Winstonn Tubbs of “Get yourself up the curve”

An Interview With Jamie Hemmings A diverse executive team is important because young professionals need to see someone like themselves in a leadership position. I was once told “If you can’t see yourself sitting at a dinner table with the leadership team, then the company probably isn’t the right fit for you.” To this day, there […]

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An Interview With Jamie Hemmings

A diverse executive team is important because young professionals need to see someone like themselves in a leadership position. I was once told “If you can’t see yourself sitting at a dinner table with the leadership team, then the company probably isn’t the right fit for you.” To this day, there are still too many leadership teams that don’t reflect their employee bases or the communities they serve. People of color need more leadership that looks like them — leaders who can observe and understand the bar, the skills, the accomplishments, and the alliances necessary for being promoted to a senior level.

As a part of my series about “Lessons From Inspirational Black Men In Tech”, I had the pleasure of interviewing Winstonn Tubbs, Senior Product Marketing Manager, Enterprise at, creators of the world’s leading cloud-based video collaboration platform.

Prior to, Winstonn held product marketing and strategy leadership roles in-house at companies including Percolate, Seismic, and Neustar, and agency-side at Wunderman. He developed his expertise through diverse experiences spanning many industries, including advertising, technology, e-commerce, media, hospitality, and financial services.

Winstonn earned his MBA in Strategy & Marketing from the University of Maryland — Robert H. Smith School of Business. He is an explorer who searches for inspiration through music, film, art, and the outdoors.

Thank you so much for joining us in this interview series! Before we dive in, our readers would love to learn a bit more about you. Can you tell us a story about what brought you to this specific career path?

I love the work of product marketing and spend a lot of my time thinking about strategy and launches. It sits at the intersection of numerous business-critical functions, requiring a healthy balance of science and art. Just about every path to a product marketing career is unique. Mine is no different.

I fought off the lure of marketing while in college and early in my career. Although I had a great understanding of the space, it seemed like part of the family business since my mom worked as a marketer at IBM for many years, and my brother ran his own digital marketing company. I felt the urge to chart my own path and explore the field according to my perspective.

I started my career in commercial banking. I was good at it, but I still found more joy while helping my brother with his company on the side. The trajectory of my career changed when he had the opportunity to pitch a popular food and beverage company. We put in countless hours of research, workshopping, and rehearsals to prepare for the meeting. We didn’t win the business but I fell in love with the process, especially after seeing the company execute a digital marketing campaign later that year that was very similar to the idea we had pitched. It was confirmation that I was in the wrong place and needed to pivot my career ASAP.

I decided to bet on myself and make a transition to marketing. I pursued an MBA at the University of Maryland, College Park, using that experience as a playground where I could experiment with my ideas and explore my interests outside of the classroom. I took on freelance work, leveraged practicums to work with companies on real-world problems, and earned an amazing opportunity to intern at Marriott International to help launch a global proof of concept. Following my MBA, I joined Wunderman as Sr. Experience Strategist, where I led day-to-day digital and engagement strategy for multiple large-scale accounts, and had the opportunity to work on marketing challenges big and small.

But something was missing. I knew that no amount of my insight would help influence the evolution of the product we were marketing. I needed to be at the intersection of marketing, product, and customer experience. Luckily, I was introduced to product marketing by a recruiter. I instantly felt a connection with it because it required the same strategic thinking I used at Wunderman, but was also closely aligned with the product development lifecycle.

I had come full circle. I was introduced to technology products as a kid by my mother, and became intrigued with “WHY” and “HOW” people used the products. I’d say that mindset is essential to being a product marketer.

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

One of the principal reasons I was drawn to is because it is a B2B company that shows a lot of B2C love. Its users are part of the company’s DNA and its success so far. The company takes a Product-Led Growth (PLG) approach, opening up the product to the end-user and focusing on the user experience as a primary driver of adoption and expansion across our enterprise customers. Complemented by a strong internal team, it had driven significant adoption, fast organic growth, and great customer satisfaction. Reaching and maintaining this high level of customer satisfaction is a dream for most SaaS companies.

