SalesTechStar Interview with Kate Ahlering, Chief Revenue Officer, Calendly

What sales experiences should B2B salespeople focus on retaining while trying to close every deal at a quicker pace? Kate Ahlering, Chief Revenue Officer, Calendly shares some helpful tips:


Welcome to this SalesTechStar chat, Kate. Tell us more about your sales journey in the B2B Tech marketplace and what inspired you to be in sales?

Today I am the chief revenue officer at Calendly, a profitable scheduling automation company making it easy to schedule, prepare, and follow up on external meetings. However, if I go back to when it all began two decades ago, a career in sales was not something I deliberately chose or dreamed about. Both my parents worked in sales and revenue leadership positions and yet landing in sales wasn’t something I had planned. I found myself debating whether or not to pursue a career in sales or marketing. In my first job interview after college, I was asked if I knew the difference between the two. After struggling to answer, the interviewer went on to make the decision for me by responding, “I think you should be in sales.” The rest was history.

My first dive into a sales role began at ACTIVE Network, a global tech platform powering activities and events, where I went on to eventually become a boomerang employee. Shortly after I left for Blackboard, an edtech SaaS company, where I worked as a strategic account manager. Things became really interesting when I transitioned to Glassdoor, where I spent nearly a decade before wrapping up my time as chief sales officer to join Calendly.

What I find most inspiring about sales is the ability to control your own destiny and the opportunity to engage with buyers. You are leading the charge when it comes to driving growth and impact at not only your organization, but also at your customers’. As a former athlete, I find there are numerous similarities between sports and this space, from strategizing goals, to feeding off the energy of competition, to working with teammates, to the dynamics of keeping score. Sales is the heartbeat of the business, and it’s where I thrive as a professional and leader. The work is interesting, fun, high-pressure, and it’s completely correlated to the organization’s success.

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As Calendly’s new CRO, what are some of the immediate processes/goals you’re focusing on? What do you feel incoming CROs should be doing as they take over new teams?

I was attracted to Calendly for many reasons – one of which was the growth and stage of the company and another was the inspiring vision of our founder and CEO Tope Awotona, a non-coder, former enterprise sales representative. The global total addressable market for scheduling is $20 billion; that’s a massive opportunity. Calendly is already profitable and creating a new category for the modern tech stack by essentially solving a universal problem at work when it comes to scheduling.

As I think about all of that, one of my primary focuses coming into this role quickly became accelerating Calendly’s momentum in the enterprise. We launched our Calendly for Enterprise plan nearly a year ago, and today it’s one of our fastest growing segments with companies like Asana, Okta, US Foods, La-Z-Boy, and adopting to drive better productivity and collaboration when it comes to meetings. We need to continue to cultivate more and deeper relationships to help organizations realize the value of enterprise-wide scheduling automation. My second focus boils down to the fact that you’re only as good as the team behind you. Hiring and scaling our sales team is a top priority. Lastly, building the GTM infrastructure that powers our sales and customer success teams to serve our customers as efficiently and effectively as possible is critical to Calendly’s long-term success. As a product-led growth (PLG) company, enterprise sales is a newer muscle we need to learn to flex in order to attract customers with thousands and thousands of end-users.

My words of advice to an incoming chief revenue officer are to be committed, be authentic, and be transparent. These traits are essential to a leader’s success and establishment of trust. In today’s hybrid-remote work environment, it’s important to overcommunicate, be clear with expectations to guarantee alignment, and don’t discount the impact culture and values have on team morale.

Calendly is a remote-first, values-driven company of nearly 400 employees. Culture is something we talk about extensively and we take extra care as a leadership team to create a workplace where we are living it and breathing it every day, even remotely. While competition is in our DNA, so is spirit and camaraderie. Sales is equally about having fun, being collaborative, and being a team player.

Over the past few months, what are some of the revenue generation/sales improvement tactics you’ve relied on to drive team output and business goals?

Calendly is by far a hypergrowth company and we don’t see demand slowing any time soon. There is something to be said about embracing the power of PLG as a tactic when your product’s initial success was founded on the basis of virality. Our customers can harness the value of Calendly in a trial, which is a very effective strategy for upselling and driving users to commit to becoming paying customers. The conversations we end up having with them typically turn into a question about how we can help them scale the platform so they can create an even deeper impact inside their organizations. The success of one department usually grabs the attention of the other departments because Calendly’s value proposition is so evident. It’s clear how the platform transforms the ways they work when it comes to productivity, connection, and collaboration.

