LLenny's Podcast
← All episodes
Casey Winters, Eventbrite21 July 2022

How to sell your ideas and rise within your company

6Frameworks
14Insights

Episode overview

Casey Winters explains how product leaders can communicate upward by framing a coherent story, anticipating each executive's questions, and de-risking important meetings through rehearsal and pre-meetings. He discusses preserving product simplicity at scale, winning support for hard-to-measure improvements, and treating operations teams as temporary mechanisms for eliminating inefficiency. The conversation also covers the strategic skills required to reach senior product leadership and Casey's distinction between early “kindle” growth tactics and scalable “fire” strategies.

Key ideas

  • Communicate trade-offs upward early so executives can improve the circumstances, understand the context, and evaluate outcomes fairly.
  • Begin an executive presentation at the last point already obvious to its audience, then build a complete story from strategy and metrics to assumptions and decisions.
  • Rehearse important meetings, anticipate the questions of individual executives, and use pre-meetings to surface objections before the main decision forum.
  • Preserve perceived simplicity by making advanced functionality easy to discover for people seeking it but unobtrusive for everyone else.
  • Win support for performance, stability, user experience, and developer-velocity work through aligned peers, custom metrics, small tests, principles, and downside framing.
  • Operations roles should identify inefficiencies and remove them through better process or software instead of becoming permanent owners of manual work.
  • Execution is essential early in a product career, but independently writing strategy and driving decisions becomes the key filter for senior leadership.
  • Use non-scalable “kindle strategies” to discover scalable “fire strategies,” then hire growth specialists after a repeatable growth loop has been unlocked.

Transcript available · source text is retained privately and is not published

Frameworks in this episode

Communication4 steps

De-Risking the High-Stakes Meeting

Turn important meetings from big-reveal gambles into pre-worked, question-proof conversations.

Read →
Strategy4 steps

Justifying Non-Sexy Product Investments

Fund performance, UX and velocity work by making the invisible measurable and the downside of neglect concrete.

Read →
Marketing4 steps

Kindle and Fire Growth Strategies

Non-scalable kindle hacks exist only to unlock the scalable fire strategy worth hiring for.

Read →
Innovation4 steps

Perceived Simplicity

Keep advanced power in the product but discoverable only to those who go looking — invisible to everyone else.

Read →
Leadership4 steps

The Product People Spectrum: Innovators to Executors

Great product careers get filtered at strategy — deliberately move executors toward the strategic middle.

Read →
Communication4 steps

The Story Chapters Framework for Executive Communication

Find the last obvious point for your audience, then build from there — skip neither the setup nor the basics.

Read →

People & resources mentioned

Attributed to the moment in the episode. Timestamps are approximate.

People · 5

  • Lenny RachitskyMentionstoday we've got another very special compilation episode something I've been pulling on more and more with the podcast and the newsletter

    “casey welcome to the pod i feel like every time that we chat i leave with at least one new perspective”

    ▶ Watch at ~3:30approx.
  • Casey WintersMentionswho's had the most influence on you in your career well we mentioned him before so I gotta bring him back up Casey Winters

    “casey welcome to the pod”

    ▶ Watch at ~3:30approx.
  • Casey WintersMentionswho's had the most influence on you in your career well we mentioned him before so I gotta bring him back up Casey Winters

    “so now i've been doing that for three years now”

    ▶ Watch at ~6:00approx.
  • Matt DamonMentionsas a joke they invite matt damon to this business meeting and they just talk and code as a prank on him

    “as a joke they invite matt damon to this business meeting and they just talk and code as a prank on him”

    ▶ Watch at ~9:00approx.
  • Scott BelskyCoinedHe's a former founder starting a company called Behance that he sold to Adobe where he worked up the ranks to chief product officer

    “scott belski who's the chief product officer of adobe he has this concept of the product life cycle”

    ▶ Watch at ~19:30approx.

