💳 How Stripe Turned 7 Lines of Code Into a $95B Empire

AI Agents For The Entire Customer Journey

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Featured Job Listings

🏆 Top Picks of the Week (Hand-Picked, High-Impact Roles)

🔹 Head of Business Operations (early hire)
Company: Doctronic
Location: Remote
Apply: Apply here

Doctronic is building AI-native diagnostics for primary care—think “GPT for doctors” but grounded in clinical evidence, not just slick demos. Co-founders come from Google and Stanford and just raised a stealth round from heavy-hitter VCs. This BizOps style role is part strategic ops, part product-minded glue—turning ambiguity into roadmap, chaos into clarity. You'll work directly with the founders to scale operations, fundraising, GTM, and team culture. Ideal if you’re the kind of person who builds process just enough to keep momentum, not slow it down.

🔹 Head of Events
Company: Brex
Location: New York, NY (hybrid)
Apply: Apply here

Brex reinvented corporate cards and expense management for the modern enterprise, and now they’re doubling down on events as a pipeline engine. As Head of Events, you’ll lead the global strategy for experiences that connect Brex with CFOs, founders, and ops leaders—from field activations to major tentpoles. This isn’t swag-and-balloons stuff; it’s high-conversion, brand-aligned storytelling in physical space. You’ll report to the VP of Comms, collaborate across GTM, and own vendor strategy, creative direction, and P&L. Must love logistics and narrative arcs.

🔹 Vice President of Operations (Healthcare Segment)
Company: Sodexo
Location: Midwest (MI, IN, OH)
Apply: Apply here

Sodexo is known for facilities and food—but in healthcare, they’re delivering outcomes, not just meals. This VP of Operations will oversee a major Midwest healthcare region, managing multi-site teams delivering patient dining, environmental services, and logistics. It’s a leadership role with high autonomy and real scale—think $40M+ in portfolio value. You’ll need to drive standardization, client relationships, labor efficiency, and contract renewals. If you’ve led complex healthcare operations and want to shape what “service excellence” looks like at scale, this is your playbook.

🔹 VP, Operations (Title: Vice President of Internal Operations)
Company: BenefitWallet (an HSA provider backed by Conduent)
Location: Remote (U.S.)
Apply: Apply here

BenefitWallet manages over $2B in health savings accounts—and their bet is that the future of consumer-directed healthcare needs better infrastructure. As VP of Internal Ops, you’ll own customer onboarding, service, claims, and partner management—essentially the operational heart of a platform serving millions. You’ll report to the President and shape the org’s long-term scalability across teams and processes. Think Lean Six Sigma meets fintech meets healthcare reform. Bonus: it’s a fully remote leadership seat.

🔹 Senior Director, Technical Program Management
Company: PayNearMe
Location: Remote (U.S.)
Apply: Apply here

PayNearMe powers payments for rent, loans, utilities, and more—especially for the underbanked. Their platform processes billions annually, and now they need a TPM leader to scale delivery with precision. Reporting into BizOps, you’ll build the TPM function from scratch, lead high-stakes cross-functional initiatives, and drive operational excellence with engineering and product partners. This is a strategic, hands-on leadership role with real impact—and they’re not shy about comp: base ranges from $200K–$250K. High leverage, low ego, mission-forward.

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Bots Take the Wheel

🤖 Track Project ROI Like a Finance Pro

Pain Point: You're delivering projects on time and on budget, but you can't prove business impact. When budget season comes around, your team gets cut because "we can't measure the value."

Solution: Build an automated ROI tracking system that captures business metrics alongside delivery metrics, so you can speak the language of business impact.

• Use Case 1: Capture Business Metrics at Project Kickoff

Logic: When you create a new project in Jira or Asana, use Make.com to automatically create a corresponding "Business Impact Tracker" in Google Sheets. The sheet includes fields for projected revenue impact, cost savings, efficiency gains, and risk mitigation. This forces stakeholders to quantify expected value upfront.

• Use Case 2: Automated Progress Updates with Business Context

Logic: Set up a weekly Make.com scenario that pulls project completion percentages from Jira and combines them with business metrics from your tracking sheet. It then generates a stakeholder update that shows both delivery progress ("75% complete") and business impact progress ("projected to deliver $2.3M in cost savings by Q4").

