Finding and Honing Opportunities Amidst Uncertainty: Four Insights from Today’s Tech Leaders

Aug 6, 2020
min read

Today, in virtual boardrooms across the country, we’re seeing leaders facing unprecedented uncertainty. They’re having tough and exciting conversations with investors, employees, and customers around what the future holds, and helping their teams learn to not only adapt, but foster new opportunities during some very big changes. 

Last night at our Innovator Series, we hosted a number of tech industry leaders to talk about what leading through uncertainty means for them, and how they’ve managed to foster opportunities during a global pandemic.

The evening kicked off with a panel discussion filled with incredible perspectives from both startup founders and corporate innovators: Amanda Greenberg, Cofounder and CEO of Balloon, the world’s first insight mobility platform; Andrew Stroup, Founder of LVRG, an intelligent supply chain management platform; Founder and Executive Director of N95, the National COVID-19 clearing house for PPE and critical equipment; Bocar Dia, Cofounder and CEO of Aplayr, a performance intelligence platform for sales teams; and Jeanne Jang, Head of Ventures and Labs at E*TRADE, enabling E*TRADE to create new businesses and solutions across digital and emerging technologies.

We then welcomed Tien Tzuo, Founder and CEO of Zuora, and Rowan Trollope, CEO of Five9, for a fireside chat where Tien told us about the founding story of Zuora, what it’s like to lead a company through uncertainty––both today and in the past––as well as how startups can foster opportunities during uncertain times like today.

Here are the top four insights and words of advice we garnered from the conversations: 

1. Build trust through transparency

There is a lot of stress and uncertainty for people right now. In this reconciliation process of reimagining what work will look like going forward, building trust, relationships, and community from afar is of the utmost importance. 

“One of the things we’re finding effective as leaders is to be transparent, honest, and open, and identifying new modes of communication with our teams, our customers, and our investors”, explained Amanda Greenberg, Cofounder and CEO of Balloon. “That includes being open with when there is an answer and when there isn’t, and as you get new information, sharing it out to the team, and keeping everyone focused.” 

Jeanne Jang, Head of Ventures and Labs at E*TRADE, told us that they’ve built trust with teams by over communicating, and being extra deliberate about being transparent. Andrew Stroup, Founder of LVRG and N95, echoed that “building a communication model around transparency is key.” And he’s seen the impact come to life. When he gets on the phone with a front line worker to sell them PPE, they tend to ask him “what should we pay?”. They are fully trusting him and his team to know this and be fair. 

Rowan Trollope, CEO of Five9, explained that in addition to transparency, it’s incredibly important to stay connected to employees at all levels of the company during digital-first times. “I’ve tried doing office hours on Zoom, but there were too many people to be productive or for people to feel comfortable being honest. Now I use an app called Donut on Slack that pairs me up with folks randomly for a digital coffee. I also have a 24/7 AMA channel in Slack, and I send a weekly email that asks questions to get direct responses from employees.”

2. Stay mindful of the effects of change on employees

While entrepreneurs might be excited about all of the opportunities, their teams might be less so. Some of us are working from home for the first time, others aren’t as good with change in general. Leaders need to be able to meet people where they are in this journey. 

“We have tried to be mindful of the individuals that we’re trying to introduce new things to, and recognize the changes they’re going through, their ability to digest at the rate and pace we need, especially if they aren't entrepreneurial”, Jang explained.

Greenberg went on to talk about the heightened need for vulnerability. “As a leader and across the team, the need for stronger communication is so important.”

Tzuo, who led Zuora through the 2008 financial crisis and now through the COVID pandemic, told us that “in a time of uncertainty, people need to feel some level of stability. Crisis management rule number one is to find the floor––a point of stability you can depend upon, and then you can start planning”. Tzuo explained that it’s been a blessing that they run a subscription business, as business is still going, so it’s not a disaster scenario for them. They are in a good position to be able to be a point of stability for their employees. They are treating this as priority number one––giving people a sense of what’s going on. And after that, it’s about helping people understand that eventually this will pass, although it will take some time, so they should settle in for a bit. 

Tzuo also explained that they are finding ways to take care of those groups that are in more difficult positions––dual working parents with kids and no support, or single folks stuck at home that aren’t able to see anyone. 

Stroup explained a theory called cognitive closure: the need for people to reconcile during major disasters. “As our team continued to grow, and normalities were removed, there was definitely a sense of disenfranchisement. At both N95 and LVRG we’re thinking about how we can support our teams and customers as much as possible”. 

3. With opportunities come challenges

For those of us who work in the startup or innovation world, we can’t help but see a multitude of opportunities during times of change. It’s in our nature. However, it’s important to remember that there are also challenges that come with the territory that need to be considered in how you approach those opportunities. 

“My immediate team - the people in labs and ventures - sees a ton of opportunities given how much the world has changed; and we get really excited about it”, Jang told us. “We have a lot of ideas, a lot of things we want to do. However, we’re in the middle of an acquisition AND a pandemic, so we can’t exactly move quickly on those right now”. 

“Mckinsey surveyed a wide range of organizations in the US before COVID-19 hit, and found that 92 percent thought their business models would need to change given digitization”, Dia explained. “When I listen to that with my startup hat on, I see a lot of opportunity if you can find ways to help companies adapt to this new reality. However, companies are really only focusing on one or two big priorities right now, so startups will need to hone in on those when they’re selling, otherwise they’ll hit a wall.”

When it comes to finding opportunities, Tzuo advises that entrepreneurs look at two things: (1) what the problem was before and (2) what changed in technology or behavior that fundamentally rewrites the rules––for example, the Internet, IOT for manufacturing, the iPhone, AI––and what is the opening that has come up. For example, everyone is staying home now for work and school, what is lost and gained from this, and where are the opportunities? 

4. Innovate TOGETHER as a team 

With uncertainty comes opportunity to innovate, and a lot of nimble startups are taking advantage of that. Greenberg talked about how as a leader, she feels a strong need and passion these days to innovate, to move forward, to shift, to be more strategic. And she has decided to ensure she is innovating with her team to help people ground themselves through stressful times. 

“The amount of disengagement with people feeling all kinds of stress is at a new level. The need for psychological safety amongst teams is huge. And if priorities are not clear, or if it’s unclear what direction the company is going in, people will panic.

“At Balloon, we create psychological safety by setting clear direction and then being productive together, innovating together and moving in that direction together.”

While we’re in the midst of unprecedented uncertainty, we learned that there is a lot of room for opportunities, but leaders need to spend time helping their teams navigate change by building trust, staying transparent, innovating together, and staying mindful. 

To watch a video of this panel and fireside chat, click here.

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