Chicago Ventures
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Chicago Ventures

Rising to the Challenge: Lessons from the Frontlines of Today’s Startups | Volume 3

Over the past few months, 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 sharing a series of articles explaining how startups are managing and thriving during this challenging time.

For this post, we asked portfolio companies (thanks to Ashish V. Shah at Dina, Samantha Strube at LogicGate, Carolyn Montgomery at Pangea Megan DePorter at HealthJoy!) to share their experience and advice around communication. Check out their insightful feedback below, and review our previous two stories on “Managing Morale Through a Crisis” and “Managing Productivity.”

Volume 3: Communications & COVID

Q: What are some of the ways that your team typically communicates key announcements and updates?

“All-Hands.” From the start, we developed a three-point plan to address employee health, the state of the business, and the rapidly changing COVID-19 environment. We have a weekly Monday morning “all-hands” meeting where I report on our progress toward that plan, and share key data on the pandemic — i.e., case rates, status on reopening, and key developments on vaccinations/testing/contact tracing. Recently, we’ve encouraged people to take these meetings over the phone during a walk vs. zoom-small nudge to help people stay active during these unique times.

Additionally, we still have our Friday weekly “all-hands” meeting where we recognize our “Stud of the Week” and catch up on all parts of the business. Like everyone else, we’re hosting Zoom happy hours, coffees and lunches as another way to stay connected. In the past, we’ve hosted an annual summer company party, and we’re looking for creative and safe ways to get together and get out of our work-from-home routine.

-Ashish Shah, CEO, Dina

We hold two major events per year, correlating with fiscal start and our midpoint. We use those two occasions to get the team jazzed about where we are going and level set on where we are currently. We also have a normal monthly cadence of an All Hands where different teams get to showcase the work they’ve done, the value they’ve added to our clients as well as make announcements.

-Samantha Strube, Director of People Success, LogicGate

Pre-COVID, our CEO held monthly all-company breakfasts to share updates and answer questions from the team. We’re still doing all-company meetings via Hangouts but have also implemented a few new weekly programs since going remote including recorded video updates from our CEO, major initiative status reports from our General Manager, and customer updates from our Director of Customer Experience.

-Carolyn Kwon Montgomery, VP of People @ Pangea Money Transfer

Q: How much have you had to adjust the way you communicate with your team during these last few months?

A lot. We rarely worked from home pre-COVID, so we had to implement remote norms right away to make sure we stayed connected. All meetings are held via video Hangouts, and we try to keep our Slack status updated to signal to people if we’re on a walk, eating lunch, or spending time with family. We’ve also implemented Donut to help facilitate informal check-ins with teammates you might not generally work with day to day.

-Carolyn Kwon Montgomery, VP of People @ Pangea Money Transfer

Self-care is something we feel a great deal of responsibility to facilitate. Most of our team already was working remotely two days a week, but now that everyone is remote full time, we’ve found that it is our responsibility to coach everyone on how to manage through this transition. It’s acceptable to place boundaries around your home life and work life. It’s ok to make time for yourself and your personal self care. It’s ok not to be online 24x7. We have an overwhelming sense of responsibility to help our people work through this transition. It starts with me… I need to emphasize this self-care mindset, demonstrate it for others with my own actions, and then reiterate the message every opportunity I get. It’s critically important for people to take care of themselves in this unprecedented moment in history.

I’ve also noticed that our team has further galvanized during this pandemic, and we are seeing incredible process innovation between our product and customer success teams in particular. We have encouraged our people to make pragmatic changes quickly without getting in their way. We’ve never been more productive.

-Ashish Shah, CEO, Dina

Not too much, but everyone has had to become more tech-savvy. We try to be more cognizant of time zones as some of our employees leave the Chicago area temporarily. Generally, our policy is to communicate early and often and via multiple channels. Repetition is truly key!

