In Depth

Amber Feng, Co-founder and CTO of Cocoon, shares her insights from eight years at Stripe. She discusses the unexpected traits of high-achievers in engineering and the debate between honing technical skills versus management roles. Amber highlights the importance of understanding user perspectives and effective communication in tech. As a first-time founder, she reveals lessons learned from Patrick Collison and provides advice for engineers looking to launch their own startups, emphasizing the need for a complementary team and adaptability.

Today’s episode is with Meka Asonye, a Partner at First Round Capital. This week marks the one year anniversary since he joined, making the transition from seasoned GTM leader to full-time early-stage investor.Prior to First Round, Meka served as the VP of Sales & Services at Mixpanel, where he ran the more than 100-person global revenue team and owned the customer lifecycle from first website visit to renewal. Meka also spent four years at Stripe as it scaled from 250 to 2000 people and matured its sales org. When he first joined in 2016, he served as one of the payments company’s early account executives, leading their first attempts to go upmarket and land enterprise logos. For the next three years, he headed up Stripe’s Startup/SMB business.In today’s conversation, Meka starts by digging into his playbook for founder-led sales, from what a great first customer conversation looks like, to how to self-diagnose what went wrong. He also shares advice for founders making their first hire, including the leveling mistake that’s easy to make, and what to ask in the interview and in reference calls. He also offers thoughts on comp and the leading indicators to look for after onboarding.We then dig into structuring early pilots, from what makes for a good design partner, to how to make sure your ICP is well defined enough. We also cover helpful tactics for customer success, which Meka finds is often the most overlooked aspect of go-to-market. Throughout the conversation, we also touch on how Meka’s experiences have translated into his first year as a VC. We end on his advice for startup folks looking to transition into venture.To read more of Meka’s go-to-market advice for founders, check out his article in the First Round Review: https://review.firstround.com/this-gtm-leader-turned-investor-crowdsources-early-lessons-from-stripe-figma-and-more You can follow Meka on Twitter at @BigMekaStyle. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.

Today’s episode is with Max Rhodes, the co-founder and CEO of Faire, an online wholesale marketplace that connects independent retailers and brands.Prior to starting Faire in 2017, Max spent several years at Square, where he was a founding member of Square Capital, the first product manager on Square Cash, and a Director of Consumer Product for Caviar.In today’s conversation, we dive deep into how startups can get international expansion right. After launching in the U.K. and Netherlands in March 2021, Faire company expanded into countries like France, Germany, Italy and the Nordic region. They’re now in 15 markets, with over 700 employees in 10 offices around the world. After sharing the company’s origin story and initial strategy, Max offers a helpful analogy that helped him decide when to go international, and details some lessons he learned from other companies like DoorDash and Airbnb.Next, Max takes us through the nuts and bolts of how the Faire team approached their first international launch, from staffing and operations, to how they thought about local competitors. Max also walks us through the operating cadence and strategic planning process that powered Faire’s international growth. We also talk about the human side of scaling internationally, and the growing pains that come along with it. To help mitigate the effects, Max shares how he’s implemented the concepts from the First Round Review article on “Giving away your Legos.” Read the article here: https://review.firstround.com/give-away-your-legos-and-other-commandments-for-scaling-startups You can follow Max on Twitter at @MaxRhodesOK. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.

Today’s episode is with Jeanne DeWitt Grosser, Head of Americas Revenue and Growth for Stripe, where she’s responsible for all sales functions and leads the company’s enterprise strategy. She joined Stripe after a career in sales at Google and also serving as Dialpad’s Chief Revenue Officer.In today’s conversation, we dive super deep into all things pricing. To start, Jeanne outlines the trade-offs when it comes to usage-based pricing versus SaaS pricing, and how usage-based gets your company more closely aligned with the customer. She also debates the merits of hybrid or tiered pricing that Stripe has implemented and provides tips for other companies looking to go this route.Next, she explains her philosophy of treating pricing like a product, and how this shows up in Stripe’s org design. Jeanne outlines some of the pricing experiments that have had the biggest impact on how the company does business, and her tips for getting a steady drumbeat of customer feedback.To wrap up, she shares her advice for founders when it comes to treating pricing as an art and a science. If you’re in sales, or are a founder just starting to think about pricing your product, you won’t want to miss Jeanne’s insights she’s picked up over the course of her career. She’s got plenty of ideas for small startups and larger companies alike. Along the way, Jeanne provides plenty of examples from her time at Stripe to illustrate her playbook in action.You can follow Jeanne on Twitter at @jdewitt29You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

Today’s episode is with Ravi Mehta, who is formerly the Chief Product Officer at Tinder, and taught product strategy as an Executive in Residence at Reforge.In today’s conversation, we dive exceptionally deep into product strategy, starting with what Ravi sees as the most common disconnect between product strategy and what product teams actually work on day-to-day. In the bulk of our discussion, we walk through the core tenants of what he calls the product strategy stack, which includes the company mission, company strategy, product strategy, product roadmap, and product goals.Next, he unpacks his alternative approach to OKRs, called NCTs. He makes the case that outlining narratives, commitments, and tasks sidesteps some of the most common headaches when it comes to OKRs, and gives suggestions for implementing NCTs within your own product teams.Strategy is often misunderstood and has come to mean all sorts of different things. What struck me about Ravi is how clearly he’s able to articulate these amorphous ideas like “mission” or “vision.” He’s also got plenty of examples from his own career at TripAdvisor and Tinder, plus his work as an advisor for other fast-growing startups.You can follow Ravi on Twitter at @ravi_mehta.You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

Today’s episode is with Arielle Jackson. For the past 7 years, she’s helped hundreds of companies build their positioning and brands from the ground up, both as our Marketing Expert in Residence here at First Round and in her own consulting work.Before helping early-stage startups, Arielle started her career in Product Marketing at Google, where she helped launch and grow Google Books and AdWords before leading marketing for Gmail. She then joined Square, where she led the launch of the Square Stand. She then headed up marketing & communications at Cover, an Android app that was acquired by Twitter.Given that she’s worked with so many companies, Arielle is a pro at spotting common patterns when it comes to early marketing, so today we spend our time digging into the challenges and missteps she’s seen so many founders run into.From category creation and company purpose, to messaging, brand personality and launch strategy, Arielle details both common pitfalls to avoid and the exercises and frameworks that she shares with founders in her consulting work.Whether it’s about not falling into the trap of focusing too much on other startup competitors, relying on emotional instead of functional benefits, or coming with unrealistic PR expectations, Arielle has tons of examples to bring these concepts to life. If you are looking to learn more, Arielle has turned the brand strategy work she does at First Round into a cohort-based course, powered by Maven. The course runs in February and applications close on Jan 28th – find out more and apply here.Additionally, here are the resources we talked about in the episodeArielle’s First Round Review articles:- Positioning Your Startup is Vital — Here’s How to Nail It- ​​Three Moves Every Startup Founder Must Make to Build a Brand That Matters- So You Think You’re Ready to Hire a Marketer? Read This First.The books on the subject that Arielle recommends:- Positioning: The Battle for Your Mind- Play Bigger: How Rebels and Innovators Create New Categories and Dominate Markets- Alchemy: The Dark Art and Curious Science of Creating Magic in Brands, Business, and Life- Predictably Irrational: The Hidden Forces That Shape Our DecisionsYou can follow Arielle on Twitter at @hiiamArielle. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.

Today’s episode is with Adrian McDermott, CTO of Zendesk.Adrian started at the company back in 2010, when they were only 50 employees. Since then, he’s led product management and engineering teams as the company has gone public and scaled to over 5000 employees.Our discussion digs into the challenges that come from scaling startups. We start off by diving into a common decision point: whether to continue with what's working or try to make a change. Adrian goes much deeper than the “what got you here won’t get you there” advice you hear all the time in startups.Next, we cover the struggle over exploring new product areas, while still continuing to make the central product brilliant, with Adrian sharing how they use the zone to win frameworks at Zendesk.Then we dive into another classic startup dilemma: whether to build or to buy. Adrian walks us through the origin stories of several Zendesk products, from the wins to the lessons learned. In addition to sharing his perspective on the role of competition in product strategy, he also offers up his definition of a truly great product.In the back half of our conversation, Adrian shares what he’s learned leading both product and engineering teams, as well as some of the go-to-market lessons he’s picked up along the way. We end on team building and recruiting. Adrian’s interviewed more than a thousand engineers, and shares more about how he’s approached hiring at the different phases of scale at Zendesk.You can follow Adrian on Twitter at @amcdermo. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson

Dharmesh Shah, co-founder and CTO of HubSpot, shares insights from his 15-year journey building the company. He emphasizes the importance of compatibility between co-founders and outlines critical conversations to ensure a successful partnership. Dharmesh discusses how he approaches feedback and culture as an engineering process, innovating even as an introvert. He also explains the organic development of company values, like transparency, and the significance of clear roles and mutual respect in fostering a productive work environment.

Today’s episode is with Zach Kitschke, CMO of Canva, an online design and publishing tool. Since launching in 2013, Canva has grown from an Australian startup to a global company, with 60 million monthly active users, over 2,000 employees, and a $40 billion valuation.Zach was one of Canva's first employees, leading comms efforts around their initial launch and fundraise. But since then, he’s done everything from answering support tickets and cooking the team lunch, to serving as a product lead and spinning up the people function. This career history gives Zach a unique vantage point on why Canva worked. The discussion starts off focused on the early days — from unpacking all the work that went into their launch, to how they improved the early product and focused on the use case for social media managers and content creators. Next, we dig into supporting and scaling the team during hypergrowth. Canva has several unique practices around onboarding, learning and development, and keeping the team connected — from vision decks, strategy docs and a specific skills framework, to their ‘chaos to clarity’ spectrum and ‘season opener’ ritual for making company planning more fun.Zach also shares what he figured out personally along the different chapters in his career at Canva, including how to leverage advisors and when to bring someone else in to take over your role. Whether you’re a marketer, a founder, a people leader, or a product manager, there are tons of helpful takeaways for everyone in this conversation.You can follow Zach on Twitter at @zachkitschke. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.

Today’s episode is with Hareem Mannan, who was a product design leader at Segment for nearly four years, and joined Twilio as a Senior Director of Product, Enablement & Design following the company’s acquisition of Segment.In today’s conversation, we deeply explore Hareem’s three pillars of what makes a great designer. To summarize, they are a product quality ambassador, serve as the glue across product areas, and intricately understand the go-to-market motion. We peel back the layers for each of these pillars to excavate why each is critical, and how folks can build up their skills in every pillar.Next, she takes us through her hiring loop and how she probes for core competencies in each of these three areas. Hareem also flags some of her own mistakes she’s learned from as a hiring manager. From there, she explains her favorite onboarding rituals, like unexpectedly pairing new designers with a solutions engineer, and crowd-sourcing a “Dear New Designer” document that’s become a huge hit on her team.We then turn our attention to her biggest lessons on leading a high-impact design org. She unpacks the aha moment that her fear of micromanaging had unintended consequences, and how she’s leveraged rituals like office hours and team bonding events to set a high bar for design quality.To learn more about the “Dear New Designer” onboarding document, visit Hareem’s Medium page: https://medium.com/segment-design/dear-new-designer-1fd006fc7390You can follow Hareem on Twitter at @hareemmannan.You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson