had to adopt a dynamic approach through 2020 to serve customer and prospect pain points despite the business or daily work challenges surrounding the global pandemic; Cheryl Boeckman, Senior Vice President of Global Sales, Terra Dotta takes us through Terra Dotta’s experience through the year while sharing a few interesting tech sales tips:

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Can you tell us a little about yourself, Cheryl? We’d love to hear about your most exciting / memorable moments from your time in global technology sales.

Wow, tough question! My career has spanned almost 30 years of providing technology solutions to solve customer’s business needs and alleviating pain points, including experiences that have taken me to all corners of the world. My favorite part has been all the wonderful people and cultures I have experienced along the way, as well as the friends I have made on my incredible journey, many of whom I have had the privilege of serving and working with for decades.

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How have you seen the B2B / Tech marketplace, especially sales teams (processes / roles) change over the years?

When I first began working in technology sales, I was surprised by how many companies were trying to sell something that their customers did not need or at least not badly enough to part with their hard-earned money. This approach wasn’t especially compelling or sustainable. Because of this, I think what has changed is the approach – if you are helping to solve a problem for your clients, then your goal is not to sell something but rather to help them solve their problem. By acting as a business “doctor” who is diagnosing problems for your client and enabling them to understand the underlying contributing factors, you can then help them reduce or alleviate their pain through the use of technology. Another change is that technology to support solution teams has changed/improved exponentially, allowing them to be more effective and productive working with their customers in a manner which is the best fit for the customer.

Could you talk a little about selling during the Covid-19 pandemic: what are some of the biggest strategies or methods you / the team are relying on during this time?

I think the biggest thing is to avoid being tone deaf across marketing and sales and to understand that things are tough for everyone, everywhere. We have spent considerable time connecting with and educating our clients and prospects on what is possible and making sure our clients are leveraging what they already use from Terra Dotta to their fullest capability. We also understand that compliance is a big issue and staying up to date on product features that drive compliance and government regulations are very important and the need to stay on top of compliance is not going away. Also, even in the midst of the pandemic, there is still a high degree of business pain that we can help address for our customers and prospects. Many of our clients are using this “lull” to complete projects they did not have time for in the past as well as helping them to be ready for the business recovery when we turn the corner.

In what ways are you seeing the Covid-19 pandemic impact global sales and marketing processes for B2B / Tech companies?

Global sales and marketing processes must continually adapt to customers’ current and ever-shifting pain points. For instance, we are seeing a huge impact around compliance for international visitors and international students and scholars who are under even closer scrutiny to make sure students, travelers, institutions and businesses are compliant to federal immigration regulations. There is also a high level of uncertainty from organizations and institutions around their risk management processes, procedures and policies; their constituents are demanding that Duty of Care is a top priority. We’ve ensured that our sales and marketing processes incorporate these key issues and are ahead of the curve in providing guidance and solutions. Also, from the beginning of COVID-19, our college and university customers were focused on tracking where their students/faculty and staff were when the travel shut-down started and could communicate through text, chat, email and our AlertTraveler app to make sure their people were safe. With the current lockdowns and the inability to travel, we are now helping them shift focus. This includes helping them pursue virtual options as well as ensuring the right agreements are in place to support expanding institutions’ global footprint moving forward — and preparing for new opportunities in a tougher travel environment.

 How, according to you, should sales leaders use this time to reevaluate their structure and processes as well as the sales technologies they use to enable their teams today?

Sales enablement technology is extremely important, as is keeping track of how your customers and prospects prefer to communicate with you so you can connect effectively and with the right frequency. Above all, sales leaders should respond quickly and with empathy. It is important to remember that our job as sales professionals is to find a solution to the customer’s business issues or pain points, communicate that solution as clearly as possible, and ensure the solution helps drive efficiencies, makes life easier for their employees and supports an excellent constituent experience. The sales structure doesn’t matter as much as ensuring an effective process to determine how to help solve the pain points. If there are no pain points, it’s time to move on to addressing another issue.

