Sullivan Learning Group

Thinking Like a Staff Data Engineer

New Relic

Hydrolix

Virginia Tech

Dan Sullivan

Dan Sullivan is a data engineer and architect,  O’Reilly author, and educator.

Compare how a strong senior engineer and a staff engineer approach the same ambiguous data-platform problem.

See the difference between senior and staff-level thinking

Use an evidence-based scorecard covering the six skills essential to thinking like a Staff Data Engineer

Assess your skills in six areas needed by staff engineers

Identify one skill to practice and one opportunity to apply it

Choose a staff-level experiment for the next 90 days

Build a robust toolkit of techniques to level up your influence, scale your impact, & show value as a design leader without direct authority

Staff Product Designer with 15+ YOE

Asana

Etsy

SoundCloud

Nasdaq

Catt Small

Staff Product Designer with 15+ YOE at Etsy, Asana, SoundCloud, & more.

Cohort 7 - July 2026

Cohort 8 - February 2027

Identify and navigate roadblocks that keep most senior designers from leveling up, all with guidance from an expert.I'm a Staff Product Designer with years of hands-on, high-impact leadership at both small and large companies. Over the past 15+ years, I've surpassed these challenges:🙃 Struggling to understand why I was stuck at senior🙃 Fighting for strategic influence, but still being left out🙃 Role ambiguity as a Staff Designer🙃 Being overwhelmed by busywork, not having visioning time🙃 Enjoying the leadership and mentorship parts of management, but not the HR part After finding clarity for myself, I decided to create this course to help others.Through digital lessons and conversations with me and your fellow Maven classmates, you'll discover tactics to become a more impactful, influential, and strategic individual contributor and leader. You'll connect with designers from across the industry and build a shared understanding of the role of a Staff+ designer.I've given over 260 designers the tools to navigate their own challenges and reap the career rewards. Let's work together to chart your path forward.

Stop being a paintbrush, start being a visioner

Clarify expectations of a Staff+ Designer

Influence strategy as a non-manager

Shift from reactive to proactive

Advocate for the Staff+ Designer role

Identify and fill your own gaps

Staff and Principal Designers who need new tactics to shift from reactive to proactive, build more leadership skills, and influence strategy

Senior Designers who want to get promoted to Staff, or learn about the role before choosing between individual contributor (IC) and Manager

Design Leads, Managers, and Directors shifting back to hands-on IC work who want to know how their skills translate

Stop being the “number explainer.” Build the stories, systems, and credibility to lead with clarity and confidence in the age of AI.

Data & AI Leader, 19yrs of scaling data

Wayfair

Scotiabank

Wunderflats

ZEAL Network SE

Pier Martin

Data & AI leader with 19+ years scaling global teams, Executive coach 

Cohort 9

Cohort 11

Do you lead a data or analytics team and you keep asking yourself:<ul><li>How do I get executives to act on my insights instead of nodding and moving on?</li><li>How do I influence Product, Marketing, and Finance when none of them report to me?</li><li>How do I build real credibility on AI without just demoing tools?</li><li>How do I get my team seen as a trusted partner, not a ticket shop?</li></ul>If those are your questions, you're in the right place. The work is strong. You are just not in the room yet when the decisions get made.Here you fix that by building your own AI Operating System. A working system that keeps supporting you long after the course ends. It remembers every stakeholder you map, drafts in your voice, pressure-tests your decisions before the room, and gets sharper every time you use it. One person, operating like a team.So you turn data into stories executives repeat. You turn AI pilots into business cases that win support. And the system keeps compounding, carrying more of your load as you take on more. You own it for life.

Get in the room with the decisions - taught by a VP who still runs a data team.

How to Make Executives Act on Your Insights

How to Lead AI Change Without the Fear

How to Run a Data Team That Scales

How to Decide What Matters Under Pressure

Folks who are early in their career, focused only on technical execution, or looking to break into data/analytics should not enroll.

This course is NOT FOR everyone

It is designed for data managers, analytics leads, and heads of data already managing teams and facing leadership challenges.

This is NOT a beginner-level technical course

The Overlooked Data Manager: you ship dashboards but get talked over in strategy rooms, and want to be trusted for impact, not output.

The Stretched Head of Data: you lead 5 to 15 people, firefight all week, and need a system that shows control and builds credibility.

The New Data Leader: just promoted from IC, strong technically but light on storytelling and presence, ready to lead in the AI era.

Transform from consumer of analytics to independent operator - asking sharp questions, validating answers, shipping decisions.

