As part of Chicago Latino Network’s 2026 vision, 5 Questions highlights leaders shaping Chicago’s business, civic, and cultural landscape.
Each edition features a respected voice responding to five questions—offering perspective on leadership, decision-making, and the ideas shaping what’s next.
Today, we feature a leader shaping how brands evolve—and how they connect with people in a rapidly changing world.
Our Featured Leader Jennifer Vianello
Former Chief Marketing Officer, Cars.com Now Co-Founder & Managing Partner, MachMachines Musical Instruments
Jennifer served as Chief Marketing Officer at Cars.com, where she led brand, growth, and marketing strategy for one of the most recognized platforms in digital automotive retail. In this role, she oversaw an enterprise transformation that unified a fragmented portfolio into a single, cohesive brand—strengthening market position, accelerating growth, and modernizing how the company connects with consumers and partners.
Today, Jennifer is Co-Founder & Managing Partner of MachMachines Musical Instruments, where she brings together more than two decades of experience at the intersection of media, technology, data, and consumer behavior to build a modern, independent brand rooted in craftsmanship and community.
MachMachines is an independent maker of guitars, basses, and ukuleles, co-founded by Jennifer and luthier David Showalter—rooted in Chicago’s music culture and focused on instruments crafted for fit, feel, and lifelong use.
Her work reflects a distinctive approach to brand building—combining digital transformation with human-centered storytelling to create products and experiences that resonate on a deeper level.
With leadership roles spanning global agency networks, public companies, and entrepreneurial ventures, Jennifer brings a strategic and forward-looking perspective to marketing, growth, and organizational design. Across each chapter, her focus remains consistent: aligning brand, product, and experience to drive meaningful connection, long-term value, and sustained impact.
Jennifer shared these perspectives while serving as Chief Marketing Officer at Cars.com.
1. You’ve led marketing transformations across media, auto, and consumer brands. Looking back, what leadership lesson took you the longest to learn, but has made the biggest difference in how you lead today?
I can be anything I want to be, but I can't be everything I want to be all at the same time.
2. As a digital-first CMO, how do you balance innovation and experimentation with the pressure to deliver near-term business results, especially in moments of uncertainty or change?
These concepts aren't mutually exclusive. Innovation for innovation's sake is a waste of resource - any experiment should always be in service of a business goal. Innovation in marketing is typically tactical, while goals are strategic. The key is to be very clear on your strategy and KPIs and then get after the tactics with the best tools available. Marketers should always test, learn, fail or scale in service of business outcomes.
3. You’ve built and led teams at scale while also mentoring and giving back through board service and pro bono work. How do you think about developing talent and creating cultures where people can do their best work?
As a leader, my role is to set the strategy and goals, create predictability in my expectations for the caliber and cadence of work, and then largely get out of the way unless there are questions - then celebrate people when they exceed expectations. In other words, my job is to set the floor, never the ceiling. Culturally, I believe there is an enormous amount of psychological safety and job satisfaction when people feel like they can progress the right work without drama.
4. Marketing continues to evolve rapidly with AI, data, and new media platforms reshaping the landscape. What capabilities do today’s leaders need to prioritize now to remain relevant and effective over the next decade?
Core marketing strategy capabilities have been diminished as so many marketing roles have become hyper-specialized in the past 10-15 years. The people with the greatest upside are generalists who understand marketing fundamentals like segmentation, targeting, and positioning, rather than specialists who can't stretch beyond optimization of a specific channel or workflow. Those who understand the craft of marketing and how it can be applied to commercial outcomes have a lifelong skillset. You can always learn a new tool.
5. Outside of your corporate role, music, the arts, and community engagement are clearly important to you. How have these passions influenced your perspective as a leader, and why do they matter in business leadership?
I could spend a lot of time on this topic! But what I'll say here is that it was always my career goal to work in arts management. However, in 2007 it was very clear that digital was disrupting both my function (marketing) and my industry (arts and entertainment), and if I wanted to be a strong marketer I would have to learn new tricks from within - which I could take back to my preferred industry in the future. I have spent the last 18 years in the media and technology world at the tip of the spear of marketing and digital business transformation, and I am thrilled that in just a few months I will be finally returning to my roots to bring those skillsets into our family business - MachMachines - which is a musical instrument manufacturing startup with cultural hub aspirations.
5 Questions is part of CLN’s ongoing effort to bring forward voices shaping our communities and industries.
