Ashley Kramer is the CMO and CSO at GitLab, a publicly listed DevSecOps platform. Ashley took a unique path into her CMO role. She started out in software engineering before becoming a product leader, and eventually, a marketer. Most recently, Ashley was the CPO and CMO at Sisense, a data analytics company last valued at over $1b.

—

In today’s episode we discuss:

—

Where to find Brett Berson:

—

Where to find Ashley Kramer:

—

Where to find First Round Capital:

—

Referenced:

—

Timestamps:

(00:00) Intro

(02:34) Marketing in closed vs open source companies

(07:40) The role of marketing at GitLab

(09:23) The tensions of being a commercial, open source company

(12:36) Advice for nurturing community and dealing with disagreements

(15:02) GitLab's main marketing metrics

(20:26) The thinking behind GitLab’s org structure, in and around marketing

(28:19) Selling to enterprise as an open core company

(29:53) The difference between open core and open source

(30:39) Serving many different customer segments

(35:10) GitLab's planning process

(39:22) An example of GitLab’s marketing in practice

(42:12) How marketing collaborates with product

(45:55) Marketing lessons from working in an open core company

(49:46) Examples of GitLab's focus on transparency

(52:22) Why GitLab is transparent about their marketing

(54:59) 2 examples of GitLab's uniquely transparent culture

(58:35) The downsides of being a transparent company

(60:13) GitLab's meeting structure and cadence

(62:04) Benefits of having an engineering and product background as CMO

(71:09) People who made an outsized impact on Ashley's career

Colin Zima is the co-founder and CEO of Omni, a business intelligence tool that has raised over $26.9m. Prior to starting Omni, Colin was Chief Analytics Officer and VP of Product at Looker, which was acquired by Google for $2.6b. Colin was an early employee at Looker, and stood up its high-touch customer support arm, which turned into a cornerstone competitive advantage for the company.

—

In today’s episode we discuss:

—

Referenced:

—

Where to find Brett Berson:

—

Where to find Colin Zima:

—

Where to find First Round Capital:

—

Timestamps:

(00:00) Introduction

(02:30) Colin's unique entry into Looker

(04:35) How Colin talks to users

(08:20) How Colin's scope at Looker expanded

(10:53) Why and how to provide white-glove customer support

(20:25) Which companies should invest heavily in customer support?

(22:49) Hiring for and hiring from customer support

(27:40) The #1 thing for making customer support effective at scale

(29:32) The culture of customer support at Omni

(32:57) Insights on product strategy

(41:33) The role of intuition vs data in product decisions

(44:25) The merits and downsides of an intuition-driven approach to product

(48:36) Insights from hitting every goal for 24 quarters straight

(55:07) The founding story of Omni

(58:10) How Colin maintains intellectual honesty as a founder

(60:02) How Colin thinks about what to copy vs not copy from Looker

(63:25) How to pick which startup to join

(66:07) The most underrated trait in early stage startup employees

(68:11) Colin's take on founder-market-fit

(69:42] Unpopular opinion on how to hire good PMs

(72:28) The people who made an outsized impact on Colin's career

Wade Foster is the Co-founder & CEO at Zapier, a platform for building workflow automations without a developer. Zapier was started during 2011 in Columbia, Missouri, and by 2021, it was valued at $5b, having only raised $1.3m. Prior to founding Zapier, Wade had just two professional jobs, and had never managed or hired anyone. He worked as a PM on a web app used by 20k students, and as an Email Marketing Manager at Veterans United - a role that had a significant influence on Zapier’s eventual success.

In today’s episode, we discuss:

Referenced:

Where to find Brett Berson

Where to find Wade Foster

Where to find First Round Capital:

Timestamps

(05:46) The fascinating story of Veterans United

(06:55) Lessons from Veterans United

(08:35) The most important things Zapier got right

(10:13) How Zapier built their powerful distribution engine

(16:56) Why Zapier didn't move to focusing on enterprise

(19:06) How Wade thinks about product market fit

(24:26) The role of skill vs luck in Zapier's success

(26:23) What was hard about building Zapier

(30:03) Key lessons on people management

(32:35) Rule of thumb: "don't hire ‘til it hurts”

(36:42) Zapier's #1 hiring mistake

(42:50) How to test for scrappiness in the hiring process

(44:31) Do hiring playbooks transfer between companies?

