Finding Success Against the Odds

I’m so excited to share Madelyn DePrey's incredible story and reflections on this past year during the pandemic. Madelyn's journey illustrates the power of empathy and how it leads to product innovation and deeper relationships that can become the foundation of your future business.

You can find more articles from the #InclusiveInnovation series here, and sign up for the CS Insider Report here.

Finding Success Against the Odds

by Madelyn DePrey

When the world shut down in March 2020, I found myself grabbing the last flight from Sydney to Los Angeles. A friend and I were celebrating our 30th birthdays for two blissful weeks in New Zealand when our trip was cut short by global lockdowns. The virus transformed almost overnight from some far-off tragedy to a global pandemic.

When I look back on the situation, global doesn't feel like the right word to describe it.  Global is too broad, too removed. This was personal, and about to change everything about life as I knew it. My husband lost his job on March 16 as the restaurants here in New York City shut their doors for what we thought would be a few weeks. I boarded an eerily empty flight and enjoyed the rewards of years of business travel with an upgrade to the most luxurious first-class cabin I would ever experience. 

I had a hunch that my glamorous globetrotting life was coming to an end with a jarring halt. The N-95 masks my mother shipped to me before the trip no longer represented her maternal exaggerated anxiety, but had become a coveted commodity. After the 20 hour apocalyptic trek back to JFK, I was greeted with empty gates and hazmat suits. I far too easily hailed a cab and glided through traffic-less streets, and settled into a new reality in our 600 square foot New York apartment. We sanitized everything from our groceries to our mail. Despite jetlag, I immediately buried myself in work. 

We all have some version of this early pandemic tale, but as a Customer Success professional in hospitality, I want to share some learnings through the lens of an industry devastated by global lockdowns.

Some background: I work for a post series B startup called ALICE. We are a technology platform that caters to the behind-the-scenes workings of a hotel operation. One of the unique things about ALICE is the diversity of our user base. The housekeeper to the CEO of a hotel, and everyone in between uses our system. I had the great privilege of joining the company in the early days. As one of the first dozen employees, I jumped at the opportunity to leave hotel management and join the alluring (albeit intimidating) ranks at a SaaS startup to be one of two members on the Customer Success team. At the time, I didn’t know what Customer Success was. In fact, I asked my hiring manager if we could be called “Hospitality Success Consultants” instead. I thought it was a gentler term for our hotel clientele. Thankfully, he grinned and assured me that Customer Success was an emerging industry ripe with opportunity, and thus I would be called a Customer Success Manager. Five years later, the customer success team had grown into a robust multi-layered organization.  

Back to March 2020: as I settled into my new kitchen counter home office, I was greeted with a flood of depressing emails. Our customers all over the world were shutting down. A Parisian boutique hotel manager wrote, “We have just learned that the hotel will be closing to guests for the unforeseeable future.” A seasoned Housekeeping Manager in Aruba inquired about “suspending our services until the government allows us to run our operation again.” Most painful of all were the messages like this one from a twenty-year Les Clef d’ors veteran concierge in Las Vegas “I have been laid off, and wanted to say goodbye. It was such a pleasure working with you over the years, and I hope you and your family are staying safe.” 

Reality was quickly setting in.

By this time, our Customer Success team had grown from a duo to 35 talented, hard-working individuals who sat in our New York or home offices all over the world. As travel halted and customers stopped operating, we all started to wonder about our job security. And then we started to wonder about the survival of the company. My team desperately needed direction on how to handle discount and suspension requests. Our Implementation team was aching for things to do since in-person training was now unsafe. Conservative models were put in place to protect the bottom line. I was advised by leadership that my job was safe, but we needed to start making hard decisions to drastically reduce costs. Have you ever received good news for yourself coupled with bad news for people you care about? It’s sort of like taking a shot of Jameson and feeling a nice buzz and then puking your guts out (blame my Irish heritage for this graphic metaphor). The only thing the CS leadership team and I could do was bury ourselves in our work. 

Leadership decided that due to our industry being demolished within days, cuts would have to be immediate. While ALICE is based here in New York, we were already set up for a remote workforce with our employees based in 16 countries. It was time to say goodbye to our loft-style Flatiron Office (with my Empire State Building View), as well as a large percentage of our employees. 

I was no stranger to recession. When I graduated from college in 2011, I had a hard time finding a job as the economy continued to recover from its 2008 crash. However, I was fortunate to participate in a strong economy for most of my professional life. I had never been fired or fired anyone before, and neither had most people on my team. 

One morning, shortly before our All-Hands meeting, I got confirmation that the CEO would be announcing layoffs and that individual calls to employees from leadership would immediately follow. I was sick to my stomach. We started the Zoom as we normally would, but waited anxiously for the announcement. Then it came time to run through my employee roster and give the dreaded news. 

My team handled the heartbreak with maturity and grace. Some even apologized to me for having to lead such a difficult conversation. I learned of spouses also losing their jobs, and even had an employee share for the first time that his wife was expecting. Within days, my team had shrunk down to two Customer Success Managers. 

