Published by Calendly - March 29, 2018

Making the dream work with cross-department alignment

Calendly builds a brand with constant collaboration.

If you’re an avid user of Calendly or an admirer of our brand, you’ve probably heard us say that we’re obsessed with providing an elegant, delightful experience for our customers. And it’s true—delivering the optimal customer experience shapes how we develop, design, market and support.

We work hard, move fast and pitch in across departments—and always make time to celebrate our accomplishments. Collaboration isn’t just jargon for us; it’s key to our success.

Many believe that in a small company like Calendly silos or information vacuums can’t exist, but that’s untrue. Sheer proximity and a small headcount don’t provide us with the resourcefulness and agility we need to produce an outstanding product. You can have an “open door policy” and limitless happy hours, but these attributes alone don’t provide the structures and processes that support cross-departmental collaboration.

If you don’t have two-way communication between all your departments—whatever your business size—you’re killing your organization slowly every day.

At Calendly, we make it a priority to hire a diverse workforce of versatile individuals who genuinely want to work as a team to solve problems. We cultivate humility, transparent communication and a spirit of celebration in our people to ensure collaboration across the company.

Cultivating humility with cross-department learning and development opportunities

Like many SaaS companies, Calendly is product-first—meaning delivering the highest quality service to customers is our number one priority. The only way this is possible is by ensuring that every employee, from finance to sales, understands our customers’ pain points and how our product resolves them.

New hires have the opportunity to go through Happiness University, which is a crash course on our product that exposes them to customers’ needs and provides the opportunity to resolve support tickets. New employees become well-versed in how Calendly works and the simplest ways to communicate solutions.

In 2017, our company rolled out an internal demo certification program. Calendly employees trained, practiced and performed a sales demo to pass certification and prove their familiarity with our customers’ needs and our product’s benefits. As a result, employees are becoming brand advocates, but more than that, each department gets deeper insight into how to talk about our product. Designers and engineers learned to simplify the language they use when referring to the product’s features and components. Marketing team members learned how to position messaging, differentiate from competitors and only present information specific to the exact audience. For anyone from finance to HR, demo certification cultivated deeper connection to our work and pride in our brand that transcends department barriers.

Lunch and learns have become another big part of the way we share and disseminate information. The product team conducts demos at our monthly all-staff meetings, which gives the rest of the company time to ask questions and get briefed on the newest features we’re testing and shipping. We also like to present the latest we’ve learned from our professional development within our teams. For example, the marketing team has a working lunch every month to share what they’ve learned from readings, webinars and courses so they can synthesize and add to the collective knowledge of the team. It’s an efficient way to stay educated!

Encouraging all our employees to interact with our customers to get insight and leverage that data allows us to build a product people love and—in turn—our people become masters of Calendly. We rely on each other to learn more about the business from every angle so we can make it thrive together. As a result, our workforce is well-rounded, nimble and interdependent.

Communicating transparently with frequent touchpoints and a flexible work environment

Calendly is able to communicate 24/7, 365 days a year, thanks in a big part to Slack. With channels for each department, squad, project and interest, we’re able to disseminate information quickly and respond to anything urgent. Slack also allows us to connect on a more personal level and show our appreciation for one another as well as keep things humorous.

We also use weekly departmental update emails, all-staff monthly meetings and department roundtables to stay in communication. Other teams are welcome to join in on standups to ask questions and learn more about another side of the business. And we conduct panel interviews when we’re vetting a potential new leader to ensure that anyone who would work with the person has a voice at the table.

“As we continue to grow, communication is important. We have to be unafraid of asking questions. We can’t fear bureaucracy or politics. We want to be both direct and thoughtful.” – Felix Hu, Director of UX

Our customer happiness team has taught us a lot about maintaining professional communication that builds up the team. They have a motto of “presuming positive intention,” which means: give each other the benefit of the doubt when receiving new information or feedback.

“Ask questions and get clarity whenever necessary. Keep each other in the loop and have each others’ backs.” – Tiffany Cosgrove, Director of Customer Success

But cross-departmental collaboration isn’t always about being heard. Some communication happens in the background.

“For the majority of our job responsibilities, if we’re doing our jobs right, we’re not seen.” – Cailey Ryckman, Director of Finance and Operations

Some teams—like accounting and office management—are doing their jobs best when they’re not noticed. If a problem doesn’t exist and operations are running smoothly, you may not notice the person behind the curtain pulling the strings. These team members are equally valuable contributors so companies may need to take extra care to shine a spotlight on the unsung heroes who are quietly supporting the work of multiple departments.

And just like our people have to communicate well with one another, our tools do too! Part of what makes our lean team so productive is our focus on integrating and leveraging a strong tech stack.

Being a data-driven company allows us to simplify our communication. The more objective you can be, the less there is to argue about. It takes the arm-wrestling and ego out when you look to the data to guide your decisions.

Valuing achievements with celebrations

At Calendly, we believe in each person owning their own successes and failures. There’s room for mistakes because nothing great ever came without risk. We just ask our team to recognize those mistakes and seek to learn from them. And while we don’t dwell on the day-to-day hiccups that come with building something new, we do want to take a step back and celebrate when something noteworthy occurs.

