Forgotten Post-it notes fall away from a Q1 goal board. The break room vending machine hums for an empty audience. Across the sprawl of identical cubicles, an abandoned office plant’s foliage withers into a yellowing heap as if begging for water.
2020 painted a bleak picture for organizations across every industry when the pandemic uprooted the modern work structure, forcing teams to work remotely for an indiscernible amount of time. Even with 2022 rapidly approaching, many organizations still remain out of the office. The sad truth is, not every business made it through the isolating effects of Covid-19 after scaling back operations or temporarily shutting their doors.
The ones that did, however, pivoted fast, implementing new plans of operation and discovering fresh ways of smashing goals by embracing technological innovations on the fly in order to stay resilient and connected.
A commonly recurring theme for teams that stayed resilient against 2020’s tumultuous reign? Togetherness.
“Having a foundational understanding of the individual on the other side of the monitor has built a connection, an openness and a desire to support one another,” said Dani Schufeldt, an engineering manager at Teachable.
For a host of New York City tech organizations, camaraderie and tight bonds helped build a wall of protection around their engaged teams to weather whatever storm came their way. That’s why Built In NYC caught up with four local leaders who’ve added the art of resilience into each company’s culture, helping them power through the tribulations of 2020 and beyond.
How do you, as a leader, model resilience for your team?
For me, resilience is not only about handling and adapting to challenges but sharing that experience openly and being vulnerable about it. I try to model that by being transparent with my team about the challenges I’ve faced and sharing what’s worked and what hasn’t.
A recent example I’ve shared with the team is my transition from working at more traditional organizations to a startup in a different industry. I’ve talked about some of the challenges I’ve had adjusting to a different mindset and trying to be open about not always having the answers. I like to talk about examples of things that went well and also talk through mistakes I’ve made or ask for feedback on how I might approach things differently.
The team has greatly supported me in this, and I can now proudly say that I know the difference between Air Jordan 1s and Air Jordan 4s — and can identify Rick Owens out in the wild.
What are some actions you take to keep your team engaged, happy and motivated to come to work every day?
I’ve always been a big believer in getting to know folks and understanding what makes them who they are and how they are looking to grow. Then, once I know more about what they’re interested in or the skills they want to build (whether it be part of their current “day job” or not), I try to connect them to opportunities that can help grow that interest or skill set.
Grailed is an excellent place for this because we move quickly and there are so many exciting things happening. While my team’s “day job” is focused on keeping the platform safe and building trust through operations, we have many fashion aficionados, and there are so many opportunities for cross-functional work.
There are many things to consider. If someone is interested in marketing, can we connect them to someone in marketing who’s working on a new collection? If someone is interested in product, can their experience be helpful for a new feature that’s being developed? How can we best help to prepare folks for their next role, whether it is on my team or not? I think it’s essential to listen and understand for people to remain engaged and motivated.
Working remotely can sometimes feel transactional, and I try to counter that by building connections.”
What are some activities or rituals your team does to strengthen bonds and create the kind of team camaraderie that supports resilience?
I think what’s important is getting people out of their “work” selves and getting to know people beyond task updates. This is more difficult in a remote world, which I’m sure is a challenge that many of us are facing.
One thing we’ve instituted in our team meetings is an icebreaker where each person shares something about themselves. Each week, a different team member picks the discussion topic. While it’s not a mind-blowing, unique ritual, we’ve had some interesting conversations, and I think it’s helped the team get out of their comfort zones and learn more about each other. Some of my favorites were “Who is your favorite cinematic villain?”, “What’s your hidden talent?” and “What animal would you choose to be in the afterlife?” If you haven’t heard of a mantis shrimp, you’re in for a treat.
Shout-outs are also a great way to encourage the team to share appreciation. Working remotely can sometimes feel transactional, and I try to counter that by building connections. We can definitely do more here — one of my goals is to do more of these activities while remaining mindful of the time and commitment. I’m looking forward to next year when we can maybe meet in person!
Grailed is a luxury peer-to-peer fashion marketplace.
How do you, as a leader, model resilience for your team?
