Fast CCO Jason Alderman on Leading and Communicating with Empathy

Editor’s note: This interview is part of Mission North’s Communications Pathfinders series, an ongoing forum with communications leaders who are sharing their perspectives about adapting to a new reality.

One-click login and checkout startup Fast announced its Stripe-led $20M Series A on March 26, 2020 – about exactly two weeks after COVID-19 hit hard and the country started shutting down. It would be six months before the company would launch its game-changing online checkout product, so Fast’s leaders had to figure out how to build a stand-out brand with sustained momentum, all while the world had more than enough to pay attention to. Even with more and more people shopping online, Fast had to communicate that it would make that experience better than ever.

And they did — Fast’s launch in September was an enormous success that rode in on an impressive wave of buzz and anticipation. Working hard on this effort was Chief Communications Officer Jason Alderman, whose varied career in corporate communications has included leadership roles at Clover Health, DraftKings, Visa, and staff positions with multiple politicians and members of Congress. 

In a lot of ways, there’s very little that Jason hasn’t seen — but no one has experienced, let alone launched a company during, anything like the current pandemic. We were grateful to talk to Jason about the unique challenges and opportunities for early-stage startups during COVID-19, prioritizing for success, and putting empathy for consumers and employees above all else.

You have an extensive background in corporate communications for some really large and well-known companies. What attracted you to an early stage startup, and to Fast in particular?

I’ve found that the older I get, the more willing I am to take career risks. After living through a couple of recessions, I felt I could take on a really interesting challenge and make a big bet on myself with a new company. 

There’s a joy in creating a government relations and corporate communications program from the ground up. At a big company, you have a big stage – but that stage is already built. At a startup, you build the stage and the auditorium while writing the script for the play.

I was drawn to Fast because I relate so much to the problem we’re solving: making people’s lives dramatically better when they transact online. It’s a ridiculously cumbersome process today. I was also blown away by our co-founders’ passion, intellect, dedication and decency. If I can measurably move the needle for a company and work with good people, that’s the right combination for me.

Fast announced its funding within the first month of the COVID crisis, and launched its product this fall in the thick of the pandemic. How do you stand out as an emerging brand to watch in an environment like this? What have you done to strengthen your presence and build a community around the brand?

Like many startups, we didn’t have a product ready for market when we announced our funding. Part of our goal was to bring in great talent to help us create the product as we started signing up sellers. Meanwhile, the world’s attention was on health matters and other seismic changes in society. 

We had to get creative about keeping our name front and center to begin building awareness and trust among influencers, merchants, thought-leading consumers and potential partners. To do that, we brought out a lot of tools – every tool, in fact. There wasn’t one left in the toolbox.

We had a great foundation with our co-founders’ (Domm Holland and Allison Barr Allen) strong Twitter presence. They talked a lot about their personal stories, the product’s promise and what it means in a world where e-commerce is a necessity. We also did consumer surveys to start establishing ourselves as experts on shopping and e-commerce. To attract top talent, we distinguished ourselves with things like our work from home policy. In essence, we spotlighted all the unique aspects of our company to keep people excited for when we launched the product.

At a big company, you have a big stage – but that stage is already built. At a startup, you build the stage and the auditorium while writing the script for the play.

Fast is an early-stage startup in a critical phase, where you have to increase the company’s profile. But it’s also a very difficult time for many people, and you need to be conscious of what might be happening in your audience’s lives. How do you approach the balance of bold and conscientious in your communications strategy?

This is the golden age for empathy. Communications professionals have always said that, but we haven’t always delivered on it. I began my career answering letters and phone calls to Members of Congress from their constituents and I learned that often, people just need someone to listen. Treating other people like human beings is crucial. That belief has guided me throughout my career, and this is the moment where we all need to practice it.

At Fast, we wanted to make sure people understand that what we’re building can really help them right now, by making their online transactions much easier. But we certainly don’t want to make people think we’re a big winner when the whole world is a big loser, or to undermine all the pain and suffering people are going through. To convey that, we make sure to be factual and make it clear that what we’re doing benefits everyone in e-commerce. We don’t talk about it like we’re celebrating the home team’s big win. This isn’t the time for that.

If we can get the empathy aspect right and be respectful and understanding of how people are feeling right now, we’ve done our jobs.

What is the role of comms in attracting top talent, especially as an early-stage startup competing with larger companies, and during a crisis when people might be more careful about taking a chance on a new company? 

This is such an emotional and scary time. Even people with secure jobs feel uneasy. We didn’t want to gloat about our position, but to understand people’s worries and provide reassurance that whether you like to go spelunking into the unknown with your career, or you’re the type of person who stays at one company for decades, Fast can be the place for you. 

We focused on showing that we’re well capitalized and solving the problem of the moment. This is a great place to work for people who like to take on new challenges and see their work have a real impact. We’re also in a secure place with a bright future, and coming here isn’t an undue risk. It can mean building, from the ground up, a solution that tackles a major problem of the last 30 years and is an even bigger problem in this moment. They can do that while having enormous support and investment. 

If we can get the empathy aspect right and be respectful and understanding of how people are feeling right now, we’ve done our jobs.

Given how many unknowns there are in the world right now, how are you approaching your communications planning for the next year or half year? 

We’ve continued building plans and roadmaps, and being opportunistic at strategic times. You can’t just throw up your hands and say, “anything could change at any time, so why bother making plans?”.

We want to build a seaworthy craft that can make it through when the next monsoon hits – take on a little water, but keep going. We stay true to our roadmap, but pivot and take advantage of new opportunities when they appear. When COVID hit, we started doing surveys to see how people felt about shopping online versus going into stores. That opportunity presented itself on short notice, and there will be many more like it. Our goal is to have a clear roadmap, but stay nimble.