Data Driven Leadership

The strongest data leaders know that their value goes beyond clean data and accurate reporting. They build relationships, understand how the business makes money, and help teams turn data into better decisions. In this episode, Jess Carter sits down with Celina Wong, head of data and analytics at Pearl, to talk about what it takes to build a data function from the ground up. Celina shares lessons from becoming the first data hire multiple times, creating alignment across teams, and helping organizations connect data work to revenue, strategy, and long-term business goals. As AI makes it easier for anyone to access and analyze data, Celina explains why strong data relationships and governance matter more than ever. She also shares how leaders can use AI to accelerate their work without losing the human judgment and verification needed to make trustworthy decisions.  In this episode, you'll learn: How data leaders can build trust and align teams around business priorities Why every data request should connect to measurable business impact How leaders can use AI while keeping data governance and accuracy intact Things to listen for: (00:00) Introduction to the episode with Celina Wong (02:33) The first thing you should do as a data hire (09:06) Educating the team as a data leader (14:29) Aligning teams around priorities and resource constraints (17:53) Asking better questions to become a strategic data partner (24:05) Preparing data for acquisitions and business decisions (29:09) Data governance in the age of AI Celina's LinkedIn: https://www.linkedin.com/in/celinaw/ Learn more about Pearl: https://hellopearl.com/  

The best data leaders know how to turn ambiguity into clarity, influence business decisions, and communicate insights in a way that drives action. In this episode, Jess Carter sits down with Shailvi Wakhlu, a data leader and author with a career that includes leadership roles at fast-growing startups. Shailvi shares what she learned while scaling Strava's analytics and machine learning team, contributing to long-term business planning, and leading through periods of rapid growth.  As AI makes analysis more accessible, Shailvi asserts that leaders still need to understand where data comes from, how trustworthy it is, and how to communicate its limits clearly.   In this episode, you'll learn: How data teams can contribute to business direction What leaders should understand before relying on an AI-generated analysis Why communication and self-advocacy matter for technical leaders   Things to listen for: (00:00) Introduction to the episode with Shailvi Wakhlu (07:06) Scaling an analytics team through hypergrowth at Strava (11:49) Moving from data execution to business strategy (14:44) Data literacy in the age of AI  (19:03) Why asking the right questions matters more than finding answers (25:25) Helping data leaders advocate for themselves   Shailvi's LinkedIn: https://www.linkedin.com/in/shailviw/   Learn more about Shailvi: https://www.shailvi.com/  

Technical expertise can only take you so far. At some point, career growth depends on earning trust, asking better questions, and learning how to see beyond your own area of expertise.  In this episode, Jess Carter sits down with Colleen Tartow, Senior Director of Enterprise Data Engineering at Capital One. After starting her career as an astrophysicist, Colleen moved into enterprise data engineering. She shares what that transition taught her about leadership, trust, and making better decisions. Jess and Colleen also discuss what it means to be truly data-driven and why the best leaders are willing to change their minds when the evidence points in a new direction.    In this episode, you'll learn: How to balance confidence in your expertise with humility  When to go deep into technical details and when to focus on the bigger picture How evidence should shape strategy instead of simply validating it   Things to listen for: (00:00) Introduction to the episode with Colleen Tartow (04:00) How astrophysics mirrors modern data engineering (11:25) Building trust quickly in new companies and industries (14:54) Why listening is a critical leadership skill (17:34) The transition from IC to leadership roles (27:34) How to tell if a company is truly data-driven or not   Colleen's LinkedIn: https://www.linkedin.com/in/colleen-tartow-phd/  

Every AI hallucination, every bad output, and every broken dashboard traces back to the same root cause. Your data was never ready in the first place.   In this episode, Jess Carter sits down with Mark Marshalek to talk about why data governance is having a major comeback in the age of AI. Drawing on his leadership experience at Farmers Insurance and his work as a Senior Lecturer at The Ohio State University, Mark explains how governance, curiosity, and flexibility can help teams experiment with AI responsibly. He also shares why stronger data discipline is essential for AI readiness.   In this episode, you'll learn: Why data discipline matters for AI adoption How leaders can make governance feel practical instead of bureaucratic Why curiosity and flexibility are critical skills for the future of work   Things to listen for: (00:33) Introduction to the episode with Mark Marshalek (02:48) Why data governance is becoming more important (06:29) Connecting governance to business value (15:54) How leaders can encourage teams to use AI (27:00) AI adoption in highly regulated industries (30:28) Mark's advice for the next generation of workers   Mark's LinkedIn: https://www.linkedin.com/in/mark-marshalek-11543721/

In this episode, Jess Carter sits down with Nicola Smith, senior AI advisor at Southwest Airlines, to explore how organizations can operationalize AI strategically and build a workforce ready for the future. Nicola shares her insights on AI literacy, human-centered design, and creating a mindset of abundance that empowers employees rather than creating fear.    In this episode, you'll learn: How to develop an enterprise AI strategy that works across departments The importance of building AI literacy programs How AI can enhance creativity, innovation, and decision-making   Things to listen for: (00:00) Introduction to the episode with Nicola Smith (04:44) Building enterprise and departmental AI strategies (07:30) Bottom-up innovation and employee-driven AI use cases (09:51) Adoption through AI literacy programs (13:24) Combating fear and cultivating a mindset of abundance (22:22) Storytelling and transparency in AI-driven organizations (27:49) Future AI initiatives and emerging technologies Nicola's LinkedIn: https://www.linkedin.com/in/nicolasmith22/   

