Leading an Education Startup Through Layoffs and COVID-19

Aug 19, 2020

In early March, just as the first COVID-19 wave started in the U.S., I went to Texas to attend SXSW EDU and talk with potential partner schools about Project Wayfinder, the social-emotional learning curriculum company I run. Prior to leaving the San Francisco Bay Area, I had a horrible feeling. People were pulling out of SXSW, and companies were just starting to shift to remote work. By Friday, March 6, the conference was cancelled, my meetings were over, and I laid in bed freaking out: “This is going to change the whole trajectory of education. How is Wayfinder going to fit in?”

I had no idea how big a deal this pandemic would be. None of us did. But our world is different, and if you’re leading a school or startup through this time, it has been harrowing.

Prior to COVID-19, I had never led an organization through a crisis. I had never laid anyone off, pivoted an entire organization in months, or tried to make decisions based on information that simply was not available. Below is what I’ve learned over the past six months—what to do and what not to do. My aim is to help other startup and education leaders make wise decisions through this incredibly tumultuous period.

Be Transparent With Your Staff and Customers

I learned this one the hard way. During our first and only round of layoffs in April, I tried to sugarcoat things for my staff. I wanted to assure everyone who was staying that it was going to be alright—that we would make it through this. I wasn’t as blunt and direct as I should be about the fact that we were going to have to make layoffs. Later, I didn’t lay out the rationale for why we choose to cut certain roles and not others.

My staff did not take this well. I had never done this before—and I did a poor job. Ultimately, they understood that we couldn’t keep all of our current staff, but they would have appreciated it if I had been more honest about the cutbacks upfront, and then delivered a message of reassurance.

After receiving feedback, I decided to create a process of clear financial transparency. Over the past five months, we have done monthly financial updates with the whole team that include what our burn rate is, how our cash runway is looking, whose job was on the line, and what financial milestones we had to hit by when to keep everyone onboard. This transparency rallied the staff; everyone felt like we were on the same team. We all understood the consequences of failure and how each of us could contribute to our organization’s success.

Our employees are adults. Telling them the truth empowers them to feel like they can be part of the solution. So tell them the truth. As leaders, we don’t have to bear all the responsibility of the bank account on our shoulders.

This pertains to your customers as well, especially returning ones. In our case, I was very straightforward, telling them: “If you want us to be able to serve you in the future, working with us this year will be critical. If most of our schools don’t return as customers this year, we are not going to be around in the future. Half my team will be out of a job.”

This message was both true and effective. One school in particular responded especially well. We worked out a one-time COVID-19 deal to continue working with them next school year. As a result, our partnership became stronger, not weaker. If customers value your organization and your work, be real with them too; your honesty can deepen long-term relationships and build trust.

Adaptability Is Crucial

Prior to COVID-19, we were a print-digital hybrid curriculum company. We also did all of our professional development and trainings in-person. (Remember those days?)

As soon as the pandemic started to take hold, we did two things: Made all our trainings virtual, and transitioned our curriculum fully to digital. We hired an engineer, moved around roles, and designed the content of our new curricula for remote learning environments.

But pivoting doesn't just mean moving fast. It means taking your values and comparative advantage and incorporating them into the ways you’re changing and adapting. For example, people loved our in-person trainings because of the connections they made with their peers. We had to think incredibly hard about how to do this successfully in a virtual environment. If we didn’t, we would lose our brand.

After weeks of prototyping and planning, we designed an online version of our signature Summer Institute with powerful results. One Australian participant who had previously attended an in-person training said this virtual format kept a sense of community and that the experience rivaled, if not exceeded, the physical format.

Since March, we’ve adapted many times. We raised a funding round, rethought our messaging, and migrated our curriculum to our new online platform. This was necessary but also on mission: Project Wayfinder teaches students resilience, creativity and adaptability. We had to walk the walk and practice what we preach. The ability to move nimbly and be decisive are critical to navigating crises successfully, but so is being thoughtful and aligning the changes with your organization’s core values.

Have a Vision for Post-Crisis

Though we don’t yet know when this pandemic will end, it’s worth our time as leaders to develop a vision for what it looks like on the other side of the crisis. “We’ll just go back to the way we did things before the crisis” is neither inspiring, practical, nor a likely option. If you succeed through the crisis, it will be because you adapted and changed your organization to meet the moment.

My vision was to use the crisis as an opportunity to position ourselves to help more students in a digital age with an online curriculum that has the same beauty and aesthetic design as its paper form. So far, that has proven the case: our digital product has opened up many doors. Because we could be more flexible on pricing and delivery is easier, it is now easier to reach lower income and international students, which has always been a priority for us.

It’s All About Your Team

Let me repeat that: It is all about your team. The constant throughline between all types of great leaders is that they pick great people. We wouldn’t be able to get through this crisis without our staff. People say people show their true colors during crises. I’m very proud that everyone on my team is rock solid and rose to the occasion.