Leaning into data more heavily has also increased the team’s performance. Having quantitative insights to help the team prioritize their time is key. For example, Calendly’s product data helps sales teams prioritize where to spend their time and how to build new or existing relationships with customers.

As a sales improvement tactic, we’re spending lots of time designing and codifying processes. A sales organization didn’t exist at Calendly until last year. We’re building the sales architecture to support our growth and opportunity to scale. This means spending significant time on formalizing the sales process, playbooks, and trainings so that as we hire we have a unified approach to share and replicate across new team members.

What kinds of sales tech has helped you and your teams?

The speed of execution can make or break a deal’s chances of closing. Any time we can identify tools that free up our team’s availability so they can focus on more selling, as well as enable our sellers to make more insightful decisions, is a good thing. Without a doubt we rely on tools like Salesforce and Zoom, but also LinkedIn Sales Navigator, Salesloft, and Clearbit to help with data enrichment. We’re in the business of delivering value and connection to our customers, which means showing up to first-time conversations with smart, informed ideas about how Calendly can help grow their business. Tools that give us this kind of rich intent data help us achieve that.

Calendly is another great example of a technology that not only helps shorten the sales cycle, but also makes it more convenient for your prospect on the receiving end. For example, we use Calendly across our sales and customer experience teams to seamlessly book demos with multiple stakeholders via our Round Robin Event Type, easily schedule onboarding sessions that work for our customers’ schedules, and plug Calendly into our inbound lead funnel to drive better conversion.

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Can you share a few thoughts on how you feel revenue teams need to shift their processes and core plans to achieve value through 2022?

In a virtual setting, sales teams have to work 10x smarter and faster to get in front of prospects and customers. The sales game has changed dramatically over the last decade. Those that adapt to this new process of automation will win; those who hold tightly onto outdated views on what sales is with little interest in technology to supplement their team’s efforts will be left behind.

Calendly is one way sales teams can close more deals faster and connect with prospects before the competition does, which means driving more revenue for your company. It’s one of our most popular departmental use cases. Our platform enables customers to speed up their pipeline, seamlessly coordinate team scheduling, automate manual data entry via our Salesforce integration, and reduce no-shows and cancellations through workflows such as automatic text and email reminders. And we’re hearing from our customers directly that Calendly delivers real ROI, everything from increasing the number of demos their SDRs schedule to reducing the amount of time it traditionally takes with hand-offs to account managers.

With this in mind, we recently announced a new way for sales representatives to more efficiently and seamlessly schedule meetings and demos on LinkedIn, where they’re already conversing with prospects. With our Calendly for Chrome and Calendly for Firefox browser extensions update, customers now have the ability to schedule meetings with prospects and their broader communities seamlessly through LinkedIn messaging. This is just one way we’re evolving our platform to meet customers where they’re already working to remove the friction and help them increase their sales pipeline.

Beyond the technology, there is also a cultural argument to be made. In today’s most competitive labor market sales leaders need to double down on smart engagement and retention strategies. As a sales leader, your ability to grow your business is in large part a function of your ability to motivate, engage, and develop your team. Engage your people in a meaningful way, give them opportunities, commit to developing their skillet, and you may find they want to stick around. The employee is in the driver seat, which is challenging companies to be better.

Please share some final takeaways or digital sales/customer communication tips and best practices before we wrap up!

We’re increasingly transitioning into a digital-first world. That doesn’t mean we should forget the basics of sales or become robotic ourselves. One of our company values is “Start with human” and it’s how we approach selling and relationship-building with our customers at Calendly. With a scheduling link, you’re saving the person on the receiving end time, but like any information you send, providing context is critical to showcase that value. Whatever technology or strategy you’re applying to your sales process, optimize your recipient’s time, but in a human way.

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Calendly helps individuals, teams, and enterprises automate the meeting lifecycle by removing the back and forth with scheduling. Today, over 10 million users across 116 countries use Calendly to simplify meetings, collaborate more effectively and efficiently, and drive business forward.

Kate Ahlering is the chief revenue officer at Calendly, where she leads Calendly’s sales, sales enablement, revenue operations, and partnerships functions. Recently, she was the chief sales officer at Glassdoor, where she helped grow the company from less than $10 million in revenue to several hundred million and through a $1.2 billion acquisition. She’s a Limited Partner for Stage 2 Capital.

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