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/