Cris Dobbins has built a career leading cross-functionally—without a traditional tech background—and she’s the go-to strategist teams call when they need clarity, momentum, and strategies that actually stick. We sat down with Cris to talk about embracing a nontraditional path, translating across functions, and why speaking everyone’s language is the real key to leadership.
🎨 The Early Days: Cris Dobbins’ First Steps in Digital Creativity
Cris’s introduction to tech came early, through her mom, a world-renowned photo retoucher who taught hand-painting on photographs before Photoshop existed.
When Photoshop launched, Cris got her hands on one of the first beta versions and quickly became her mom’s unofficial assistant, editing thousands of wedding photos. She started using Photoshop to create art, logos, and branding, an early spark that shaped her creative future.
💡 From Opera to UX: How Cris Dobbins Found Her Way Into Tech
Cris’s path to tech wasn’t conventional. Classically trained in opera, she simultaneously nurtured a passion for design, using Photoshop and Illustrator for branding projects on the side.
A pivotal moment came at South by Southwest in the early 2000s, when the tech side of the festival was still small and intimate. Meeting innovators there introduced her to Silicon Valley’s tech scene, inspiring her to shift from building websites to web apps, and eventually into product and user experience design.
Two decades later, Cris’s career reflects a journey of curiosity and adaptability.
🎤 Owning Your Nontraditional Path in Tech
Without a typical tech background, Cris leaned into her strengths and continued learning. At this year’s ICON Conference, she’s leading a breakout session for those who’ve felt like outsiders in tech, especially in non-technical roles.
Her talk, The Least Technical Person in the Room and Still the Most Needed, will share a tactical roadmap for growing influence, earning a seat at the table, and leading confidently. Cris emphasizes the power of speaking your audience’s language—whether that’s ARR, product metrics, or fiscal quarters—to bridge gaps and shine as the essential connector on engineering-driven teams.
🧠 What Does a Strategic Advisor Actually Do?
Cris’s role varies widely across startups. One day she might focus on product strategy, the next on go-to-market planning or user experience tweaks.
“Context switching” is a constant, as she moves between prototyping features, conducting user research, and analyzing funnel metrics to solve complex problems. Throughout, her goal is translating developers’ needs into human-centered solutions that drive real impact.
🧩 The Secret to Driving Impact? Speak Everyone’s Language
Cris works with sales, product, marketing, engineering, and content teams. Clear communication tailored to each group’s priorities is essential. She pinpoints core issues like onboarding, documentation, product-market fit, and then crafts messages that resonate: revenue and quarters for sales, metrics and PRDs for engineers. This approach establishes her as a trusted partner and speeds progress.
📊 Build Trust with Proof, Not Just Passion
Trust comes from measurable outcomes, not just enthusiasm. Cris focuses on metrics and real user feedback, connecting every initiative to tangible results like increased sales calls or improved retention. If a project isn’t moving KPIs, it’s time to pivot.
She embraces experimentation, setting realistic expectations that some KPIs will be missed—and that’s part of the learning process. For Cris, leadership means continuous testing, learning, and improving.
🤝 Creating a Culture of Learning and Celebration
Cris champions psychological safety where teams can make mistakes without fear. She models progress over perfection and encourages celebrating “micro wins” every two weeks—small victories that keep momentum high.
When engineering, sales, product, and design teams celebrate successes together, it strengthens connection and fosters ongoing energy.
Career Advice Cris Wishes She’d Heard Sooner
“It’s more important to be someone people want to work with than to do everything exactly how you think it should be done.”
Cris reflects on her early perfectionism, which sometimes hindered collaboration. Now, she focuses on “we” over “I,” inviting input, letting go of control, and emphasizing teamwork as the fastest path forward.
Why Cris is Excited for ICON
“I’m most looking forward to meeting everyone and hearing their stories. Building community is powerful. Being a woman in tech can feel isolating, and it’s energizing to be surrounded by others on the same journey.”
Curious to hear more?
Check out the full recording of our conversation with Cris Dobbins, where she dives deeper into her journey and shares insights on leading without a traditional tech background.
You can also meet Cris at this year’s Tech Ladies ICON Conference, she’ll be leading a breakout session titled The Least Technical Person in the Room and Still the Most Needed. This session is designed especially for anyone who’s ever felt like an outsider in tech—particularly those in non-technical roles. Cris will explore why having a cross-functional thinker on your team is essential and share practical strategies to help you bridge gaps, build influence, and become the vital connector that propels engineering-driven teams forward.
