SalesTechStar Interview with Tina Dobie, Chief Customer Officer, Calendly

Tina Dobie, Chief Customer Officer, Calendly has a candid chat with SalesTechStar on her new role and what it takes to drive better customer success initiatives in today’s B2B marketplace:


Hi Tina, welcome to this chat, tell us more about yourself and your new role at Calendly!

Thanks for having me, Paroma! I joined Calendly – a modern scheduling platform helping teams and individuals automate the meeting lifecycle – in September as the company’s first Chief Customer Officer. In my role, I am responsible for the team of Customer Experience experts who onboard our customers, drive product adoption, and deliver world-class customer education and support. Our priority is to ensure our customers are successful with Calendly.

I am deeply passionate about the experience customers have with a product and the value they receive from it so Calendly was a natural, exciting transition for me. Calendly is a game-changer for anyone who schedules external meetings. The combination of a high-value product, a loyal customer base, and an incredible team made this position and company an attractive opportunity.

Read More:  E2open Named A Leader In The 2021 Nucleus Control Tower Value Matrix For Seventh Consecutive Year

For someone who’s usually been in customer facing roles, what are some of the biggest learnings you’ve come away with?

My biggest learning over the years is that companies who deliver an exceptional customer experience are able to do so because they hire the right people, truly invest in their growth, and ensure strong collaboration. Teams who work together – who help each other in service of the customer – create a positive environment that customers can feel in every interaction.

Can you tell us about the different ways in which you’ve driven better customer success and customer experiences through the years?

The pace of business has changed over the years, and therefore, the ways customers want to engage with companies have also changed dramatically, especially as new communication and interactive technologies have emerged. When customers have a question or are stuck, they don’t have time to wait for an emailed response. Organizations that want to deliver a superior customer experience must engage in real-time across the many channels where their customers are in a way that is personalized and empathetic to their situation. As an example of a technique, companies’ use of live chat can deliver excellent engagement and resolution quickly to result in remarkably high customer satisfaction scores.

Another way to drive customer success is to deeply understand your customers’ usage of your product, and apply that rich data to create a monthly scorecard that demonstrates the specific value that is being delivered from your products and services. Customers who receive this type of personalized content, along with recommendations for how to further maximize their investment, respond favorably to a company’s support team, have higher renewal rates, and are more open to opportunities for future expansion.

For today’s customer success and customer service officers, what are some of the biggest observations and challenges you notice teams struggle with and what sales technologies and best practices would you recommend to them to address this?

Fast-growing technology companies such as Calendly, who innovate rapidly, must ensure that teams are armed at all times with the right knowledge and tools to help customers. This is true for all customer-facing roles, including CX and Sales teams.

More specifically, the most successful companies do a couple things particularly well. First, they integrate their Sales & CX systems to get a 360 degree view of the customer across their lifecycle. Second, they create a tremendously strong knowledge-management function that is tightly aligned across the company, where educational content is created for both internal training and continuous learning, as well as customer self-service documentation and in-app contextual help. Applying some of these best practices across your team is critical for increasing and retaining customers in today’s highly competitive, distributed workforce.

Read More:  SalesTechStar Interview With Mary Pat Donnellon, Chief Revenue Officer At CallRail

At Calendly, what are some of the biggest initiatives/plans you’re looking to follow through on as part of your new role?

As cliche as it may sound, our customers are at the heart of everything we do. Calendly is at a pivotal moment in its evolution and within the working world at large. We have a responsibility to make sure our customers are successful across the meeting lifecycle with the right tools, onboarding, knowledge, and support readily accessible. This, along with growing our CX team to better serve our global customer base, is my number one priority.

As Calendly continues to grow and serve millions globally, my primary focus will be on continuing to help our customers be successful with the platform and strengthening the teams who service them. We need to understand where we are doing well and where we have room to improve when it comes to customers choosing to adopt and how they feel about engaging with our platform. Feedback is a gift; as a leader, I strive to listen, understand, and build off our strong existing CX foundation to ensure we are investing in the whiteglove services and initiatives our customers expect of us.

One of the ways we’ll become stronger is by expanding our internal team so we have the resources and people to meet needs and demand. We’re growing rapidly, and our plan is to grow the customer experience team by more than 25% before the end of the year.

For sales leaders looking to scale their customer service processes, what top thoughts would you share?

Meetings accelerated throughout the pandemic. Our customers are proof of that; over the last year, we saw the number of users double across the platform. We see this trend continuing as people transition to a hybrid workforce, which means becoming more efficient with tasks like scheduling will be critical. This will be particularly true for those in customer success and sales roles, where the recipe for success entails being the first to interact; engaging with customers in a seamless manner; improving conversion, retention, and customer satisfaction rates; trading out manual processes for synchronized and integrated systems; and creating a positive experience with your product and support team from the start.

As companies continue doubling down on digital transformation across their organizations in preparation for the hybrid-work future, leaders in these fields should look to automate the redundancies or tasks creating friction so they can focus on inspiring and scaling more continuous human touchpoints. Shameless plug, but a platform like Calendly helps maximize your team’s time while enabling them to focus on creating a stronger relationship with your customers. We’ve seen such strong traction across sales and customer support teams because you can save time with manual tasks like sharing your availability for an onboarding meeting instantly via your personalized link, using team-based event types and Workflows to automate evenly distributing lead requests for demos or sending thank you notes and meeting reminders; and engaging customers post-meeting with a survey link or request for feedback. Befriend the technologies and processes that will help you drive long-term satisfaction among your customers.

If you hadn’t been in a sales/customer service role, what else would you see yourself as?

That’s a hard one! I’ve been working with customers and leading teams to deliver customer success for so long simply because I love it. If I wasn’t directly operating in a customer-facing role, I would most likely work with people early in their careers as a coach and mentor. I would help people discover their passions and guide them to understand what is expected of them so that they can exceed expectations and earn that next promotion. I am filled with gratitude and pride when I see an individual contributor who I hired early in their career grow into a leadership role at an exceptional company. It makes all the hard work so worth it!

Read More: Usability: The Key To RevTech Success

Calendly is a simple, yet intuitive cloud-based platform that helps 10M+ users across 116 countries automate the meeting lifecycle by removing the back and forth with scheduling. Calendly connects with tools like Salesforce, Zoom, HubSpot, and Stripe to automate scheduling workflows and help users, such as sales and customer support teams and professionals, be more productive.

Tina Dobie is the Chief Customer Officer at Calendly, where she brings over 25 years of experience in the SaaS and management consulting industries. She’s built and scaled global teams at high-growth organizations, most recently as the Chief Customer Officer at WP Engine and before that, as the Vice President of Client Services at Bazaarvoice.

Catch our Latest Episodes of The SalesStar Podcast!

Episode 97: B2B Marketing Trends And The Changing Face Of The B2B CMO: With Dave Dabbah, CMO, CleverTap

Episode 96: B2B Sales Intelligence Trends And Best Practices With James Isilay, CEO At Cognism

Episode 95: Enterprise Sales Best Practices With Damien Swendsen, VP Sales At InsideView



B2B marketplaceCalendlycustomer experiencecustomer satisfaction scoresDigital Transformationinteractive technologiesinterviewsPersonalized Content