Dive Club 🤿 — "Ryan Scott: The Skills That Get Designers Promoted"

Host: Ridd
Guest: Ryan Scott
Date: November 7, 2025

Overview

This episode of Dive Club zeroes in on the evolving landscape for designers, specifically the nuanced, business-oriented skills that move designers from being "hired" to being "promoted." Host Ridd sits down with Ryan Scott—veteran of DoorDash and Airbnb, MBA graduate, and educator—to dive deep into how designers can think more strategically about their careers, stop chasing outdated differentiators, and develop the high-ROI, cross-functional abilities that are increasingly valued in top companies. From leveraging data, to cross-pollinating with PM and engineering skills, to tactically selling the impact of your work, this episode is packed with actionable frameworks and anecdotes.

The Changing Job Market for Designers

• Market Uncertainty:
  Ryan addresses the confusion and exhaustion many designers are experiencing amidst layoffs, the rise of AI, and hyper-specific hiring criteria.

  • Quote:
    “No one knows what’s going on in the current market. ... We’re having a difficult time contextualizing the signals.”
    — Ryan Scott (01:24)

• Extreme Specialization is the New Hiring Norm:
  Companies are seeking candidates who fit ultra-narrow profiles, not just ‘the best designer.’

  • Example: Rejection for managing 5 direct reports instead of the required 6 (04:38).

• The Competition Fallacy:
  It’s less about too much competition; it’s about companies filtering for overly specific “puzzle piece” fits, leaving many designers excluded (04:38).

Selling Yourself: From Designer to Business Asset

• Selling to the Right Audience:
  Designers often err by pitching themselves to design managers, not realizing product leaders or executives are the final decision-makers.

  • Quote:
    "We need to be selling the right thing, that impact, and thinking about who the ultimate approver is. And it might not be the designer we think it is."
    — Ryan Scott (06:33)

• Craft, Visual Skill ≠ Promotion:
  Visual craft may get you hired, but business impact gets you promoted.

  • Focus your story on measurable outcomes, not just beautiful outputs.

• How to Frame Your Work:

  • Reframe your portfolio or interview story from “I redesigned X for Y company” to “I implemented X, which drove Y outcome, resulting in Z business value” (08:50).
  • Don’t rely solely on metrics—highlight holistic business impacts like team efficiency, market positioning, or enabling key clients (10:33).

• Storytelling Tip:
  Use a 'shock and awe' approach—list multiple forms of value created, not just numbers (14:23).

Transitioning Skills: The Two Paths for Designers

1. Technical/Engineering Crossover

• Embrace AI and ‘vibe coding’ to gain autonomy, especially for front-end polish or shipping smaller features (16:12).
• Designers can now ship things themselves, reducing friction with engineers.

2. Strategic/Product Crossover

• Move toward product strategy: opportunity finding, competitive analysis, business impact thinking.
• Key Metaphor: If PMs and engineers are learning design skills, designers should learn PM/engineering skills: “We all have more overlap with each other. … We are valuable partners, but we are also, in some ways, competing for influence.” (16:12)

Navigating the New Collaboration Lines

(26:07)

• With role boundaries blurring, open dialogue is essential.
  • Expect trial and error.
  • Explicitly negotiate responsibilities with PMs and engineers.
  • Acknowledge: “People across the spectrum are probably feeling a little insecure right now. Everything’s changing.” — Ryan (22:43)

Building High-ROI, PME (Product-Manager-Engineer) Skills

Finding and Pitching Opportunities (28:02)

• Opportunity Spotting:

  • Don’t limit yourself to user research; use competitive analysis, business modeling, market trends.
  • Example: At DoorDash, Ryan identified the need for faster Dasher payments by combining empathy with competitive analysis and user surveys.

• How to Pitch Upwards Effectively (32:07):

  • DON’T: Skip team buy-in and strong-arm ideas via exec endorsement.
  • DO: Socialize ideas casually, seek early adopters, build coalitions before formal pitches.

Prioritization Frameworks (35:14)

• Move beyond traditional “RICE” or conversion-only metrics.

