Rippling

Matt MacInnis is the chief product officer and former longtime COO at Rippling, a unified workforce management platform valued at over $16 billion. We discuss: 1. Why “extraordinary results demand extraordinary efforts” 2. Why you should deliberately understaff projects, and how to know when you’ve gone too far 3. Matt’s transition from COO to CPO and what surprised him about leading product 4. The “high alpha, low beta” framework for evaluating people, processes, and products 5. When founders should quit their startups (hint: much earlier than VCs want you to) 6. How to fight entropy in your organization through relentless energy and intensity — Brought to you by: Google Gemini—Your everyday AI assistant: https://ai.dev/ Datadog—Now home to Eppo, the leading experimentation and feature flagging platform: https://www.datadoghq.com/lenny GoFundMe Giving Funds—Make year-end giving easy: http://gofundme.com/lenny — Transcript: https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths — My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/181916584/my-biggest-takeaways-from-this-conversation — Where to find Matt MacInnis: • X: https://x.com/stanine • LinkedIn: https://www.linkedin.com/in/macinnis • Email: macinnis@rippling.com — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Matt MacInnis and Rippling (04:38) The importance of extraordinary efforts (08:37) The challenges and rewards of relentless effort (10:11) Your job as a leader is to preserve intensity (12:39) You learn far more from success than failure (16:34) Transitioning to chief product officer (19:54) Fixing product management at Rippling (25:27) The “high alpha, low beta” framework (28:55) The PQL framework (35:16) Hiring frameworks and team dynamics (36:52) A helpful interview tactic (40:00) Leading as a COO vs. a CPO (42:34) The reality of product-market fit (46:38) The problem with venture capital (49:29) When founders should quit their startups (41:48) The immutable market (54:13) Lessons from Notion’s success (57:43) Investment strategies and narrative violations (01:00:42) The power of compounding, power law, and entropy (01:07:02) Maintaining intensity and fighting entropy (01:11:33) The importance of feedback and escalations (01:14:31) Rippling’s vision and success (01:17:48) AI’s impact on SaaS and business software (01:23:42) AI corner (01:26:23) Final thoughts and lightning round — Referenced: • Rippling: https://www.rippling.com • Sunil Raman on LinkedIn: https://www.linkedin.com/in/sunilraman • Dan Gill on LinkedIn: https://www.linkedin.com/in/dangill • Carvana: https://www.carvana.com • Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach • Parker Conrad on LinkedIn: https://www.linkedin.com/in/parkerconrad • Inkling: https://www.inkling.com • Akshay Kothari on LinkedIn: https://www.linkedin.com/in/akothari • Notion: https://www.notion.com • Conway’s law: https://en.wikipedia.org/wiki/Conway%27s_law • Seeking Alpha: https://seekingalpha.com • Dennis Rodman’s website: https://dennisrodman.com • Dancing pickle emoji: https://slackmojis.com/emojis/456-dancing_pickle • Pickle Rick: https://en.wikipedia.org/wiki/Pickle_Rick • SPOTAK: The Six Traits I Look for When I’m Hiring: https://finance.yahoo.com/news/spotak-six-traits-look-m-181335267.html • Geoff Lewis on LinkedIn: https://www.linkedin.com/in/geofflewis1 • Zenefits: https://en.wikipedia.org/wiki/TriNet_Zenefits • New banking records prove Deel paid thief who stole trade secrets from Rippling: https://www.rippling.com/blog/new-banking-records-prove-deel-paid-thief-who-stole-trade-secrets-from-rippling • Workday: https://www.workday.com • Matic robots: https://maticrobots.com • Wall-E: https://www.imdb.com/title/tt0910970 • Conviction: https://www.conviction.com • Mike Vernal on X: https://x.com/mvernal • Sarah Guo on X: https://x.com/saranormous • No Priors: https://linktr.ee/nopriors • Gemini: https://gemini.google.com • ChatGPT: https://chatgpt.com • Claude: https://claude.ai • Bryan Schreier on LinkedIn: https://www.linkedin.com/in/bryanschreier • Heated Rivalry on HBO Max: https://www.hbomax.com/shows/heated-rivalry/50cd4e99-04ee-427b-a3b4-da721ed05d9c • Fellow coffee maker: https://fellowproducts.com/products/aiden-precision-coffee-maker — Recommended books: • Pale Blue Dot: A Vision of the Human Future in Space: https://www.amazon.com/Pale-Blue-Dot-Vision-Future/dp/0345376595 • Conscious Business: How to Build Value Through Values: https://www.amazon.com/Conscious-Business-Build-through-Values/dp/1622032020 • Thinking in Systems: https://www.amazon.com/Thinking-Systems-Donella-H-Meadows/dp/1603580557 • The Effective Executive: The Definitive Guide to Getting the Right Things Done: https://www.amazon.com/Effective-Executive-Definitive-Harperbusiness-Essentials/dp/0060833459 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Matt MacInnis

COO

RipplingInkling

As a three-time founder, Parker Conrad has one piece of advice for aspiring entrepreneurs—don’t do it. The Rippling co-founder and CEO joins Sarah Guo to talk about what he learned from the crash at Zenefits, why most advice to founders is wrong, and how building a real platform—not a point solution—is the only way to win in SaaS. The two get into founder psychology, the myth of learning from failure, and what true ownership looks like inside a company. He also shares why AI won’t shrink teams anytime soon, what people misunderstand about vertical software, and why ambition trumps efficiency with long-lasting companies. Sign up for new podcasts every week. Email feedback to show@no-priors.com Follow us on Twitter: @NoPriorsPod | @Saranormous | @parkerconrad Chapters: 00:00 Introduction to Parker Conrad 00:33 Lessons from Zenefits to Rippling 01:54 The Psychology of Founding a Company 07:56 Rippling's Ambitious Vision 10:41 Building a Platform Company 15:05 Challenges and Strategies in Scaling 30:36 AI's Impact on Software Development 42:06 Public vs. Private: Rippling's Future 44:19 Conclusion

Parker Conrad

Co-founder & CEO

Rippling

Matt Plank is Rippling's Chief Revenue Officer where he oversees all Sales and Account Management functions in the US and Internationally. Matt joined Rippling in the very early days when Parker Conrad (founder) was building V1 in a basement with $0 in revenue. Today the company is a market leader with 100s of $Ms in ARR. Prior to Rippling, Matt was a Sales Director @ Zenefits where he helped the company scale to $70M in ARR. In Today's Show with Matt Plank We Discuss: 08:25 Challenges and Strategies in Outbound Sales 10:29 Building Effective Sales and Marketing Partnerships 13:37 Founders and Sales Playbooks: Who Should Create Them? 20:45 Pricing Strategies and Customer Success 24:43 Discounting and Urgency in Sales 33:57 Building Relationships for Successful Deals 34:22 Effective Deal Reviews: Asking the Right Questions 35:30 Pipeline Reviews: Frequency and Participants 35:59 Handling Deal Slippage: Acceptable vs. Non-Acceptable Reasons 39:17 Maintaining Morale in Volatile Times 42:14 Outbound Sales Strategy: Lessons Learned 46:03 Scaling Sales Teams: Hiring and Promoting 47:15 Challenges and Strategies in International Markets 01:00:45 Signs of Scaling Issues in Sales Leadership

Matt Plank

Chief Revenue Officer

Rippling

Guest: Matt MacInnis, COO of Rippling One of the most important things a non-founder can do, says Rippling COO Matt MacInnis, is to learn how to operate in the context of the company they’re joining. His CEO, Parker Conrad, “spikes” in certain skill areas, and the rest of the executive team needs to maximize his ability to thrive while “taking care of the rest of it.” Matt likened the work to being a hobbyist airplane pilot, who can’t get a license without knowing all the minute details about their plane’s engine and aerodynamics.  “You can’t be a good pilot if you don’t understand the engine, because if something goes wrong, you want to be able to troubleshoot it,” he says. “An executive coming in to fly your airplane better learn the engine.” Chapters: (01:08) - Telling Rippling’s story (04:27) - Founding & failing at Inkling (09:30) - Different types of hard (13:55) - Discipline and stamina (15:22) - Meeting with Steve Jobs (19:20) - Definitely, give up! (22:29) - Product-market fit (27:15) - Founders and culture (33:24) - Executive instincts (36:06) - Talent Signal and AI (40:06) - 150 former founders (44:08) - Zero to one projects (48:06) - The failure of Silicon Valley Bank (55:25) - Routines and discipline (59:37) - Disagreeing with Parker (01:02:25) - Who Rippling is hiring (01:03:37) - What “grit” means to Matt Mentioned in this episode: Parker Conrad, London Breed, Apple, Sequoia Capital, Sapphire Ventures, Tenaya Capital, digital textbooks on iPad, Oricom, Netscape, Peter Cho, Eddy Cue, John Couch, iBooks, Slack, Airbnb, Paul Graham, Brian Chesky, “founder mode,” Larry Ellison, Ivan Zhao and Notion, Intel and ARM, Salesforce, United Airlines, LLMs, GitHub, DocuCharm, Peter Thiel, Mamoon Hamid, Expensify, Navan, Costco, Comcast, HBO’s Silicon Valley, Jensen Huang and NVIDIA, and Taylor Swift. Links: Connect with Matt LinkedIn Twitter Connect with Joubin Twitter LinkedIn Email: grit@kleinerperkins.com  Learn more about Kleiner Perkins This episode was edited by Eric Johnson from LightningPod.fm

Matt MacInnis

COO

RipplingInkling

HR software is big, big business. And no one understands that better than Parker Conrad the CEO and co-founder of Rippling, a global HR company that offers global payroll, onboarding, time tracking, benefits management and more. This week, Equity is bringing you an episode of our sister show, Found. The Found crew talk with Conrad about what goes into building a leading HR tech company—from what it’s like building out features companies love, to dealing with fierce competition in this ever growing landscape. Conrad also gets into the power imbalance that can arise between VCs and founders and the drama at his previous company that inspired him to build Rippling.  Found posts every Tuesday. Subscribe on Apple, Spotify or wherever you listen to podcasts to be alerted when new episodes drop. Check out the other TechCrunch podcast: Equity . Subscribe to Found to hear more stories from founders each week. Credits: Equity is produced by Theresa Loconsolo with editing by Kell. Bryce Durbin is our Illustrator. We'd also like to thank the audience development team and Henry Pickavet, who manages TechCrunch audio products. Learn more about your ad choices. Visit megaphone.fm/adchoices

Parker Conrad

Co-founder & CEO

Rippling

SaaStr 760: CRO Confidential: Rippling's Top 3 Growth Tactics for Driving Revenue at Scale with Rippling CRO Matt Plank and Former CRO at Brex Sam Blond At this year's SaaStr Annual, Rippling's CRO, Matt Plank, chats with Sam Blond, host of the SaaStr CRO Confidential and former CRO at Brex, about Rippling's top 3 growth tactics, which have led to the Rippling becoming a $14B company with several hundred million of ARR. A few years ago, Matt was making cold calls from CEO Parker Conrad's basement, and he's helped bring Rippling to where it is today. The three growth tactics that worked for Rippling can be categorized into three different stages: Outbound Increasing closed-won revenue rates Serving customers and expanding revenue in the base -------------------------------------------------------------------------------------------- SaaStr hosts the largest SaaS community events on the planet. Join us in 2025 at: SaaStr Annual: May. 13-15 in the SF Bay Area. Join 12,500 SaaS professionals, CEOs, revenue leaders and investors for the world's LARGEST SaaS community event of the year. Get your early bird tickets TODAY. -------------------------------------------------------------------------------------------- This episode is sponsored by: Pendo This episode is sponsored by our good friends at Pendo the all-in-one product experience platform. Pendo brings together product analytics. Guides discovery and replay. So you can improve your product experiences for every customer and employee try Pendo for free at Pendo.io/saastr. -------------------------------------------------------------------------------------------- This episode is sponsored by: remote.com Ready to expand into new markets with confidence? Remote's comprehensive HR suite propels your growth from the ground up. From setting up new entities and managing intellectual property, to overseeing contractor compliance Remote makes scaling effortless.With their platform and partnership, your business grows not just bigger, but smarter. Transform your growth today with remote at Remote.com.

Matt Plank

Chief Revenue Officer

Rippling

In this episode of No Priors, Sarah and Elad sit down with Matt MacInnis, COO of Rippling, to discuss the company’s unique product strategy and the advantages of being a compound startup. Matt introduces Talent Signal, Rippling’s AI-powered employee performance tool, and explains how early adopters are using it to gain a competitive edge. They explore Rippling’s approach to choosing which AI products to build and how they plan to leverage their rich data sources. The conversation also delves into how AI shapes real-world decision-making and how to realistically integrate these tools into organizational workflows. Sign up for new podcasts every week. Email feedback to show@no-priors.com Follow us on Twitter: @NoPriorsPod | @Saranormous | @EladGil | @Stanine Show Notes:  0:00 Introduction 0:32 Rippling’s mission and product offerings 2:13 Compound startups 3:53 Evaluating human performance with Talent Signal  13:19 Incorporating AI evaluations into decision-making at Rippling 14:56 Leveraging work outputs as inputs for models 18:23 How Rippling chose which AI product to build first 20:53 Building out bundled products 23:26 Merging and scaling diverse data sources 25:16 Early adopters and integrating AI into decision-making processes