(50:01) The 12 year evolution of Zapier's product

(53:20) How Zapier makes product decisions

(55:40) How Zapier thought about competition

(60:11) How to foster intellectual honesty in yourself and your org

(65:35) The people who most impacted Wade's worldviews

Laura Behrens Wu is the Founder & CEO at Shippo, a company that has raised $100m+ and was last valued at $1b in 2021. Shippo provides an API and dashboard that makes shipping easy for e-commerce businesses, marketplaces, and platforms. Prior to starting Shippo, Laura graduated from Harvard University, and was heavily influenced by a short internship at LendUp, which exposed her to Silicon Valley and startup culture. 

In today’s episode we discuss:

Referenced:

Where to find Todd Jackson:

Where to find Laura Behrens Wu:

Where to find First Round Capital:

Timestamps

(02:36) The Shippo origin story

(06:57) Why they pivoted into Shippo

(11:01) How they got their first customers

(13:27) The role of timing in Shippo's early success

(14:40) The value of being an outsider

(17:49) When founder-market-fit is and isn't necessary

(19:07) The path to product-market-fit

(22:06) What kept the Shippo team persisting

(24:41) Advice on talking to users

(29:28) Shippo's fundraising journey

(34:26) Finding product-market-fit again and again

(37:54) The 3 Horizons Framework

(45:04) Shippo's culture and early team

(49:17) Hiring people you can learn from

(50:40) Laura's most impactful hires

(52:12) Frank Slootman's "Sunday Email”

(55:43) Laura's #1 piece of advice for founders

(57:34) The most memorable influences on Laura's career

Dan Siroker is the co-founder and CEO at Rewind AI, a personalized AI powered by everything you’ve seen, said, or heard. Dan launched Rewind to an emphatic response on Twitter, and used a public pitch video to fundraise at a $350m valuation. Prior to starting Rewind, Dan co-founded Optimizely, which reached $120m ARR before being acquired by Episerver, a content management company. Dan was also the Director of Analytics for Obama’s first presidential campaign.

In today’s episode, we discuss:

Referenced:

Where to find Dan Siroker:

Where to find Todd Jackson:

Where to find First Round Capital:

Timestamps

(02:25) Rewind's origin story

(04:04) How Rewind works

(07:24) Managing scope when building Rewind

(13:47) How Dan thought about early user feedback

(17:08) Rewind's cultural mantra for shipping and validating fast

(18:35) Product positioning as a category creator

(20:39) Lessons from being a 2nd time founder

(26:11) Cultural values at Optimizely and Rewind

(28:22) How Dan defines and operationalizes Product Market Fit

(32:06) Audience segmentation

(34:32) Measuring Product Market Fit

(36:23) Dan's take on the current AI hype

(38:11) What makes a "wrapper" thin vs thick?

(39:50) Where founders should and shouldn't build within the AI ecosystem

(43:22) Trends in consumer expectations around data privacy

(46:59) What AI might look like 10 years from now

(51:09) Dan's one-of-a-kind public Twitter fundraise

(59:40) What's next for Rewind?

(61:26) The influence of Paul Graham

(62:47) Dan's #1 piece of advice

(64:23) Dan's #1 book recommendation

Sprig is an AI-powered user insights platform that has raised over $88m. Today’s discussion features two key individuals in Sprig’s journey so far: Ryan Glasgow, Sprig’s CEO and founder; and Kevin Mandich, Sprig’s Head of Machine Learning. Before Sprig, Ryan was an early PM at GraphScience, Vurb, and Weeby (all of which were acquired), and Kevin was an ML Engineer at Incubit, and a Post-Doctoral Researcher at UC San Diego.

In today’s episode, we discuss:

Referenced:

Where to find Ryan Glasgow:

Where to find Kevin Mandich:

Where to find Brett Berson:

Where to find First Round Capital:

Timestamps

(02:50) Intro

(04:57) What attracted Kevin to Sprig

(05:53) Kevin's background before Sprig

(07:56) How Ryan gained conviction about Kevin

(09:55) Key technical challenges and how they solved them

(18:46) How to overcome AI skepticism

(21:47) The early difficulties of building an ML-enabled product

(25:06) Evaluating new models and knowing when to switch

(35:09) Using Chat GPT

(37:23) Product development in the pre vs. post-LLM world

(39:53) The impact of AI hype on Sprig's product development

(45:36) Balancing AI automation with user-psychology

(48:47) Do recent LLMs reduce Sprig's competitive advantage?