Resources · 32

  • CodaUsessoftware · Coda

    “i actually use coda myself every day”

    ▶ Watch at ~1:30approx.
  • MixpanelMentionssoftware · Mixpanel

    “this episode is brought to you by mixpanel offering powerful self-serve product analytics”

    ▶ Watch at ~2:00approx.
  • Apartments.comUseswebsite

    “i started my career as an analyst at apartments.com on the marketing side”

    ▶ Watch at ~4:00approx.
  • LinkedInUseswebsite · LinkedIn

    “just looking at your linkedin trying to scroll through linkedin”

    ▶ Watch at ~4:00approx.
  • GrubhubUsescompany

    “i basically worked on growing the demand side of that business from series a to ipo”

    ▶ Watch at ~5:00approx.
  • PocketUsessoftware

    “i started doing some more advising you know with airbnb on the demand side with pocket”

    ▶ Watch at ~5:30approx.
  • AirbnbUsescompany · Brian Chesky, Joe Gebbia, and Nathan Blecharczyk

    “i started doing some more advising you know with airbnb on the demand side”

    ▶ Watch at ~5:30approx.
  • PinterestUsescompany · Pinterest

    “it wasn't until i went to pinterest that i was actually formally labeled a product person”

    ▶ Watch at ~5:30approx.
  • ThumbtackUsescompany

    “independently started working as a full-time advisor with companies like you know eventbrite tinder thumbtack canva”

    ▶ Watch at ~6:00approx.
  • Greylock PartnersUsescompany

    “then i went to a vc named greylock partners and worked with their companies on on growth and scaling”

    ▶ Watch at ~6:00approx.
  • TinderUsescompany

    “independently started working as a full-time advisor with companies like you know eventbrite tinder thumbtack canva”

    ▶ Watch at ~6:00approx.
  • CanvaUsescompany · Melanie Perkins, Cliff Obrecht, and Cameron Adams

    “independently started working as a full-time advisor with companies like you know eventbrite tinder thumbtack canva”

    ▶ Watch at ~6:00approx.link ↗
  • Ocean's TwelveMentionsfilm

    “i don't know if you've ever seen ocean's 12”

    ▶ Watch at ~9:00approx.
  • AdobeMentionscompany

    “scott belski who's the chief product officer of adobe”

    ▶ Watch at ~19:30approx.
  • Uber EatsMentionsproduct · Uber Technologies, Inc.

    “unbundle it over time like facebook messenger uber eats have done”

    ▶ Watch at ~20:00approx.
  • Facebook MessengerMentionssoftware · Facebook

    “unbundle it over time like facebook messenger uber eats have done”

    ▶ Watch at ~20:00approx.
  • WhatsAppMentionssoftware · Meta

    “the company that i feel like has always done the best job of this is whatsapp”

    ▶ Watch at ~22:00approx.
  • WhimsicalMentionssoftware · Whimsical

    “this episode is brought to you by whimsical”

    ▶ Watch at ~27:00approx.
  • FacebookMentionscompany · Meta

    “we were a fast-growing startup that stopped growing due to some changes in in the market related to facebook”

    ▶ Watch at ~28:30approx.
  • IntercomRecommendscompany · Intercom

    “intercom has a really good blog post on this from a while back around their business operations team”

    ▶ Watch at ~33:00approx.
  • The GoalMentionsbook · Eliyahu M. Goldratt and Jeff Cox

    “it mapped to my mind better as someone who's like really influenced you know by the book the goal”

    ▶ Watch at ~38:30approx.
  • CamblyMentionscompany

    “i was inspired from talking with omar who who runs product at cambly”

    ▶ Watch at ~41:00approx.
  • ReforgeUsescompany · Brian Balfour

    “i built some programs for reforge around product strategy”

    ▶ Watch at ~44:00approx.
  • AppleMentionscompany · Steve Jobs, Steve Wozniak, and Ronald Wayne

    “especially with facebook and apple's platform changes”

    ▶ Watch at ~52:30approx.
  • Cyberpunk 2077Usesproduct · CD Projekt Red

    “i'm currently playing cyberpunk 2077 on the ps5 which is fun”

    ▶ Watch at ~53:00approx.
  • PlayStation 5Usesproduct · Sony

    “i'm currently playing cyberpunk 2077 on the ps5 which is fun”

    ▶ Watch at ~53:00approx.
  • Horizon Forbidden WestRecommendsproduct · Guerrilla Games

    “i recently finished horizon forbidden west and that was excellent really great science fiction game”

    ▶ Watch at ~53:00approx.
  • BroadcastRecommendsother

    “one of my favorite bands this band called broadcast”

    ▶ Watch at ~53:30approx.
  • BBCMentionscompany

    “a bunch of their live sessions that they recorded on the bbc”

    ▶ Watch at ~53:30approx.
  • Casey AccidentalCoinedwebsite · Casey Winters

    “blog caseyaccidental.com”

    ▶ Watch at ~54:00approx.
  • EventbriteRecommendscompany · Eventbrite

    “if you're searching for a cool event check out the eventbrite app”

    ▶ Watch at ~54:30approx.
  • Lenny's PodcastCoinedpodcast · Lenny Rachitsky

    “you can also learn more at lennyspodcast.com”

    ▶ Watch at ~55:00approx.