The sting of the layoffs lingered while the world continued its screeching halt around me. I decided to step away from my computer and go for a run. Masked up and zigzagging from one side of the street to the other to avoid other possibly infected pedestrians, I thought about my customers and colleagues who had lost their jobs and the challenges ahead for all of us. I passed a city playground with its swingset and slides blockaded with caution tape, a place once bouncing with innocence and joy, now dressed as a crime scene. Life was looking bleak, but I was starting to feel inspired in my cardio-induced state. As I thought about the impact of the virus on our industry, it dawned on me that Customer Success had never been so important. Fiercely protecting and connecting with our customers on an entirely new level would be crucial to the success of our company. Furthermore, it was going to be critical to invest in, and protect my lean team. It was time to get to work!  

That human touch… 

In the weeks that followed the cutbacks, we found ourselves much busier than expected. The proactive customer success strategies we’d spent the last few years building immediately went out the window. Hundreds of emails and calls were flooding in, and our team of three had to balance helping our customers while protecting our bottom line. As the businesses we serve were suddenly restricted from operating, it became clear that this could be one of the most devastating events in the history of the hotel industry (and it is an archaic industry!). 

In the early days of the pandemic, the situation was fluid. Most of our customers were optimistic that things would get back to normal soon, and we weren’t inundated with cancellations. Instead, most of the requests were for billing suspensions or discounts. Our business model is largely based on 12-24 month contracts that auto-renew and we don’t offer a pause button on subscriptions like Netflix or Hulu. Our intention was to continue to provide our services and invoicing, whether a hotel was able to operate or not.

Instead of automatically offering a mass discount to all customers, we handled these conversations on a case-by-case basis. When they came in, we did our best to call the customer, learn about their situation, come to a mutual agreement about compensation, and schedule a future touchpoint. We took our time in understanding our customers’ situations by asking about things like their families before their businesses. This approach gave us the opportunity to level with the customer on a human level and allowed us to offer compensation in a manageable way. This was a big strain on our little team managing much larger books of business than we were used to; however, it was incredibly effective. We built empathy and provided our partners with deferred payment plans, subscriptions, or discounts. 

The other reality was that our customers newly had time on their hands. They weren’t busy greeting guests or running around putting out fires. They were home on Zoom with kids on their laps, dogs barking, watching Fauci, and ferociously hand sanitizing. Just like us. Suddenly, despite being all around the world, we had plenty in common with folks in Dubai, Mexico, or Japan. Those Zoom calls gave us an unexpectedly intimate look into our customers’ lives. We included them in over virtual happy hours and even met their kids bouncing on their laps during the workday. We learned more about each other during this time of crisis than we did meeting them in person or walking the halls of their hotels. I asked the team to track these personal connections so they can ask about children by name or refer to a favorite sports team on future calls. Customers reciprocated by asking about us, showing gratitude, and keeping us informed as their statuses evolved. 

Pivoting to customer needs 

One of the challenges during this time of crisis was getting a pulse on our global customer base as the world shut down. Outside of the customers who reached out to let us know they were closing, we didn’t have a natural pulse on everyone’s status. I dove into extensive customer research including frenzied Googling and cold calling. I even enlisted the help of my newly unemployed husband to help research what hotels were open as well as legal restrictions by state and country. At the peak of the lockdowns, a whopping 92% of our customers could not run their businesses. Needless to say, we had our work cut out for us.

Our first big product change was to dive into new territory and launch a Freemium product line that centered on the current needs of our customers. The focus was on shutting down their operations, protecting their assets during the closure, deep cleaning, and eventually, reopening. We worked with a consultant to understand the critical aspects of maintaining a building with limited staffing, and incorporated the CDC cleaning guidelines into our functionality. This not only offered new value to our existing customers, but also generated new sales leads, press, and industry buzz. 

We also quickly adapted to the changing environment and needs of our end users. Many hotels went from an army of employees running a busy operation to one or two individuals taking care of an empty building. We needed to show users and decision-makers innovative ways to pull value from our product. Working cross-functionally with Product, Sales and Executive leadership, we generated blog posts, newsletters, and case studies about these evolving use cases. 

Customer-centricity isn’t limited to Customer Success 

During this unprecedented time for our industry, protecting the customer was more critical than ever. As a rapidly growing startup, we had historically been pretty focused on new revenue streams. This was an opportunity to generate customer-centricity across the entire company. 

As our entire industry was turned on its head, we needed to demonstrate the continued value of our team to our internal stakeholders. We used metrics like engagement, risk, product line, ARR, and discounts to provide weekly updates to our CEO. This has since grown into a weekly CS org-wide executive report. Not only does this show the executive team successes and challenges, but it also holds all of the CS leaders accountable for owning their updates and metrics. 

Additionally, we used our All Hands Meeting to drive company-wide buy-in to the health of our customers. We shared high-level metrics and invited customers to share their direct feedback and current operational details. Everyone from DevOps to HR got to engage firsthand with our customers, increasing investment in their success. 