• Use Case 3: Post-Launch Impact Measurement

Logic: 30 days after project completion, Make.com automatically sends a Slack reminder to project stakeholders asking them to update the actual business impact in the tracking sheet. It then generates a "Project ROI Report" comparing projected vs. actual impact, which gets shared with leadership and archived for future reference.

Visionary Voices 

📝 Cristina Cordova - The Platform Builder Who Scaled Stripe Infrastructure

The year was 2017, and Stripe was processing billions in payments annually. But behind the sleek API that developers loved was a growing nightmare: infrastructure that was buckling under exponential growth.

Cristina Cordova joined Stripe as a Staff Software Engineer with a reputation for solving the unsolvable. She'd previously built distributed systems at Twitter that handled millions of tweets per second. But Stripe's challenge was different—and arguably harder.

The Pain Point That Changed Everything

When Cristina arrived, Stripe's engineering teams were drowning. Simple code deployments took hours. Database queries that once ran in milliseconds now timed out. Customer support tickets about payment failures were piling up faster than they could be resolved.

"We were successful, but our success was literally breaking us," Cristina recalls. "Engineers were afraid to ship code on Fridays because they might spend their weekend fixing outages."

The company had grown from processing thousands of payments to handling millions, but the underlying platform architecture hadn't evolved to match.

The Agitation Moment

Things got worse before they got better. During Black Friday 2017, Stripe experienced its most serious outage to date. Payment processing slowed to a crawl just as e-commerce traffic peaked globally. Major customers—including Shopify, Lyft, and hundreds of smaller businesses—couldn't process transactions.

Cristina spent 72 straight hours in the war room, coordinating with teams across time zones to restore service. "I realized we weren't just fixing a technical problem," she said. "We were rebuilding the foundation of the internet economy in real-time."

That weekend changed everything.

The Intrigue: A New Perspective on Platform Engineering

Most companies approach infrastructure scaling by throwing more servers at the problem. Cristina saw it differently. She proposed something radical: instead of just scaling up, they needed to rebuild their platform to scale intelligently.

Her vision wasn't about handling more traffic—it was about creating infrastructure that could adapt, learn, and optimize itself.

"Traditional scaling is like adding more lanes to a highway," Cristina explains. "But what if instead, we could build roads that automatically reroute traffic, predict congestion, and even create new paths when needed?"

The Positive Future Vision

Cristina began designing what would become Stripe's next-generation platform architecture. She envisioned:

• Self-healing systems that could detect and resolve issues before they impacted customers

• Intelligent load distribution that could predict traffic patterns and pre-scale resources

• Developer tooling that made complex distributed systems feel simple to work with

• Real-time optimization that continuously improved performance based on actual usage patterns

The goal wasn't just reliability—it was to make Stripe's infrastructure invisible to developers while being incredibly robust underneath.

The Solution in Action

Over the next three years, Cristina led the transformation of Stripe's entire infrastructure stack. Here's what she built:

The Adaptive Platform Layer Instead of static configurations, Cristina's team created dynamic systems that could automatically adjust based on load patterns, geographic distribution of requests, and even seasonal business cycles.

Developer Experience Revolution She introduced internal tooling that abstracted away infrastructure complexity. Engineers could deploy code globally with a single command, and the platform would handle optimization, scaling, and monitoring automatically.

Predictive Scaling Systems Using machine learning models trained on historical data, the platform could predict traffic spikes hours in advance and pre-scale resources accordingly.

Zero-Downtime Architecture Perhaps most importantly, Cristina designed systems that could be updated, patched, and evolved without any service interruption—even during peak traffic periods.

The Measurable Impact

The results speak for themselves:

• 99.99% uptime achieved and maintained even during record-breaking traffic periods

• 10x improvement in deployment speed and reliability

• 50% reduction in infrastructure costs through intelligent resource optimization

• Developer productivity increased by 300% as measured by features shipped per quarter

But the real measure of success came during the COVID-19 pandemic. As e-commerce exploded overnight, Stripe's infrastructure seamlessly handled a 200% increase in traffic without a single major outage.

The Leadership Philosophy

What sets Cristina apart isn't just her technical brilliance—it's her approach to platform thinking.

"Most engineers optimize for the problem in front of them," she explains. "Platform builders have to optimize for problems that don't exist yet. You're building the foundation that will support innovations you can't even imagine."