Spot an error or want something removed? Request a correction or removal.

Insights & moments

The myth-busts, hot takes, explainers, and tools worth keeping.

Hot Take· 5

Hot Take07:30

Escalating Issues Is Leadership, Not a Failure

Casey noticed managers at Eventbrite tried to handle tough situations on their own instead of raising them, then complained he didn't understand the circumstances. He argues escalation is often the right move because it lets an executive change the circumstances, or at least evaluate outcomes with proper context. People chronically under-communicate upward and then wrongly conclude executives are out of touch.

  • Managers often treat 'handling it alone' as leadership when escalation is the correct move
  • Escalating lets an executive change the circumstances or at least judge results fairly
  • Executives can't evaluate a situation they were never told about
  • People under-communicate upward, then complain leaders are out of touch

“these people on my team thought that being a leader was you know handling it the best they could given the circumstances when you know…”

Casey Winters · 08:00

“people just way under communicate upward inside of companies and then they'll complain that executives are out of touch you know when they aren't telling…”

Casey Winters · 08:30
#management#communication#leadership
Hot Take28:00

At Scale, You Can Lose What You've Already Built

Non-sexy work like performance, stability, and developer velocity gets chronically underfunded because it's hard to measure — what gets measured gets managed. Casey's key argument for funding it: early-stage companies only think about adding growth, but once you've built a real business you can actually lose it. Showing leaders what a hard-won conversion rate or engagement level would look like if it eroded is powerful.

  • Hard-to-measure work (UX, performance, dev velocity) gets chronically underfunded
  • 'What gets measured gets managed' explains why unsexy work is skipped
  • At scale the risk flips from failing to grow to losing gains you already have
  • Show leaders concretely what a lost conversion rate or engagement level would cost

“when you're at scale you can actually lose what you've built”

Casey Winters · 28:30
#growth#product-strategy#prioritization
Hot Take32:00

Standing Ops Teams Are Often a Sign You're Inefficient

Casey's spiciest take: functional ops roles are a hack for an underlying functional problem, and normalizing them as permanent, stable functions is a form of empire building. He ran a double-digit-million marketing budget at Grubhub without marketing ops by investing in automation and process. Eventbrite's ops team is great precisely because its job is to find inefficiencies and build software to root them out — then move on.

  • Functional ops roles are a hack for a deeper functional or efficiency problem
  • Making ops a permanent standing function is a form of empire building
  • He ran a large Grubhub marketing budget with no marketing ops via automation and process
  • Good ops eliminates its own work, then people move to other roles they're wanted for

“having marketing ops means you suck at marketing and obviously that's a bit of hyperbole”

Casey Winters · 32:00

“in general functional ops roles whether it's product ops or marketing ops or you know whatever they're a hack to deal with some sort of…”

Casey Winters · 33:30
#operations#org-design#efficiency
Hot Take49:30

A Scalable Acquisition Loop Is Part of Product-Market Fit

Casey sees founders building growth loops into their product before they find product-market fit — not to prematurely scale, but so distribution is ready the moment PMF arrives. His stronger claim: scalable acquisition is a requirement for product-market fit. A product that retains well but can't find more users isn't, in his view, actually at product-market fit.

  • Founders increasingly build growth loops before PMF, not to scale early but to be ready
  • The goal is built-in distribution advantage the moment PMF is found
  • Scalable acquisition (an acquisition loop) is a requirement for PMF
  • A product that retains but can't find more users isn't truly at product-market fit

“if you've got a product that retains well and you can't find more users for it i don't think that's product market fit”

Casey Winters · 50:00
#growth#product-market-fit#founders
Hot Take52:00

Data Network Effects Are Still Underrated

Casey thinks people confuse data network effects with selling data as a product — and most businesses, especially SMBs, can't be charged for data they don't know how to use. Real data network effects mean using product-usage data to make the product itself stronger over time, like Pinterest's personalized results or Eventbrite's ad targeting. With Facebook and Apple platform changes, a product generating its own data is a real edge.

