20Product Shopify's VP Product on Why the Founder is Always the Head of Product, What Makes Truly Special Product Managers, Why The Majority of Product Managers Need to Change, Why TopDown DecisionMaking in Product is Good & How Shopify Will Be Bigger

In this episode, the host enthusiastically welcomes Glenn Coates, VP of Product at Shopify, who shares his journey from a computer science graduate to a key player in Shopify's expansive ecosystem. Coates details his transition from video game development to e-commerce, founding Handshake, and ultimately joining Shopify through acquisition. He emphasizes the importance of storytelling in product marketing, the challenges of managing up, and the necessity for product managers to focus on decision-making and execution over process. Coates also discusses Shopify's strength in innovation speed and its unique position with a powerful buyer aggregation engine. He reflects on strategic mistakes, like misjudging technology's progress with Handshake, and praises Microsoft's bold strategy with AI and Bing. The episode also highlights Miro and Mixpanel, tools that facilitate collaboration and analytics for startups, underscoring the significance of direct audience access and the potential impact of AI on search.

• Effective PMs exhibit a relentless drive and determination akin to a freight train.
• They are builders with a clear vision and a sense of urgency.
• Standing in their way is to risk being overcome by their momentum.

"Best pms have this feeling about them where it's like a freight train that like, if you try and stand in front of this thing, you're gonna get fucking flattened. The best pms have this sense of, I'm building this thing. It's gonna be great. Stand in front of me, you're fucking peril. Let's go."

The quote emphasizes the unstoppable nature and the powerful forward momentum of the best product managers, likening them to a freight train that cannot be easily halted.

• Glenn Coates is the VP of Product at Shopify, overseeing the core commerce platform, developer platform, and partner ecosystem.
• He transitioned from a computer science graduate to a VP at Shopify with a unique career path.
• Glenn's journey included international moves, a stint in video game development, and entrepreneurship.

"Glenn Coates is the VP of product at Shopify, leading the development of Shopify's core commerce platform. He also oversees the core developer platform and Shopify's partner ecosystem, which includes over 10,000 publicly available apps in the Shopify App Store."

The quote outlines Glenn Coates' current position and responsibilities at Shopify, highlighting his leadership in the development of key areas of the company's product offerings.

• Glenn Coates founded Handshake, a SaaS B2B eCommerce platform, which was later acquired by Shopify.
• The acquisition led to Coates joining Shopify and eventually becoming the VP of Product.
• Handshake specialized in wholesale eCommerce, complementing Shopify's offerings.

"Glenn then joined Shopify in May 2019 when the company acquired Handshake, and he's since been in the vice president role since October 2020."

The quote describes the transition from Handshake's acquisition to Glenn's leadership role at Shopify, indicating the trajectory of his career following the merger of the two companies.

• Gaming experience may contribute to the development of analytical and competitive skills beneficial for founding companies.
• The iterative process of improving at games parallels the challenges of company building.
• Gaming can foster resilience and a mindset of continuous improvement.

"That's an interesting question. I guess you have to have a very analytical mind and a very competitive mind to want to keep basically smashing your head against the wall at the same thing over and over and over again and getting better and better and better at it in a way that's usually very frustrating but fun at the same time."

The quote connects the skills developed through gaming, such as analysis and competition, to the qualities needed for successful entrepreneurship, highlighting the persistence and iterative learning common to both.

• Shopify's structure in 2020 consisted of multiple product lines with full-stack teams.
• Challenges arose when collaboration across divisions was necessary, particularly for checkout.
• Code Red at Shopify signifies a high-priority project requiring cross-team collaboration.

"And so when you have this that's cut on all these lines, it suddenly gets really hard to coordinate solutions that bridge the lines."

The quote explains the difficulties Shopify faced due to its organizational structure, emphasizing the need for better coordination across different product divisions.

• Coates' framework consists of defining outcomes, assumptions, and principles for product development.
• Outcomes determine how success will be measured once a project is completed.
• Principles guide decision-making during the project, especially for difficult choices.

"So the framework that I try to have people think about, I like to ask people to sketch out your outcomes, your assumptions and your principles at the start of a project, because these are the places where things can go off the rails and it's really good to catch those things early because you can just find, oh, let's get ahead of this, because you're going to go off in the wrong direction here."

The quote introduces Coates' product framework, which is designed to preemptively address potential issues in product development by establishing clear guidelines and objectives.

• Conflict often arises within teams, especially in large organizations like Shopify.
• It is crucial to align the team early on to prevent divisions and self-destruction.
• Establishing a clear direction for the entire team to follow is essential when conflicts are anticipated.

"It's really bad if half the team is taking one side and half the team is taking the other."

This quote emphasizes the importance of team unity and the negative impact of a divided team on project success.

• Trade-offs are common, especially between different stakeholders.
• Conflicts may arise between the interests of small and large merchants.
• Anticipating and addressing conflicts is important for businesses with broad missions like making commerce better for everyone.

"And it's not always between those three constituents. You might even have trade offs between small merchants and large merchants."

The quote highlights the complexity of balancing different stakeholders' interests and the need for strategic trade-offs.

• Team members may have differing foundational assumptions leading to disagreements.
• Assumptions about the future, like the rise of mobile web traffic, can significantly influence product development.
• Clarifying assumptions helps resolve conflicts and align product vision.

"We have some foundational assumption about reality that's different, which explains why we are talking past one another."

This quote underlines the significance of identifying and reconciling differing assumptions to improve communication and decision-making.

• Measuring outcomes for core features of a platform is challenging due to indirect financial impacts.
• Dependencies within a platform make it difficult to attribute specific financial results to changes in user experience.

"It's really hard to tie. Like, oh, we made this part of the UX better and this many more dollars came in."

The quote discusses the difficulty of directly linking user experience improvements to financial outcomes.

• Setting objectives that are not easily manipulated is a challenge.
• Metrics should reflect meaningful progress and not just easily achievable numbers.
• Quality of leads and customer retention are as important as acquisition numbers.

"I think the hardest thing that I've learned actually on objectives and goal setting is not making them gameable."

This quote stresses the importance of setting goals that truly reflect the value and progress of the team's efforts.

• The responsibility to build for the future increases the closer one is to the bottom of the stack in a platform.
• Long-term thinking is crucial for foundational platform features that will shape the industry for years to come.

"The closer you are to the bottom of the stack, the more responsibility you have to build for the future."

This quote highlights the strategic consideration required when making decisions that affect the fundamental aspects of a platform.

• Progressive disclosure and an app ecosystem are key to serving a wide range of customers while keeping the core product simple.
• High-quality third-party apps are essential for a successful app ecosystem.
• Shopify functions allow third-party logic to run securely on Shopify's servers, enhancing performance.

"The only two pieces of leverage you really have to allow that stretch is one is extremely good execution of progressive disclosure in the core products."

This quote explains the strategies used to maintain simplicity in a product that serves a diverse customer base.

• Reorganizing teams to improve alignment can be counterintuitive, such as dividing a combined team back into smaller teams.
• Adhering to the Dunbar number facilitates manageable team sizes and better collaboration.
• The restructured team alignment allows for escalations to be handled more appropriately than reaching the CEO directly.

"The first thing I did was I split core into eight teams."

This quote reveals the practical approach taken to restructure teams to improve efficiency and manageability within the organization.

• The leadership team at Shopify includes heads of various departments who focus on understanding team dynamics, resolving conflicts, and making decisions that guide the direction of the company.
• The role of leadership is to provide clarity and direction, preventing confusion and prolonged disagreements among teams.
• Decisions are made to ensure that the various products within the company work cohesively, similar to how Apple's products integrate seamlessly.

"We sit above these ten teams, but we consider our jobs to be understanding what's going on in these teams, handling the escalations, making sure that when kid a and kid b both want to go to university, we're like, you know what? You get to go to university. You get to be happy. You get to be sad. But the good news is, no one's confused about what we're doing."

This quote highlights the leadership's role in providing guidance and making decisions that benefit the company as a whole, while also acknowledging individual team desires and needs.

"The value of that suite is to a large extent, the way it all works beautifully together. And if all the decisions are coming from the edges, the chance that it's all going to work together and feel like it came from hand of a single creator just goes through the floor."

The speaker emphasizes the importance of having a unified vision and direction for the product suite to ensure a cohesive and high-quality user experience.

• The concept of "disagree and commit" is discussed, where team members may not fully agree with a decision but will still commit to executing it.
• The effectiveness of this approach can vary, with some individuals possibly not performing as efficiently as if they were in full agreement.

"Oh, I don't think they don't move down the field quite as fast, but there is a difference between moving downfield at 80% speed and literally digging your heels in."

This quote explains that while there may be a reduction in the speed of progress when team members "disagree and commit," it is still preferable to complete inaction or resistance.

"Sometimes that's a problem with the person who's disagreeing and not really committing, and maybe they just have to say, I disagree with this way of running a company. I disagree with this product direction. I should just leave the company."

Here, the speaker acknowledges that sometimes the "disagree and commit" philosophy may not work if an individual is fundamentally opposed to the company's direction and may need to consider leaving.

• Storytelling is a crucial skill for leaders to convey the vision and rationale behind decisions.
• A compelling story can create emotional connections and make concepts more relatable and memorable for the team.
• The ability to craft a story that resonates with various personas and stakeholders is key to effective communication and leadership.

"If you do not tell someone a story that they can see themselves in and they can empathize with, you can say all the numbers in the world, you can describe all the processes and analysis in the world. No one gives a shit."

This quote emphasizes the importance of creating an emotional connection through storytelling to engage people effectively, beyond just presenting facts and figures.

"The best stories work for everyone. They don't make two versions of Aladdin. There's one version of Aladdin. Great stories work until you can get there, you're not really doing your job."