Her team at Stripe became known for their "future-first" methodology:

• Design for 100x scale, not 10x

• Assume requirements will change, and build adaptability into the core

• Prioritize developer experience as much as system performance

• Make complex systems feel simple, not the other way around

The Ripple Effect

Cristina's work at Stripe didn't just solve their scaling challenges—it became a model for how modern platform engineering should work. Her approaches have influenced infrastructure decisions at companies from startups to Fortune 500 enterprises.

She's now a sought-after speaker at engineering conferences, where she shares insights about building platforms that can evolve with business needs rather than constraining them.

The Vision Continues

Today, Cristina continues to push the boundaries of what's possible in platform engineering. She's working on the next frontier: infrastructure that doesn't just scale automatically, but actually gets more efficient and intelligent as it grows.

"We're moving toward a future where infrastructure becomes truly adaptive," she says. "Where the platform learns from every request, every failure, every success, and continuously optimizes itself."

For Cristina Cordova, the most successful platform is the one you never have to think about—because it's busy thinking for you.

✨ Weekly Recommendations

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This brutally honest list reveals dozens of things society tells you that you "must" do—but actually don't have to do at all, from reading the news to having a five-year plan.

Salary negotiation expert Josh Doody shares the exact strategies that help his clients increase their first-year compensation by an average of $47,273, including why you should never share your salary expectations.

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Professional Development

📚 The Transaction Model Revolution - What Stripe Taught Us About Pricing Strategy

Why 2.9% + 30¢ Changed Everything

When Stripe launched with their simple transaction-based pricing (2.9% + 30¢ per successful charge), they weren't just setting rates—they were making a philosophical statement about how technology services should be priced. Instead of the traditional model of upfront fees, monthly minimums, and complex tier structures, they aligned their success directly with their customers' success.

The Psychology of Aligned Incentives

Traditional payment processors made money whether your business succeeded or failed. Monthly fees, setup costs, and minimum transaction requirements meant they got paid even if you processed zero transactions. Stripe flipped this model: they only make money when you make money. This alignment created trust and removed friction from the buying decision.

How This Applies to Your Delivery Projects

The transaction model offers lessons for how we structure and communicate the value of our delivery work:

Think Outcomes, Not Outputs

Instead of measuring success by features shipped or projects completed, focus on business outcomes achieved. If you're implementing a new CRM system, don't just track "go-live date"—track "sales cycle reduction" and "lead conversion improvement."

Align Your Metrics with Business Success

Stripe's pricing model works because it scales with customer success. Your project metrics should do the same. If you're building an e-commerce platform, track revenue per user, not just uptime. If you're implementing automation, measure cost savings, not just tasks automated.

Simplify Your Value Communication

Stripe's pricing is transparent and easy to understand. Your project proposals should be equally clear. Instead of complex technical specifications, lead with simple business value statements: "This project will reduce customer support costs by 40% within six months."

The Compound Effect of Small Percentages

Stripe's 2.9% might seem small, but it compounds at scale. A $1M business pays Stripe about $29,000 annually. A $100M business pays $2.9M. This scalability is what turned Stripe into a $95B company. Your delivery projects should have similar scalability potential.

Building Trust Through Transparency

Stripe publishes their pricing openly, with no hidden fees or complex calculations. When you're proposing projects, be equally transparent about costs, timelines, and expected outcomes. This builds trust and makes decision-making easier for stakeholders.

The Network Effect Advantage

As more businesses used Stripe, the platform became more valuable for everyone. Each new integration, each new feature, each new market expansion benefited the entire ecosystem. When you're designing delivery projects, think about how they create network effects within your organization.

TL;DR:

Stripe's transaction model succeeded because it aligned company success with customer success, simplified pricing decisions, and scaled naturally with business growth. Apply these principles to your delivery work: focus on business outcomes, align your metrics with stakeholder success, communicate value simply, and build projects that create compound benefits over time.

How I can Help

Wanna chat IRL? Connect with me on LinkedIn and we can set up some time.

The Delivery Career Decoder shows why you’re already qualified for more—and how to prove it.

I love feedback. If you have topics you want to see? Or thoughts or ideas on how to serve the community better, please hit reply or email [email protected].

Until next time,

The Business of Delivery

Quiet moves. Bold Careers.