Rising to the Challenge: Lessons from the Frontlines of Today’s Startups | Volume 1

Over the past few weeks, companies both small and large have had to quickly adapt to COVID-19. From moving from offices to remote work, to helping employees navigate the mental strain of a global pandemic, these have been challenging times for business leaders, especially the ones responsible for employee morale. To share lessons learned from across the Chicago Ventures portfolio, we’re kicking off a new series explaining how startups are thriving during this challenging time. We’ll start by exploring how teams are managing employee morale.

For this post, we asked the head of people operations at several of our portfolio companies to share their experience and advice. Check out their insightful feedback below, and look out for more stories like this in our new series: Rising to the Challenge: Lessons from the Frontlines of Today’s Startups.

Volume 1: Managing Morale Through a Crisis

Q: How have you kept morale high with employees during challenging times prior to COVID-19?

We rely on consistent, honest communication. If times are tough, we want everyone to feel connected to the mission and motivated to get to the other side together. Everyone needs to feel that their day to day work is connected to the company’s objectives. We also make sure to celebrate wins along the way.

– Carolyn Kwon Montgomery, VP of People, Pangea Money Transfer

It all comes down to thoughtful communication and an inclusive engagement strategy. On communication, we’ve kept up our normal cadence of monthly company meetings and stand-ups where we’ve tried to be very transparent about where we are as a business. Additionally, we’ve tried to incorporate more storytelling and narratives around where our customers derive value from our product – our employees need to see and know that what we are doing matters!

In terms of inclusive engagement, we’ve rallied a great group of employees that have risen to the occasion and have helped us action various initiatives around working from home successfully and Mental Health Awareness Month. We’ve done everything from storytime for kids to cooking nights, weekly virtual workouts, and even a talent show. Honestly, the talent show may have been THE BEST company event I’ve ever participated in.

– Samantha Strube, Director of People Success, LogicGate

We have regular all team meetings and hold virtual company events like spirit weeks and post pictures in Slack, brown bag lunches and encourage teams to gather their groups together for fun events like happy hours and game hours.

– Anonymous

Q: What makes this particular time more or less challenging when it comes to maintaining morale?

I believe the greatest challenges facing us are 1. motivation 2. burn out and 3. isolation.

It’s critical for leaders to check in with their team members to provide an increase of whatever motivator resonates with their team: structure, stimulus, or acknowledgment. Zoom fatigue is real and there are less clear lines between work and home. We’ve been encouraging employees to #tapout when they need to and strive for 80% right now. Lastly, our employees miss each other. They miss the camaraderie they have with their teammates and just the casual conversations they have around the office.

– Samantha Strube, Director of People Success, LogicGate

The lack of natural ‘water cooler’ moments has been difficult to replicate while working remotely. We also realize many employees are not able to work from home as easily as others. Whether it’s a poor internet connection, childcare, or other distractions, everyone is battling their own issues with finding work-life balance in this new normal.

– Carolyn Kwon Montgomery, VP of People, Pangea Money Transfer

Q: May is Mental Health Awareness Month. What are some ways that your company is supporting employees’ mental health during this time?

We have shared many Mental Health resources with employees, but the biggest way that we are supporting employees is encouraging everyone to take a Mental Health Day. We have really pushed for all employees to take a day and fully unplug from Interior Define. We ask them to sign out of email, turn off their slack notifications, even uninstall the apps on their phone if they find it too tempting. Even if we can’t leave our homes it is important to take the time to focus on ourselves. It is very easy to put in 10 hour days right now, if only out of boredom. We recognize that and have really encouraged employees to step back and focus on their health.

– Casey Darnell, Interior Define, Head of People

We’ve put a lot of effort into this one. We’ve been sharing tons of resources on Slack and in our weekly WFH newsletter. Promoting physical health initiatives like a walk/steps challenge as well as yoga. Additionally, we’ve trained all People Leaders on signs of mental health issues like anxiety, etc and equipped them with a tool kit to have supportive conversations with those in the team. Lastly, we’ve launched a Slack campaign, asking people to tag the Mental Health Awareness green ribbon emoji by their names for the month.

– Samantha Strube, Director of People Success, LogicGate

We implemented a company-wide holiday on May 1st in honor of Mental Health Awareness Month. We wanted to break the stigma of mental health in the workplace and make sure our teams knew it was OK to take time off without the excuse of going on vacation (or leaving their homes at all).