Communication and psychological safety are key factors in building a resilient team. As a leader, I foster that environment by being open and transparent in nearly everything I do: planning, adapting to change and seeking input on the work I’m doing.
As a team, we talk openly about the challenges and opportunities that come up. Software is more flexible and forgiving than we often remember. I advocate to release software early and often, gather user feedback and incorporate it into our plan. We have a roadmap, but we also accept that we’ll uncover things as we go and should accommodate change.
Additionally, I wholeheartedly believe in the concept of failing fast and celebrating the lessons learned from those experiences. Every morning at standup we don’t give status updates; instead, we talk about blockers and support we might need to move forward. We pair and provide insightful reviews of our code to have a collective understanding, which enables the entire team to support the product. We can adapt and persevere through whatever comes our way if we’re comfortable addressing the impact that those changes might have.
What are some actions you take to keep your team engaged, happy and motivated to come to work every day?
One of the best ways to motivate and keep a team engaged is to make sure they feel empowered by the work they’re doing. I actively ensure engineers have a seat at the table and can influence our work. We collaborate closely with product and design to evolve what we’re creating, leveraging technical insights and also an individual’s domain experience. Engineers are strongly encouraged to advocate for tech debt to be incorporated into our planning.
In addition, I make space for people to work on activities outside of our team goals and trust them to manage their time appropriately to support this. There’s no shortage of ways to contribute to our code, culture and the overall employee experience, so finding an initiative that motivates someone is extremely rewarding.
I also believe that it’s important to call out that as humans, we might not be happy every day. It’s essential to recognize, especially as leaders, that we are collectively going through a lot — at work, in our personal lives and during a global pandemic — and this reality impacts us all. I want to empower my team to openly acknowledge that it might not be someone’s best day, and we’re here to support each other in whatever way we can.
It’s essential to recognize, especially as leaders, that we are collectively going through a lot.”
What are some activities or rituals your team does to strengthen bonds and create the kind of team camaraderie that supports resilience?
As a distributed team, we’ve been especially intentional in finding ways to get to know each other, even though we’re not physically together. Our team rotates our meeting facilitator every week, providing leadership experience, shared responsibility and empathy. Every Monday, we ask lighthearted icebreaker questions to learn more about each other and don’t solely focus on software delivery.
Recently, we were asked about our favorite Halloween costume, which led to hilarious photos being shared within the team! We use Slack as a space for problem solving and also casual conversation; we have daily prompts set up which invite us to share memes (mostly TikToks), cute animals and even what we’re having for lunch. The “What’s for lunch?” prompt eventually evolved into a recurring cookie exchange where we each send a teammate our favorite treat.
Having a foundational understanding of the individual on the other side of the monitor has built a connection, an openness and a desire to support one another. I believe these activities have bonded us as a team — regardless of any challenges thrown our way, we feel confident in tackling anything together.
Teachable is an online expertise course platform.
How do you, as a leader, model resilience for your team?
No matter the industry, people in all consumer spaces have felt the supply chain challenges that the pandemic brought on — and in the meantime, everyone adopted a dog. While this time has allowed us to grow quickly, it presented an increased challenge for our operations team. When problems pop up and employees look to you for solutions, they mimic your reaction.
It’s important to find the humor in small moments and to continue prioritizing the broader missions. It’s also important to be prepared for challenges, and to react to those challenges with a calm tone and thoughtful response. Thinking about what the right action item is and accepting the problem at hand instead of wallowing in frustration allows your team to motivate to solve the problem.
Be ready to dive in and support — even if it means keeping people company on Zoom while they work through an issue after-hours. Redundancy planning helps make problems easier, but either way, people will look to you as a leader to find the confidence and drive to keep overcoming challenges versus wallowing in them.
What are some actions you take to keep your team engaged, happy and motivated to come to work every day?
As a leader whose schedule is probably back-to-back Zoom calls, you tend to want to jump right into work topics on each Zoom call so you can then move onto the next one. Force yourself to acknowledge everyone on the call in the beginning, tying in personal notes or breaking the ice while waiting for people to join. A mental jolt of personality in a Zoom world goes a long way.