How can business and IT leaders align on AI and make smarter decisions together? Jess Carter reflects on conversations with business, IT, and data leaders across industries, sharing common themes she has observed around AI adoption. She discusses the disconnect between technical teams and business stakeholders, and offers practical advice on how to bridge that gap, build confidence with AI, and focus on real business value. In this episode, you'll learn: How data leaders can better connect AI initiatives to business outcomes Why developing hands-on experience with AI tools is critical How business leaders can experiment with AI while managing risk and cost   Things to listen for: (00:00) Introduction to the episode (02:16) The two types of IT and data leaders approaching AI (06:25) Prompt engineering and AI experimentation (09:20) Managing data security and tool limitations (14:06) Why AI adoption looks different for every organization Jess's LinkedIn: https://www.linkedin.com/in/jessicaccarter/  Not sure if your AI efforts are actually paying off? Take this free quiz and find out where your business stands: https://info.resultant.com/ai-value-scorecard

When times get tough, we rely on leaders to make the hard decisions. That's why their character is so critical—it can make or break a team, a company, or even an entire organization.  In this episode, Jess Carter sits down with Ernest O'Boyle to explore the "dark triad" of leadership and how these toxic traits can quietly sabotage a workplace. Professor Ernest shares his research on how these traits often go unchecked, leading to manipulation and a toxic culture. They discuss how leaders with dark triad traits can distort data, influencing outcomes and undermining trust in data-driven decisions. In this episode, you'll learn: How toxic leadership traits impact team performance The effects of narcissism and Machiavellianism in leadership dynamics How to build and maintain a positive workplace culture despite challenging behaviors   Things to listen for: (00:00) Introduction to the episode with Ernest O'Boyle (02:00) The dark triad traits in leadership (06:45) How narcissism and psychopathy show up in the workplace (10:25) Leadership in high-pressure environments (14:10) Managing manipulative behaviors in teams (18:00) How organizational culture shapes leadership behavior (22:15) Ethical dilemmas in decision-making (27:30) Can toxic leadership traits be reformed? Ernest's LinkedIn: https://www.linkedin.com/in/ernest-o-boyle-4547a729/ 

AI can make decisions fast. But weak data foundations still slow everything down. In this episode, Jess Carter sits down with Senior Director of Data Platform & Governance at Hungryroot Ben Ganzfried to discuss what it takes to build trust in data as companies grow. At Hungryroot, data does more than support reporting. It informs recommendations, recipes, and inventory decisions. Ben shares lessons on building data foundations that help teams move faster with more confidence. He explains why governance should reinforce accountability, not create friction, and why unclear ownership becomes a bigger risk when more decisions depend on data.  In this episode, you'll learn: Why data governance is crucial for business growth Best practices for managing data security and accessibility How to foster a data-driven culture within your organization Things to listen for: (00:00) Introduction to the episode with Ben Ganzfried (02:41) How Hungryroot uses data to personalize the customer experience (08:39) Making faster decisions through better governance (14:15) The rise of data and AI leadership roles (19:23) Why ambiguity becomes a risk as systems scale (23:38) Curiosity as part of data-driven leadership Ben's LinkedIn: http://linkedin.com/in/ben-ganzfried-1a5a8620a/?skipRedirect=true Links from the episode -  https://www.cdomagazine.tech/opinion-analysis/lessons-in-ambiguity-data-ai-and-the-limits-of-informal-coordination  https://benganzfried.com/f/the-nature-of-data-the-foundation-we-forgot-and-why-it-matters  https://benganzfried.com/f/the-year-the-margin-for-error-disappeared  https://www.cdomagazine.tech/opinion-analysis/lessons-in-ambiguity-data-ai-and-the-limits-of-informal-coordination  

Some moments define the kind of leader you are. When the stakes are high and the data is incomplete, your character becomes the strategy. In this episode, former FBI agent Herbert Stapleton joins Jess Carter to explore the role of integrity, decision-making, and leadership in high-stakes environments. Drawing from his two decades of experience in federal law enforcement, Herb shares his insights on how character and effective leadership are essential when the stakes are life and death. He discusses the importance of honesty, accountability, and the challenges of making tough decisions with incomplete information. In this episode, you'll learn: How to lead with integrity under intense pressure The importance of humility and confidence in leadership Ways to foster trust and loyalty within your team during crises Things to listen for: (00:00) Introduction to the episode with Herbert Stapleton (02:20) Herb's journey from law school to the FBI (06:34)  Leadership development in the FBI (10:03) Decision-making with incomplete information (14:32) How to deal with crises in corporate settings (17:35) Prioritizing wellness in your team (22:21) Developing character in the age of AI (28:33) Can integrity be taught? Herb's LinkedIn: https://www.linkedin.com/in/herb-stapleton-b94a19126/  https://www.dinsmore.com/  

Many organizations are adopting AI tools at record speed. Few are stepping back to ask whether they are meaningfully transforming how work gets done. In this episode of Data-Driven Leadership, Jess Carter sits down with Sindhu Venkata, Vice President of Technical Delivery at Resultant, to discuss what intentional AI leadership looks like. Sindhu introduces the idea of the "AI speed trap" — the cycle of moving faster, producing more, and slowly eroding quality, trust, and critical thinking along the way. She explains why AI failure is rarely a technology problem; it's a leadership problem. This episode is especially relevant for executives, data leaders, and operators navigating AI adoption across their teams. In this episode, you'll learn: The difference between operational AI and transformational AI Why the AI speed trap creates fatigue and poor outputs How leaders can adopt AI without losing critical thinking   Things to listen for: (00:00) Introduction to the episode with Sindhu Venkata (08:02) The AI speed trap and work slop (17:57) AI licenses vs. transformational strategy (23:57) Trust erosion and AI hallucinations (27:55) Leading AI adoption with intention Sindhu's LinkedIn: https://www.linkedin.com/in/sindhuvenkata/