Matt MacInnis

COO

RipplingInkling

Parker Conrad has spent the last 8 years building Rippling into a $13B company, marking his redemption after being ousted from Zenefits. In his second appearance on the podcast, Parker and I discussed Paul Graham's "founder mode" essay and how he operationalizes it at Rippling. He also reflected on the key lessons he's learned throughout his career, highlighting the differences in how he ran Zenefits compared to Rippling today. Additionally, Parker shared his candid views on the challenges of having investors as board members and why he believes much of VC "value add" is overrated. (00:00) Intro (01:31) Parker's Leadership Principles at Rippling (02:16) The Importance of Anecdotal Evidence (04:09) Balancing Founder Mode and Team Collaboration (05:08) The Risks of Over-Extrapolating Founder Mode (06:56) The Reality of Sales Compensation (08:15) Hiring Founders for New Products (11:10) The Pace of Execution in a Company (11:21) The 'C on a Box' Dilemma (12:07) The Speed vs. Quality Debate (13:56) The Viral Tweet Incident (16:51) Governance and Board Dynamics (20:04) Choosing the Right Investors (29:57) The Role of Career VCs as Board Members (33:43) Misaligned Incentives Between Founders and Investors (35:43) Navigating Business Challenges (36:27) Sam Altman's Crucial Support (38:45) The Role of Venture Capitalists (40:06) The Value of Y Combinator (43:16) Fundraising and Valuations (01:00:39) Lessons from Past Ventures (01:06:05) Building Compound Software (01:09:33) The Future of Compound Software Businesses (01:10:04) Microsoft's Unassailable Approach (01:10:40) Building Narrow vs. Compound Software (01:12:16) Investment Decisions in New vs. Existing Products (01:14:42) Platform Development and Resource Allocation (01:16:32) The Journey from Chem Major to Software Visionary (01:18:34) Challenges and Strategies in Multi-Product R&D (01:25:32) Improving Customer Support Metrics (01:28:50) The Role of a Founder in Product Management (01:31:23) Hiring and Cultivating Executive Talent (01:39:07) The Motivation Behind Rippling's Success (01:41:58) Conclusion and Final Thoughts Executive Producer: Rashad Assir Producer: Leah Clapper Mixing and editing: Justin Hrabovsky Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA 🎥 Subscribe on YouTube: https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=1 Follow on Socials 📸 Instagram - https://www.instagram.com/theloganbartlettshow 📱 X - https://twitter.com/loganbartshow 🎬 Clips on TikTok - https://www.tiktok.com/@theloganbartlettshow About the Show Logan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode of The Logan Bartlett Show, we sit down with the people behind today’s most important startups and extract the tactics, lessons, and frameworks they’ve learned the hard way. Conversations span hiring to GTM, product, growth, fundraising and everything in between - collectively forming the ultimate playbook to make you a better CEO, investor or board member. Tap follow and enable notifications to stay ahead of the game.

Parker Conrad

Co-founder & CEO

Rippling

Ashley Kelly is the VP of Global Sales Development at Rippling, the all-in-one platform for HR, IT, and finance. Before Rippling, Ashley played a crucial role in scaling Brex's outbound sales from $2M to over $300M in ARR, and has hired over 800 SDRs during her time in some of the best tech companies in Silicon Valley, including Lever and Zenefits. In Today's Episode with Ashley Kelly We Discuss: From NASCAR to Silicon Valley SDR How did Ashley make her way into the world of sales? Why does Ashley think the best AEs and leaders start off as SDRs? What is Ashley's advice to new SDRs starting their jobs today? Age of AI: Is SDR Outbound Dead? Does Ashley agree that outbound is dead today? Is SDR dead? How will AI change SDR? Why is Ashley hesitant to adopt AI? Why does Ashley think founders should always build the first sales playbook? What did Ashley mean by SDR is the 3rd pillar between sales and marketing? What does Ashley think most companies get wrong about outbound? SDR Hiring: Who, What, When & How When does Ashley think founders should hire their first SDR? How does Ashley structure the hiring process? What questions does she ask? What profile does Ashley look for when hiring for an SDR? How does Ashley structure the finance package? How is it different for each team? Why did Ashley avoid hiring SDRs with SDR experience? Why has she changed her mind? What was Ashley's biggest hiring mistake? What were her takeaways? Onboarding New SDR Hires How does Ashley onboard new SDR hires? What is her onboarding timeline? How does Ashley set targets for new hires? When should they be fully productive? When does Ashley know if a new hire isn't working? What are common traits among Ashley's most successful hires?

Ashley Kelly

VP of Global Sales Development

Rippling

In this memorable episode from our podcast archives, we revisit our conversation with Parker Conrad, Co-Founder of Rippling and former CEO of Zenefits. Parker opens up about his entrepreneurial path, detailing everything from fundraising challenges to his departure from Zenefits and the founding of Rippling. We also discuss the dynamics between VCs and founders, including what founders really value from investors, as well as the many entrepreneurial lessons Parker has gained from growing four companies (including two that reached unicorn status). This episode was originally aired in May 2022. (00:00) Intro (01:25) Parker's Early Life and Education (02:08) Parker's Experience at Harvard and Early Career (05:21) Parker's Journey to Entrepreneurship (08:27) The Founding of Sigfig and Challenges Faced (10:15) The Birth of Zenefits and its Rapid Growth (13:13) The Downfall of Zenefits and Lessons Learned (19:12) Parker's Perspective on Media Narratives and VC Involvement (35:48) The Power of Investors and Branding (37:22) The Influence of Media on Investment Success (38:42) The Role of Venture Capitalists and Founders (39:39) The Impact of Social Media on Business (40:48) The Rise of Andreessen Horowitz (41:18) Introducing Rippling: A New Approach to Business Software (41:32) The Power of Employee Data in Business Software (49:47) The Advantages of Compound Companies (56:13) The Role of Founders in Business Units (01:09:20) The State of San Francisco and the Tech Industry Executive Producer: Rashad Assir Producer: Leah Clapper Mixing and editing: Justin Hrabovsky Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA 🎥 Subscribe on YouTube: https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=1 Follow on Socials 📸 Instagram - https://www.instagram.com/theloganbartlettshow 📱 X - https://twitter.com/loganbartshow 🎬 Clips on TikTok - https://www.tiktok.com/@theloganbartlettshow About the Show Logan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode of The Logan Bartlett Show, we sit down with the people behind today’s most important startups and extract the tactics, lessons, and frameworks they’ve learned the hard way. Conversations span hiring to GTM, product, growth, fundraising and everything in between - collectively forming the ultimate playbook to make you a better CEO, investor or board member. Tap follow and enable notifications to stay ahead of the game.

Parker Conrad

Co-founder & CEO

Rippling

SaaStr 714: From Zero to Hero: How to Dominate Outbound SaaS Sales with Rippling and Founders Fund on CRO Confidential. Hosted by Sam Blond, Partner at Founders Fund. With Ashley Kelly, VP of Global Sales Development at Rippling. In the latest episode of SaaStr's CRO Confidential series, host Sam Blond, partner at Founders Fund and former CRO at Brex, sits down with Ashley Kelly, VP of Global Sales Development at Rippling. For context - Ashley had previously helped Sam scale Brex's outbound sales from $2M to over $300M in ARR as Senior Director of SDR. Together they discuss: Scaling outbound sales and SDRS (sales development representatives) from 0 to $100M and beyond How to hire the right outbound sales team The SDR interview checklist How to create an environment to set up outbound sales reps for success Which KPIs to measure and matter most in outbound SaaS sales Increasing the quality and closed-won revenue with your outbound sales team Listen now! -------------- SaaStr hosts the largest SaaS community events on the planet. Join us in 2024 at: SaaStr Annual: Sept. 10-12 in the SF Bay Area. Join 12,500 SaaS professionals, CEOs, revenue leaders and investors for the world's LARGEST SaaS community event of the year. Podcast listeners can grab a discount on tickets here: https://www.saastrannual2024.com/buy-tickets?promo=fave20 SaaStr Europa: June 5-6 in London. We'll be hosting the 5th SaaStr Europa in London for two days of content and networking. Join 3,000 SaaS and Cloud leaders. Podcast listeners can grab a discount on Europa tickets here: https://www.saastreuropa2024.com/buy-tickets?promo=fave200 -------------- This episode is sponsored by: Northwest Registered Agent When starting your business, it's important to use a service that will actually help you. Northwest Registered Agent is that service. They'll form your company fast, give you the documents you need to open a business bank account, and even provide you with mail scanning and a business address to keep your personal privacy intact. Visit https://www.northwestregisteredagent.com/saastr to get a 60 percent discount on your next LLC.

Ashley Kelly

VP of Global Sales Development

Rippling

Guests: Parker Conrad, CEO of Rippling, and Mamoon Hamid, partner at Kleiner Perkins How long did it take for Parker Conrad to stop wanting revenge? “I’ll let you know when it switches over,” the Rippling CEO and co-founder jokes. He resigned from his last company, the buzzy HR unicorn Zenefits, in 2016 and then quickly realized that the company’s new leaders would never return it to its former glory. He still loved the problems he had been trying to solve, and launched Rippling because “there was an opportunity there, [and] if it works ... it’s going to be fundamentally and foundationally better as a product.” It worked. As of March, Rippling has been valued at more than $11 billion, more than double Zenefits’ peak. In this episode, Parker, Mamoon, and Joubin discuss what happened at Zenefits, avoiding press coverage, FOMO and expectations, Paul Graham, fixing corporate insurance, Ryan Peterson’s “revenge portfolio,” CEO coaches, Mike Vernal, approving expenses, anecdata, and the Costco of SaaS.  In this episode, we cover: How Parker and Mamoon met (00:56) The Zenefits Series B (06:29)  “Stuck in a nightmare” (09:20)  Entrepreneurship is “soul-destroying” (12:46)  Parker’s first company, SigFig (17:17)  Starting a company for the right reasons (21:02)  Starting over after Zenefits (27:06)  Avenging Zenefits (31:57)  Rippling’s unusual Series A (38:40)  What it does well (43:13)  “Go and see” (46:35)  The compound startup (51:44) Who Rippling is hiring and what “grit” means to Parker (01:00:39)  Links: Connect with ParkerTwitter LinkedIn Connect with JoubinTwitter LinkedIn Email: grit@kleinerperkins.com  Learn more about Kleiner Perkins This episode was edited by Eric Johnson from LightningPod.fm

