Breaking the Marketing Mold: Lisa Kraynak Of The League On 5 Innovative & Non-Traditional Marketing Strategies That Can Engage Audiences Like Never Before
An Interview With Chad Silverstein
Differentiate. So many businesses have relatively low barriers of entry or are in categories that are over saturated. Really think through what makes your brand truly unique.
Traditional marketing methods are insufficient in today’s dynamic and fast-evolving market. To truly engage and captivate audiences, businesses must think outside the box and adopt innovative and non-traditional marketing strategies. What are these strategies, and how can they transform audience engagement? I had the pleasure of interviewing Lisa Kraynak.
Lisa Kraynak is the Senior Vice President and Head of Marketing at The League, where she leads strategy and execution across brand, social, PR, partnerships, and events, connecting ambitious singles through innovative in-app features and exclusive real-life experiences. With over 20 years of experience driving growth at Fortune 100 companies and VC-backed startups, Lisa has held leadership roles at NBCUniversal, iVillage, Carbon38, and Viacom, among others. She is a trusted advisor, board member, and adjunct professor at USC Annenberg, bringing expertise in scaling mission-driven companies through innovative business models, brand-building, and digital transformation.
Thank you so much for joining us in this interview series! To start, could you share when and how you got started in marketing?
The early part of my career included being part of the founding team at iVillage, where we were among the first to pioneer the creation of online communities, content, and commerce at scale. Since then, I’ve held senior roles across media, entertainment and e-commerce businesses. I also teach luxury marketing at the University of Southern California at the Annenberg School of Communication and Journalism.
In my role as Head of Marketing at The League, I am responsible for strategy and execution across brand, social, PR, partnerships, and events, all with a focus on connecting ambitious singles in meaningful ways.
What has been the biggest shift in the marketing industry and can you give us an example of how it impacted you?
The biggest shift has undoubtedly been in the digital arena, which has fundamentally transformed nearly every aspect of daily life — including dating. The rapid evolution of technology affects me daily as we continually adapt to new capabilities, leveraging them to enhance both operational efficiencies and the consumer experience.
Can you explain why it’s essential for businesses to break away from traditional marketing and embrace new strategies?
In a saturated digital landscape, standing out requires moving beyond traditional marketing. Consumers now seek meaningful, interactive experiences rather than passive advertisements. By embracing new strategies, businesses can engage audiences in unexpected ways, fostering stronger connections and building vibrant communities.
Could you share and briefly explain the first major change you made to break the trend of traditional marketing that was not so common?
One of the most impactful initiatives we launched at The League was what we’ve termed Influencer 3.0. This strategy redefined traditional influencer marketing by partnering with inspirational individuals who are not just prominent in their fields but also actively dating on our platform. Instead of collaborating with conventional influencers who promote brands as a primary career, we focused on aspirational figures excelling in their respective professions — people achieving extraordinary things and aligning with the ambitions of our target audience. The League attracts driven, high-achieving individuals with big goals and an appetite for a vibrant life, so it was natural to showcase partners who embody those qualities. From an Olympic fencer to accomplished doctors, lawyers, and chefs, we featured single professionals whose lives and pursuits resonate with the aspirations of our community. By authentically representing our members’ values, this campaign strengthened our brand identity and deepened engagement with our audience in a way that felt both genuine and inspiring.
What specific results did you see after implementing this change?
The results have been amazing. Consumer engagement has been through the roof and the positive sentiments have been off the charts.
How do you ensure that these new marketing strategies resonate with your target audience?
From a business perspective, we track downloads, but we also closely watch consumer reaction. This is one of the benefits of a “social-first” campaign. We can see immediately how consumers are reacting and responding.
Can you share an example of something you tried that didn’t deliver expected results or ended up becoming a financial burden, and what you learned from that experience?
As a team, we are constantly pushing boundaries and experimenting with new ideas and strategies. Whenever possible, we use a test-and-learn approach to minimize risk while uncovering opportunities. However, we also recognize that certain situations call for bold, decisive actions when we strongly believe in the potential impact of an idea. A great example is our work in performance marketing. Every day, we rigorously test different elements — targeting, messaging, and creative assets — to refine our approach and maximize effectiveness. Not every experiment delivers the desired results, but we see those moments as opportunities to gain valuable insights. By being disciplined in analyzing what didn’t work and why, we’ve built a culture of iteration that allows us to turn initial setbacks into eventual success. This mindset of continuous learning and adaptability has been instrumental in driving meaningful growth and innovation.
