Meet Amy Gershkoff Bolles, the mind behind Bitly’s data & insights division



In this feature, we are pleased to reflect on the frame of mind of a seasoned technology executive and pioneer in the technology industry, Dr. Amy Gershkoff Bolles, the Chief Data Officer of Bitly, Inc., and GM of BitlyIQ, who believes that when someone tells you ‘it can’t be done’, it’s a challenge rather than a conclusion.  

When we say ‘Seasoned’

From a young age, Amy had a passion for quantitative analysis and ended up pursuing a Ph.D. at Princeton University in this field. Looking back at it, she exclaims, “I owe my entire career to my dad – he was the one who encouraged my interest in analytics. When I was in college, he suggested (well, actually, insisted) that I take courses in statistics, data mining, and econometrics. Those courses ignited my passion for data and analytics.” 

After completing her education, Amy moved to Washington, D.C., where she used her data science skills to work in politics. During her time there, she led data and analytics strategy for several Congressional campaigns, U.S. Senatorial candidates, and prominent governors. She also had the honor to serve as the Head of Media Planning and Analytics for President Barack Obama’s re-election campaign.  

Amy also co-founded and led a tech company: Changing Targets Media. Within just two years, she turned a $50,000 ‘Friends and Family’ cheque into a profitable enterprise with $9 million in ARR. This company helped advertisers optimize their media planning using software called PrecisionBuy, built by Amy. She shares, “It was an amazing journey to build a company from scratch, and I learned a tremendous amount from that experience.”  

After the Obama re-election campaign, Amy was hired by the largest media conglomerate of the time, WPP, joining their subsidiary Burson-Marsteller to establish and lead their Data and Analytics practice. She shares, “After a little over a year, I had built the Data & Analytics practice into a highly profitable, 8-figure business, and was promoted up to Chief Data Scientist for WPP, Data Alliance. In that role, I worked across all of WPP’s then 350 operating companies, helping them establish Data & Analytics practices similar to what I had built at Burson-Marsteller, designing custom data and analytics solutions for WPP’s marquee clients.” 

After this, Amy joined eBay, where she built and led the Customer Analytics & Insights team that developed eBay’s first personalization engine, which significantly increased conversion rates and incremental revenue for the company. For her remarkable contribution, she was later promoted to the Global Head of Data Science at eBay. She later served leading organizations like Zynga and Ancestry as their Chief Data Officer before she finally joined Bitly in 2018.  

“It was an amazing journey to build a company from scratch, and I learned a tremendous amount from that experience.”

Building BitlyIQ, Bitly’s Data and Insights division, was not an easy journey and Amy was faced with plenty of skepticism along the way, but she embraced every challenge to pave the way forward. “Building a successful business from scratch is never easy – there are always numerous obstacles along the way. For example, to build BitlyIQ, we had to figure out how process hundreds of machine learning models against billions of datapoints in a fraction of a second.  We had to build an architecture that would enable us to scale to be able to process petabytes of data while still maintaining reasonable computing costs. We had to build a search engine that could search billions of pieces of content based on themes, not just based on keywords – and we had to do it in 148 languages.  Internally and externally, many people were skeptical that we could overcome some of these difficult technical challenges, and build a successful business, but we did. Throughout this journey [building the BitlyIQ business], my team and I have often been underestimated. But we always deliver because we are a strong, innovative team, we are determined to succeed, and we work together.” 

Dr. Amy Gershkoff Bolles, Chief Data Officer, Bitly, Inc., and GM, BitlyIQ.
Dr. Amy Gershkoff Bolles, Chief Data Officer, Bitly, Inc., and GM, BitlyIQ.

“Don’t let the negative experiences define you. But instead, choose to focus on the positive. Positive people always advance further and have a better experience along the journey.”

Driving business results 

BitlyIQ was established in 2018 as a new division of Bitly, Inc., which was founded in 2008 as a SaaS company that provides a link shortening utility. Bitly, Inc., has been in business for 12 years, headquartered in NYC, and has offices in San Francisco and Denver as well. The vision behind BitlyIQ is to create unique, privacy-friendly insights about digital trends, leveraging Bitly’s unrivaled understanding of the Internet landscape. Bitly’s platform is the 5th most visited destination on the Internet, receiving more traffic every day than Amazon, Netflix, Instagram, and Twitter combined; billions of people click on Bitly shortened links every month. Having such a significant portion of global internet traffic under their belt, BitlyIQ was created to generate custom analyses of relevant digital trends and behaviors from the Internet for clients.  BitlyIQ insights leverage fully anonymized trend data from Bitly’s unparalleled dataset,  overlayed with industry-leading machine learning algorithms.  BitlyIQ’s insights help their clients defend their brand, optimize their content strategies, gauge messaging impact, monitor competitors, and gain a deepened understanding of their customers.  

