Chicago Ventures
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Rising to the Challenge: Lessons from the Frontlines of Today’s Startups | Volume 2

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 several of our portfolio companies (thanks to Cameo, SpotHero, Pangea, and LogicGate!) to share how they are managing and tracking productivity. 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. (You can view Volume 1: Managing Morale Through a Crisis, here!)

Volume 2: Managing Productivity

Q: What was your remote work policy or philosophy before COVID-19?

Our official policy was one work-from-home day per month. If employees needed more time for personal reasons, we made efforts to support them. Ultimately it was about trust and productivity. We don’t have a lot of redundancies at Pangea, so regardless of where you’re working — if you aren’t getting your job done — it’s obvious.

-Joshua Gordon-Blake, GM, Pangea Money Transfer

Our policy was flexible but it was team specific. For instance, our tech team members were typically remote one day each week but our finance team was in the office every day.

-Nikki Facchini, VP of People, SpotHero

Our policy was rather loose. If it made sense for employees to be remote then we had no problem with it. What mattered to us then remains what matters to us now: outcomes.

-Samantha Strube, Director of People Success, LogicGate

We allowed remote work as needed by corporate employees, but our sales team needed to be in the office to work with customers.


Q: How challenging was it to move to a remote working model for your company?

It was not challenging to complete our work. It was more challenging to be away from each other because our teams are so close.

-Nikki Facchini, VP of People, SpotHero

We tested it pre-COVID, so it was a fairly seamless transition.

-Katie Burgoon, Head of People, Cameo

We established some work from home norms right away — all meetings on video, keep your routine if possible, take care of your mental and physical health. All of these have been easier said than done. Some find it difficult to find a quiet place to take video calls, others have completely changed their working hours in order to balance taking care of their children, and all of us have struggled with taking care of ourselves at some point during this. The best response we’ve found so far is to preach empathy. Pangea has worked hard to support employees through whatever challenge they’re facing during this time.

-Joshua Gordon-Blake, GM, Pangea Money Transfer

Fortunately, it wasn’t difficult. We had to do some education around best practices but since about 10% of our employees were remote prior to COVID, organizationally we had familiarity there.

-Samantha Strube, Director of People Success, LogicGate

Q: How do you typically measure productivity? Are you doing anything differently now?

It’s a tricky question! It is really dependent on the teams themselves but we track it through communication streams such as 1:1s, stand-ups as well as programmatically through OKRs and by setting clear expectations and deadlines. One feature of our performance management tool that I’ve been finding very useful allows for my team to send me weekly updates on what they focused on last week, bandwidth, problem areas, and priorities for the coming week.

-Samantha Strube, Director of People Success, LogicGate

We measure productivity against roadmaps and project management. We have followed the same model while remote.

-Nikki Facchini, VP of People, SpotHero

We publish performance dashboards for all employees to access on Looker. When we were in the office, TV screens cycle through those dashboards. Now, we’re reporting out via email, Slack, and video. Leadership is dedicated to making sure employees know how we’re performing, and how their work is tied to it.

The entire organization knows the activities that each team is working on every week, and we communicate what was and was not completed. We publish company KPIs that are impacted by those activities. By reporting out not only activities but the impact of them, we’re holding everyone accountable to outcomes, and ultimately, the success of our business.

-Joshua Gordon-Blake, GM, Pangea Money Transfer

Q: How has working remotely impacted your team’s productivity?

I actually think we have been more productive in many ways.

-Nikki Facchini, VP of People, SpotHero

It’s been amazing to see what we’ve been able to accomplish with such a lean team. The crutch of feeling like we’re aligned just because we’re working next to each other no longer exists. So, even though we haven’t seen each other in months, the team feels to be marching in the same direction now more than ever.

The amount of work getting done has not been an issue — with our team largely confined to their homes. Instead, it is coordination that has needed new attention, and it’s remarkable the improvement that the team has shown week-over-week. We’re starting to adjust to the new normal.

-Joshua Gordon-Blake, GM, Pangea Money Transfer

I think everyone goes through phases of higher or lower productivity, which is normal, but generally our productivity as a company has remained more or less consistent.

-Samantha Strube, Director of People Success, LogicGate

We have seen an uptick in productivity. We sent out a remote work survey and a large number of people have felt that without the distractions and interruptions that comes with an office they are able to focus on their work and accomplish more in a day than they had previously been able to.


Q: With the boundaries between work and home now blurred, how are you making sure your teams aren’t getting burned out?

People are working more. It seems like the time employees used to spend commuting or socializing is spent working. We’re lucky to have a dedicated team, but of course, we worry about burnout. Everyone in leadership is responsible for checking in with people — not just their direct reports. We’re also doing more frequent employee surveys. This has led to making more flexible work schedules for those who need it, implementing a company-wide mental health day, and more mental health resources.

-Joshua Gordon-Blake, GM, Pangea Money Transfer

We’re doing lots of check-ins and encouraging our team to take PTO.

-Katie Burgoon, Head of People, Cameo

We make an effort to ensure people are taking time off, taking breaks during the day and ensuring there is a clear end of the workday.

- Nikki Facchini, VP of People, SpotHero

We have set specific guidelines for all employees to follow which include setting working hours on their calendar and slack notifications, and the executive team has been very vocal about the need to unplug.


We took a company-wide Health Day on May 1st to encourage people to check in with themselves and re-calibrate. Generally, most people are not scheduling meetings after 4pm to encourage people to get out and enjoy their evenings.

-Samantha Strube, Director of People Success, LogicGate

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

The tone really starts from the top. 2020 has certainly been difficult to navigate. As an organization, we have been good about recognizing the difficulty, giving employees a few extra days off to avoid burnout and sustain productivity.

-Nikki Facchini, VP of People, SpotHero

For us, the keys are: (1) focus on outcomes, (2) over-communicate, and (3) be empathetic. Boundaries have been destroyed: kids join conference calls and sweatpants are the new business casual. And, we’re doing all of this while dealing with a global pandemic in the background.

Focusing on outcomes helps us all have a feeling of building toward a less chaotic future.

Over communicating makes sure that no one is confused about where they stand, and the health of the company.

Empathy allows us to handle the bumps in the road — we are all going through something that we’ve never done before and we are figuring all of this out together.

Luckily, by the nature of being a venture-backed startup, we’re accustomed to facing the unknown together. Now we’re leaning on those same muscles for a whole new challenge.

-Joshua Gordon-Blake, GM, Pangea Money Transfer

We do weekly Pulse Surveys and a lot of virtual cultural and cross-organizational events. Those have been incredibly helpful.

-Katie Burgoon, Head of People, Cameo

Check back next week for Volume 3: Communication & COVID

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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