TechBytes with Jacob Ross, President at PebblePost

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TechBytes with Jacob Ross, President at PebblePost

Tell us about your role and the team/technology you handle at PebblePost?

I joined PebblePost as President, in April. In my new role, I’ll partner closely with CEO Lewis Gersh and the team to drive growth and innovation for the company’s digital-to-direct mail marketing platform.

I have been in the AdTech and MarTech space for many years, and have been fortunate enough to be on the cutting edge of digital marketing becoming more addressable, performance-driven and also accountable (although the latter is very much a work in progress, as I’m sure most industry insiders will agree).

After five years at MediaMath, most recently as Chief Product Officer, I recognized the huge opportunity that PebblePost had harnessed in the space: where the digital world and the physical world intersect. As marketing becomes more digital and digital marketing becomes more addressable, the next frontier is being explored where those worlds come together: television and connected TV, radio and streaming audio, out of home and digital out of home, and, of course, direct mail and Programmatic Direct Mail (a term PebblePost coined as inventors of the space).

PebblePost has identified a unique market position, and we’re just getting started. My role is to take our CEO Lewis’ enduring vision of ‘bringing good marketing home’ and make it a reality, with the right strategy, plan, and team to fully realize it. We have a responsibility as the category leaders to build great experiences for both brands and consumers that are effective, respectful and relevant. Given that remit, most of the team will roll up to me, from engineering to sales to Business Intelligence.

How did you start your journey in the Technology industry?

I fell into this wonderful, unique industry by chance. I was working on Wall Street, putting my Literature degree to good use, as a trader and analyst on a trading desk. I have always had a passion for markets of all sorts, and technology. When a friend told me about Right Media (the first real ad exchange), I was immediately hooked. He described it as a real-time marketplace for the buying and selling of ads, using cutting edge technology, that did more volume than all the world’s stock exchanges combined and ran 24/7/365. My first job was convincing publishers and agencies to adopt a bid-based philosophy and technology (we didn’t call it ‘programmatic’ quite yet) to help them run their businesses more effectively.

I had a chance to work with a series of other leading companies in the years since, from Demand Media to Criteo to MediaMath; each of them has played a critical role in pioneering the evolution of digital advertising and creating new solutions for our young but rapidly maturing industry.

What is the current technology roadmap to build powerful ROI-centric Marketing, Sales and Advertising stacks?

Great question. Many companies struggle with actually providing clear ROI. The solution has a few necessary components. First, there must be clear, measurable goals, and the technology has to be able to hit that goal. Second, there has to be a way to measure performance. Third, the entire offering and experience must be grounded in how companies measure success and need their marketing departments to drive that success, so at the heart of it all, we solve a company growth problem, not just a mathematical equation.

In PebblePost, I’ve already seen evidence of all three. We have developed intellectual property to harness and use digital data signals that results in highly effective (and respectful) mail. The solution is fully integrated. We are solving more and more parts of this brand measurement challenge with each product release.

The challenge we came to in the early days was that the performance was so good that the results were hard to believe! We invested heavily here, developing strong data science and BI team with experienced leadership in Hongyan Jing and Bridget Gola, and we committed to holding ourselves accountable to both ROI and incrementality. Incrementality is so powerful – it is a way to measure the precise impact of a marketing tactic on overall ROI. PebblePost has consistent positive incrementality – that means the more our brands spend with us, the more they drive revenue, and we can prove that.

Finally, our brands are looking for more than a report, they need to know that we deeply understand their business objectives and that their marketing efforts are making the impact that they need. When we get to know a new brand we try to understand this upfront, and when we share the results we make sure it aligns with what we are aiming for. We talk about ROI, ROAS, etc. But what we aim to deliver in every brand engagement is improved business outcomes. That is ‘true ROI.’

What are the key Advertising Analytics/metrics that Digital Advertising and Marketing teams should be keenly following?

We start with what most of our brands are measuring. They are looking to acquire new customers and delight their current customers. They want to achieve this effectively and respectfully. With all the fragmentation present in the industry today, all proxy metrics (and self-judged results) should be looked at with some skepticism. That’s why we believe strongly in metrics directly impacting business outcomes: sales. Our brands are measuring sales by looking at ROI, ROAS, and other metrics. We believe strongly in incremental lift measurement as well, and we conduct transparent incrementality analysis for almost all our brands now.

The other challenge we have seen is that digital-only metrics are often not sufficient. Our Transaction Match Analysis, a proprietary study we do for every brand we work with now, looks at true sales holistically, wherever the customer was, to understand the true impact. We do this transparently for the brand. This gives our clients more confidence that their marketing efforts are really working, without smoke and mirrors.

