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In Depth

Latest episodes

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Mar 31, 2022 • 58min

A crash course on comms for founders — Nairi Hourdajian’s early-stage advice from Figma & Uber

Today’s episode is with Nairi Hourdajian, the VP of Communications, Content and Community Marketing at Figma.Prior to joining Figma, Nairi was the Chief Marketing Officer at Canaan, an early-stage venture capital firm. In 2013, she became Uber’s first communications person and spent the next 3 years building out the function. Before getting into tech, Nairi came from the world of politics. She was a VP at Glover Park Group, a communications consulting firm started by former Clinton officials, and she also served as a policy director for the Democratic Senatorial Campaign Committee and as a staff assistant to then-Senator Joe Biden.Our conversation focuses on what a great communications strategy looks like at early-stage startups. Nairi breaks down the basics for founders who aren’t familiar with this function, and shares advice for thinking beyond just announcing your Series A funding. She shares lots of thoughts on crafting foundational messaging for different audiences and shaping the company narrative — with examples from both Uber and Figma, as well as startups she’s advised.Next, we get into the nuts and bolts of building relationships with reporters. Nairi shares her take on handling negative stories about your competitors, and offers tons of tactical pointers on how to prepare for a media interview.We ended on her advice for assembling the team that can help you shape and execute on your comms strategy — from working with agencies and freelancers, to making your first full-time comms hire.You can follow Nairi on Twitter at @NairiHourdaj. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.
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Mar 17, 2022 • 1h 5min

How founders can get executive hiring right from startup to scale — advice from Lattice’s Jack Altman

Today’s episode is with Jack Altman, co-founder & CEO of Lattice. There were so many topics we could have gotten into with Jack as it relates to scaling as a founder and CEO, but we decided to dive deep on executive hiring, a huge challenge for founders. The conversation starts with how the hiring profile for executives changes as the company grows. Jack is a strong believer that you should focus on hiring someone who’s a great fit for the next 18-24 months, not the next 5 or 10 years. (Here's the blog post he mentioned about the different stages a CEO faces.)He also talks about the traps of hiring “too big,” whether that’s over indexing on BigCo experience, or focusing on seniority and titles that don’t match your startup’s current challenges. Instead, Jack shares more about why founders should focus on getting good at assessing and taking a chance on more junior, undiscovered talent. Next, we dig deep into his end-to-end hiring process, from how he sources folks and what he asks in interviews, to why he sometimes does references on a candidates’ references. Whether it’s diving into how a leader might build out their team, or the red flags that signal that an executive candidate doesn’t have an ownership mentality, Jack shares tons of tactical pointers.We also get into where executive hiring errors come from, as well as the leading performance indicators to look for and what to do when a new executive leader doesn’t work out. We end by chatting about promoting internally versus hiring externally, and why you should think about your executive team like you’re constructing a portfolio.You can follow Jack on Twitter at @jaltma. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.
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Mar 10, 2022 • 57min

IC? Manager? Technical Founder? How to chart your engineering career path — Stripe & Cocoon’s Amber Feng

Today’s episode is with Amber Feng, who is the co-founder and CTO of Cocoon, and was previously an engineering leader at Stripe for eight years.In today’s conversation, we pull on threads from Amber’s engineering career to weave together lessons for other engineers charting their own path. Although Amber’s spent the majority of her career at Stripe, she’s had all sorts of different experiences — from individual contributor, to engineering manager, to heading up entire orgs, and then back to individual contributor again. We begin by discussing the unexpected traits that differentiate the most high-achieving engineers up and down the org chart.We also get into the debate that most engineers face during their career — whether to hone your craft and become an expert IC, or go the management route. Amber’s gone back and forth between the two, and shares the advice she gives to other folks who are considering where their strengths may be best leveraged.Finally, we turn the page to the most recent chapter in her career journey — becoming a first-time founder. She shares the lessons from Stripe’s Patrick Collison that she’s applying to her own company Cocoon and shares words of wisdom for other engineers with interest in starting their own company from 0 to 1.You can follow Amber on Twitter at @amfengYou can read the First Round Review article Amber mentioned with the co-founder questionnaire here: https://review.firstround.com/the-founder-dating-playbook-heres-the-process-i-used-to-find-my-co-founderYou can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson
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Mar 3, 2022 • 1h 6min

Never done sales before? Meka Asonye shares GTM playbooks from Stripe, Mixpanel, and backing founders at First Round

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.
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Feb 10, 2022 • 1h 1min

The startup playbook for expanding internationally — Advice from Faire CEO Max Rhodes

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.
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Jan 27, 2022 • 50min

Usage-based? Hybrid? Tiered? Which pricing model is right for you? — Stripe’s Jeanne DeWitt Grosser

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
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Jan 20, 2022 • 1h 3min

The Product Strategy Playbook that Powered Growth at Tinder & TripAdvisor — Ravi Mehta

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
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Jan 13, 2022 • 1h 25min

After building hundreds of startup brands, Arielle Jackson shares 6 early marketing missteps to avoid

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.
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Dec 9, 2021 • 60min

Buy or build? Focus on the core product or innovate? Zendesk CTO Adrian McDermott's advice for scaling

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
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Dec 2, 2021 • 54min

The biggest lessons from building Hubspot, from co-founder harmony to engineering the culture — Dharmesh Shah

Today’s episode is with Dharmesh Shah, the co-founder and CTO of Hubspot. In today’s conversation, we deeply explore some of the marquee moments along the 15-year journey building Hubspot. To start, Dharmesh unpacks the very specific way he and his co-founder Brian Halligan approached evaluating their compatibility as co-founders. He’s got tons of advice for other potential founding pairs to increase the likelihood of success and smoother sailing.Next, he points to some of the foundational building blocks that keep him jazzed about his role at Hubspot still to this day, including the way he elicits feedback through “bug reports.” He also explains the reasoning behind his decision to never take on any direct reports and remain an individual contributor as a co-founder.Finally, Dharmesh tells the story about how he came to own culture at Hubspot, even as the self-described least social person at the company. He walks us through how he approached culture as an engineering exercise, which continues today in his assessment of the culture as a product.You can follow Dharmesh on Twitter at @dharmesh.

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