(51:00) The importance of "selling the vision" to customers

(54:40) How Sprig structures teams

(57:25) How Sprig upskills all team members on AI

(60:25) 3 key tips for companies trying to navigate AI

(66:05) Major limitations with LLMs right now

(70:27) The future of AI and the future of Sprig

Saumil Mehta is the GM of Square’s flagship point-of-sale business, as well as CRM, Square Staff, and Square Online. Before Square, Saumil was the Founder and CEO of LocBox, which raised over $5.1M, and helped offline/local businesses run multi-channel marketing campaigns, all from one universal dashboard. Saumil has now been a leader at Square for 8+ years, and has overseen many complex re-orgs. These experiences have shaped Saumil into an all-round org-design expert.

In today’s episode we discuss:

Referenced:

Alyssa Henry, CEO at Square: https://www.linkedin.com/in/alyssa-henry-0905692

Saumil’s 6 key principles for effective re-orgs: https://medium.com/@saumil/avoid-the-reorg-from-hell-with-six-key-principles-f8c9cbdfb0bd

Saumil’s blog post about “Building Better Products with Escalation”: https://medium.com/swlh/well-that-escalated-quickly-building-better-products-with-escalation-feb259d733c9

Square: https://squareup.com/gb/en

Where to find Saumil Mehta:

Twitter: https://twitter.com/saumil

Linkedin: https://www.linkedin.com/in/saumilmehta1/

Blog: https://medium.com/@saumil

Where to find Brett Berson:

Twitter: https://twitter.com/brettberson

LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/

Where to find First Round Capital:

Website: https://firstround.com/

First Round Review: https://review.firstround.com/

Twitter: https://twitter.com/firstround

Youtube: https://www.youtube.com/@FirstRoundCapital

This podcast on all platforms: https://review.firstround.com/podcast

Timestamps

[00:02:22] Intro

[00:04:20] The principles of effective org design

[00:04:32] #1 Align on goals

[00:06:14] #2 Separate design considerations from human considerations

[00:08:03] #3 Define clear reasons each team exists

[00:09:21] #4 Design for durability

[00:09:49] #5 Be very intentional with comms

[00:10:14] Some stories behind the principles

[00:13:55] How to know when you need a re-org

[00:16:14] Managing inevitable tradeoffs in org design

[00:20:45] Square's "GM-led" structure

[00:23:05] Why Square centralized GTM

[00:25:39] Managing pricing and packaging across a complex org

[00:29:28] Examples of Square's written principles

[00:31:19] How Square determines what each GM owns

[00:38:35] Collaboration across GMs and products

[00:40:32] Key lessons on planning and decision-making at scale

[00:43:15] Designing incentives across a massive org

[00:49:03] Two reasons GM structures go wrong

[00:52:03] 6 Step re-org walkthrough

[00:52:37] Step 1: Triggering the re-org

[00:53:59] Step 2: Sketching a proposed org design

[00:56:17] Step 3: Checking against key criteria

[00:59:22] Step 4: Finalizing approach with leadership

[01:00:04] Step 5: Planning comms

[01:01:58] Step 6: Executing comms

[01:04:20] Signals a re-org worked vs failed

[01:07:13] 5 lessons from Alyssa Henry, CEO at Square

Kellan Elliott-McCrea is a Head of Engineering at Adobe, overseeing Frame.io, a newly acquired video review and collaboration platform. He is known for his experience and expertise as an engineering leader. He was previously a VPE at Dropbox, and CTO at Etsy where he built and led a team of 300 people, from tech and platform reboot through to IPO. Kellan also built and scaled teams at Flickr, and has a coaching and advising practice for companies looking to supercharge their engineering teams. 

In today's episode, we discuss:

Referenced:

Adobe: https://www.adobe.com

Dropbox: https://www.dropbox.com/

Flickr: https://www.flickr.com/

Frame: https://www.frame.io/

How Complex Systems Fail, by Richard I. Cook, MD: https://how.complexsystems.fail/

How Etsy Grew their Number of Female Engineers by Almost 500% in One Year https://review.firstround.com/How-Etsy-Grew-their-Number-of-Female-Engineers-by-500-in-One-Year

Where to find Kellan Elliott-McCrea:

Twitter: https://www.twitter.com/kellan

LinkedIn: https://www.linkedin.com/in/kellanem

Website: https://kellanem.com/

Personal blog: https://laughingmeme.org/

Where to find Brett Berson:

Twitter: https://twitter.com/brettberson

LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/

Timestamps:

[00:02:58] Engineering orgs now vs 15 years ago

[00:05:57] Why engineering teams are bigger despite better tools

[00:10:45] How to think about engineering productivity

[00:15:50] Questioning common compensation models

[00:19:39] Slow teams are misaligned teams

[00:23:56] How to achieve alignment in engineering teams

[00:29:12] How to co-ordinate better across teams

[00:35:23] Why so few companies successfully go multi-product

[00:38:02] Which elements of successful orgs replicate?

