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Shana Opperman of Pluto: “Fundraising truly is like dating”

Pluto helps local businesses deepen and sustain relationships with their customers remotely. We’re humanizing brand relationships and scaling their sense of welcome. We do this by specializing in creating light-touch participatory moments that connect the offline and online experience, measurably increasing retention and revenue immediately. And, importantly, the approach emphasizes authenticity, respect, and fun. It’s […]

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Pluto helps local businesses deepen and sustain relationships with their customers remotely. We’re humanizing brand relationships and scaling their sense of welcome. We do this by specializing in creating light-touch participatory moments that connect the offline and online experience, measurably increasing retention and revenue immediately. And, importantly, the approach emphasizes authenticity, respect, and fun. It’s also all through text, so there’s nothing to download or get lost in email inboxes. And, why start with text? It’s the lowest barrier medium for all ages to participate, plus a recent study from Velocify found that 45 percent of businesses’ text messages receive a response, compared to only eight percent of marketing emails. Pluto utilizes text messaging to engage customers — enabling brands to text surveys, share drink recipes or recommended reading lists — cultivating conversations based on their brand and services. Our assistive AI helps brands understand what their audience data means and surfaces novel text-based activities and inspirational templates based on our MIT research. We’re like the Hitch for small business marketing (anyone else a Will Smith movie fan?). The who, what, when, where problem is solved in one place and built with the same ethos of how you’d treat your friends and family.


The telephone totally revolutionized the way we could communicate with people all over the world. But then came email and took it to the next level. And then came text messaging. And then came video calls. And so on…What’s next? What’s just around the corner?

In this interview series, called ‘The Future Of Communication Technology’ we are interviewing leaders of tech or telecom companies who are helping to develop emerging communication technologies and the next generation of how we communicate and connect with each other.

As a part of this series, I had the pleasure of interviewing Shana Opperman, CEO & Co-Founder of Pluto who was motivated by her graduate research at MIT on tech’s impact on human connection when she formed Pluto. She’s both an MIT graduate and MIT drop-out, completing her MIT MBA & MIT Media Lab research, and leaving her MIT M.S Engineering to focus on Pluto. Previously, she led technical and creative production for an experimental adtech team at Google, bringing new ideas from concept to final product. Pre-Google, she was a digital producer at Saatchi & Saatchi NY, gaining experience in consumer marketing. She builds humane AI to amplify vs replace our own humanity, as she fundamentally believes that all you really are is a collection of your memories and who you make them with. Shana is a middle sister, astronomy enthusiast, 60s/70s/80s music fan, and sans-recipes cooker/baker (except when it comes to making her Yiayia’s 30-layer baklava!).


Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

My career interests actually stem from a soccer accident that happened when I was 14 and landed me in a wheelchair for a year. That experience formed my deep interests in memory as part of identity, the importance of social connection, and brands as friends that have influenced all that I’ve done since. My career began in advertising at Saatchi & Saatchi NYC, working closely with brands like General Mills, where I learned about consumer behavior and how brands can extend beyond a product and into a lifestyle choice. Then at Google, I focused on how brands can tell stories with data, and led technical and creative production for an experimental adtech team. After Google, I got an MBA from MIT and was working to complete my second masters in software engineering. While there, I worked in the Lab for Social Machines, a part of MIT’s media lab, which uses machine learning to understand how information disseminates through social networks and the impact on human connection. I became interested in what forms a true sense of belonging and how technology can be an extension vs replacement of our humanity, ad that’s where Pluto gets its roots.

Can you share the most interesting story that happened to you since you began your career?

One of the most interesting stories came from a major failure moment. While at Google, I was working on a massive advertising campaign with Nike for the World Cup and right when it was about to go live, lawyers came sprinting, literally, into the room yelling to halt the campaign we had spent about six months working on. Millions of dollars were on the line and to save it, over the course of just six days we had to completely redo what we had worked on for six months. It was an intense week to say the least, but titles/roles went out the window and everyone stepped up in impressive ways. We amassed a team across three countries so every hour of the day, someone was working to fix this project. Happily, we salvaged the project and it ended up winning over 20 industry awards for innovation, but more importantly, I bonded so closely with my colleagues during this project and formed friendships that still stand today. This experience proved to me that the greatest innovations come at the most unexpected moments and the most interesting experiences, while horrendous at the time, can end up being some of the most memorable.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

My favorite life lesson quote comes from my dad, I call it his Always Advice. Growing up, he used to remind me of three key things.