Fight the urge to work through Slacks or other items while on Zoom calls — that “face” time is limited and really valuable. Stay engaged, ask questions and give visual cues like you would in person to show you’re listening and interested.
It’s also important to keep the surprise and unexpected acts of thanks going — a small gift card on a Wednesday or delivery of wine on a Friday as a thank-you helps people know they’re appreciated.
When problems pop up and employees look to you for solutions, they mimic your reaction.”
What are some activities or rituals your team does to strengthen bonds and create the kind of team camaraderie that supports resilience?
Small recurring non-work elements offer something to look forward to. We play a Sporcle in our weekly Friday meeting for a little friendly competition and to take minds off work for a minute. Who knew European geography could bond operations folks?
In our broader meeting with our colleagues in manufacturing, we make a point to pause and open the floor to new members for an introduction and some fun facts (and an open challenge to beat the group in weekly Sporcle). We are also doing “closing thoughts” from a different member each week so there’s engagement beyond just project updates.
Lastly, we offer happy hours periodically for those who are comfortable attending, which is great given most people aren’t seeing each other in-office yet and that normalcy goes a long way for camaraderie and a feeling of connection to a bigger organization.
The Farmer’s Dog is a fresh pet food company and delivery service.
How do you, as a leader, model resilience for your team?
At Haven Technologies, we strive to create an environment where people can tackle tough challenges while knowing that we all have each other’s backs. We take the time to clean the espresso machine steam wand for each other even as we pull together for tight release deadlines.
Even when a team knows that everyone is in it together, there is still the extra responsibility to take care of one’s own needs. I was most inspired to fill my own tank from a mentor of mine who taught me that you can’t show up for others in your life unless you show up for yourself first. That advice inspired me to fulfill my personal goal of meditating every day for 40 days, which took me a year and a half to work up to! I model for the Haven Technologies team that showing up with resilience for myself is just as important as showing up for others around me.
What are some actions you take to keep your team engaged, happy and motivated to come to work every day?
We may be a bit quirky at Haven Technologies, but we believe that a fun, supportive culture is paramount for our employees’ well-being. We want all of our colleagues to be able to show up for work motivated and excited to create every day.
To fuel this, our team has implemented a wide variety of wellness initiatives, benefits and activities including yoga and meditation sessions, gym memberships and Friday focus time (which means no meetings in the afternoon). We promote our “obsessively learning” value by offering each employee a learning stipend to encourage continued growth and learning outside the office. In true startup fashion, we make sure to provide snacks, coffee, beer on tap and games like shuffleboard, Ms. Pac-Man and ping pong in the office.
Though the perks are great, the meaningful work that we produce as an organization is what really keeps our employees engaged. Haven Technologies’ mission is to “Make life better. Together.” To us, this means that we are not only transforming the life insurance industry, but doing so in partnership with our clients to make life insurance more accessible to all.
You can’t show up for others in your life unless you show up for yourself first.”
What are some activities or rituals your team does to strengthen bonds and create the kind of team camaraderie that supports resilience?
Trust and community are at the forefront of our culture. We encourage our employees to bring their authentic selves to the office — or their computer — each day. We celebrate and learn about each other beyond our work achievements. Just recently, we celebrated three marriages, two house purchases, lots of new puppies, a mid-pandemic haircut and gathered together for an employee-led Latinx cooking demo.
The pandemic brought with it a unique opportunity to rethink the routines and rituals that we engage in as a team. Especially while working from home, we know it is important to create team togetherness. With that in mind, we shifted our monthly all-hands meetings to short weekly all-employee check-ins with our CEO, Yaron.
As a complement to the organization-wide 300-plus people meetings, many of our employees engage in Haven Hangs, an employee-created initiative to casually get to know and reconnect with other employees across the company. We believe that this sense of togetherness allows us to maintain a broad sense of resilience that we will continue to nurture long after the pandemic is over.
Haven Technologies is an advanced insurtech platform helping to make life insurance more accessible to everyone.
