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Women Leading The AI Industry: “The reality is that the AI industry needs women more than the other way around” With Heidi Messer & Tyler Gallagher

We need women founders, funders, board members and academics to be featured more in media coverage. There are many success stories that must be told — articles like this one that show that women are making a massive impact on how AI is being brought to market. The reality is that the AI industry needs women more […]


We need women founders, funders, board members and academics to be featured more in media coverage. There are many success stories that must be told — articles like this one that show that women are making a massive impact on how AI is being brought to market. The reality is that the AI industry needs women more than the other way around. Despite representing only half of the world’s population, women control the economy, responsible for 80+% of the purchases that fuel it. It’s always been mind-boggling to me that women drive a huge portion of the economy yet are left out of the tech conversation. How can you train machines to think like decision makers if you don’t have their voice at the creation stage? Women also need to participate in networks to support each other. I believe one of the most critical things we can do to engage more women in the industry is to build and support powerful networks that provide them with opportunities to which they traditionally have not had access.


As part of my series about the women leading the Artificial Intelligence industry, I had the pleasure of interviewing Heidi Messer. Heidi is the Chairperson and co-Founder of Collective[i], a pioneer in the future of work movement where technology is used to augment talent and free people from error-ridden and tedious tasks. Collective[i] helps B2B sales organizations improve productivity and grow revenue by using a network of data and machine learning to better understand their buyers and their preferences to optimize outcomes. Heidi has been an active entrepreneur and investor in the digital economy since the commercialization of the Internet. Previously she co-founded LinkShare Corporation, host to one of the world’s largest online affiliate networks representing the world’s premier publishers and merchants on the web, which was acquired by Rakuten for $425 million in 2005.


Thank you so much for doing this with us! Can you share with us the ‘backstory” of how you decided to pursue this career path?

I started in the industry working with cable companies at a time of deregulation. While there, I collaborated with some of the smartest entrepreneurs who all had worked to make an industry where nothing had stood before. When the Internet and World Wide Web was nascent, my brother, Stephen, and I saw a similar opportunity and jumped on the chance to be a part of a new revolution that might displace everything before it.

Many people thought I was foolish to leave a stable career in a more established industry but they just couldn’t see the future. Part of what makes a great entrepreneur is the ability to see potential before other people can imagine its realization. I can thank my mother, an incredible entrepreneur, for that lesson. She encouraged us to bet on the future. Stephen and I made the decision to jump in and the rest is history…or history still in the making if you look at what we are doing now.

What lessons can others learn from your story?

Transformative opportunities tend to elicit extreme reactions, especially when a technology has the potential to change the world as we know it. The irony is that the extremism, the moment when most people tell you it’s crazy to imagine that a technology will work — is the moment you know you are onto something. What distinguishes innovators from everyone else is their ability to see possibilities where everyone else sees impossibilities.

It happened when Steve Jobs said that people would use the iPhone for photos, music and just about everything else. It happened when Reed Hastings told people they would watch movies from Netflix streamed through the Internet. It happens when we tell people that Collective[i] will transform how sales professionals work and how enterprises manage revenue. The point is that you have to believe in your vision of the future and lead people there. Rejection is often the validation of a great idea.

Can you tell our readers about the most interesting projects you are working on now?

As someone who travels between tech hubs in the U.S. and abroad and has a track record of building technology companies, I’m lucky in that I get to be involved in numerous interesting projects. In my career, nothing has ever compared to the revolution that is taking place in AI/ML. Collective[i] (short for Collective Intelligence) is the most interesting and important project that I have ever been a part of and one that will have a huge impact on the world. That is saying a lot especially given the opportunities LinkShare unlocked for millions of people.

In America alone, one in eight people are in sales and the revenue they generate is what drives our economy. B2B is a market that is twice the size of B2C. The irony is that sales organizations are the engine of growth and economic stability but the technology they use, mostly CRM, actually inhibits success. Sales professionals spend more time capturing and managing data than they do generating revenue. More than a third of their time is spent doing useless data entry or the futile exercise of trying to forecast revenue off of biased and error-ridden human perception.

Without any guidance about what is happening with the real people who control revenue (the buyers!), more than half of sales professionals miss their targets and a quarter lose their jobs. For people who are paid on commission, that’s tough. For their organizations, it’s even more challenging. When a sales organization misses targets, lots of other people suffer. Often sales is the canary in the coal mine, the first to sense when a market is changing and a company needs to evolve. Unfortunately, because the data input is one-sided and often seen as self-serving, the voice of the buyer gets lost.

It’s astonishing that even the most tech-savvy companies like Facebook, IBM, and Microsoft have massively missed the mark on revenue generated from their sales teams resulting in sudden and staggering drops in their stock value.

Collective[i] disrupts this. Succeeding in sales is not about process or rules. It is about experience and judgment — things that are perfect applications for AI/ML. You can basically train a machine to be an expert in how buyers make decisions by letting it learn from millions of interactions. Experience that would take a human years to acquire can now be shared, essentially making sales professionals experts from the first day they meet a buyer.

I am excited that Collective[i] can have a huge impact on how people work and address the terrible costs (layoffs, bankruptcies, recessions) that come from the inability for most companies to spot issues and opportunities. It’s energizing to create a world where individual talents are appreciated and companies become more agile. In the end, we remove a ton of guesswork (and busywork) that inhibits creativity and success. The potential impact on people’s livelihoods, quality of work and the economy at large is staggering.

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?

When you want to change the world it can be lonely. You need people from the outside to debate ideas, act as cheerleaders and provide perspective. For me, Julian Brodsky, co-Founder of Comcast was one of those people. He “discovered” my first company and went all in.

My brother Stephen and I started LinkShare because we saw an opportunity for companies to monetize their site traffic. We knew we were on to something, but plenty of people doubted us. That’s why Julian played such a pivotal role in my early success. He believed in Stephen and me, even though we were just beginning our careers, and basically just said, “let’s do this!”. He joined LinkShare’s board and has been an incredible mentor and supporter ever since. He’s an unbelievable businessperson and negotiator. He helped me be a better negotiator, stay focused on building (networks require a huge upfront investment before you reap the rewards) and taught me to remain curious and open-minded throughout the process.

Julian once told me that whenever he had an important decision to make he would go fishing. It sounds like a small thing but when you are in the thick of something important, taking a break feels impossible. He saw it as an investment and a way to avoid the costs of making a poor decision. Like my mom, his perspective is that the best bets are made when you tune out outside noise and can think for yourself.

What are the 5 things that most excite you about the AI industry? Why?

  1. AI is exponential, which means that you think everything will take longer than it does. It literally is the tip of a massive iceberg. Technology can go from a place of limited utility to mind-blowing change in the span of a few months.
  2. AI is not like prior revolutions. In the past, everyone could watch and learn from people who got in early because there was an adoption cycle. It took the Internet 10 years to take flight. Mobile took five. AI will happen overnight. And when you fall behind in AI, there is no catching up.
  3. AI is the turning point for all humanity. It is the sum of all our trials and errors.
  4. AI will drive a new era of innovation and progress.
  5. One of my favorite quotes is one I came across attributed to Professor and Pulitzer Prize-winning author Douglas Hofstadter who said, “AI is whatever hasn’t been done yet.” AI will improve how we live and how we work in massive ways. We are on the cusp of a world where human creativity and ingenuity will drive business opportunity.

What are the 5 things that concern you about the AI industry? Why?

  1. AI will be misunderstood which will inhibit adoption.
  2. Countries that lead in AI will have disproportionate advantages and impact on global outcomes.
  3. AI can be a force for tremendous good but uninformed politicians will stifle that potential with poorly drafted regulation.
  4. Companies and people that take a “wait and see approach” to AI will be decimated and/or miss out on human talents with underinvestment in training.
  5. Like most technologies, AI is neutral but also limitless in its potential. Any bias or misuse comes from humans. Good outcomes rely on founders and leaders with integrity and a vision for humanity that is inclusive and designed to maximize human gifts.

As you know, there is an ongoing debate between prominent scientists, (personified as a debate between Elon Musk and Mark Zuckerberg,) about whether advanced AI has the future potential to pose a danger to humanity. What is your position about this?

This is a false choice because the AI train has left the station. It’s happening. When certain change is inevitable, you can either embrace the positive and play a role in making it happen or you leave it to others to shape the future and criticize. Technology by its nature is neutral, meaning the ability for extreme evil and extreme good lies in its creators and users.

In the case of AI, much of its use can’t be controlled by regulation or borders, rather, it relies on the collective judgment of all of us. For me it comes down to your view of humanity — do you believe that people are essentially good? If so, AI is incredibly exciting in the long run. The risk is people who hijack its power for nefarious purposes.

What is interesting about AI, and one reason why I believe our educational system must evolve, is that you are training machines to do things. Once they are trained, the morality and biases passed onto them go beyond the humans that created the algorithms. It is for this reason that it’s important to have debates now about the kind of society we all want, finding common ground and establishing shared values so we don’t replicate the problems and inequities of the past.