[00:41:53] How to approach a new org system at a new company

[00:45:48] The value of information sharing and coaching

[00:48:55] Best practices for communicating with and across teams

[00:51:05] How to approach disagreements

[00:54:27] What high-quality engineering management looks like

[00:58:37] How to increase organizational capacity

[00:63:20] Tactics and rituals for enabling effective teams

[00:66:05] How to build business literacy

[00:68:30] Kellan's biggest inspirations

Alex Kracov is the CEO and Co-Founder at Dock, and the former VP of Marketing at Lattice. Alex joined Lattice as the first marketer and third employee, and he helped to grow the business from seed to 1850+ customers. Prior to Lattice, Alex was a consultant at Blue State Digital — the team that elected President Obama and orchestrated projects at Google. Since leaving Lattice in 2021, Alex co-founded Dock, a B2B platform that has streamlined the customer buying experience for clients like Loom, Origin, and Instabug. 

In today's episode, we discuss:

Referenced:

Where to find Alex Kracov:

Twitter: https://twitter.com/kracov/

LinkedIn: https://www.linkedin.com/in/alexkracov

Website: https://www.kracov.co/

Where to find Brett Berson:

Twitter: https://twitter.com/brettberson

LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/

Timestamps:

[00:00:00] Intro

[00:02:45] The challenges and opportunities in early-stage B2B marketing

[00:05:13] How to think about short-term versus long-term marketing goals

[00:07:31] Allocating resources across marketing bets

[00:09:13] Signs your marketing is working

[00:11:20] The most underutilized marketing strategy

[00:13:03] Creating your company’s first website

[00:14:22] How Lattice formed its brand messaging and positioning

[00:18:22] Dock’s innovative approach to marketing software

[00:20:14] The first thing people should see on your website

[00:23:10] Lattice’s most successful early-stage marketing tactics

[00:28:05] Determining which marketing strategies are still relevant

[00:30:25] Lattice’s unorthodox million-dollar marketing campaign

[00:33:26] Why Alex had an outsized impact at Lattice

[00:37:05] Lessons from his first marketing hires

[00:39:41] When to scale your marketing team

[00:40:55] Building an effective early-stage marketing team

[00:42:30] A tough conversation with the CEO & Co-founder of Lattice

[00:44:46] Achieving early-stage marketing alignment

[00:46:20] Transitioning from employee to entrepreneur

[00:49:19] Getting the most out of conferences

[00:50:47] Selecting marketing channels in the early stages

[00:52:44] Hiring marketers for experience versus potential

[00:56:34] The 2023 SaaS marketing stack

[00:58:19] Advice for Zero to One marketing

[00:60:46] What successful B2B marketing looks like

Anique Drumright is the COO at Loom, a video communication tool for streamlining workflows. Loom has raised over $200M, and was last valued at $1.5B. Anique has a proven track record across product development, executive leadership, and building high-performing organizations. Before joining Loom, Anique was the VP of Product at TripActions, where she scaled the team over 8x globally, and she has also held multiple roles at Uber.

In today's episode, we discuss:

Referenced:

Where to find Anique Drumright:

Twitter: https://twitter.com/aniqued

LinkedIn: https://www.linkedin.com/in/anique-drumright-53978a1a

Where to find Brett Berson:

Twitter: https://twitter.com/brettberson

LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/

Timestamps:

[00:03:00] The similarities and differences between PM and executive leadership roles

[00:06:53] How Loom uses storytelling when launching a product

[00:10:01] Managing cross-functional scope and performance

[00:13:41] Goal-setting with functional leads

[00:16:59] The importance and difficulty of organizational alignment

[00:20:40] How Uber achieved alignment at scale

[00:24:06] Rituals for staying aligned

[00:25:23] Loom's winning one-on-one format

[00:27:49] When and how to help functional leads

[00:29:13] Hiring for roles outside your area of expertise

[00:32:55] Go-to interview questions for prospective leaders

[00:33:55] Changing the hiring process for roles outside your area of expertise

[00:36:09] Common patterns of failed external hires

[00:37:40] Common patterns of failed internal hires

[00:39:05] Avoiding over-promotion in your organization

[00:40:51] What inspires people in a company

[00:45:40] Tactics for getting honest answers in interviews

[00:47:12] Asking the right questions during reference checks

[00:51:29] A month in the life of a COO

[00:52:52] The importance of employee energy levels

[00:54:53] Loom's leadership dynamics and why it works

[00:57:30] People who had an outsized impact on Anique's career