Project Wayfinder’s staff gracefully switched roles, embraced our digital pivot, and made thoughtful sales pitches to educators who were consumed with crises of their own. For example, because there were no sales in March and April, our sales lead transitioned to leading virtual trainings, applying her experience with this type of work from her previous job. This was a gracious move on her part. When our digital transition was complete, she jumped quickly back into talking to schools about buying our curricula for the ’20-’21 school year.

The reason the role changes worked so well for us is because we’d built a significant amount of trust with our team before the pandemic kicked off, through weekly check-ins and deep culture-building activities in previous all-team gatherings. These long-term cultural investments went a long way towards sticking by each other when things got rough in COVID.

Listen to the Right Advisers

I had some advisers who, back in March, suggested slashing half my team. This would have been a huge mistake. Once business picked back up in June, instead of trying to rebuild a team amidst a crisis, I had folks who were ready to pick up the slack.

I had one adviser in particular who suggested the “middle path.” You can’t keep everyone, he told us, so you need to cut some of your budget. But don’t go overboard. He was correct. I’m incredibly glad I listened to him. He had been through a number of economic slumps coaching dozens of businesses. In this crisis, I’ve noticed that the best advice came from older advisers that had lived through multiple downturns.

As a founder, executive director, or CEO, you will get lots of advice during a crisis. Listen to the people who have been right the most number of times in the past. Listen to those who have experienced situations that mostly closely resemble the one your organization is currently in. Consider those who have the best track record in the specific area you’re seeking counsel about. This sounds like common sense, but in the midst of chaos it can be easy to forget. Don’t weigh everyone’s advice equally; choose wisely who you listen to.

Lean on Your Closest Allies the Most

One of the first things we did was go to our existing funders to see how they could support us through this crisis. They were all amazing and pitched into an emergency COVID-19 fund to buy us a few months’ of runway. We also went to our biggest and strongest customers and did everything we could to get them to stay onboard for next year. I also leaned heavily, emotionally and practically, on my board and executive team.

A crisis is an incredibly hard time to build new relationships. So go to those with whom you have already established strong links. One of our funders, the Peery Foundation, doubled their 2020 giving and introduced us to other foundations in the space. This was essential. Luckily, we had built and maintained a strong relationship with them before the pandemic hit, so they offered support naturally, rather than in response to a desperate, out-of-the-blue plea.

Lots of people have helped build your ship; they don’t want to see you sink or break apart. Let them help. Let them know how, and communicate consistently. I have so much gratitude for our funders, advisers, school leaders and teachers who believed in us along the way. Crisis brings people together—it certainly brought the Wayfinder education community together in a way that I had never experienced before.

Don’t try to go it alone, and pretend anything is okay, or be too scared to ask for help. Be real, communicate clearly, and share what you need. Your allies will listen and want to help.

Relentless Determination

If you’re a startup founder, you’re always hustling. It’s in your DNA. But in a crisis, the hustle has to go into hyperdrive. Customers are harder to acquire, money is harder to raise. Everything’s harder.

In January, when we made our annual plan, we set the wheels in motion to kickoff our first institutional fundraising round on March 1. The timing could not have been worse. Looking back, it was comical. We got countless “no’s” and started and stopped due diligence with numerous firms. But we kept at it, and in the end those that were still talking were by far the best investors for us. They understood the value and potential of Wayfinder to impact students’ lives and to help combat feelings of depression and loneliness exacerbated by COVID-19. They could see beyond the tunnel vision of the tumultuous April-June period. But we had to talk to so many people to come to this conclusion.

When things are in crisis, it’s on the executive leadership team to go into hyperdrive. Your team’s depending on you for their livelihoods. Because my COO and I have such a strong and long-standing relationship, we’re good at pushing one another. On our many late night Slack messages, he knew what to say to keep me going and stopped me from spiraling.

Having collaborators, advisors and supporters who know you deeply—and know how to motivate you—makes a huge difference. It is what pushes you that extra mile. Our growth consultant gave me many pep talks when I could not see school partners picking up again. In a crisis, talk to people who leave you feeling energized, clear eyed, and more motivated; not the ones who leave you anxious, worried, or frazzled.

As a startup curriculum provider serving schools, August is the end of our year. It is when our curriculum launches, takes root in schools, and we take a breather in September before we think about building for the next year.

But as schools come back into session, many school leaders and startup founders are in for the academic year of their lives. Schools are not going away, and neither is COVID-19. I hope that some of these lessons can guide you as you embark on what will likely be your most tumultuous, uncertain—and perhaps defining—year as a leader.

Godspeed and good luck. You can do this. Yes, it will be scary along the way. But keep at it. And ask for help—none of us can do this alone. Remember, people want you to succeed.


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