  • Don't confuse data network effects with data-as-a-product you sell
  • SMBs usually can't be charged for data they can't use well
  • Real data network effects make the product itself better via usage data over time
  • Amid platform changes, generating your own data instead of relying on big platforms is an edge

“i still think data network effects are underrated”

Casey Winters · 52:00

“what data network effects are is leveraging product usage data to make the product value stronger and stronger over time”

Casey Winters · 52:30
#growth#data#network-effects

Explainer· 6

Explainer09:30

Talk to Executives Like You're Telling a Story

Casey frames upward communication as storytelling: you have to start at 'chapter one' — what strategy you're working on, what metric you're improving, what assumptions guide you — or an exec won't follow. But the opposite failure is re-explaining company strategy everyone already knows. The skill is finding the last point that's completely obvious to your listener and starting just past it.

  • Non-execs often jump to 'chapter six' and skip the context that earns the right to be heard
  • The opposite mistake is spending 20 minutes re-explaining strategy everyone knows
  • Find the last point that's obvious to the listener, then go from there to less obvious things
  • The right altitude differs for a CEO, a CFO, and an individual engineer

“you haven't earned the right to tell that part of the story yet because you skipped the first five chapters”

Casey Winters · 09:30

“you want to find the last point in your story that would be completely obvious to the person you're telling the story to and then…”

Casey Winters · 10:30
#communication#product-management#storytelling
Explainer11:30

De-Risk Big Meetings Before They Happen

Rather than the dramatic 'big reveal' meeting, Casey coaches his team to de-risk beforehand. He role-plays the audience — anticipating the exact questions the CFO or CEO will ask so PMs can weave answers in early — and pushes for pre-meetings with key individuals so nobody is surprised. His memorable reframe: executive communication is really 'executives' communication,' since each leader has different styles and concerns.

  • Avoid the 'big reveal' meeting; de-risk it in advance instead
  • Role-play the audience and pre-answer the questions specific execs will ask
  • Hold pre-meetings with key stakeholders so concerns surface before the big meeting
  • Treat it as 'executives' communication' — each exec has a different style

“i think the best way to coach is actually to do it before the meeting”

Casey Winters · 11:30

“executive communication is actually executives communication you're communicating with individual executives that all have different styles and different concerns about the business”

Casey Winters · 12:30
#management#meetings#coaching
Explainer21:30

Perceived Simplicity: Hide Power Until It's Wanted

Because Eventbrite serves creators at every level of sophistication — and users move between levels — segmentation and progressive disclosure don't fit. Instead Casey's team aims for 'perceived simplicity': advanced features exist and are discoverable when you look for them, but effectively invisible to the majority who never will. He cites WhatsApp as the gold standard, where advanced features like voice and video reveal themselves only when needed.

  • Eventbrite's users span every sophistication level and shift between them over time
  • Segmentation and progressive disclosure both break for that mixed user base
  • Perceived simplicity: advanced features are discoverable on demand but hidden by default
  • WhatsApp is the exemplar — advanced features surface only when you look for them

“there are advanced features in the product and they are easily discoverable when you look for them but they're effectively hidden if you're not looking…”

Casey Winters · 21:30
#product-design#simplicity#ux
Explainer29:30

Product-Market Fit Decays If You Stop Pushing

Casey explains that user expectations rise every day and the competitive landscape keeps improving, so product-market fit isn't permanent. Stop improving your product, UX, and latency and you may — not tomorrow, but in a year or five — fall out of product-market fit entirely. That's dangerous because it takes a long time to detect and you'll have accumulated technical debt to clean up before you can catch back up.

