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

Noah Desai Weiss is the Chief Product Officer of Slack, and has an accomplished track record inside and outside of the company. He started Slack’s Search, Learning, and Intelligence division, led the Self-Service (SMB) Business, and led the Expansion and Virtual HQ product areas (responsible for Huddles, Clips, and more). Before joining Slack, Noah was the SVP of Product Management at Foursquare (raised over $390m), and was a Product Manager at Google.

In today's episode, we discuss:

Curious to learn more about Slack? You can try Slack Pro and get 50% off using this link.

Referenced:

Creative Selection - Inside Apple's Design Process During the Golden Age of Steve Jobs: https://www.amazon.com/Creative-Selection-Inside-Apples-Process/dp/1250194466

Salesforce acquires Slack: https://slack.com/blog/news/salesforce-completes-acquisition-of-slack

Thinking in Bets - Making Smarter Decisions When You Don't Have All the Facts: https://www.amazon.com/Thinking-Bets-Making-Smarter-Decisions-ebook/dp/B074DG9LQF

Where to find Noah Weiss:

Twitter: https://twitter.com/noah_weiss

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

Where to find Brett Berson:

Twitter: https://twitter.com/brettberson

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

Timestamps:

[2:46] Not all decisions should be data-driven

[3:46] When to use data vs intuition to drive decisions

[9:15] Taste and judgment are learnable

[11:47] How Slack scales intuition across their product org

[14:58] Challenges of intuition-led product building

[16:43] Matching people to data vs intuition-driven work

[19:19] underrated qualities for remote workers

[21:34] What's special about Slack's approach to product?

[23:33] Which products should focus on end-users versus executives

[26:38] What Slack learns from Salesforce

[31:44] Pricing lessons from Salesforce and Marc Andreessen

[34:10] How Slack runs product reviews

[37:02] What creates good vibes in a product team

[40:17] Managing pace vs accuracy in decision-making

[46:29] Rituals for good decision-making

[50:20] Balancing "big swings" with incremental improvements

[55:30] Slack's biggest philosophy change

[60:05] Slack's humility and why it matters

[61:43] Advice for thinking about product-led vs sales-led growth

[01:08:14] How to build product with a product-focussed founder

[01:12:46] People who made an outsized impact on Noah's career

Jack Altman is the co-founder and CEO of Lattice, a people success platform for building engaged, high-performing teams. Lattice has raised over $330M, and was last valued at $3B. He is an expert in building company culture, and wrote a book on the topic, titled: “People Strategy”.

In today's episode, we discuss:

Referenced:

Jack’s book: https://www.amazon.com/People-Strategy-Culture-Competitive-Advantage/dp/1119717043

Jack’s company, Lattice: https://lattice.com/

First Round Capital's Newsletter: https://review.firstround.com/newsletter

Where to find Jack Altman:

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

Twitter: https://twitter.com/jaltma

Where to find Brett Berson:

Twitter: https://twitter.com/brettberson

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

In this episode, we cover:

(2:40) Founders must continually grow with their company

(7:23) How to identify hiring errors vs management errors

(9:46) Managing the tension of delegation vs control

(11:51) How to cultivate self-awareness

(14:59) The one thing founders should never give up

(17:22) How to build a product org

(19:06) Hot take on micro-management

(21:05) The importance of context setting as CEO

(22:09) What founder transparency actually means

(23:43) Examples of “context setting” as a leader

(26:09) The value of uncomfortable conversations

(27:16) How to have uncomfortable conversations

(28:30) Founders must own their most difficult decisions

(31:48) Optimizing speed vs accuracy in decision-making

(33:50) The hidden biases in group discussions

(35:05) When Jack experimented with removing himself from all meetings

(37:48) The most unusual element of Jack’s leadership approach

(38:34) 4 pieces of advice for CEOs

(41:20) How to talk to customers

(42:59) The many sources of learning for CEOs

(46:45) Instructive framework for maximizing employee performance

(49:56) When long-time employees don’t scale with the company

(55:07) How to think about low-performing but “well-liked” employees

(58:19) Identifying team members that “aren’t a fit”

(59:57) Should you tell people why someone was let go?

(62:42) Managing in the challenging new economic environment

(68:18) Aligning an employee’s career goals with company goals

(74:27) You're probably underestimating your team's potential

Tara Seshan is the Head of Product at Watershed, a climate platform that companies use to measure, report, and reduce their carbon emissions. Before joining Watershed, Tara was Head of Product at Stripe throughout the launch of Stripe Billing and Stripe Treasury. As a Thiel Fellow and experienced multi-product builder, Tara brings a wealth of experience with 0-1 SaaS products.

In today's episode, we discuss:

Referenced:

Companies Referenced:

People Referenced:

Where to find Tara Seshan:

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

Twitter: https://twitter.com/tarstarr

Where to find Brett Berson:

Twitter: https://twitter.com/brettberson?lang=en

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

In this episode, we cover:

(0:00) Intro

(3:55) How Stripe navigated the path from single to multi-product

(6:00) How to allocate resources across a primary product and secondary bets

(7:46) How to launch products using small teams

(12:25) What makes a great early-stage product thinker

(13:08) Key indicators for spotting early-stage product talent

(16:33) A common fail-case when hiring for potential over experience

(18:32) 5 interview questions to unearth hidden talent among product candidates

(20:35) What Stripe got wrong when it first launched Billing

(26:00) How Stripe adapted to new buyer profiles

(28:50) Why new product teams should be treated like a startup within a company

(30:35) The importance of “definite optimism”

(31:44) How Watershed prioritizes new products in an early market

(33:53) The methodical versus analytical approach to picking new products

(40:08) Setting goals and evaluating new product bets

(41:55) How Tara runs new-product reviews

(42:10) “The Enterprise Rent-A-Car Story” and why it matters

(43:56) The 12 questions Tara asks in product reviews

(46:17) How to use product review questions pre-meeting

(46:34) The rationale behind Tara’s 12 questions

(48:13) How Tara re-focusses the questions when building products for net-new-customers

(49:43) How to collect and leverage user feedback when building new products

(51:58) Why product development must start with problem validation

(53:52) Two people who had an outsized impact on how Tara thinks about product

(54:50) Outro

Our guest today is Melissa Tan, GM of Self-Service and Head of Growth at Webflow and formerly Head of Growth and Monetization for Dropbox Business.

In today’s conversation, she unpacks the nuances between the two PLG businesses and how growth strategy changes for a more complex product like Webflow, including: 

You can email us questions directly at [email protected] or follow us on Twitter @firstround and @brettberson.