What can be done to prevent such concerns from materializing? And what can be done to assure the public that there is nothing to be concerned about?

AI is no different than any other seismic change — it breeds fear that blinds people to possibility. When the world shifted from an agrarian economy to an industrial one, people were afraid. No one realized that it would bring things like leisure time, automobiles, cures to lethal diseases, etc.

It’s our job as leaders in AI to talk about the real benefits to people and not just how the technology works or the jobs it will automate. We need to show everyone how the world transformed by AI will actually be better.

It’s imperative that we include as many people as possible in the discussion. The more people who participate in the development and use of AI, the better. At Collective[i], we spend a lot of time teaching our prospects and users about what AI actually is. Once they understand the potential it has to improve outcomes for them — be it health, professional or otherwise, it feels more like progress.

AI is a reflection of who we are and what we dream is possible. The technology is amazing because it puts a microscope on our belief systems and biases. We shouldn’t be afraid of what we see (even if we reject it) but use what we learn as a way to advance humanity. That is the foundation of all knowledge.

I worry that certain countries are treating AI like an arms race. I believe that the approach taken by Canada and the United States of open sourcing AI will prevail as a better alternative to using science as a weapon to gain power. Science should be about progress, not politics and dominance.

What matters most is that we learn fast and pivot to better outcomes. Stifling technology purely to prevent negative consequences inhibits the possible. We need to dream big and provide incentives to put AI to positive use. If we worried about how rockets could be misused, we would never have explored space. Real progress is fueled by human imagination and curiosity backed by a desire to do good.

How have you used your success to bring goodness to the world? Can you share a story?

I believe that networks are key to progress. LinkShare’s network brought an income to millions of people. Collective[i]’s network helps sales professionals learn from each other and succeed exponentially as a result. After seeing networks’ power to transform, as well as an alarming underrepresentation of women in technology and other influential sectors, I set out to build a network for powerful women.

It’s called the “All In” Network and includes the world’s most incredible leaders spanning the corporate, government, entertainment, entrepreneurial and not-for-profit sectors. What started with a small, private poker game has evolved into a powerful network of extraordinary women at the top of their fields. The waitlist to attend is currently at 3,000+. The game has created a legacy as a breeding ground for a myriad of deals, partnerships, funding and board appointments, and a whole host of other things where networks remove friction and expedite progress.

As you know, there are not that many women in your industry. Can you share 3 things that you would you advise to other women in the AI space to thrive?

  1. AI will be bigger than the Internet. Get in early and be one of the people who define the categories.
  2. Machines learn from who and what teaches them so we need to make sure that this emerging industry is diverse and well represented.
  3. Networks are essential to execution. Invest in building a strong network of friends, peers, mentors, and sponsors to help carry you through tough times and expedite your success.

Can you advise what is needed to engage more women into the AI industry?

We need women founders, funders, board members and academics to be featured more in media coverage. There are many success stories that must be told — articles like this one that show that women are making a massive impact on how AI is being brought to market.

The reality is that the AI industry needs women more than the other way around. Despite representing only half of the world’s population, women control the economy, responsible for 80+% of the purchases that fuel it. It’s always been mind-boggling to me that women drive a huge portion of the economy yet are left out of the tech conversation. How can you train machines to think like decision makers if you don’t have their voice at the creation stage?

Women also need to participate in networks to support each other. I believe one of the most critical things we can do to engage more women in the industry is to build and support powerful networks that provide them with opportunities to which they traditionally have not had access.

What is your favorite “Life Lesson Quote”? Can you share a story of how that had relevance to your own life?

“You will never be the smartest or dumbest person in anything. All you can do is focus on finding a way to make things happen.” Said by my mom. Her point was that a creative solution (which requires both curiosity and willingness to fail) is the ultimate advantage, not raw intelligence. In the world of AI, nothing could be truer. As algorithms equalize our access to intelligence, curiosity and creativity will be enormously important.

You are a person of great influence. If you could start 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. 🙂

I would start a movement to view human talent as a natural resource — and one that is under as much threat as our environment is from climate change. Every time we fail to educate a child, retrain a worker, present everyone regardless of their gender, skin color, age, etc. with equal opportunities we lose an asset. Put another way, if only a small percentage of the world is participating in the advancement of human talent, we are all in jeopardy.

How can our readers follow you on social media?

You can follow me on Twitter @heidimesser and via LinkedIn, and learn more about Collective[i] on Twitter @collectivei.

This was very inspiring. Thank you so much for joining us!

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