Parker Conrad

Co-founder & CEO

Rippling

Mamoon Hamid

Partner

Kleiner PerkinsSocial Capital

The First Rule You Know About Building Software is Wrong. Discover why with Rippling CEO and Co-Founder, Parker Conrad, and Sam Blond, Partner at Founders Fund. In this session, Parker will explain step-by-step his theory of the compound startup and how it can help you scale your SaaS company. ***** Shipping projects doesn't have to be a mess. Notion combines project management with your docs, knowledge base, and AI. So you can stop jumping between tools, and stop paying too much for them too. Get Notion Projects for free at Notion.com/SAASTR. Vention provides technology leaders with the top engineering talent they need to accelerate their roadmap, innovate faster and more efficiently, and ultimately catapult their operation to new heights. Vention developers sync with clients' in-house teams, helping them get to market 30 percent faster and saving them more than $600,000 on average. Looking for the edge to outpace your competition? Vention is your partner. Learn more at ventionteams.com. ***** Want to join the SaaStr community? We're the 🌎largest community for B2B software. Subscribe for weekly updates: https://www.saastr.com/subscribeform Twitter: https://twitter.com/saastr LinkedIn: https://www.linkedin.com/company/2724976 Quora Group: https://www.quora.com/q/cloud Facebook: https://www.facebook.com/SaaStr/ Instagram: https://www.instagram.com/saastr/ Our North American Event: https://bit.ly/2OXeAYh Our European Event: https://bit.ly/2OZTad8

Parker Conrad

Co-founder & CEO

Rippling

Orlando Bravo is a Founder and Managing Partner of Thoma Bravo. He led Thoma Bravo's early entry into software buyouts and built the firm into one of the top private equity firms in the world. Tobi Lütke is the CEO and Co-Founder of Shopify, the powerhouse company allowing anyone to start and grow their e-commerce business. Dara Khosrowshahi is the CEO of Uber, where he has managed the company's business in more than 70 countries around the world since 2017. Parker Conrad is the Founder & CEO @ Rippling, the company that lets you easily manage your employees' payroll, benefits, expenses, devices, apps & more—in one place. Jamie Siminoff is the Founder and Chief Inventor @ Ring, with Ring Jamie, created the world's first Wi-Fi video doorbell while working in his garage in 2011. The company sold to Amazon for $1BN. Martín Escobari is Co-President, Managing Director and Head of General Atlantic's business in Latin America. Martín is Chairman of the firm's Investment Committee and also serves on the Management and Portfolio Committees. Ariel Cohen is the Co-Founder and CEO @ Navan (formerly TripActions), the #1 travel management super-app used by over 8,000 companies. Tarek Mansour is the Founder and CEO @ Kalshi, the first regulated exchange where you can trade directly on the outcome of events. Brian Armstrong is the Co-Founder and CEO @ Coinbase, the easiest place to buy and sell cryptocurrency. Over the last 10 years, Brian has led Coinbase to today, a public company with over 3,500 employees and revenues of over $7.5BN in 2021. Question of the Day: What are the world's tech leaders running from?

Orlando Bravo

Co-Founder & Managing Partner

Thoma Bravo

Tobi Lütke

Founder and CEO

Shopify

Dara Khosrowshahi

CEO, Uber

Uber

Parker Conrad

Co-founder & CEO

Rippling

Jamie Siminoff

CEO

Ring

Brian Armstrong

CEO and Co-Founder

CoinbaseResearchHub

Brought to you by Miro—A collaborative visual platform where your best work comes to life | Mixpanel—Product analytics that everyone can trust, use, and afford | Lenny’s Job Board—Hire the best product people. Find the best product gigs — Jeremy Henrickson is Rippling’s SVP of Product, responsible for scaling their product and design team across three continents. Previously, as Chief Product Officer at Coinbase, he oversaw 10x growth of the product and engineering organization and transformed a scrappy startup into a global cryptocurrency platform with tens of millions of users. He began his career at Apple in the 1990s and holds a BS and MS in computer science from Stanford. In today’s episode, we discuss: • Strategies for sustaining focus and momentum at scale • The case against MVPs • The problem with frameworks • “Compound startups” and how this influences Rippling’s product development process • Advice for founders wanting to move faster • Why you don’t understand your product unless you’re “in the weeds” • Hiring practices at Rippling and how young PMs can build fruitful careers — Find the transcript at: https://www.lennysnewsletter.com/p/moving-fast-and-navigating-uncertainty — Where to find Jeremy Henrickson: • Twitter: https://twitter.com/jeremyhenricks • LinkedIn: https://www.linkedin.com/in/jeremyhenrickson/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • Twitter: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Jeremy’s background (03:24) What it was like leading product teams at Coinbase during the crypto boom (05:25) How Jeremy kept teams focused and the biggest challenges he faced at Coinbase (07:35) Advice for going through intense periods at work (08:52) Maintaining velocity at scale (12:07) An example of small teams with clear missions (14:29) A model for building products (18:03) Jeremy’s thoughts on MVPs (minimum viable products) (22:26) Designing for the most complex use case first (23:17) What a compound startup is and how it works at Rippling (27:09) Rippling’s unique culture of fast decision-making (28:14) Rippling’s leadership values (32:13) Advice for cultivating fast-decision-making teams (33:44) How deep-level thinking and working on the ground helped Rippling expand to other countries (38:42) Why product leaders need to be right (40:42) How Rippling decided where to expand to first (42:29) The case for expanding internationally before you think you’re ready (45:32) Why Jeremy isn’t a huge fan of frameworks (48:08) The differences between building product at Rippling and Coinbase (52:49) How Jeremy hires PMs at Rippling (58:29) Advice for junior PMs (1:00:19) Lessons from working with a founder who has strong opinions about what the product should be (1:02:15) Lightning round — Referenced: • Coinbase: https://www.coinbase.com/ • Ethereum: https://ethereum.org/en/ • Parker Conrad on Twitter: https://twitter.com/parkerconrad • Rippling: https://www.rippling.com/ • Excellent Advice for Living: Wisdom I Wish I’d Known Earlier: https://www.amazon.com/Excellent-Advice-Living-Wisdom-Earlier/dp/0593654528 • Matt MacInnis on Twitter: https://twitter.com/stanine • Rippling’s leadership principles: https://www.rippling.com/life • Airbnb cereal story: https://www.cnbc.com/2023/04/18/airbnb-ceo-says-he-wooed-first-investors-with-boxes-of-cereal.html • Guidewire: https://www.guidewire.com/ • Jira: https://www.atlassian.com/software/jira • Kyle Boston on Twitter: https://twitter.com/KyleB • Quicksilver (book one of the Baroque Cycle series:) https://www.amazon.com/Quicksilver-Baroque-Cycle-Vol-1/dp/0060593083/r • Consider Phlebas (book 1 of The Culture series): https://www.amazon.com/Consider-Phlebas-Culture-Iain-Banks/dp/031600538X/ • The Last of Us on HBO: https://www.hbo.com/the-last-of-us • The Game on Paramount+: https://www.paramountplus.com/shows/the-game-2021/ • Tenet: https://www.imdb.com/title/tt6723592/ • Corsair H60 CPU cooler: https://www.amazon.com/CORSAIR-Hydro-Liquid-Cooler-Radiator/dp/B00A0HZMGA • Focal Bathys headphones: https://www.amazon.com/Focal-Over-Ear-Bluetooth-Headphones-Cancelation/dp/B0B93YKQT3 • Pandemic: https://www.amazon.com/Z-Man-Games-ZM7101-Pandemic/dp/B00A2HD40E • Gloomhaven: https://www.amazon.com/Cephalofair-Games-CPH0201-Gloomhaven/dp/B01LZXVN4P — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Jeremy Henrickson