Great. Now, let’s dive into the heart of our interview. Could you list “5 Innovative & Non Traditional Marketing Strategies That Can Engage Audiences Like Never Before”?
1. Be relentless about authenticity. Our “You Don’t Want to Date Me” campaign resonated because it featured real people talking about their real lives and true selves.
2. Don’t be afraid to be a bit irreverent. Obviously this depends on the category, but I think a lot of brands take themselves too seriously. Being overly precious about brand communications can lead to an inauthentic consumer connection or just plain boredom.
3. Mine for meaningful consumer insights. It always surprises me how little time some leaders spend thinking about what their target audience truly needs or wants.
4. Differentiate. So many businesses have relatively low barriers of entry or are in categories that are over saturated. Really think through what makes your brand truly unique.
5. Be clear and be bold. Regardless of what your business or brand is, you are fighting for consumer mindshare. Hone in on your core value proposition and make sure you are telling a crisp and memorable story.
What challenges might companies face when transitioning away from traditional marketing strategies, and how can they overcome them?
One of the biggest challenges companies face when moving away from traditional marketing strategies is the need for agility and adaptability. Non-traditional approaches, such as experiential and digital-first campaigns, require faster response times, a willingness to experiment, and a more data-driven mindset. This shift can feel risky, especially when results aren’t immediately measurable.
To overcome this, companies should start small with test campaigns, gather real-time feedback, and be prepared to iterate quickly. Building a flexible, cross-functional team with a mix of traditional and digital expertise is essential. Embracing data analytics as part of the process allows brands to refine their strategies based on what resonates, ultimately creating more impactful, non-traditional marketing initiatives.
How do you measure the success and ROI of these new marketing strategies?
We use a mix of qualitative and quantitative metrics, from engagement rates and social sharing to customer feedback. For example, with the ‘Date Me’ links, we track shares and profile visits, allowing us to see direct ROI in terms of new member sign-ups.
Looking forward, how do you see the role of innovative marketing evolving in the next 5–10 years?
In the next 5–10 years, I see innovative marketing becoming increasingly immersive and personalized. With advancements in AI, VR, and AR, brands will be able to create experiences that feel deeply tailored to individual interests and lifestyles. Data-driven personalization will continue to evolve, allowing brands to anticipate audience needs and deliver value in real-time, whether that’s through interactive content, unique in-person experiences, or seamless digital engagement. Marketing will move further toward building communities rather than just customer bases, with brands fostering real connections and loyalty through transparency and shared values.
What advice would you give to business leaders who are hesitant to move away from traditional marketing methods?
I think there is still a role for traditional marketing methods, however the media landscape is evolving at an accelerated rate. It is critical that brands ensure that they reach their target customers where they are. Clearly this includes digital platforms, but it also includes the physical places that consumers want to be. Breaking through the clutter requires creativity and sometimes involves being someplace unexpected or collaborating with another brand who at first look may not seem obvious.
Can you share any upcoming initiatives or plans you have for further innovating your marketing strategies?
To continue to innovatie our marketing strategies, we are focused on blending digital and in-person experiences that resonate with our ambitious community. We’re expanding The League’s hybrid approach by creating exclusive, real-world experiences for our members.. Recent examples include high-end activations such as our Blade Hamptons summer experiences, our “Ultimate Second date“ to the US Open and a special VIP Mariah Carey concert experience lined up for the holidays.
Additionally, the ‘You Don’t Want to Date Me’ campaign is just beginning. While the campaign was launched as a “digital first” initiative, it was so successful that we expanded into TV and are now looking at new platforms. The League will be dropping new talent over time, featuring notable personalities who embrace their quirks and redefine what it means to be ‘dateable.’ We’re always exploring more ways to connect people, whether in-person through our luxury partnerships or online through campaigns like ‘You Don’t Want to Date Me,’ to create deeper connections both online and offline.
How can our readers follow your work and learn more about your approaches to modern marketing?
The League is available for download on the App Store and Google Play. You can follow The League on our social media channels, including Instagram ,Tik Tok and Linkedin.
This was great. Thank you so much for the time you spent sharing with us.
About the Interviewer: Chad Silverstein is a seasoned entrepreneur and Thought Leader with over 25 years of business experience. He has founded, operated, and exited multiple companies and now builds into a handful of high impact CEOs. Chad has launched multiple online communities, including a recent leadership development platform, and also serves as a strategic advisor for Authority Magazine’s thought-leader incubator program.
To learn more and connect with Chad visit: chadsilverstein.io
Breaking the Marketing Mold: Lisa Kraynak Of The League On 5 Innovative & Non-Traditional Marketing… was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.