Laura Baldwin of O’Reilly Media: “Sell direct rather than through distribution partners, where appropriate”

Take advantage of today’s cloud solutions, which have democratized AI and data science for all. I think this is the biggest game changer in the Digital Transformation race these days. You no longer have to employ an AI engineer to take advantage of machine learning. Those features are built into today’s cloud solutions. By hosting […]

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Take advantage of today’s cloud solutions, which have democratized AI and data science for all. I think this is the biggest game changer in the Digital Transformation race these days. You no longer have to employ an AI engineer to take advantage of machine learning. Those features are built into today’s cloud solutions. By hosting your own business in the cloud, you have access to the latest and greatest technologies that were previously reserved for the few large companies that could afford them. Your job is to do the homework and see where you can use those technologies in your specific business. Just go back to answering the first questions I posed: Can your products become digital or digitally enabled, can you find new markets via social media, and can you interpret your sales data to build a better product?


As part of our series about “How To Use Digital Transformation To Take Your Company To The Next Level”, I had the pleasure of interviewing Laura Baldwin.

Laura Baldwin is the President of O’Reilly Media, the premier source for insight-driven learning on technology and business. Laura started with O’Reilly in October 2001 as chief financial officer, added chief operating officer to her responsibilities in October 2004, and became O’Reilly’s first president in March 2011, taking on responsibility for the company’s worldwide businesses. Prior to O’Reilly, she was a consultant to the publishing industry and managed several large consulting engagements across all genres of publishing and media.


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?

I was always a math person, but banking is where I learned how to marry those skills with process and business. Banking led me to roles in cash management and finance — always for companies whose products I loved. It was at luxury retailer and perfume company Giorgio Beverly Hills that I learned finance was really telling the story of the operational decisions made every day in service of the business. That observation was a game-changer for me. Even as a financial analyst and, eventually, a controller, I engrossed myself in the business operations of every company I was fortunate enough to work for. That personal curiosity around business decision-making and strategy development led me to my current role at O’Reilly. When I joined the company as CFO, I intentionally led the team through an operational, decision-making lens. That resulted in a promotion to COO and then president. The story of my career path has really been a combination of my love of numbers and my natural curiosity.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lessons or ‘take aways’ you learned from that?

When I was a financial analyst for Giorgio Beverly Hills in the mid-eighties, the company purchased its first desktop computer. We were all a bit nervous as no one had any idea how to get started. I volunteered to jump in and learn a program called Symphony, which was a combined word processor and spreadsheet software solution. Now, that was the heyday of luxury retail, and our owner, Fred Hayman, was traveling the country to meet with the CEOs of major high-end chains and stores. I worked so hard to figure out that software. After many sleepless nights, I proudly announced that I had moved all of our manual reporting over and we were now “computerized.” I carefully printed out all of the sales reports Mr. Hayman would need for his trip and off he went. Unfortunately, I wasn’t quite the expert I thought I was. My boss got a call that we had just disclosed the incorrect (and in some cases competitive) sales data to every account he visited, causing great embarrassment. I was mortified. I got called into CFO David Horner’s office, fully expecting to be fired. Instead, I was told, “You’re not working hard enough if you’re not making mistakes.” That simple lesson has set the tone for my entire career.

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?

I’ve been fortunate to have several mentors throughout my career. At Giorgio Beverly Hills, David Horner taught me if I wasn’t making mistakes I wasn’t working hard enough, and Fred Hayman taught me that presentation was everything. Jack Jensen and Nion McEvoy at Chronicle Books taught me an eye for design and a passion for taking care of the talent that made our work possible. At O’Reilly, Tim O’Reilly taught me about running a mission-driven business. However, the mentor that affected me the most didn’t even realize she was acting as a mentor.

Kathy Franzen was the CFO of Giorgio Beverly Hills following David Horner. This was the late eighties, and it was definitely still a man’s world. I watched her navigate the all-male senior team with grace and dignity. She never deferred to the male leadership in the room as I had previously seen women do in the workforce. Instead, she challenged them — which made them and everyone around her better. She gave me opportunities because she saw potential in my hard work. She elevated those that earned it. I learned how to lead and grow talent simply by watching her. It was a gift.

Is there a particular book, podcast, or film that made a significant impact on you? Can you share a story or explain why it resonated with you so much?

I love to read both business books and fiction, so I could make a long list to answer this question. But a few years ago I read Little Fires Everywhere by Celeste Ng. The two main characters are mothers, one’s from a privileged family and the other’s struggling to raise her daughter, and the book really digs into the effects their situations have on how they raise their children.

Then last year, Little Fires Everywhere was made into a Hulu series starring Reese Witherspoon and Kerry Washington. It took the concept of privilege further, emphasizing racial inequalities — Reese portraying well-off white mother Elena and Kerry struggling Black mother Mia. At one point in the series, Elena says, “Good mothers make good choices.” Mia’s response: “You didn’t make good choices. You had good choices.”

As a mother myself, and one who proudly puts family first in everything I do, it really made the concept of privilege hit home. And it added such an important layer to the novel’s scrutiny of it — particularly in a year that saw widespread protests about racial injustice brought on by the killings of George Floyd and so many others. The power of that quote struck a chord within me, but this past year amplified it. Greatly.

I’m fortunate to have had good choices myself. Today, as president of O’Reilly, I’m in the unique position to recognize where I can actively work to make a difference and offer “good choices” to others. Reading Little Fires Everywhere actually coincided with O’Reilly’s push for diversity in our in-person event speaker lineup. We were trying to abate the “brogrammer” culture that was proliferating in Silicon Valley at the time by including more talented women from a wide range of underrepresented groups as speakers at our events. We made a concerted effort, and within two years 30% of our keynote speakers were women; within five years 100% of speakers at our virtual open source event were women. In 2016, we created a diversity and inclusion scholarship program that allowed people from underrepresented communities to attend our events. That scholarship is one of the best ideas I’ve brought to the company.

Yet even after doing all of that as an organization, Celeste Ng’s novel and that impactful quote from the series were wake-up calls that remind me there’s more to do and I still have a lot to learn.

Extensive research suggests that “purpose-driven businesses” are more successful in many areas. When your company started, what was its vision, what was its purpose?

I took the reins of O’Reilly from the company’s brilliant and iconic owner and CEO, Tim O’Reilly, in 2011. It was Tim who taught me about running a purpose-driven business. For 33 years, the company had served a community of technology and business visionaries with its educational books, leading Publisher’s Weekly to declare on a cover, “The Internet Was Built with O’Reilly Books.” In 1997, the company launched its first conference series, eventually creating several global conference franchises including our best-known Strata Data and AI Conferences. Every event brought leaders together worldwide to promote a culture of learning around the most impactful areas of technology. The company also launched a web-based platform in the early ’90s, which has grown to a 2.5 million member learning solution used by some of the world’s leading organizations — the real movers and shakers who are out there changing how we live our lives and interact with each other. While our learning modalities have evolved over the company’s 43-year tenure, the purpose of empowering professionals with lifelong learning tools and skills has remained at the core of O’Reilly. It’s no doubt why we’ve been able to not only survive but thrive over the years.

Are you working on any new, exciting projects now? How do you think that might help people?

Artificial intelligence is a hot topic, and we’re fully on the AI bandwagon at O’Reilly. While there’s still an underlying fear of machines taking jobs away from humans, we see it differently. We’ve doubled down on our online learning solution, investing millions to help enable — not replace — workers and arm them with the skills they need to navigate the jobs of tomorrow. This goes beyond providing the tools and learning materials on a subject; we’re actually helping businesses and users understand why certain trends or technologies are important and will shape our work and personal lives. We’ve dubbed this the “O’Reilly Radar,” and it’s built into the DNA of our entire organization. We provide a learning environment that helps people put this technology-driven world into context and sheds some light on what’s possible to give them a brighter outlook for the future.

For example, according to a recent study, 85% of employees lose at least 1–2 hours of productivity a week searching for information. That insight led us to launch our new AI-powered Answers feature in October. It uses an advanced natural language processing engine to deliver quick, contextually relevant answers to challenging technical questions posed by users through O’Reilly online learning. So our members can quickly uncover relevant highlights and snippets from our library of expert content across thousands of O’Reilly titles — pointing them directly to only the most applicable resources (and eliminating noise). So now they can get those 1–2 hours back each week and put them to better use. It’s just one example of how AI can help augment people’s ability to work, not put them out of a job. It’s also an example of O’Reilly walking the walk into the new economy, and helping others to do so too.

We’ve also committed to experiential learning, as our 2019 acquisition of Katacoda proves. We’ve since incorporated the technology into our learning platform so our members could get hands-on experience with tech like Kubernetes, Docker, Python, Java, and more in a live dev environment. So again, we’re adding new tools to help our members “pivot and move” through today’s fast-paced world so they’re ready for the jobs of tomorrow. You don’t have to be afraid of what’s coming when you’re ready for what’s next.

Thank you for all that. Let’s now turn to the main focus of our discussion about Digital Transformation. For the benefit of our readers, can you help explain what exactly Digital Transformation means? On a practical level what does it look like to engage in a Digital Transformation?

I find Salesforce’s definition a useful starting point: “Digital Transformation is the process of using digital technologies to create new — or modify existing — business processes, culture, and customer experiences to meet changing business and market requirements.” I like this definition because it encompasses more than just the technical aspect of overhauling previously manual processes and moving them online. At its core, Digital Transformation impacts all facets of a business — your employees, your customers, and how day-to-day business operations are performed. So it’s important to take a holistic approach and consider the impact a transformational project may have on anything it touches. To give one example, the customer data you collect is of no value if the appropriate team members don’t have access to it. You could also be in for a world of hurt by regulatory and legal standards if the wrong people do have access to it. Likewise, that great new software you invested in to streamline the billing process is useless if employees aren’t properly trained to maximize its benefits — not to mention the question of how clients will be impacted by it. On a practical level, engaging in a Digital Transformation requires your entire workforce to think beyond themselves. It’s a team effort and it can’t succeed if everyone isn’t on board.

Which companies can most benefit from a Digital Transformation?

All companies can benefit from a Digital Transformation. And it doesn’t have to be a complete systems overhaul or a transition to a completely online format. Something as simple as a local business starting to use social media to reach potential customers can have a huge impact on business success — and ultimately could lead to further transformation. But for technology companies, Digital Transformation isn’t only a benefit; it’s essential for survival and growth. And there’s a lot to know in order to stay ahead of it all. That’s why O’Reilly is always offering new subject matter from the most sought-after experts and adding new features on O’Reilly online learning to enhance our member’s ability to keep up with what’s next.

We’d love to hear about your experiences helping others with Digital Transformation. In your experience, how has Digital Transformation helped improve operations, processes and customer experiences? We’d love to hear some stories if possible.

The core of what we deliver through O’Reilly online learning are the techniques and tools necessary for Digital Transformation. At its heart, Digital Transformation is about taking advantage of opportunities and really understanding what’s possible for your business. Through our case studies, conference talks, Meet the Expert sessions, and more, we help our members see what’s possible in their digital future. They can then craft a vision of where they need to be going, and we help get them there.

Too often, companies think about Digital Transformation as a holistic business project but don’t take the time to evaluate the barriers so they can address them head-on. But time spent upfront thinking through roadblocks pays off in the end. A simple example is something we did for a very large tech company a few years back. They were trying to move their entire employee population into what they called an “agile mindset.” Unfortunately, the term “agile” has so many different meanings and connotations in tech that they were struggling. We helped them create a baseline definition for what agile meant (for them) and then socialized that via our platform through training and content. It took a few months, but ultimately 80K employees were finally operating from the same playbook, which allowed them to move forward with a more unified vision.