SVP of Product

Rippling

Zach Lawryk is Head of Solutions Consulting @ Rippling, what is solutions consulting? They are the product expert in the solution that ties a business value to help support the sales rep in the execution of their quota. And there is no one better than Zach, prior to leading the solutions consulting team at Rippling, Zach was VP of Solutions Consulting at Slack where he scaled the SE team from 10 to 200. Before Slack, Zach was Head of Solutions Engineering @ Optimizely and before that was Director of Sales Engineering at Box. In Today's Episode with Zach Lawryk We Discuss: 1. ) WTF is Solutions Engineering: What is Solutions engineering and why is it important? How does a software developer turned lawyer become one of the OGs of Solutions Engineering? What is the single biggest piece of advice Zach gives to graduates entering the workforce today? 2.) When and Who: Building the Foundations: When is the right time to hire your first solutions engineer? Should this be a senior hire or a more junior hire? What experience is ideal? Would Zach rather have someone who has sold to the same customer segment or sold to the same deal size? What are the challenges with each? 3.) Making the First Hire: The Process: What is the right hiring process for solutions engineers? Which members of your existing team should be involved in the process? What are some of Zach's favourite questions on the candidates past to determine quality? What are the best case studies and tests to give potential hires to test their aptitude? What are the biggest red flags in the hiring process for solutions engineers? 4.) Integrating into the Team: Making it Work: What is the optimal onboarding process for solutions engineers? Why does Zach think it is important they spend time with customer success in their first month? What is the right way to measure the effectiveness of SE's? How should the entrance of SE's impact the close rate and comp structure for AE's? How can sales leaders prevent division and friction between AEs and SEs?

Zach Lawryk

Head of Solutions Consulting

Rippling

In today's CRO Confidential, Sam chats with Rippling VP of Sales Matt Plank. Matt was employee #5 and the first sales hire at Rippling. In this episode, he shares how he built and scaled Rippling's sales team. Video: https://youtu.be/yAloXeNI1Qw Blog post: https://www.saastr.com/saastr-cro-confidential-founders-fund-partner-sam-blond-rippling-vp-sales-matt-plank-pod-617-video/ Want to join the SaaStr community? We're the 🌎largest community for B2B software. Subscribe for weekly updates: https://www.saastr.com/subscribeform Twitter: https://twitter.com/saastr LinkedIn: https://www.linkedin.com/company/2724976 Quora Group: https://www.quora.com/q/cloud Facebook: https://www.facebook.com/SaaStr/ Instagram: https://www.instagram.com/saastr/ Our North American Event: https://bit.ly/2OXeAYh Our European Event: https://bit.ly/2OZTad8