As the world progressed into an unpredictable patchwork of closings and openings (and sometimes closings again) we launched a Reactivation Task Force. This group of cross-functional leaders met on a regular basis to ensure we were reinvigorating our customers’ use of our product. We built a Reactivation Toolkit, complete with self-serve user training guides, blog posts emphasizing the increasing importance of technology, and best practices for using the system for things like “Contactless Guest Communication.” Additionally, we measured usage and system load to ensure our product could handle the evolving strain on the product. 

One of the most challenging aspects of this effort was turnover in points of contact. The hotel industry is already ripe with turnover, as leaders often move from hotel to hotel. The pandemic brought this to new heights, requiring continued efforts to obtain new champions, decision-makers, and user details from all of our customers. 

Driving Internal Compassion and Work-life Balance 

As customer-facing professionals, there is an inevitable emotional impact on our work. The pandemic and its effect on our industry raised the already high requirement for empathy, resulting in an absolute rollercoaster ride for our team. The CSMs’ days were filled with difficult customer conversations, stress over the impact on our business, and challenges at home. 

In order to reduce the emotional burden, I worked hard to increase communication and deepen our relationships. We implemented informal events like a weekly happy hour, including a “make a cocktail from the contents of your fridge” class taught by my husband, a career bartender. I encouraged my team to start conversations to help make decisions and break through barriers. This allowed us to bond, laugh, and share the burden the pandemic placed on us. 

Our company offered free group therapy sessions, yoga classes, and summer Fridays. While these things had some impact on employee well-being, I think the most relief was offered by our deepening relationships with customers. Our shared experiences about mask-mandates or child care challenges grew our trust and strengthened our bond. As leaders, we also made an effort to give the most transparent updates we could and shared metrics in a way that kept the team focused and motivated. 

Support didn’t end with our employees. We also found creative ways to connect with our former colleagues, as well as our customers who suffered pandemic layoffs. We held career workshops and wrote letters of recommendation. When parts of the world started to open back up, we helped connect customers to new job opportunities with other customers or prospects. This was a rewarding experience, and it was wonderful to watch my customer success network grow. 

Diversity & Inclusion also became a focus both personally and across the team. As a Minneapolis native in a mixed-race marriage living in Harlem, the events resulting in the murder of George Floyd hit home in some complex ways. I felt the company's early efforts to address it seemed insincere until we brought in a guest speaker who challenged us to talk about it freely and openly. Being able to hear perspectives from my colleagues who physically live all over the world and bring diverse socioeconomic backgrounds and family lives was incredibly moving. I learned the importance of addressing the elephant in the room instead of bottling it up or ignoring it. For years, I had taken for granted the gift of diversity in our company. I am so happy that we started to celebrate it and swap stories about our culture and diversity. We also found ways to respectfully ask our customers to share their stories. This brought a sense of trust and respect to our daily Zoom lives. 

My team of all-female CSMs was absolute champions during this unpredictable year. I am so grateful for their work around the clock to pivot our strategies so sharply (to tasks like collections instead of EBRs), often while homeschooling their children. Personally, I had never been so challenged in my career. There was a slew of pandemic babies, and at one point I was helping to cover three maternity leaves while juggling a much leaner team. While this meant long hours (literally going from my desk to the bed most nights), I am so grateful to have had the opportunity to take on new leadership responsibilities. Our sales team managed to close some exciting business during this time, and we were able to bring a few heads back. The days were long, to say the least, but the learnings were vast. 

Now, as we celebrate vaccines and reopenings and pent-up travel demand here in the states, we must remember that the situation is not the same globally. We have colleagues in India who are experiencing the worst of it now, customers in regions that are still locked down, and hotels that may never reopen. It’s important to consider the evolving situation across the world and continue empathy and inclusivity. The hotel industry has not stopped evolving and our customers are now also working with leaner teams. While this journey continues to be bittersweet and unpredictable, one thing is certain: Customer Success is of critical importance. 

Reflecting on all this now, I can summarize the strategies we took as follows: 

• Deepened customer empathy 
• Practiced agility and responsiveness to evolving customer needs
• Generated company-wide customer investment 
• Drove internal compassion and work-life balance

We didn’t realize it at the time, but these tried and true Customer Success principles were pivotal to our success even in times of chaos. Many customers are so grateful for our hard work and continued product development during the last year, that they are expanding their product lines with us and referring us to others. Had we not drilled into protecting our customers, and deepening our relationships (often with long hours and an emotional strain) we wouldn’t be in the successful place we now are as a company. On a personal level, it is remarkable to see New York alive again! My husband had his pick of job opportunities coming out of lockdown, and I am filling up my hazmat-suit-free travel schedule. Time with loved ones has never been so treasured, as really all comes down to those human connections. 

Madelyn DePrey is the VP of Account Management team at ALICE, a hotel technology platform. An avid runner, former (amatuer) child actor, and NYC enthusiast, she found her calling in Customer Success. She incorporates her background in nonprofit management and hospitality to passionately lead a team of Customer Success professionals. Her goal is to continue to encourage companies to act with a customer-centric mindset. 

Jan Young is a CS Insider Community Thought Leader and Consultant with The Success League. If you have something to share with our community about customer-centric, employee-centric or DEI practices in Customer Success, DM Jan on LinkedIn. If you’d like to read more from this series, you can find it here.