In Depth

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

Today’s episode is with Max Mullen, co-founder of Instacart.He started as a generalist, running everything from product to payroll, but as the company has grown over the years, he’s come to focus on one particular area: culture. Since Max is also an active angel investor, he’s also been able to partner with tons of founders and help them think about architecting their own culture at the early stages — which is exactly what we dive into in today’s episode.In the first half of our conversation, we dig into company values. Max shares both the process the Instacart team used to come up with unique values like “Every minute counts,” and his advice for making sure values actually guide behavior. He has tons of creative tactics for making employees feel more connected to them, as well as lots of helpful advice on hiring for values early on. After getting into measuring culture and better surfacing feedback from employees, we end our conversation by chatting about some of the pitfalls when it comes to culture — the mistakes that are easy for founders to make, the factions that can develop between early employees and newcomers, and the onset of politics and bureaucracy as the company gets bigger.There’s lots of great advice here on how founders can take a more deliberate role in shaping culture from the very beginning — we hope you enjoy the episode.You can follow Max on Twitter at @Max. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. If you're interested in learning more about how Cocoon makes employee leave easy, visit https://www.meetcocoon.com/

Today’s episode is with Alisa Cohn, an executive coach with nearly 20 years of experience working with companies like Etsy, Venmo, InVision, The Wirecutter, Google and IBM. Her new book, From Start-Up to Grown-Up: Grow Your Leadership to Grow Your Business, just came out this week. In our conversation today, we focus on what founders and startup leaders can learn from Alisa’s experiences as a coach. We start by getting into self-awareness, and how tough it can be for executives to get truly candid feedback. As an expert in the art of conducting 360 feedback, Alisa shares the right questions to ask, as well as tips for getting at the root of what people are actually saying in their feedback. We also dive into what to do with what you hear, from why not every piece of feedback is useful, to her tips on how to actually enact change in your day-to-day routine. Next, we tackle the most common opportunities for growth that she’s seen time and time again in her coaching practice, from communication and decision-making, to how the CEO’s own personality is often unconsciously reflected in the company culture.We wrap up by covering how to have effective conversations about layering and letting people go, as well as the reflection ritual that she recommends every founder incorporate into their daily routine.This episode will be helpful for those who are making the transition from scrappy founder to established CEO, but it’s a great listen for any startup leader who’s struggling to give away their Legos.You can follow Alisa on Twitter at @AlisaCohn. You can email us questions directly at review@firstround.com or follow us on Twitter @FirstRound and @BrettBerson.

Today’s episode is with Gretchen Howard, COO of Robinhood. Gretchen joined Robinhood in early 2019 as the company’s COO and just its second executive hire. She climbed aboard the Robinhood rocketship after 5 years building CapitalG, Alphabet’s investment fund.In today’s conversation, we dive really deep into what she’s learned about executive hiring. To start, she explains how to align the hiring profile to the trajectory of the business to make sure you’re investing in the right places. She also unpacks her hiring philosophy as it pertains to Robinhood, including balancing financial industry expertise with an innovative, hands-on mindset that’s critical for startups.Next, she walks us through the executive interview process she’s crafted at Robinhood, including the three traits that are always at the top of her wish list for candidates — including sussing out whether someone has a “knower” versus a “learner” attitude. She also explains her complicated feelings towards certain interview exercises and how she leverages reference checks. Finally, she shares her tips for successfully onboarding new executives so these hires don’t result in what she calls “organ rejection.”If you’re struggling with your executive hiring — whether it’s coming up with the right candidate profile, aligning on culture fit, or finding that your interview process doesn’t seem to be surfacing the best candidates, this conversation is a must-listen.You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettbersonLearn more about how Cocoon makes employee leave easy by visiting https://www.meetcocoon.com/

Today’s episode is with Giancarlo 'GC' Lionetti, the former CMO of Confluent and VP of Self-Serve Growth at Dropbox. (GC also previously spent 6 years at Atlassian, as a sales engineer and product marketing manager for developer tools.)He describes his career as more of a maze than a ladder, and this functional diversity combined with his deep experience at standout B2B companies gives him a unique perspective. In today’s conversation, we dig deep into why he advocates for a hybrid go-to-market strategy that brings together more traditional selling with modern product-led growth.We start by mining lessons from GC’s time at Atlassian and Dropbox, including his takes on the differences between their business models and what it takes to make a multi-product go-to-market motion work.Then we dive right into his advice for a hybrid approach, covering everything from his litmus tests for picking the right metrics, to the structure of his weekly meetings. GC explains how he sinks tons of time into understanding the customer journey, mapping out the delta between reality and the ideal vision. He also shares plenty of pro-tips about pricing, packaging, and activation, as well as a broader diagnostic framework that he’s developed to evaluate a company’s go-to-market strategy. We wrap up by focusing on team building for a hybrid go-to-market strategy — from hiring profiles to team structure.It’s a great listen for founders, product and go-to-market leaders, with tons of examples of specific impactful experiments he ran, metrics that did or didn’t work out, and common traps that he sees teams falling into. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. 

Today’s episode is with Sandr Oh Lin, founder and CEO of KiwiCo, which creates hands-on learning kits for children. Sandra started KiwiCo over ten years ago, after a career with executive positions at PayPal and eBay. She was looking for ways to give her own kids more hands-on projects to exercise their creativity, which led her down the path to become an entrepreneur and create KiwiCo. Today, KiwiCo has expanded to include 8 different lines of crates that are shipped out monthly. In the first half of today’s conversation, we excavate some of the thornier challenges that come with creating a physical product — and Sandra’s biggest aha moments as a first-time founder. She talks about creating the first KiwiCo crate, including the product development process and spinning up a supply chain and shipping department. Sandra also walks us through how KiwiCo approaches new product lines, particularly in the last year when KiwiCo demand skyrocketed. She also discusses how the team gathers quality consumer feedback when your customer is often a toddler. In the second half of our interview, she talks about some of the cultural practices at KiwiCo that all sorts of companies can learn from. Sandra’s a big believer in manager training for everyone from folks that manage just one person, to executives that have been managing for decades. She outlines the specific management training modules they leverage at KiwiCo and makes the case for having everyone at the company fill out a motivations spreadsheet. Finally, she discusses the specific tactics she leans on for creating a feedback-rich environment for herself as a CEO. You can follow Sandra on Twitter at @sandraohlin. 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 Maya Spivak, the Head of Marketing at Mux, which is ​​an API for developers to build video experiences. Maya recently joined Mux after five years at Segment, where she was the company’s second marketer and its Head of Global Brand Marketing and Communications, as well as a stint at Wealthfront as a marketing director. In today’s conversation, she takes a magnifying glass to the core components of a startup’s marketing org. She starts by breaking down the three pillars of marketing roles — product, brand, and growth. She explains the leading indicators that your startup is ready to hire folks within each of these pillars — which starts with analyzing your sales motion and sizing up the founders’ strengths and weaknesses. Next, Maya pulls back the curtain on how she architects interview loops for each of these different roles, and the unique capabilities that separate good candidates from great, must-hire folks. Finally, she reflects on her experience as one of the earliest marketing hires at Segment, and how she built the marketing org in the first couple of years to keep up with the shifting needs of the growing startup. Today’s conversation is of course a must-listen for marketers, particularly marketing leaders and hiring managers that are trying to pluck out the best and the brightest to join their org. But there’s a ton for other folks to learn from this interview, which explains some of the nuances of startup marketing you may not fully appreciate. You can follow Maya on Twitter at @papayamaya. You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson