Leadership Q&A: Shelby Bolinger, Director of Marketing at Cloverleaf
- 3 days ago
- 6 min read
Leadership doesn’t always follow a straight line—and Shelby Bolinger's journey is a great reminder of how clarity, curiosity, and trust shape strong leaders over time. As Director of Marketing at Cloverleaf, Shelby brings a thoughtful, people-first approach to building teams, aligning marketing with revenue, and creating space for real growth.
In this Q&A, she reflects on her career path through high-growth startups, how her leadership style has evolved, and why personalized development isn’t just a nice-to-have—it’s essential. Her insights offer a candid look at what it means to lead with intention, transparency, and impact.
Can you provide an overview of your career journey and highlight key transitions?
For most of my career, I’ve been a marketer at early- to mid-stage startups, typically in the 30–200 employee range. A large portion of my experience has been within HR tech, somewhat accidentally at first, but it turned out to be incredibly valuable. Working across multiple companies with similar buyer profiles has allowed me to build deep expertise in the space and sharpen how I think about messaging, demand, and go-to-market strategy. Working for high growth startups has given me the opportunity to work across nearly every facet of marketing, from brand and demand to product marketing and sales enablement.
Early on, I discovered a strong affinity for content marketing, which became my core skill set and foundation. As the companies I worked for scaled quickly, I saw firsthand how marketing could be a primary driver of revenue growth which pushed me to think more strategically about impact. That shift marked a pivotal transition in my career. I began working closely with sales leaders and go-to-market teams to align strategy, improve execution, and drive measurable revenue outcomes. Over time, this evolved my role from an individual contributor focused on content into a marketing leader responsible for building and guiding teams with a clear revenue mandate. Today, my focus is on leading marketing functions that meaningfully support sales teams and contribute to revenue growth every single day.
How would you describe your current leadership style, and how has it developed over time?
I would describe my leadership style as supportive, approachable, and rooted in trust. Throughout my career, I’ve been fortunate to work for leaders who gave me a high level of ownership while also challenging me to continuously improve. That balance had a lasting impact on how I think about leadership, and I try to mirror it with my own teams today. I genuinely enjoy helping marketers hone their craft and expand their skill sets, whether that’s deepening expertise in an area they already love or exploring new facets of marketing altogether. My goal is to create an environment where people feel safe asking questions, trying new things, and pushing themselves beyond what they thought they could do.
One of the biggest evolutions in my leadership style over time has been how I approach feedback. Earlier in my career, I was more hesitant to be direct, thinking I was being kind. I’ve since learned that avoiding clear feedback can actually limit growth. Now, I’m intentional about sharing constructive, actionable feedback so people clearly understand where they can improve and what’s required to take the next step in their role or career. I see that transparency as one of the most supportive things a leader can offer.
What has inspired your path and leadership approach?
My career path and leadership approach have been shaped largely by the people I’ve worked for over the years—both the great examples and the challenging ones. Seeing firsthand what made certain leaders effective, and where others fell short, gave me a clear sense of the kind of leader I wanted to become and the environments I wanted to create for my teams. I’m also deeply inspired by the leadership team I work alongside at Cloverleaf.
We operate with a high level of openness and honesty, and watching how my peers navigate difficult conversations, ambiguity, and moments of tension has been incredibly influential. Those experiences continually push me to reflect, improve, and think more intentionally about how I show up as a leader.
Finally, my time at Cloverleaf—and the purpose behind the product itself—has fundamentally shaped how I think about leadership. It’s reinforced the idea that every person I manage is unique in what they need to do their best work. What motivates one team member may not resonate with another, and what support looks like can vary widely depending on their goals, values, and even what’s happening in their day-to-day work.
Having the tools and insights that help me better understand those differences has pushed me to move beyond having a “good” leadership style and toward delivering real, individualized value as a leader to every person on my team.
What role do the company's values play in shaping its culture, and how do you reinforce them?
At Cloverleaf, our values are deeply embedded in how we operate and how we show up for one another every day. What makes Cloverleaf especially unique is that our platform itself is built to support personalized people development at scale, which means I’m able to reinforce our values not just through conversations or leadership behaviors, but by using our product as part of our daily work.
Our employees are empowered to do the same, which creates a shared responsibility for shaping our culture. We recognize that every employee has a unique working style and is navigating their own challenges and opportunities. While it’s essential for leaders and managers to provide guidance and support, our product also emphasizes ownership and self-development. Cloverleaf enables individuals to take those moments into their own hands by giving them insights and learning opportunities that help them grow in ways that feel relevant and actionable.
Through tools employees already use—like Slack, Microsoft Teams, and email—Cloverleaf delivers daily learning moments that help people better understand themselves and the colleagues they work with. These insights help break down communication barriers, encourage growth in key areas, and provide practical support for giving and receiving feedback. Over time, those small moments add up to stronger relationships, better collaboration, and a healthier culture overall. I feel incredibly fortunate to work for a company that not only lives its values internally through strong leadership and intentional culture, but also builds a product designed to help other organizations do the same.
How do you invest in growth, and what advice do you have for aspiring leaders?
I invest in growth primarily by doing. Throughout my career, I’ve learned best through hands-on experience, which is why working at high-growth startups has been so formative for me. Those environments created constant opportunities to stretch, experiment, and learn quickly, and that approach continues to shape how I think about my own development. When it comes to the teams I lead, I’m intentional about having open, ongoing conversations around growth—where people want to go, what skills they want to build, and how they learn best. That understanding allows me to support them in ways that are actually meaningful, whether that’s through new responsibilities, feedback, or opportunities to step outside their comfort zone.
At the foundation of all of this is trust.
I believe growth happens fastest when people feel trusted to make decisions and take ownership of their work. When I lead with trust, it gives my team the confidence to try, to learn from mistakes, and to push for what’s next in their role or career. For aspiring leaders, my advice is to lean into discomfort and raise your hand before you feel fully ready. You won’t grow unless you give yourself the chance to try—and that means accepting that you might fall along the way. The goal isn’t to avoid failure, but to fall forward, learn from the experience, and use it to keep moving ahead with more clarity and confidence.
Looking ahead, what excites you about the future?
What excites me most about the future of the industry—and Cloverleaf in particular—is how we’re using AI to deliver truly personalized development at a scale that hasn’t been possible before. Much of the conversation around AI in our industry has focused on efficiency—saving time, automating tasks, or optimizing workflows. Those use cases are valuable, but they’re not what excites me most.
What sets Cloverleaf apart is how our platform helps HR and talent teams amplify the development programs they already believe in and make them a meaningful, daily part of an employee’s journey. Instead of one-size-fits-all training or sporadic development moments, Cloverleaf is able to coach employees in real time on what matters most to them, while factoring in what they’re experiencing at work. Historically, that level of personalization simply wasn’t achievable due to limited team sizes and resources.
This is the kind of AI that energizes me—the kind that doesn’t replace human connection, but strengthens it. Technology that helps people better understand themselves and each other, supports growth in moments that matter, and ultimately helps humans be more human. That’s the future I’m excited to help build.
Shelby’s perspective reinforces an important truth: great leadership is less about having all the answers and more about creating the conditions for people to do their best work. From leaning into discomfort to embracing individualized growth, her approach mirrors the mission behind Cloverleaf itself—helping people better understand themselves and one another in the moments that matter. As organizations continue to navigate growth, change, and the evolving role of AI, leaders like Shelby remind us that the future of work is still deeply human.