Principal Data Scientist @ Ontra 

Stripe

Nextdoor

PwC India

Ontra

AppFolio

Shane Butler

Principal Data Scientist @ Ontra | Ex-Stripe, Nextdoor, PwC, Appfolio

Data Science Leader |Ex-Microsoft

Microsoft

eBay

Grammarly

Superhuman

Sravya Madipalli

Data Science Leader@Superhuman (Prev. Grammarly)| Ex-Microsoft, eBay, Nextdoor

Head of Data @ Ontra AI | Ex-LinkedIn

LinkedIn

Pinterest

Hai Guan

Head of Data @ Ontra | Ex-Nextdoor, LinkedIn, Pinterest, Meta

Cohort 3

Cohort 4

As AI reduces the value of deep domain silos, the people who thrive will be the ones who can work across disciplines and ship. Analytical independence - the ability to validate your own ideas and make data-informed decisions - remains the missing skill in most builders' toolkits.AI can conduct the analysis, but it can't tell you what to ask or whether the answer makes sense. That requires analytical judgment.This course teaches you to think like a senior Product Data Scientist. You'll learn the frameworks used at FAANG companies to frame problems, choose the right metrics, diagnose root causes, execute the analysis, and turn insights into decisions.-&gt; <a target="_blank" rel="noopener noreferrer nofollow" href="https://join.slack.com/t/dataneighbor/shared_invite/zt-3ox4drc3r-3g0ptSthytkgv0sD6ovvqg">Join AI Builders Slack Community!!</a> &lt;-What makes this different: No SQL. No stats lectures. Five weeks of hands-on real scenarios. You'll build end-to-end, metric specs, deep dives, experiment plans, stakeholder readouts.The result: You become analytically self-sufficient. The last dependency removed from your toolkit. Make data-informed decisions in hours, not weeks.

Ask Better Questions, Make Faster Decisions - with AI as Your Analyst

Frame Problems Like a Senior Data Scientist

Design Metrics That Actually Drive Decisions

Diagnose Root Causes Without Guessing

Design Experiments That Ship

Turn Analysis Into Action With AI as Your Copilot

Synthesize Insights and Prioritize for Impact

Product Managers, engineers, and operators who need analytical independence and frameworks to measure success and drive decisions.

Designers and researchers stepping into strategy roles who need to quantify impact, run experiments, and influence with data-driven insights

Data professionals who want to frame better questions, delegate technical execution to AI, and drive impact with agentic analytics tools.

Go from shaky in design reviews to the engineer everyone trusts to architect the hard stuff

Staff Software Engineer, 500+ mentees

Ehsan Gazar

Staff SE. 500+ mentorship sessions. 5.0 rating. Systems at scale.

The architecture skills that get senior engineers promoted. Live, 6 weeks, small cohort.

Cohort 1

November 2026

You're a strong engineer. You ship reliable code, you debug fast, your PRs get approved. But when a system design question comes up in an interview, design review, or promotion conversation, something shifts.You know the concepts. You've read the articles. But under pressure, your thinking gets fuzzy. You're not sure where to start. You hedge. You cover too much or miss what matters. And afterwards, you can't always explain why.This is the gap that holds senior engineers back. It's not about intelligence or experience. It is that system design is a skill no one explicitly teaches you on the job. You're expected to absorb it. Most don't.I've worked through this with 500+ engineers. The pattern is always the same. Once someone understands how to structure their thinking, frame constraints, drive trade-offs, and justify decisions out loud, everything changes. Interviews get clearer. Design reviews get easier. Promotions follow.This cohort is four weeks of doing exactly that, live, with feedback. Not theory. Not another article to bookmark. A repeatable way to think that works under pressure, in interviews, on the job, and at the next level.

System design taught by someone who designs systems for a living.

Structure any system design problem confidently

Lead architecture discussions without doubt

Clear the system design interview round

Make trade-offs that hold up to scrutiny

Think at the level your next promotion requires

Build a repeatable design process

Solid coder, shaky on architecture. Keeps getting passed over for staff. Knows something's missing but can't name it.

Strong track record, rusty on design rounds. Needs a structured approach before facing a FAANG or scale-up loop

Not waiting to be promoted. Building staff-level skills now to compress the timeline from L4 to L6.

Agentic AI

Coding with AI

AI Workflows

Claude Code

OpenClaw

Vibe Coding

AI Evals

AI Transformation

RAG & Search

AI for PMs

AI for Engineers

AI for Designers

AI for Marketers

AI for Founders

Product Sense

Product Discovery

User Research

Prototyping

Growth

Analytics

Tech Foundations

Strategy

Influence

Leadership

Career Growth

Machine Learning

LLM Ops

Context Eng

Security

System Design

Figma

Design Systems

Visual Design

Design Strategy

Automation

Content Marketing

Demand Gen

Go-to-Market

Product Marketing

Positioning

Social Media

Brand

B2B Marketing

SEO & AEO

AI for Leaders

AI Governance

Communication

Management

People Operations

Exec Presence

Storytelling

Goal-setting

Personal Brand

Fundraising

Everyone

Operators

Data Scientists

Business Analysts

User Researchers

Customer Success

Project Managers

HR Professionals

Sales People

Lawyers

Finance

Investors

Real Estate

Educators

Creators

Engineers and engineering leaders who build, deploy, and scale software systems.

Getting promoted, navigating job transitions, and advancing to the next level in your career.

Developing leadership skills — inspiring teams, building culture, navigating organizational complexity, and driving results through others.

Designing scalable, reliable software systems — architecture patterns, distributed systems, and technical tradeoffs.

Thinking Like a Staff Data Engineer

What you'll learn

Why this topic matters

You'll learn from

Dan Sullivan