Has integrating Digital Transformation been a challenging process for some companies? What are the challenges? How do you help resolve them?

While Digital Transformation is necessary for most businesses, by no means is it an easy journey. Change is hard. My own experience leading O’Reilly through a Digital Transformation was no different. When I stepped up as president 10 years ago, it was clear that the world of publishing was changing dramatically. I knew that in order to survive and grow, we had to adjust our long-term strategy and become a true media business. But going from a book publisher to a media organization and an online learning platform…well you can’t digitally transform much more than that — and it was a tectonic shift for O’Reilly. A complete rethinking of the business model while leveraging our existing talents and expertise. It was also the most difficult time in my career, as I was met with pushback against new ideas I didn’t anticipate. However, the experience taught me to trust my instincts and to make the right decisions for the organization as a whole. I’ve always framed my role as balancing an ecosystem of shareholders, customers, and employees. At times, the decisions that kept that ecosystem in balance emerged from listening and responding to that pushback. The lessons learned during that time are still the basis of how we think and operate as an organization today.

I applied those lessons once again when we made the difficult decision to shutter our live events business in 2020. Our in-person conferences accounted for 30% of our global business, and they were what many people associated the O’Reilly name with. Even before COVID-19, we’d started to consolidate some of them, like our popular Strata Data and AI Conference franchises. But the pandemic led us to really question the future of highly produced multi-day (sometimes weeks long) in-person events. We knew learning in the flow of work was the best way to promote skills building, so why shouldn’t our events reflect the same ease and accessibility for attendees? We quickly shifted our model to shorter multipart virtual “Superstream” events on the same critical technology topics our in-person events had covered, now hosted throughout the year. What once took a week and required getting on a plane now takes hours and is as simple as opening a laptop. By the end of 2020, more than a million members had registered for O’Reilly virtual events and live online training courses, including over 30,000 for the Superstream series. Did we make the right decision? Absolutely. Was it painful? Certainly. Did it require a Herculean effort by team members across the entire organization? Undoubtedly. And I’m so proud of them all. You will be too when you embark on your own Digital Transformation. Don’t lose sight of your vision and remember to carefully balance your ecosystem of shareholders, customers, and employees.

Ok. Thank you. Here is the primary question of our discussion. Based on your experience and success, what are “Five Ways a Company Can Use Digital Transformation To Take It To The Next Level”? Please share a story or an example for each.

When I talk to our customers about Digital Transformation, they all seem to think it’s some huge undertaking — one that they’re simply unable to tackle. My response is always the same: Digital Transformation doesn’t have to be all-encompassing if you think about it as taking advantage of a series of opportunities. When you break it down like that, there’s always room to tackle the changes Digital Transformation requires to better position your organization for today’s digital economy. Even for a small business.

Digital Transformation 5 ways:

1.) Use social media to open your business to new customers and reward your loyal base.

One example that comes to mind is a small dry cleaning chain that claimed their customers loved the personal attention they gave. They prided themselves on their best-in-class customer service, after all, and didn’t need a social media site because word of mouth had worked for them for 50 years. But little by little, those customers (who no doubt loved their local dry cleaner) started migrating to the dry cleaner that sold their offering on social media with discounts and home pickup through an app they had developed. Customers simply had to sign in and provide their address and their clothes would be picked up and dropped off at their convenience. And just like that the definition of best-in-class customer service had changed because of social media awareness coupled with a digitally enabled business model. In today’s busy world, customers will always choose the business that better caters to them and makes their lives easier. Social media is a powerful tool you can leverage to be the better solution for your customers and prospects.

2.) Digitize your physical product or complement your physical product by digitally enabling it.

This doesn’t apply to everyone, but it should be top of mind for all businesses. For O’Reilly, it was selling ebooks versus staying focused on our print product. The answer will be different for each business, but the question everyone should be asking is, How could this work online?

3.) Sell direct rather than through distribution partners, where appropriate.