-Samantha Strube, Director of People Success, LogicGate

Q: Are you opening up new channels for your employees to communicate ideas, stress levels, or other challenges?

It’s important to maintain connectivity in the workplace (but not overdo it). We 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, Director, People Ops, HealthJoy

We are looking at leveraging new tools for engagement such as Donut. We also utilize a performance tool called Lattice that has a great feature called ‘Updates’ that helps keep teams in the loop as well as track mood.

-Samantha Strube, Director of People Success, LogicGate

We’ve shifted from semi-annual surveys to monthly, and added more open-ended questions so employees can share ideas for us to improve. Our leadership team is hyper-aware of stress and work-life balance. We’ve added extra all-company days off for mental health and Juneteenth, and are sending managers more frequent PTO reports so they can manage for potential burnout.

-Carolyn Kwon Montgomery, VP of People @ Pangea Money Transfer

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.


Phone calls. I started one-on-one check-ins with the team to connect and hear how they’re doing personally, and I’ve encouraged all our managers to do the same. We tend to rely on Slack as a way to communicate, and I’ve encouraged our team to replace some of their online meetings with one-on-one conversations, despite how busy we may be. We are really emphasizing phone calls that people can take on a walk vs. stationary zooms, if at all possible. In addition to all of this, we are continuing with our regular skip-level review process, as well as ongoing monthly employee surveys, to ensure we have many open lines of communication at all times.

-Ashish Shah, CEO, Dina

Q: When it comes to communication, what is the single most important thing your leadership team prioritizes?

TRANSPARENCY. Full stop. We try to be as transparent as possible. I think that’s really the key. There are things we literally can’t share, things we’ll definitely share but need to suss out further before doing so, but everything else is up for grabs!

-Samantha Strube, Director of People Success, LogicGate

Consistency. Every communication is an opportunity to further underscore our values, why we do what we do, and strengthen the trust we have developed with our internal and external stakeholders. In times of crisis, leadership must provide consistent, frequent and transparent communication that invites proactive, constructive feedback.Operating with this mindset allows us to be much more dynamic, activate the full weight of our team, and deal with issues openly before they become much larger. We’re a growing team and everyone has a lot on their plate. In addition to our “all-hands” forums, we’ve found that frequent post-project debriefs are a good way to identify what works and what we can do better to support our team.

-Ashish Shah, CEO, Dina

Engagement. No matter how many emails or all-company meetings we have, none of it matters if the team doesn’t feel connected or well informed. The team’s perception of the communication programs we put in place is everything. Our employee surveys measure the team’s approval of company communication, a rating that has gone up 51% since we started collecting feedback on it.

-Carolyn Kwon Montgomery, VP of People @ Pangea Money Transfer

Any final thoughts or tips that you would like to share?

These are unprecedented times with lots of change and uncertainty. We have been able to make meaningful progress with our business by leaning even more heavily on our values than ever before. Everyone in our company has stepped up and operated like a leader, and I believe this is because our values have been well socialized, emphasized in every major decision we make, and further underscored through frequent communication to our stakeholders. Make no mistake — this pandemic sucks — but we are emerging stronger than ever by relying on the basics in how we support one in another.

-Ashish Shah, CEO, Dina

It’s impossible to act like it’s business as usual when there are so many important movements happening in the world. Communication plans can and should change to make room for important conversations about Black Lives Matter and LGBTQ rights.

-Carolyn Kwon Montgomery, VP of People @ Pangea Money Transfer

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.


This completes our series of 3, thank you for reading!

(For more, check out Volume 1: Managing Morale and Volume 2: Managing Productivity, with additional insight from SpotHero and Cameo!)

We believe generational companies can be built anywhere, by anyone. We lead seed rounds before it’s obvious, and serve as active, operationally-involved partners during a company’s earliest days.

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Chicago Ventures

Chicago Ventures

We believe generational companies can be built anywhere, by anyone. We lead seed rounds during a company’s earliest days.

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