– Carolyn Kwon Montgomery, VP of People, Pangea Money Transfer

HealthJoy’s mission is to provide a better healthcare experience, and to be the most trusted source of healthcare guidance; therefore, employee health, wellbeing and happiness is always top of mind for us. We kicked off the month launching a 30-day wellness challenge to promote healthy habits that feed our physical, emotional, and mental wellbeing. In an effort to motivate one another and share progress, a #maywellnesschallenge slack channel was created to foster collaboration and encouragement. In addition to the wellness initiative, we are hosting virtual Zen Sessions with a local yoga instructor.

Lastly (shameless plug), HealthJoy recently launched an EAP offering last summer, which is also offered to our employees. This gives them access to licensed counselors, social workers, and psychologists for short-term consulting 24/7.

– Megan DePorter, HealthJoy, Director, People Ops

Q: What are some ways you have worked to maintain your company’s culture despite employees being distributed and working remotely?

We have multiple, planned touchpoints with all employees every week, all via different mediums (video, email, Slack, newsletter). Senior leadership is responsible for their own set of weekly engagement KPIs that we hold each other accountable to. We started using Donut, a slack integration that randomly pairs you with a coworker for a virtual coffee once a week. We’re also sending out more frequent, relevant engagement surveys to employees to better understand how we can improve their experience during this time.

– Carolyn Kwon Montgomery, VP of People, Pangea Money Transfer

Lots of Zoom activities! We have hosted cocktail making classes, cupcake decorating lessons, plenty of trivia games, Call of Duty groups, and are working on a Bravo-lebrity themed moderated debate! Anything that employees are into, we want to share with the larger team. It’s an opportunity for us to learn from one another, and usually have a much needed laugh at what we can come up with to entertain ourselves.

– Casey Darnell, Interior Define, Head of People

It’s important to maintain connectivity in the workplace (but not overdo it). Our Operations Manager, Mallory Fritz, has done a tremendous job launching monthly initiatives like cooking classes, trivia, spelling bees, donut-connects, lunch & learns, etc. Additionally, we’ve been making an effort to check in on employees; it’s important to be human, this is a stressful time for everyone, so acknowledge that. Ask them questions like “how has your week been?” or “how you are feeling today?” Those simple questions go a long way. We also host monthly company meetings where our leaders provide updates around COVID and the state of the business. They’ve been extremely transparent throughout this entire transition to ensure employees are clear on expectations.

– Megan DePorter, HealthJoy, Director, People Ops

Q: When you think about employee morale and mental health, are there any bright spots from this time that you would like to share or highlight?

We’re rallied around the impact of the virus on our customers, and how important our service is to them. Many of our customers are sending money via Pangea’s apps to put food on the tables of their family members abroad, or to pay their medical bills. Being trusted with and responsible for that kind of transfer keeps us going.

– Carolyn Kwon Montgomery, VP of People, Pangea Money Transfer

I think many employees are feeling more comfortable expressing their needs and concerns. Being vulnerable is a knock on effect of building trust. For me, that is the silver lining — I’m building deeper relationships in many ways.

– Samantha Strube, Director of People Success, LogicGate

Our employees are truly there for one another, whether business or personal, there is a bond. All for one and one for all.

– Anonymous

I have gotten very positive feedback from employees for simply recognizing and calling out the need to unplug. Having the leadership team reinforce this and truly encourage people to take real-time away from work has made employees feel recognized for their hard work and recognized that we are all only human.

– Casey Darnell, Interior Define, Head of People

Final thoughts and best practices:

Being a leader is hard right now. I have had many moments over the last 10 weeks where I just wanted to crawl into my IC hole. BUT now is your time to shine as a leader. It’s tough but you will come out even stronger, more compassionate and more agile. Being there for people is the hard route but the most worthwhile!

– Samantha Strube, Director of People Success, LogicGate

Virtual happy hours aren’t for everyone. We learned pretty early on that the same people that choose not to attend happy hours in the office are the same ones that choose not to attend the ones on google hangouts. They’re great for those of us who attend, but culture isn’t just about happy hours 🙂

– Carolyn Kwon Montgomery, VP of People, Pangea Money Transfer

The most important reminder that I would add is that we need to continue these initiatives. At the beginning of COVID, every company was focused on keeping employees engaged. As we have settled into the remote working normal, I worry that some of the initiatives and efforts that companies have put into place will fade away. If anything, we need to become more committed and intentional about creating spaces for employees to connect as we continue to navigate through this.

– Casey Darnell, Interior Define, Head of People

Read Volume 2: Managing Productivity, here.

Lindsay Knight


Posted On

May 27, 2020


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