Can you share a few ways in which you’ve used sales tech to create better remote sales processes during this time?

Terra Dotta’s team leverages multiple technology tools to help advance sales productivity, ranging from CRM, customer support and business intelligence to online meeting and webinar technologies, lead database providers and proposal solutions. Ultimately, our goal is to use technology in a way that enables our sales reps to use their time as efficiently as possible while empowering them to build meaningful relationships with customers to help solve their business problems. For example, our CRM solution provides valuable information on our customers and prospects, which helps us communicate with our clients according to their preferences. Information that we collect starts on day one.  This information is also shared with our implementation teams – including important discovery information from conversations throughout the client/prospect decision process. This critical information flow cuts out unnecessary time that would have otherwise been wasted rehashing information, thus allowing us to implement our customers faster so they realize the value of their investment with us much sooner.

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We also use a customer support system that is available 24/7/365 for our customers, allowing them to use self-service electronic support tickets, an expansive Knowledge Base including relevant “How To” video libraries, and of course, live phone support. Terra Dotta has been operating in the cloud for years, and in this time of COVID, our customers can access our solutions with a simple internet browser. We support single sign on for added security and other industry-standard security measures are in place. Many of our newest customers have told us they made the change to go to Terra Dotta because their legacy “on-premise” solutions were not available to them or their VPNs were either non-existent or problematic, which made it difficult or impossible to do their job remotely. We have used live video platforms before COVID 19 but now use it for all our meetings until in-person meetings become possible again.

What are some of the biggest takeaways sales, customer success, marketing teams should grab from this entire experience of working and living through a global pandemic?  

There are many, but I think the most important one is that we are all in this together, we can help each other get through this and we will come out the other side much stronger because we have empathy for each other. We are partners through thick and thin. We are listening and will adjust to whatever this pandemic throws at us. Teams should let their customers know that they aren’t going anywhere and are committed to helping them through the global pandemic. At Terra Dotta, we’ve been around for 20 years and we are committed to our market – our strongest message is that we are here to support our clients.

Another key takeaway for teams is that time management and prioritization is now more important than ever. Before COVID-19, we were sitting on a plane for hours and socializing with clients or prospects in person at conferences or meetings; we must make sure our time is still invested in client and prospect relationships. Teams should think creatively about how to maintain current and build new connections virtually.

What are the five tips you would share with tech sales and marketing teams to prepare better for 2021, in the new normal?

  • Don’t Choose Technology for Technology’s Sake – The issues you are trying to solve should support the price tag – both for the people and software.
  • Be Flexible and Nimble – There will be many more curve balls thrown at us during and after this epidemic. Be flexible enough to react and react in time to help clients when they need it.
  • This Too Shall Pass – Enable the future users and constituents to benefit from your software solution. In our business, the students who have always yearned to study abroad, attend a university as an international student, or travel for research or otherwise on behalf of their institution are not going away. We are here to educate them on the risks and help them do all these things within regulations as safely as humanly possible.
  • Maintain Your Reputation – Keep your credibility high in the marketplace and keep trying hard to understand the key business issues at hand.
  • Be A Problem Solver – Focus on the continual changes and challenges that clients face now and post-COVID and work to solve those issues.

A few secret tips to sales success you’d share with B2B tech sales reps?

We hire and train professionals who want to solve our customers’ business problems and want to build a partnership relationship rather than just serving as a vendor. Our team truly cares and has empathy for our clients and strives to be a trusted advisor. With this approach, clients will know that their partner is in the foxhole with them – and that they will be by their side in good times and bad.

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There’s more to B2B and Tech Marketing and Sales than meets the eye in 2021 and Beyond! Catch more here where leaders from Ness Digital, TeamViewer, JotForm, Xactly and others weigh in!




Terra Dotta

Terra Dotta provides higher education travel, study abroad and international program management solutions.

Cheryl Boeckman is the Senior Vice President of Global Sales at Terra Dotta