How is PebblePost’s strategy transforming the way modern brands do their Marketing and Sales?

PebblePost is helping to connect the physical and digital worlds and make-at-home marketing a more effective, relevant experience. We do that by using data and decisioning to ensure that we only send mail to the most interested consumers, and we help mail move closer to the speed of digital. Brands who work with us are looking for modern solutions to modern problems, and we are working to deliver that every day. With brands like Dyson,, Parachute and many more we’ve already delivered – but we’re just getting started.

Tell us more about your expertise in AI and Machine Learning initiatives for Marketing and Sales Intelligence.

So much has been said about Machine Learning, so I want to try to say something new and useful here as a business leader, as opposed to a technical expert. I’ve been fortunate to work in innovative companies with very smart teams who are at the forefront of how to use data science to make better decisions, at scale.

At Right Media, we used various Machine Learning techniques to predict the probability a user would take a certain action that, among other things allowed us to innovate a new pricing type: dynamic CPM (dCPM). This conferred great benefits to brands and publishers because it allowed a ‘true price’ to be paid.

At Demand Media, we built an incredible content platform. We were publishing 10,000 articles per day, and our content technology allowed us to predict and optimize how useful each piece of content would be for the 150MM+ visitors to our sites each month. This informed what content we would create, allowing AI to guide our content strategy, as it were. Of course, we integrated our ad strategy into this stack.

At Criteo, we employed incredibly powerful Machine Learning to predict both how likely a user would be to convert on an ad that they saw, and the actual content that the ad showed. This powerful personalization and targeting drove incredible performance.

Finally, at MediaMath, we built both prediction and recommendation algorithms that could be used in a variety of scenarios, but we also built a Machine Learning platform that allows others to plug in their own algorithms. As the market has progressed it’s less about having one great Machine Learning algorithm, but more about allowing the variety of use cases and technologies out there to learn and compete for the best insights and performance out there. I’m still very excited about the partnership that MediaMath has with IBM’s Watson.

At PebblePost that evolution continues, with the machine learning being laser-focused on driving the best performance in the digital-to-physical worlds. It’s incredibly powerful, and we’ll be sharing a lot more about this topic soon.

What are the biggest challenges in measuring the ROI of Marketing and Advertising?

Aside from the technical and analytical challenges we discussed above, we are looking at a moment of real maturation for the industry, in MarTech and tech more broadly.

None of us will be successful if we don’t take consumer privacy and the security of consumer’s data seriously. Between the increasingly central role large tech companies have in our society, consumers who are fed up with the feeling that their data is out of their hands, and changing behaviors overall, we have arrived at incredibly important crossroads as an industry.

At PebblePost we put consumer privacy and security first as we believe that how we approach these challenges in the next year or two will determine how effectively we can make marketing a progressive force for good and growth.

How do you prepare your team to leverage analytics and technology for Search, Display, and Programmatic?

PebblePost is a technology company, and in that, we have to be at the forefront. In addition to the technical expertise we have in our engineering, data science and BI teams, we’ve adopted tools and processes and training to help ensure those technical skill sets are married with a deep understanding of industry context.

What is your prediction on the disruptive application of Video and TV Advertising Analytics in B2B and B2C marketing initiatives?

The home is certainly a huge focus for many in the space: how do we market effectively and respectfully to consumers as devices proliferate, everyone spends more time online, and ways of consuming content continue to become more personal and tailored?

I predict the trend will continue and accelerate, although new measurement standards will need to emerge that are omnichannel in nature, and purpose-built for the world we live in today.

PebblePost is pushing the envelope on this frontier as well, focused on better at-home marketing experiences for consumers. We welcome the innovation we see in this space and will be building new offerings for our brands alongside TV, radio, and other at-home focused solutions.

Jacob will be responsible for accelerating PebblePost’s growth even further, and to prepare the company for the next stage. He is responsible for the near-term success of the business managing sales, customer success, marketing, operations, business intelligence, product, and engineering. Given the rapid growth this New York headquartered leading digital-to-direct mail marketing platform company is experiencing, another priority is to bring people in to help them with the next phase of growth.

pebblepost logo

PebblePost is the leading digital-to-direct mail marketing platform. We capture online interest and intent data to send relevant direct mail that activates buying decisions at home and drives conversions everywhere.

We invented Programmatic Direct Mail® to help brands convert more shoppers into buyers using advanced targeting, algorithmic optimization, attribution and quantitative analysis. PebblePost® is a venture-backed company based in NYC.

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