• Use the triad: Value, Cost, Risk

  • Value: All forms of business value—not just metrics, but customer experience, team enablement, brand positioning.
  • Cost: Not just engineering hours, but organizational complexity, cross-team dependencies.
  • Risk: Human and business risks—morale, legal, technical, or reputational pitfalls.
  • Quote:
    “You can use value, cost, and risk as a way to move people towards an idea or emphasize what’s being left if we don’t pursue an idea. ... It’s not a really PME type framework you have to memorize, you can think about it at a human level.” (40:28)

• Anecdote:

  • At Airbnb, Ryan’s calendar redesign for hosts balanced massive revenue implications against risk (Brian Chesky’s personal involvement) and organizational cost.

Getting Comfortable With Data (44:14)

• Level 1: Build Relationships

  • Accessing business data is often a people problem, not a tooling problem—build trust with PMs, data science.

• Level 2: Understand Your Team’s Core Metrics

  • Learn the success KPIs for your project, not just general metrics.

• Level 3: “Go into the tool.”

  • Observe user behavior, not just outcomes. Spot unusual data or funnel outliers, then hypothesize the underlying human reason.

• Examples:

  • DoorDash: Noticed a spike in order-status page views, deduced anxiety, and proposed live order tracking, now an industry standard (49:07).
  • Airbnb: Noted modal for checkout fees improved conversion—pushed for single-step booking, leading to measurable gains pre-IPO (51:46).

Advancing in Business Skills — Notable Quotes

• On Promotion:
  "Visual skills get you hired, but it's this more product strategy/business skills that get you promoted." – Ridd (56:50)
• On Careers:
  “The only designers in trouble are the ones that are standing still.” — Ryan Scott (15:32)
• On Value:
  "You are an investment that they're making and they want to understand what they're getting for that investment." — Ryan Scott (56:50)

Ryan Scott’s Education & Courses (54:46)

• Ryan’s Maven courses focus on business skills for designers:
  • PM Masterclass for Designers: Opportunity finding, assessing, pitching ideas with data, stakeholder negotiation, and launching impactful work.
  • Designed for designers who want to be strategic, drive business value, and get promoted.

Timestamps for Important Segments

• [01:24] — Why the job market feels so erratic for designers
• [06:33] — Rethinking who you’re selling to (design manager vs. business leader)
• [10:33] — Telling your story when you lack perfect metrics
• [16:12] — The two career paths: technical vs. strategic
• [28:02] — How to find and surface new business opportunities
• [32:07] — Getting buy-in for ideas without alienating teams
• [35:14] — Value/Cost/Risk: Human-centric prioritization frameworks
• [49:07] — Data as insight: Real stories from DoorDash and Airbnb
• [54:46] — Business education for designers and how to go deeper

Memorable Moments & Quotes

• “No one knows what’s going on in the current market.” (01:24)
• “We need to be selling the right thing, that impact, and thinking about who the ultimate approver is.” (06:33)
• “I've literally just gone to the CEO of a company ... and I got buy-in, but ... ended up pissing off a lot of people.” (32:07)
• “You can use value, cost, and risk as a way to move people toward an idea or emphasize what’s being left if we don’t pursue it.” (40:28)
• “If cost goes down, maybe that impacts value, maybe that impacts risk.” (44:14)
• "Designers really excel when we think about things on human levels." (40:28)
• “Visual skills get you hired, but it's this more product strategy / business skills that get you promoted.” (56:50)

Takeaways for Designers

• Start thinking and talking in business outcomes, not just design craft.
• Learn to frame your work’s impact in language executives and PMs understand.
• Seek out opportunities to build trust and collaboration across roles, especially as boundaries blur with AI and new tools.
• Use holistic frameworks like value/cost/risk to prioritize and advocate for design work.
• Develop comfort with data—not just numbers, but the human behaviors behind them.
• The designers who keep learning, adapting, and moving are the ones who will thrive in the years ahead.

For deeper knowledge and resources, explore Ryan’s PM Masterclass for Designers via Dive Club. You'll find details and discounts through the show’s links.