Although many companies today already use social media monitoring or listening, there are significant gaps in using it as the only tool to manage their brand.  Amy explains, “First, social listening can only provide limited data from a handful of social media platforms, and the data are siloed into “walled gardens,” – Twitter data are separate from Facebook data, etc. – whereas BitlyIQ provides data across a much larger number of platforms and de-silos the data so you can get a comprehensive, “one-stop-shopping” view of all online conversation about your brand and industry. Second, these days, social listening data are much less reliable because such a high number of interactions on social media are bots – many industry experts estimate that bots comprise more than 50% of all social media activity. So, it’s very difficult for a company to tell what online conversation about their brand is real. At BitlyIQ, we leveraged our extensive 12-year training dataset and industry-leading machine learning algorithms and built a world-class bot-detection engine that our benchmarking shows is among the very best in the industry. This bot detection technology allows us to cleanse our clients’ data of bot traffic, giving them a clear view of the true digital conversation about their brand, company, or industry.” 

Some BitlyIQ customers are leveraging BitlyIQ’s insights trend data to predict aggregate consumer demand market by market.  With the ongoing COVID pandemic causing dramatic changes in consumer behavior, real-time predictive data on consumer trends has become very valuable.  Amy explains “The BitlyIQ trends data can provide real-time signals of consumers’ intent, giving our clients a leading indicator of sales on a market by market basis, which can be enormously helpful for marketing, sales, and overall strategy.”

When leadership is action, not position  

Amy has a few key ways of working that have helped her achieve success as a leader and an innovator.  First, she says it is important to secure some time just to do the ‘thinking work’ instead of packing the entire week with meetings. Second, she asserts, “It’s important to broaden your perspective outside of the day-to-day experiences at your company. This is one reason why I’ve enjoyed my roles advising other companies over the last decade, in addition to my full-time, primary role. The experience of seeing how other companies and leaders handle certain opportunities and challenges ensures that you continue to keep your perspectives broad and diverse.” Another rule that she has is if two or more people have more than five messages back and forth about a topic, it needs to become a meeting. This is because critical information can easily be lost over email or Slack, and reading the other person’s non-verbal cues and body language is crucial to reaching the best resolution.

Amy also believes teamwork is far more essential than any number of individual great ideas. This ideology further extends to the way every team member should behave. Speaking of which she asserts, “Treat people the way you want to be treated- Theoretically, we all learn this rule as children, but many adults in the workplace do not follow this mantra. Living by this Golden Rule in the workplace means delivering tough feedback with compassion, saying no gracefully, speaking up respectfully. Teams that live by the Golden Rule always deliver better results because people feel respected and are able to deliver their best work.”   

Even when it comes to hiring, Amy has her criteria before she brings someone on board and it has less to do with what they bring to the table and more about how they serve it. She says, “Whenever I hire someone onto the team, I have them meet with a variety of key leaders and team members, and always have the last meeting be with the most junior person on the team – this could be the executive assistant, or an intern, or very junior analyst. I have had candidates who passed all other interviews with flying colors but were rude or disrespectful to the junior interviewer, and I never hire these people, no matter how qualified he or she may seem based on other criteria or assessments by other interviewers. All work is a team sport and every member of the team matters equally – anyone who doesn’t believe that is not someone I want on my team.”  Using this approach, Amy has built a strong team at BitlyIQ that is capable of delivering industry-leading technology under tight timeframes in an agile fashion. Amy shares, “The engineers, data scientists, and analysts on the BitlyIQ team are among the best I’ve worked with in my career, and the technology we’ve built together has been revolutionary, allowing us to analyze broad digital trends culled from billions of digital engagements in just a fraction of a second. We’ve had many successful client projects over the last 18 months leveraging the new technology we’ve built. The next 18 months are about continuing the very strong growth trajectory that we’ve had so far.”

Keep going 

When it comes to motivating her team, Amy is just as considerate and employs a personalized approach depending on the individual’s drive. Her consideration comes from her years of experience in the industry and the struggles she has faced to break through the glass ceiling as a woman. According to her, “While diversity is incredibly important, inclusion also matters just as much. Everyone deserves to be treated fairly in the workplace and be given equal access to promotions, compensated fairly, and treated with respect.” Although Amy has repeatedly faced discrimination during her career, Amy’s advice for women striving to reach the next level in their careers is to not dwell on these unfortunate incidents: “Don’t let the negative experiences define you. But instead, choose to focus on the positive. Positive people always advance further and have a better experience along the journey.”  

To conclude, “The expression ‘nothing ventured, nothing gained’ rings true – if you stand still, you will never learn and grow. I’ve always learned more from the entrepreneurial experiences than I ever could have learned by playing it safe,” says Amy. 

Flying High: Women Leaders, 2020 ​.

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