  1. Always be ready for the pass (ready to catch any curveball thrown at you!)
  2. Always assume positive intent
  3. Always do the right thing, even if no one will ever know

These are mindset choices and when I started Pluto, I shared them with each teammate I recruited. To this day, we include them as part of our company values and they guide how we interact with each other and make decisions.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

While in college, I was an intern at an advertising agency and served as an executive assistant to the CEO and COO, both incredible women. While there, the head of digital production was a man named Tim and one day, rather randomly, he asked if I was familiar with project management (I wasn’t at all). He said he’d noticed how I tended to get things done and thought I had an instinct for it, then offered to teach me more about project management as a skill and potential career pathway. He would stay with me after hours, during lunch and even early mornings to walk me through programs, techniques and his tips/tricks. It was special that he would help me just for the sake of helping. The project management skills he taught me got me some of my first big roles in my career and still influence how I bring my team together to tackle solving problems. Like Tim, there have been so many people in my career that have been willing to take a chance on me and help me grow. Those chances really helped me overcome my insecurity of feeling like I didn’t know what I was doing. People don’t always realize that the small things they do can make a huge impact — and I am thankful Tim took the time to teach me when he did.

How have you used your success to bring goodness to the world?

I grew up near a redwood forest in CA and it made an impression on me about the unseen interconnectedness of things. Redwoods, while they may seem to stand alone, are connected by an elaborate underground root system. I try to look at all of my interactions through this lens, it’s related to The Butterfly Effect — one small, positive interaction with someone I come in contact with could brighten their mood, and they could then pass that positivity to those they encounter. People get caught up in believing that to “do good” in the world, it must be a huge effort to be impactful. But people want to be seen, heard and feel appreciated and it does not require much effort on anyone’s part to make a friend or stranger feel valued. We can’t always control how what we do will impact others, but we can control the energy and efforts we put out into the world and I try to live by this to hopefully have a series of small, positive impacts, that I see or not, that can then hopefully ripple to others like dominos.

This approach has shaped how I operate in my everyday life, how I run my business, and honestly formed the basis for my business. Pluto enables businesses to create meaningful interactions with their customers, and at the end of the day, shared experiences of all kinds shape how we look at the world.

Ok wonderful. Let’s now shift to the main focus of our interview. Can you tell us about the cutting edge communication tech that you are working on? How do you think that will help people?

Pluto helps local businesses deepen and sustain relationships with their customers remotely. We’re humanizing brand relationships and scaling their sense of welcome. We do this by specializing in creating light-touch participatory moments that connect the offline and online experience, measurably increasing retention and revenue immediately. And, importantly, the approach emphasizes authenticity, respect, and fun. It’s also all through text, so there’s nothing to download or get lost in email inboxes. And, why start with text? It’s the lowest barrier medium for all ages to participate, plus a recent study from Velocify found that 45 percent of businesses’ text messages receive a response, compared to only eight percent of marketing emails. Pluto utilizes text messaging to engage customers — enabling brands to text surveys, share drink recipes or recommended reading lists — cultivating conversations based on their brand and services. Our assistive AI helps brands understand what their audience data means and surfaces novel text-based activities and inspirational templates based on our MIT research. We’re like the Hitch for small business marketing (anyone else a Will Smith movie fan?). The who, what, when, where problem is solved in one place and built with the same ethos of how you’d treat your friends and family.

How do you think this might change the world?

There’s a famous saying that the quality of your relationships determines the quality of your life. I believe this applies to how you sustain relationships with friends and family, as well as how businesses do so with their customers. Businesses, after all, are just a collection of people behind them. It’s an honor to take someone’s attention, so you better provide value and we want to bring this humility and humanization to how brands and their fans interact. We’re also mindful there is a fine line between technology amplifying a community’s humanity versus replacing it, and Pluto’s goal is to offer an easy way for businesses to maintain and strengthen their relationships authentically. We’re here to help more businesses foster connections with their customer bases and do so in a light, effective way with a dose of delight and respect. This is changing the way small businesses and their fans are spending time together and creating better, more human connections, even from afar.

Keeping “Black Mirror” in mind can you see any potential drawbacks about this technology that people should think more deeply about?

Our team has a monthly “Pluto Sci Fi” night to talk about what we want to be, what we do not want to be, and potential unintended consequences of what we do. It’s critical to our entire Plutoon team that we stay vigilantly intentional and mindful of where we want to head with Pluto’s technology and what we want to see this become. A recurrent “Black Mirror” topic we track is to always ensure we are not outsourcing thoughtfulness. It is not about just automating daily interactions and making things easier — we’re about making human connections more possible, accessible and fun. People should think deeply about what they want to do with their communications technology — we’re against gathering and scraping information so that it can be used to upsell. Rather, we want to create technology that helps others become their best self, i.e. following through on intentions, not creating ones they would never have.

Was there a “tipping point” that led you to this breakthrough? Can you tell us that story?

