Sep 22, 2021 · 43m · 20vc
Welcome 20Growth: How To Hire a Head of Growth? What are Signs of World-Class Talent? How To Structure the Process? How To Onboard Growth Teams? The Relationship Between Head of Growth and CEO and more with Casey Winters, Chief Product Officer @ Eventbrit
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In the inaugural episode of '20 Growth,' host Harry Stebbings speaks with Casey Winters, CPO at Eventbrite and former growth lead at Pinterest and Grubhub, about building, hiring, and structuring high-performing growth teams. They discuss candidate evaluation frameworks, cross-functional organizational alignment, CEO-growth relationship dynamics, and strategic execution lessons from leading tech startups.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 22.5% of the talking time here. How this is scored →
Harry as informed peer 2.4 Guest teaching 4.9 Guest disagreement 1.1 Harry pushing back 1.1
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 15:02 Playfully guarding proprietary interview questions
When Harry asks Casey for the exact questions he uses to test data fluency, Casey playfully refuses to give away all his battle-tested secrets on air before yielding two detailed examples.
Hardest push from Harry ▶ 19:40 Challenging executive case study normsHarry pushes back on standard executive recruiting processes, questioning whether asking senior growth leaders to complete case studies is impractical or insulting for early-stage founders.
Biggest teaching moment ▶ 27:35 Reframing executive alignment with founder visionCasey corrects a common misconception among product executives, educating Harry that CPOs and Growth leaders are hired to execute the founder's vision rather than run their own independent show.
Harry holds his own ▶ 14:45 Drilling into candidate assessment mechanicsHarry demonstrates strong practical interview grounding by pressing Casey past high-level principles to explain exactly how to test a candidate's data orientation in an interview.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Casey Winters' Career Trajectory in Growth | 1 | 2 | 0 | 0 | Harry invites Casey to share his career story spanning Apartments.com, Grubhub, Pinterest, and Eventbrite. Casey provides a smooth monologue outlining how performance marketing and product hybrid roles evolved into modern growth leadership. Harry listens intently with minimal intervention beyond expressing awe at Grubhub's early Series A metrics. | |
| Defining Growth and Structuring the Growth Function | 2 | 5 | 1 | 1 | Harry prompts Casey to define growth and evaluate integrated versus standalone team structures. Casey offers a clear reframe, defining growth as connecting users to existing product value rather than building new features. The dynamic remains conversational and friendly as Casey outlines structural trade-offs. | |
| Determining the Right Timing for Growth Hires | 3 | 6 | 2 | 2 | Harry presses Casey on tactical interview techniques for evaluating a candidate's data fluency. Casey jokingly guards his best proprietary questions before sharing specific case scenarios like diagnosing metric drops and identifying comparative baseline trends. Casey educates the audience on distinguishing kindling strategies from fire scaling strategies. | |
| Evaluating Growth Layers, Subject Matter Skills, and Candidate Case Studies | 3 | 6 | 1 | 2 | Harry challenges the practical aspect of asking senior, pedigreed executives to complete case studies without alienating them. Casey reframes the issue, explaining that case studies protect both parties and if a candidate views a case study as beneath them, they are a bad cultural fit for the role. Casey also breaks down the McKinsey horizons growth layer cake across product, performance, and brand marketing. | |
| Onboarding Growth Leaders and Fostering Internal Alignment | 2 | 5 | 1 | 1 | Harry asks how to effectively onboard growth leaders and eliminate friction between product and growth departments. Casey details how growth leaders must over-communicate their goals to dismantle internal skepticism and build cross-functional trust. Harry listens and prompts with follow-ups on organizational harmony. | |
| Navigating the Head of Growth and CEO Relationship | 2 | 6 | 2 | 1 | Harry asks about meeting cadences between CEOs and growth leaders. Casey gently points out that Harry's suggested meeting structure is a bit light and provides a lesson on executive alignment, noting CPOs and Heads of Growth often mistakenly think it's 'their show' when their job is executing the founder's vision. | |
| Handling Metric Volatility, Strategic Pivots, and Data Dependencies | 3 | 5 | 1 | 1 | Harry asks Casey to share a time he made a growth decision based purely on gut instinct rather than data. Casey transparently admits that almost every intuitive decision he made without data failed, citing examples from Grubhub and Pinterest. Harry guides the conversation with good probing questions about strategic pivots. | |
| Angel Investing Insights and Assessing Execution Speed | 3 | 4 | 1 | 1 | Harry guides a crisp quickfire round touching on angel investing, obsolete tactics like organic social and SMS, and common founder hiring mistakes. Casey criticizes founders who track vanity activity metrics like MAU instead of core value usage. The segment maintains an agreeable, efficient cadence. |
Statements from this episode (25)
Casey Winters scaled Pinterest signup conversion 5x via SEO
“At Pinterest, Casey turned SEO into a scalable acquisition strategy, increasing conversion to signups, five X.”
Grubhub expanded from 3 to over 1,000 cities prior to $7.3B exit
“Casey played an instrumental role in scaling Grubhub from three cities to over a thousand, and from a one million dollar series A to an IPO and a 7.3 billion dollar exit.”
Winters: Pinterest grew from 40M to 150M MAUs during his tenure
“Stayed there from about forty million monthly actives to a hundred and fifty million monthly actives.”
Winters: Growth connects users to existing value, not new features
“Growth is about connecting people to the value that's already been created by the business, you know, either through Product or services or whatever. So growth is not about building totally new features, totally new products. It's about once we have those and …”
Winters: Isolated growth teams fail long-term without organizational alignment
“While that can be really good at going fast, a lot of times by going fast, you're not going far because you're not as default biased to keeping the rest of the organization in loop with what a growth team is doing.”
Casey Winters: Startups must build growth capabilities immediately after product-market fit
“As soon as possible after product market fit, that's when growth becomes the number one concern of most startups, and that's where you need to be building out that capability.”
Casey Winters: Experienced growth leaders won't join until startups prioritize growth internally
“There are perhaps 50 people that are capable, that have shown previous, like, head of growth experience, and they're not going to join your company until they've seen that you've already prioritized growth and shown that you value it.”
Winters: Do not hire a Head of Growth for initial traction
“You don't want to bring it ahead of growth to start Kindling things. You want to bring it ahead of growth to like really start the fire.”
Winters: Scalable startup growth is limited to four core strategies
“Fire strategies, there's really only a few of them, right? You know, you could scale via sales, you could scale via performance marketing, you could scale, you know, content loops, or you could scale via virality.”
Casey Winters: Brand marketing is unmeasurable and speculative for early startups
“Brand marketing, which is neither measurable nor scalable and requires money. It's not a bad idea. It's just usually has a longer return, a more speculative return. So generally startups wait longer before they invest in that.”
Casey Winters: Product-driven growth requires one-week experimental projects over six-month builds
“A lot of what product driven growth requires is someone that can figure out a grand opportunity and then break it down into really small chunks that help them learn that they're not, you know, putting forth a six month project. They're putting forth a one week…”
Casey Winters: Refusing interview case studies signals poor fit for startup roles
“Interviews should be for both sides, right? If I feel like that case study is beneath me, that's a problem. That means I'm probably not a good fit for the job right now, and you should be hiring someone more junior, right?”
Winters: Growth leaders must talk to users, not just analyze data
“Cause if our job as like a growth leader is to connect people to the core value of the product, we need to understand that core value almost better than anyone at the company. We need to know how to talk about it. We need to know the steps that get them introd…”
Winters: Startup executives must resolve inter-departmental conflict themselves
“I see a mistake a lot of executives make, and this is outside of growth too, where they're like, they'll expect their manager or the CEO to like take care of their problems for them. And it's like, no, that's not what happens. Like you got to go solve those pr…”
Winters: Visionary product founders prioritize core product evolution over metric optimization
“Visionary product founders, they are going to naturally spend more of their time thinking about how the core product evolves, rather than thinking about how can I move this metric up one, two percent, five percent, 10%, et cetera.”
Winters: Growth leaders exist to execute founder vision, not create strategy
“What a lot of product leaders make a mistake of, as well as growth leaders, is they think it's their show. They get to create the vision. They get to create the strategy. And it's like, not really. You're there to execute on the vision and strategy of the foun…”
Casey Winters: Growth teams must prioritize learning velocity over short-term results
“You can't focus entirely on the results. What you really want to focus on is the learning. Are we continuing to learn how our users operate, how this business operates, and what our scalable growth strategies are? As long as that learning loop is quick, that's…”
Casey Winters: Facebook Open Graph changes temporarily killed Pinterest's viral user acquisition
“When Facebook changed the way the open graph worked, all of a sudden we stopped getting any new users.”
Pinterest signed up over half the US population via Google SEO
“So as we did that, that was really successful, and we ended up signing up, you know, like over half of the US up to Pinterest with, you know, a pretty high retention rate.”
Casey Winters: Enterprise SaaS companies should not copy Facebook's growth strategy
“So much of this is context-specific, and so few people in the startup community know even which context they're in. So they might, oh, I read Facebook does it this way, and it's like, great, you're an enterprise SaaS company. What Facebook does has, like, no m…”
Winters: Founder execution speed is the top factor when angel investing
“In other companies, like I could rely on my rate of execution, you know, like my speed, my learning loop, but now it's become this different element of, I'm really trying to gauge how quickly they learn, how quickly they execute. And that's like the biggest fa…”
Winters: Organic social reach as a growth channel is dead
“Generally, anything organic, social related, just doesn't exist anymore, because the social networks are so good at taxing any reach that you want to have on the social channels. So that's one that feels relatively dead.”
Winters: Scaling growth requires deep engineering work, not quick hacks
“Growth is done in a team, and it's not just hacks or experiments. Like, it requires understanding the growth model of the business, where the constraints are, and potentially doing quick hacks, but a lot of times deep engineering work to actually scale the bus…”
Winters: Performance marketing over-reliance fails within five years without network effects
“The default towards performance marketing is the only channel that matters. It creates a lot of issues long term, especially if you're not network effect driven, where It's going to work really well in year one, not as well in year two, and in year five, you'r…”