It’s important for team morale and transparency to know how the business is doing. That’s why we ring a cymbal when a big deal gets closed and we run a countdown to big milestones like revenue marks and user sign-ups.

We also make sure that employees feel recognized and known. It may seem easy for a small company to do this, but it’s tempting to not worry about employee recognition until it becomes a problem. By that point, scaling your processes to try and flip your culture is an uphill battle that takes far more work than if you had built it from the beginning.

“The culture at Calendly is unlike anywhere I’ve worked previously. We celebrate each other’s success and work together through challenges. We have each other’s backs, and everything we do keeps the product and—more importantly—our customers top of mind.” – Rachel Hobbs, Head of Content

Every month, a survey goes out to all employees, asking them to vote for one person to receive the Scheduling Ninja Award. This person is someone who has provided value by doing their job well and also making contributions outside their job description to support other team members throughout the month. It’s someone who has gone above and beyond. A bit of shameless bragging: we have a lot of months where there are multiple ties because our employees are just that incredible. Turns out, when you expect your employees to do more—they deliver!

The Scheduling Ninja is announced at the all-staff meeting by our CEO and presented with a golden ninja trophy and a prize. It’s important to note that it’s our CEO Tope who reviews the nomination feedback about employees and he presents the award.

Employees want to be recognized by their leaders. We all feel great when we’re liked and respected by our peers, but when it comes to building a career within a company, we all know that our leaders hold a lot of influence. So it means something to not only be nominated by the “bros” in the trenches with us, but also to be seen by our leader(s). Recognition instills a drive to work for more opportunities to do great work and take on more responsibility. This cultivates leaders who know how to collaborate without ever being instructed to do so.

Keeping your team motivated takes more than Barney Stinson-crafted inspirational posters all over your office. Delivering feedback and results to your team that ties directly to their work gives employees purpose and job satisfaction. Our customer happiness team is one of the best support teams in the world. They’re an incredibly positive crew. Seriously—they’re some of the happiest people you’ll ever meet. But even they need routine affirmation and reinforcement.

Trying to stay positive can be difficult for support teams. They’re barraged with complaints, anxieties and snarky comments all day. It’s easy to forget that not all feedback is bad. So our customer happiness team runs a channel dedicated to positive customer feedback. For them, it’s not just a way to collect UX research. Showcasing customers’ gratitude and positivity keeps the happiness team—well… happy. And that makes our customers happy too!

Similarly, we always celebrate our teammates’ birthdays, work anniversaries and graduations.

Making time for recognition and celebration is a huge part of working together. If we all wanted to work alone, we could, but our work would be so much harder. When a new person chooses to work at Calendly and devote their time to helping us build the best scheduling brand, we want to make that person feel appreciated from day one. Their commitment to us in a competitive job market, like tech, is a vote of confidence that we don’t take lightly. Our goal is to keep up that sense of mutual appreciation through our culture and operations so that collaboration is a natural output.


As a result of working together, Calendly is experiencing incredible growth from the inside out.

Our sales team has become more efficient by constructing processes that are repeatable and scalable. Now that lead engagement is focused on building relationships by automating logistics, they’re seeing twice the revenue with half the team size.

Marketing is succeeding by building out the team, partnering with sales and creating assets that serve all departments. They share customer success stories so that other departments see the value in their work and feel connected to the Calendly mission. And by creating reference materials and content libraries that scale, they’ve been able to unify Calendly messaging and strengthen the brand.

The growth and capacity of individual customer happiness team members have increased due to their department’s focus on agility, transparency, passion, initiative and supportiveness. Instead of trying to endlessly tame a rogue support ticket “box,” they’ve created processes with other departments that are scalable so they can pick up the pace and deliver more value to customers.

With the data provided by each department, the operations team is able to track metrics against our company goals to ensure we’re growing in a fiscally conscious way.

Our product department is organized into cross-functional teams. Danny Miller, Head of Engineering, counts the team structure as a major driver towards reaching Calendly’s goals because decisions are made with diverse context and data from multiple departments. This means the product team works on the most important things faster and the rest can wait.

“We end up building the right things which has a direct impact on business growth.” – Danny Miller, Head of Engineering

“Collaboration also contributes to better hiring and job satisfaction. When we’re all on the same page we’re able to do our jobs better and candidates will hear that message and experience the same culture and expectations in their first few weeks—not a bait and switch.” – Kelly McDonald, Head of Recruiting and People Operations

When our people are happy, we attract other happy people.

Cross-departmental collaboration all starts with aligning individual department’s objectives to Calendly’s business goals and finding the areas where each team can help support the other.

“Each department will have to use different communication cadences with other departments dependent on its own goals and needs.” – Rachel Williams, Director of Sales

Regardless of a company’s size or industry, collaboration is a key driver of growth. Without it, you’ll be hard-pressed to scale or maintain your market share. Invest early on in processes that encourage open communication and cross-functional teams. You won’t survive on a fun and inclusive culture alone. Instead, be intentional about your organization’s design and operations and you’ll create a positive and productive culture naturally.

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