  • User expectations and competitor quality both rise continuously
  • Standing still means eventually falling out of product-market fit
  • The failure is slow and hard to detect, making it especially dangerous
  • Recovery is costly because technical debt piles up while you fall behind

“user expectations just continue to go up every day right in terms of their expectations on user experience”

Casey Winters · 30:00

“you might find yourself fall out of product market fit entirely and that's a really dangerous place to be”

Casey Winters · 30:00
#product-market-fit#product-strategy#growth
Explainer41:30

The Spectrum From Innovators to Executors

Casey describes product people on a spectrum rather than a two-by-two. On the left are crazy innovator types with endless ideas — most bad, but one in ten is a game changer — who struggle to execute. On the right are executional PMs who turn strategy into value but don't track the industry or generate ideas. Everyone wants the rare middle; as a product leader Casey biases toward strong executors, while a VC should bias toward the idea generators.

  • Product talent sits on a spectrum from innovators to executors, not a 2x2
  • Innovators generate many ideas — mostly bad, occasionally game-changing — but struggle to ship
  • Executors deliver value but need direction and miss industry shifts
  • Leaders should prefer executors; VCs should prefer idea generators

“i generally will take people who are good at execution over people who are good at generating ideas”

Casey Winters · 43:00
#product-management#hiring#talent
Explainer48:00

Product-Led Growth: Merge Sales and Product Loops

Casey argues the real growth edge isn't new channels but getting leverage on existing ones. At Eventbrite they unified separate direct-response and lead-gen flows, lowering CPAs while letting sales pick up high-value product-qualified leads. He calls this 'product led' — fusing self-service product loops and sales loops into one larger cross-functional engine — and predicts an explosion of B2B companies that learn to unlock it.

  • The edge is leverage on existing channels, not brand-new channels
  • Eventbrite unified direct-response and lead-gen flows for better CPAs
  • Sales picks up high-value product-qualified leads with the data to justify it
  • 'Product led' fuses self-service and sales loops into one cross-functional engine

“you can unify self-service loops in a b2b business which are typically driven by product and your sales loops into one more complex giant loop…”

Casey Winters · 48:30
#growth#b2b#product-led

Takeaway· 3

Takeaway16:30

Prep Until You Can Answer Every Possible Question

Asked how much time to spend preparing, Casey says the real metric isn't hours but whether you truly know the material and what your audience cares about. He recounts Pinterest product reviews where Jack would open with data questions — miss one and you cast doubt on the whole meeting. You need to map the entire universe of how a meeting can go, which can take dozens of hours.

  • The metric isn't hours spent, it's how deeply you know the material and audience
  • At Pinterest, failing to answer a leader's opening data question undermined the whole review
  • Map the full universe of questions that could be asked and prepare answers with data
  • Thorough prep can take dozens of hours but sharply lowers the odds of a bad outcome

“if you haven't thought through all the questions that might be asked from the document that you're sharing or the presentation you're about to present…”

Casey Winters · 16:30

“you need to know the entire universe of how that meeting can go and that may take you dozens of hours”

Casey Winters · 17:00
#meetings#preparation#product-management
Takeaway39:00

How He Reached CPO: Company-First and Never Specialize

Casey says the CPO role is more a company leadership job than a functional one — you optimize for the whole company even at your own team's expense, which new executives struggle with. Two things served him: he'd worked with executives since his first job and learned to speak their language, and he refused to specialize, combining skills to work on the most important problems. That slowed his visible title progress but sped his path to a true executive role.

  • A CPO optimizes for the whole company, even against their own team's interests
  • Learning to speak executives' language early was a durable advantage
  • Treat exec questions as attempts to learn, not tests trying to catch you out
  • Refusing to specialize slowed title growth but sped the path to executive scope

“you're expected in this role to optimize for the entire company even at the expense of what's good for your team”

Casey Winters · 39:00

“the other element that served me well was just refusing to specialize”

Casey Winters · 40:00
#career#leadership#product-management
Takeaway45:30

Strategy Is the Great Filter for Senior PMs

Casey says early-career PMs win by shipping things customers like, but leveling up to run a business unit requires writing the strategy doc yourself. Many people simply can't take that step, and when a CEO expects it and they can't deliver, their careers cap hard at senior PM or group PM. The industry lacks good ways to turn great executors into great strategists, which is why he invests in Reforge programs and mentorship.

  • Early on, shipping products customers love matters most
  • Leveling to leadership requires writing the strategy doc independently
  • Failing that step caps careers at senior PM or group PM level
  • There's no reliable playbook to turn executors into strategists — the biggest skill bottleneck

“that one to get to the top is the great filter”

Casey Winters · 46:30
#career#strategy#product-management