Shortly after I joined in April 2020, I experienced my first product launch with, which was packed with critical new features for users. The best part was the ability to observe the attention to detail and collaboration across teams. I appreciated seeing everyone rally together to get high-quality work done promptly. All changes were handled fluidly and all team members successfully turned pain points into opportunities. It was no surprise that the launch immediately generated a great buzz and received an overwhelmingly positive reception. At that moment, I knew I had made a great decision.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that? runs a great onboarding process, but had to quickly shift to doing it remotely after the COVID-19 quarantine went into effect, which was just when I was hired. One of the pillars of the program is called Frame.iKnow. After new hires are given an overview of the industry, company, and product, they are assigned a series of tasks to complete throughout the week using the product — but the program had been significantly shortened for remote onboarding.

I missed that memo somehow. I was so eager to get started and dive into the product that I completed tasks in record time. I sent a note to the instructor after each task, but I didn’t receive a response until the last task was complete. His reply was, “You only needed to do half. I didn’t want to stop you because you were on a roll. Great work!” This funny mistake was a reminder of two of the nine core values:

  • Dig the hole: It’s important to take the first real step forward when faced with a complex problem. Spend less time talking and more time doing!
  • Get yourself up the curve: You must be the master of your own destiny by continuously pushing yourself to reach the next level.

Those two values are important to everyone, especially those going through a transition or tackling a complex situation.

Can you tell us a story about the hard times that you faced when you first started your journey? Did you ever consider giving up? Where did you get the drive to continue even though things were so hard?

After finishing up my final Spring term in my MBA program at the University of Maryland (College Park), I landed a great opportunity as an Intern at Marriott International and only had a few credits left. I was in a great place but things took a quick turn.

On the morning of the first day of my internship, I received a call that my father had passed away. He was my hero, my muse, and my mentor. As a middle school administrator and college professor, he taught me the significance of being a lifelong learner. We spent countless hours debating theories, data, culture, and current events. Those were some of my best memories, and in an instant, I knew those conversations would no longer be a part of my life.

Instead of shutting down, I used his passing as the motivation to work harder. I knew his spirit was still with me and it felt like a torch had been passed. I completed my internship, powered through my remaining credit to earn my MBA, and used the graduation ceremony as an opportunity to tell his story during my commencement speech.

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

There is a long list of people who have guided me with their experiences and words of wisdom throughout my career and life. However, the one person I am most grateful for is my mother.

As I made my pivot into marketing, I used to think that I needed to avoid being a generalist and must specialize in a specific area. I struggled with this because I viewed the world of marketing as a sandbox, a space where I could explore, learn innovative approaches, experiment with ideas, and share knowledge with other practitioners. Early on, I tried to focus on brand marketing — like most people. But, as I immersed myself in that space, I began to learn about digital marketing, marketing research, marketing analysis, content strategy, and many other related disciplines.

I accumulated a wealth of knowledge but I initially struggled to find a place to land in marketing and to frame my own story. Throughout several points in my career, my mother constantly reminded me that my exploration and curiosity were positives that would only make me a stronger marketer. I’ve had that same curiosity since I was a kid watching commercials with my family, trying to understand their meaning and the brand’s goal. Each job I had or the skill set I learned in my career was additive and helped me gain a unique perspective on solving problems.

She modeled the way during her long time at IBM, where she held various roles. It was because of her that I realized being a generalist was my superpower. While I initially thought I was “unfocused,” she helped me understand that I was honing all the skills I would use one day as a strategist.

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

I find a lot of power in words and there are really so many meaningful quotes I could choose from. I’d have to say that one that’s always stuck with me is, “Bring clarity to the world, the world will bring clarity to you.” This quote was shared by a panelist at an event after I asked him for advice on ways I could land more business as a freelancer or independent consultant. This quote speaks to me in more aspects of life beyond business.

A lack of clarity can create chaos and frustration, and those emotions are poison to any goal in life. It is important to take a moment to develop a specific intent, a clear vision, a plan of action, and most importantly, the courage and determination to amplify that message to the world. Everyone might not understand it, but the right people will.

Let’s now shift to the main focus of our interview. The United States is currently facing a very important self-reckoning about race, diversity, equality, and inclusion. This is of course a huge topic. But briefly, can you share your view on how this crisis inexorably evolved to the boiling point that it’s at now?

The acquittal of George Zimmerman in the murder of Black teenager Trayvon Martin in 2013 sparked the beginning of the Black Lives Matter movement. People took to social media and with the #blacklivesmatter hashtag to share their outrage and demand justice. The movement gained national attention in the summer of 2014 when police officers murdered Michael Brown in Ferguson, Missouri, and Eric Garner in New York City. After these two incidents, protesters took to the streets in several cities with calls for swift action to end systemic racism in the police force.

Since then, the Black Lives Matter movement has continued to fight for justice for Black people, but national conversations around #blacklivesmatter have only risen in short bursts when incidents of police brutality and murder occur before becoming quiet again.

However, the murders of George Floyd, Breonna Taylor, and Ahmaud Arbery in 2020 — all unarmed Black people — and videos of increased incidents of police brutality against peaceful protestors have brought rightful massive, unprecedented global attention to the Black Lives Matter movement. Racism and its impact throughout society is now unavoidable as a result of the graphic nature of George Floyd’s death, centuries of pent up anger from Black people, increased tension from COVID-19 lockdowns, and the increased volume of — and engagement with — videos of police brutality.

Unfortunately, the level of outrage doesn’t extend to everybody — including many business leaders and lawmakers who are being called upon to make changes — and we’ve also discovered that many people don’t understand the full extent of what’s happening. We are now in a critical part of this movement where the attention, momentum, and infrastructure can be harnessed to drive significant and substantial change.

This may be obvious to you, but it will be helpful to spell this out. Can you articulate to our readers a few reasons why it is so important for a business or organization to have a diverse executive team?

A diverse executive team is important because young professionals need to see someone like themselves in a leadership position. I was once told “If you can’t see yourself sitting at a dinner table with the leadership team, then the company probably isn’t the right fit for you.” To this day, there are still too many leadership teams that don’t reflect their employee bases or the communities they serve. People of color need more leadership that looks like them — leaders who can observe and understand the bar, the skills, the accomplishments, and the alliances necessary for being promoted to a senior level.

Increasing diversity on an executive team, by itself, doesn’t increase effectiveness. What really matters is how an organization harnesses the diversity of an executive team and whether it is willing to reshape its power structure. Even many Black leaders have to make difficult decisions to work through it, and to a large extent, tolerate it and internalize it, in the hope of making it easier for those that come after them. Careers are often crushed in service of the company’s needs. This has played out in all aspects of corporate America time and time again. A diverse executive team helps bring a well-rounded perspective to every scenario and results in better treatment of people and achieving better business outcomes.

Let’s zoom out a bit and talk in more broad terms. It’s hard to be satisfied with the status quo regarding Black Men in Tech leadership. What specific changes do you think are needed to change the status quo?

It’s not rocket science, it’s commitment. It is easy for leaders to be performative with their actions, while still holding on to unchecked prejudice or institutionally racist beliefs. Business leaders must use the same level of rigor with DE&I objectives and initiatives that they use with other business objectives IF they want to see real change. Business leaders must reject the notion that maximizing shareholder returns is the only thing that matters. Instead, they must embrace a broader vision of success encompassing learning, innovation, creativity, flexibility, equity, and human dignity. Getting it wrong is costly. It costs time, talent, and money.

A common excuse for not changing the status quo is that the pipeline of talented people of color is just too small. The reality is much different. Actually, the number of people of color that they know is small. Leadership must take a long-term approach and invest in a pipeline by setting aside resources to specifically focus on recruiting operations and building relationships with talent of color. Find the talent, cultivate a relationship, then find a role that fits them. Not the other way around.

As a member of the DE&I Core Team at, we outlined the company’s commitment to the Black Lives Matter movement and to making change within our company and the media industry. We’ve established new objectives along with an action plan that is monitored regularly. It’s a great step forward. However, the real challenge for us, and for every business, is to drive consistent, meaningful change over time.

We’d now love to learn a bit about your company. What is the pain point that your company is helping to address?

The media and entertainment industry is often caught up in a paradox: the technology and tools advance quickly, while adoption happens more slowly. It’s partly a function of people being so busy that they don’t have time to learn new tools, partly because people don’t have the money to keep purchasing or upgrading tools, and partly because it’s easy for them to stick to doing what they know works.

In no part of the industry is this truer than in post-production. has emerged as the industry’s leading cloud-based workflow collaboration platform. Its design is intuitive and takes little onboarding. It means that even people who are less tech-savvy can start using it immediately. But it’s also deeply functional, enabling the savviest users, from large creators, such as VICE Media and BuzzFeed, to customize their workflows across locations worldwide to thousands of users.

When remote work became the new normal, played a significant role in helping creators collaborate with their distributed teams. As a cloud-based platform, all that’s required is an internet connection to access projects, share detailed and frame-accurate feedback, and easily make changes or get approvals. is accessible, both as a Web app and for iOS, so anyone with an iPhone or iPad can access the relevant projects from anywhere. We’ve now seen numerous video creators produce high-end content from the comfort of their homes.

What do you think makes your company stand out? Can you share a story? truly understands its customer — the professional video creator.

Most collaboration in the video production space happens with technology that’s not made specifically for video. As a result, it turns out to be a slow and frustrating experience for everybody involved. Our co-founders, Emery Wells and John Traver, experienced these frustrations themselves at their post-production studio, working on everything from Super Bowl commercials to SNL shorts. Like other post-production shops, they had to deal with vague feedback, too many different tools, and files that lived in multiple locations.

In 2011, they set out to solve these challenges and ended up turning their post-production house into a technology company — The result is that our platform is built by creatives who know and understand the task of creating great videos. Now with over 1 million users around the world, we’re still focused on creating a user experience people love. It is the very reason we keep an extremely high retention rate with our customer base. Over the past year, we’ve also doubled our engineering teams to ensure we continue to invest in and stay focused on addressing the industry’s unique needs.

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

The primary aim of product marketing is to deliver the right product to the right customer at the right time. It is easier said than done because you’re typically dealing with a moving target and you can almost always rely on an unexpected event to occur.

As the new reality of COVID-19 forced most of our customers, professional video creators, to create quality content while working and collaborating remotely, one of the tools they needed was something that would allow them to transfer their large media files faster and more efficiently.

In June 2020, we decided to release a beta version of a new application called Transfer. Transfer was originally slated for release later in 2020. Transfer allows for the high-speed upload and download of large media files and folders with just a single click and is one of the fastest file transfer applications in the market.

Additionally, we’ll be launching a new technology in February — a game-changing technology for Hollywood. I can’t say much else right now. You’ll have to wait until our January announcement to learn more!

Do you have any advice about how companies can create very high performing marketing teams?

We live in a unique period of rapid change, and building a high-performing marketing team has never been more important — or more challenging. The stakes for individuals, teams, and companies are extremely high. While working in MarTech, I’ve had the opportunity to speak to customers with marketing organizations that ranged in size and maturity. The one constant challenge all of them had was creating and sustaining an agile, high-performing marketing team. Here are a few key ingredients to consider:

  • Purpose led: First and foremost, it is important for leadership to be purpose driven. The marketing team should feel connected on a deeply personal level to the vision and what they are building, creating, and putting out into the world.
  • Customer obsession: The closer marketers are to customers, the higher their team performs. This makes intuitive sense, since driving effective communications and campaigns requires customer insight.
  • Commitment to culture: The implications of culture are bigger than they seem. Culture not only dictates how you surface new ideas and bring them to life, but it also helps you attract and retain the best people. Working culture focuses on how the team works together to accomplish goals and social culture focuses on creating an environment where people know they will be working with teammates who will be accountable as well as motivate and inspire them. That’s when the magic really happens.
  • Strategic direction: A clear strategy serves as a map to guide a team’s efforts toward achieving goals. A clear, well-documented, scalable, and forward-thinking strategy outlines specific goals for the team, giving them a true north to work toward.
  • Professional development: Today’s candidates want to know that they will be developed, coached and mentored while working in a culture where they can be happy and thrive. The highest performing marketers are voracious learners who constantly push themselves to master new and interesting things.

Finally, keep in mind that it takes time to create a high-performing marketing team, and in many cases, it’s work-in-progress. The journey is long and complex, with many obstacles in the way. There will be some unpopular and difficult decisions in the road ahead, but ultimately addressing them early will pay off in the end.

In your specific industry, what methods have you found to be most effective in order to find and attract the right customers? Can you share any stories or examples?

The video production industry is full of creators that are passionate, hardworking, and highly skilled. Like many customers, they expect to use vendors that understand their space and their needs. It requires the development of a deep understanding of the customer– before positioning, framing, and GTM. This is true in any industry but especially in video production.

I believe market validation is the most critical step as it helps identify who the right customers are and what resonates with them the most. Many companies fail to do a proper discovery and analysis of the market and their potential customer before moving forward to building a product or even marketing to customers. Months, if not years, of wasted time and effort, can be saved if they focus on the practice of trying to deeply understand.

Market validation varies depending on the market and maturity of the product. For example, building a product for a new market vs. an existing market will require a greater investment in time on the top of funnel activities like educating customers about the new market, which requires additional capital and headcount. Still, the same set of steps can be followed:

  1. Discovery and analysis: Take a cross-functional approach to test your hypothesis with your target audience and getting feedback.
  2. Market sizing: Once you understand your target customer, you can then calculate the size of your addressable market and potential revenue.
  3. Industry mapping: After collecting initial feedback from discovery, you can confirm if your product solves the needs of your target customers, understand where you fit in the competitive landscape, and if the market is worth doing business in.
  4. Direct customer research: Conduct a full-scale market assessment of the potential ecosystem, business environment, product, operational impact, and approach to technical development. This will help understand the psychology of players in the market, their goals, and how they make purchasing decisions.
  5. Prioritization: At this step, you can start to really prioritize what you want to build and the messaging you want to create based on factors like scalability, customer impact, resources, PR, market response, cost, and revenue.
  6. Validation: The only way to know if you’re on the right track is to launch your product and test assumptions in different markets and regions.
  7. Market requirements: Document the capabilities of the product, functionalities, feature set, and how those features address the needs of the market. Then arm stakeholders in your organization so everyone is aligned and can use the information to inform decisions.

Following these steps provide the foundation for informing positioning, messaging, packaging, and go-to-market activities.

We are very blessed that very prominent leaders read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them 🙂

I would like to have a private conversation with Charles D. King because he knows no ceilings. In TV and Film, we are seeing a shift to a more authentic world view — one that accurately portrays the real experiences, particularly, of people of color. Near the center of this shifting landscape is Charles D. King, an agent of these changes.

Charles blazed new trails in the entertainment industry and has been the “first” on many occasions. Throughout his career, he did everything he set out to accomplish. His vision of achieving more led him to the launch of MACRO, a multi-platform media company representing the voice and perspectives of people of color. I would love to learn about his experiences and observations to understand at what moment he knew he needed to start his own venture. I would also love to learn about the infrastructure and activities that were necessary to an organization that addresses multiple business verticals, including a film and television studio, talent and influencer management divisions, a branding and creative agency, and a venture firm.

Thank you so much for this. This was very inspirational, and we wish you only continued success!

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