When we first started Pluto, we had a customer ask us to scrape data about their customers from external sources and use it to automatically send upsells on their behalf, and we said no. While it’s technologically easy to do this, we want the technology we build to be used to develop the personal connection between the customer and the company. We don’t believe in using information the brand and customer weren’t intentionally part of communicating. Our customers use Pluto to do the work to ask the customer their favorite flower, for instance, but we do not want to be purely a scraping service that pulls this information that the user never told us and automate thoughtfulness.

Above all, we need to make sure we are benefiting our customers. AI is truly a powerful tool and at Pluto our goal is to find the humanity within it and make sure that authenticity and trust stays intact.

What do you need to lead this technology to widespread adoption?

I think there needs to be a paradigm shift in how businesses view the interactions with their customers. Of course sales matters, but there’s an over-focus on the transactional parts of the relationship, which sells both the business and the customers short. If businesses were to hold the customer experience and relationship building in the same regard as a completed sale, society as a whole would benefit. Focusing on customer relationships builds brand loyalty which will ultimately lead to increased sales — but in a more personal and connected way.

The pandemic has changed so many things about the way we behave. One of them of course, is how we work and how we communicate in our work. How do you think your innovation might be able to address the new needs that have arisen as a result of the pandemic?

With Pluto we have found that we are really able to revive true human connection during a time where people aren’t able to interact closely at all. Social distancing restrictions have had devastating impacts on small businesses and the customer relationships that are their lifeblood. With a reduction in face-to-face interactions, businesses need a new approach to connecting with customers to stay profitable and maintain brand loyalty. Designed for the unique needs of small to medium sized businesses, we are helping build brand loyalty and drive meaningful ROI with light-touch, participatory text messages and help these businesses retain their customer base. As some of our customers have re-opened, they’ve seen inbound requests to keep their text circles as a permanent channel — it’s a welcomed new way to interact with local businesses.

Fantastic. Here is the main question of our interview. What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

1. It’s not a badge of success to neglect yourself

When I started, I had heard the tech startup folklore about all nighters and eating ramen over your desk that was also your kitchen table. And early on, I was running on fumes — barely sleeping, not eating well, not exercising, and I thought sacrificing my health was somehow required as a step towards tech startup success. One day I was in New York City doing customer interviews and I just collapsed on the sidewalk. And that was a wakeup call for me. The time it took for me to recover physically and emotionally, was a longer process than had I spent the time taking care of myself from the get go. I also realized that I was setting a terrible cultural example for my team and would have encouraged them to slow down if they were devaluing themselves as I was. Now, I do “Vitality hour” every morning to take time for myself and not feel bad about it. I have also decided that Pluto won’t operate during all hours of the night and over the weekend — we all need time to decompress so that we are energized and more productive when we are working. We work hard, but that respect for health and living life fully has made us even more productive.

2. Invest in values and in quality work, from the beginning

After I collapsed from sheer exhaustion during customer meetings, I completely shifted how I lived and how we ran the company. We now invest a lot in building our team culture and taking time to do silly “team dates”, fun new employee “initiations” and checking in with each other to make sure we are taking care of ourselves. When the pandemic hit and we shifted to remote work, we found that we had built such a strong team bond and trust that our team continued to work without interruption.

3. Fundraising truly is like dating

This has been a funny one — I think dating personally has prepared me more for fundraising than I ever could have imagined. The different stages are very similar; mutual attraction to building trust to discovering compatibility beyond initial interest, evaluating consistency in actions, and understanding core value alignment are all key in dating and fundraising. And, most of all, how this is a mutual choice, not a one-way sell.

4. Cultivate a network of differing opinions

I have truly come to value each of my mentors, especially as they often offer strong (and varying) opinions and perspectives. It helps me gauge my reactions, next steps and synthesize my decision. I also find value in the monthly roundtable discussions I have with members of my community — hearing from all different walks of life really helps open my eyes to experiences outside of my own and I think ultimately makes it easier for me to connect with investors and customers.

5. Take the roller coaster with a degree of humor and find ways to ground your perspective

Every day will be different, but our ability to navigate that ambiguity with grace is what we as leaders need to remember to do daily. I have a wall of astronomy photos in front of my desk to remind me we’re all running around on a floating rock and choosing how to spend our time on this planet. It changes the way I look at work; I no longer look at all of the tasks I have to do, but instead feel happy with all of the work I get to do. I try to make sure to remind myself that this is an honor and privilege and it’s important to enjoy the journey.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

It’s safe to say that 2020 was tough on everyone, but I think one positive effect of COVID has been highlighting how much we all need compassionate human interaction. So if I could inspire a movement, I think it would be to teach thoughtfulness and empathy as a critical life skill. Society wins when people are motivated to bring out the best in each other because we are all connected in the shared human experience. I have always appreciated a Henry David Thoreau quote, “To affect the quality of the day, that is the highest of arts.”

How can our readers further follow your work online?

You can find us at heypluto.com.

Thank you so much for the time you spent doing this interview. This was very inspirational, and we wish you continued success.

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