I love seeing entrepreneurs get their new inventions into a large chain store. The possibility of thousands upon thousands of new customers is just too exciting to escape. But it also comes with inventory requirements within those stores and the chain’s constant pricing and margin pressures, which can drag on a small business. But what if you started direct — selling at higher margins to fewer customers and then using the data about those sales to refine your product over time? When you sell through a partner, the customer relationship belongs to them, not you. In a digitally enabled business, the customer belongs to you. I’m not saying you never want to see your product shining brightly on the shelves at Bed Bath & Beyond. But selling directly allows you to perfect your original invention through customer feedback. And when your perfected product finally hits those shelves, you can rest assured that your customer base is already strong…not simply a wishful prayer.

4.) Own your data — digital businesses acquire a lot of data that can be used to refine your product, reward your customers, and grow your revenue.

As mentioned above, owning the customer tells you a lot. By selling directly you learn about their likes and dislikes, pricing sensitivity (by testing different price points), and what’s important to them (free shipping or faster shipping at a cost, for example). The best digital businesses use that data to refine their products and pricing over time. The prime example is Amazon. Don’t let the fact that Amazon is one of the world’s largest retailers scare you — they simply test and try out new prices all the time. Amazon uses algorithms to determine the best price, but a small business can do the same manually and learn from the data those sales render. Owning your data means you can constantly test to find the best possible product and market fit.

5.) Take advantage of today’s cloud solutions, which have democratized AI and data science for all.

I think this is the biggest game changer in the Digital Transformation race these days. You no longer have to employ an AI engineer to take advantage of machine learning. Those features are built into today’s cloud solutions. By hosting your own business in the cloud, you have access to the latest and greatest technologies that were previously reserved for the few large companies that could afford them. Your job is to do the homework and see where you can use those technologies in your specific business. Just go back to answering the first questions I posed: Can your products become digital or digitally enabled, can you find new markets via social media, and can you interpret your sales data to build a better product?

Let’s go back to our dry cleaning example. The successful company also built an app that lets a customer take a picture of their clothes and get a price estimate for cleaning. How? Using a feature called automated machine learning, the app has “learned” to discern what piece is what (based on previous pictures of blouses, pants, and dresses) and then uses that data to supply a real-time in-app experience. If a small business that was typically based on local walk-in customers can thrive in this digital world, everyone can if they make the effort.

In your opinion, how can companies best create a “culture of innovation” in order to create new competitive advantages?

You can’t cultivate a culture of innovation without learning. Give your team the tools and resources they need to upskill and reskill and a safe space to apply their newfound knowledge and innovation will follow. By investing in your employees, you’re strengthening your own business position, thereby gaining a competitive edge. Take hiring new talent, for example. Research we’ve done here at O’Reilly shows there’s a shortage of data scientists compared to the market need. As a result, businesses must pay a premium to hire people with this expertise, and for many, that’s just not feasible. Unless you’re one of the Googles or Amazons of the world — which most aren’t — why not dedicate time and resources to teaching your own team members how to acquire the skills they need to fill data science roles internally? A solution like O’Reilly online learning can give professionals access to everything from live online training to sandboxed interactive learning environments so they can really refine their new skills — and even get certifications in top programming languages. Imagine what your business could accomplish by arming your entire workforce with the ability to learn at work? It’s invaluable.

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

Tennis great Billie Jean King once said, “Just remember: Pressure’s a privilege — dream big and truly go for it.” Everything I’ve accomplished and tried to provide for others came from a position of strength and from not backing down when it was hard. When I think of the true milestones in my career, they all came after a period of difficulty and great change that required intensity of both purpose and drive. Now that I have those successes behind me, I face each new challenge with such hope and aspiration since the outcomes have all been good. But also because I do the homework.

How can our readers further follow your work?

Readers can follow along on my personal Twitter and LinkedIn accounts. For the latest O’Reilly company news and updates, you can follow us on Twitter and LinkedIn too. If you’re interested in exploring our learning solution, visit: https://www.oreilly.com/.

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