The speaker points out that the most effective stories are universal and resonate with a wide audience, and that achieving this is a critical part of a leader's responsibility.

• Repetition is important in storytelling to ensure that the core message is remembered and internalized by the audience.
• Leaders should focus on creating memorable narratives with key takeaways that stick with the team.

"You'd be shocked how fast people forget things. This is why compelling storylines with just memorable sound bites are so important, because you only get to lodge like, a few words in someone's brain before every word you add pops one out their other ear."

The speaker acknowledges the limited capacity for people to retain information and the necessity of repetition and memorable sound bites in communication.

• Product marketing is complex, especially for a diverse and growing customer base like Shopify's.
• The challenge lies in crafting a message that is authentic to the company's values while appealing to a wide range of customers.
• The goal is to create a brand that people feel a part of, rather than just a service provider.

"How do you have a message which still speaks authentically to who you are and what you actually give a shit about without alienating an unacceptably large part of your customer base?"

This quote captures the essence of the challenge in product marketing: balancing authenticity with broad appeal.

"I want Shopify to be a media company. I want to see your business owners in Hawaii surfing and their fucking life. Hawaii having coconut cocktails is paid for by their store, which is powered by Shopify."

The speaker expresses a desire for Shopify to adopt a more lifestyle-oriented marketing approach that showcases the real-life benefits and stories of its users.

• Speaker A discusses their role in managing a specific segment of Shopify's product, the platform aspect, and the importance of focusing on it without diluting their efforts by taking on more.
• There is a distinction between platform businesses and aggregator businesses, and Shopify excels at both, creating a powerful combination.
• Speaker A emphasizes the competitive advantage Shopify has due to its platform joined with a buyer aggregation engine.
• Competitors are viewed as less formidable because they are pure platforms, lacking the aggregator component that Shopify has integrated.

The part of Shopify that I run is really the platform part. And there are other parts of Shopify, namely Shop and Shopify logistics, which are more aggregator plays.

The quote explains that Speaker A is responsible for the platform aspect of Shopify, which is distinct from other parts of the company that focus on aggregation, like Shop and Shopify logistics.

We have a great platform, but we've got it joined at the hip to an incredible buyer aggregation engine, which it's hard to overcome. How powerful that is.

This quote highlights the strategic advantage of combining a strong platform with a powerful buyer aggregation engine, which Speaker A believes is a formidable combination that competitors would find difficult to match.

• Shopify is acknowledged to be in direct competition with Amazon.
• The scale and magnitude of the competition are confirmed to be significant.
• Speaker A expresses confidence in Shopify's competitive position.

I mean, Shopify competes with Amazon today... 100%, 100%.

Speaker A confirms that Shopify is currently competing with Amazon and agrees with the suggestion that the competition is significant in scale and impact.

• Speaker A shares a past strategic mistake with their company Handshake, which involved overestimating the longevity of offline functionality as a key feature.
• The assumption that users would often be offline led to a tech stack built around offline capabilities, which became less valuable as internet connectivity improved.
• The mistake resulted in immense technical debt and hindered innovation.
• Speaker A reflects on the importance of anticipating technological progress and the consequences of not doing so.

There was a mistake strategically underneath handshake that basically was an ongoing tax for its entire lifetime.

The quote describes the enduring negative impact of a strategic mistake made at Handshake, likening it to a tax that weighed on the company for its entire existence.

If you'd said to me in 2010, hey, Glenn, how long do you think it's going to be until there's literally Internet connectivity everywhere? I might have actually sat down and thought, okay, how long is that really going to be?

This quote reveals Speaker A's reflection on the failure to anticipate the widespread availability of internet connectivity, which would have influenced their strategic decisions regarding the product's reliance on offline functionality.

• Speaker A expresses admiration for the Roland V-Drum kit due to its impressive emulation of a real drum kit.
• When asked about head versus heart, Speaker A chooses heart, despite being more of a "head" person.
• The ideal relationship between CEO and VP of Product is compared to the dynamic between a lead singer and a drummer in a band.
• Speaker A warns against founders relinquishing the title of head of product, as it could signify quitting or setting up the new head for failure.
• Shopify's biggest strength is highlighted as its pace of innovation and the combination of its platform and aggregator success.
• A weakness identified for Shopify is the lack of control over the top of the shopping funnel, which poses strategic challenges.
• Speaker A criticizes product managers (PMs) who overly focus on the process and technique of their craft rather than on making good decisions and getting things done.
• Microsoft's AI strategy, particularly with Bing, is praised for its boldness and potential impact on the search market.

The best pms have this sense of, I'm building this thing. It's going to be great. Stand in front of me at your fucking peril. Let's go.

This quote illustrates Speaker A's admiration for product managers who are determined, proactive, and unafraid to pursue their vision for a product.

The way Microsoft is going at the AI thing is brilliant.

Speaker A applauds Microsoft's strategic approach to AI, recognizing their partnership with OpenAI and the innovative use of AI in Bing as smart moves that could significantly disrupt the search market.