Matt Plank

Chief Revenue Officer

Rippling

My guest today is Parker Conrad, co-founder and CEO of Rippling. I wanted to speak to Parker because he is building Rippling in a way that we don’t come across often. Rather than focus narrowly on one product, he is building a suite of interrelated products simultaneously to carry out the functions of HR, Finance, and IT for companies. He calls it a compound company and we discuss the idea, as well as some of his other non-traditional theories, in detail. Please enjoy this conversation with Parker Conrad.   For the full show notes, transcript, and links to mentioned content, check out the episode page here.   -----   This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com.    -----   This episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.   -----   Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes.    Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.   Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.   Follow us on Twitter: @patrick_oshag | @JoinColossus   Show Notes [00:02:36] - [First question] - Overview of what a compound startup is  [00:06:32] - What he’s learned about picking customers effectively  [00:08:48] - Key chapters when it comes to building a compound startup  [00:13:48] - What great looks like at the base level infrastructure of employee data [00:20:15] - His overall philosophy on product development writ large  [00:25:09] - His role as a capital allocator and distributing resources to his teams [00:27:19] - The amount of products they offer and whether or not there’s a tradeoff between time, cost, and quality when building software [00:31:36] - Possibly incorporating an app-like store on top of their existing infrastructure  [00:34:43] - Speed and the kinds of people that can sustain it for long periods of time [00:36:30] - What motivates him on a personal level and harnessing motivation in general [00:42:31] - Whether or not there’s an end to feeling hurt by false public perceptions when building in public [00:44:12] - The intersection of leadership and communication inside of a business and what he’s learned about great communication  [00:48:00] - The paradox of how focusing on non-scalable actions perpetuates growth and productivity and his views on productivity-per-person [00:50:36] - The best example of a moment that required the most grit and perseverance while building his company  [00:52:28] - How to successfully get former founders to come work for him  [00:54:47] - What good private equity investors do  [00:58:31] - The kindest thing anyone has ever done for him

Parker Conrad

Co-founder & CEO

Rippling

Parker Conrad is the Founder & CEO @ Rippling, the company that lets you easily manage your employees' payroll, benefits, expenses, devices, apps & more—in one place. To date, Parker has raised over $697M for Rippling from some of the best including Sequoia, Founders Fund, Greenoaks, Bedrock, Kleiner Perkins and Initialized to name a few. Prior to founding Rippling, Parker was the Co-Founder and CEO @ Zenefits and if that was not enough, Parker is also a prominent angel having invested in Census, Pulley and then also AgentSync and TrueNorth, alongside 20VC Fund. In Today's Episode with Parker Conrad: 1.) Entry in Startups and Zenefits: How did Parker make his way into the world of startups? How did Parker end up being kicked out of his own company, Zenefits? How did he respond? How did that experience of being kicked out of Zenefits inspire him to build Rippling? 2.) Parker Conrad: The Leader: How does Parker define "high performance"? How would Parker describe his leadership style today? Why does Parker fundamentally disagree that with speed comes a trade-off in quality? How does Parker ensure Rippling does all things fast and to the best of its ability? How would Parker break down his decision-making framework today? How does he decide what to prioritize vs not? How does he decide what to delegate vs not? What are Parker's biggest insecurities in leadership today? How have they changed over time? What does Parker do to combat and mitigate them? 3.) Rippling: The Compound Startup How does Parker define a compound startup? What types of business do this verticalized approach work for vs not work for? What does Parker believe are the 4 core benefits of this approach? What are the single biggest challenges of building a compound startup? 4.) Rippling: The Economics: How does this compound startup approach impact ability to cross-sell? How much net new ARR today comes from cross-sell? What have been some of Rippling's biggest lessons on what it takes to do cross-sell so effectively? How do the margin profiles differ across their different products? How have the margin profiles changed over time? Why does Parker not believe that most startup margins are accurate? How does the compound startup approach change the amount invested in R&D? How does that impact the fundraising requirements of the business? 5.) Rippling: The Partner Ecosystem: How does Rippling think about building out the best partner ecosystem? What will it take for that to work? Why do Rippling want to introduce services that compete with their own products? Why do they not only build their own? How do the margins differ when comparing revenue share on partner products vs Rippling products? What are the single biggest barriers to this partner ecosystem working?

Parker Conrad

Co-founder & CEO

Rippling

(00:08) Welcome Zach Weinberg (00:55) Andreessen Horowitz/Flow Carbon (10:41) Crypto Litigation Risk (16:27) Venture vs. Hedge Funds (22:25) Sequoia’s Leaked Deck (27:04) Different Kind of Crisis (28:20) Tech Companies Had It Easy (30:21) Uber vs. Lyft (34:16) Down Rounds (40:27) High Valuation Doesn’t Mean Good Employment (45:31) 2008 Work Force (49:50) Parker Conrad Intro (50:13) Working on Harvard’s Crimson (52:45) Left School for a Little Rock Newspaper (55:13) Cancer Diagnosis (57:16) Starting SigFig (58:52) Raising Money Pre-2013 (1:05:29) Challenges in Automating (1:08:36) The Public Narrative (1:10:36) Forced Out of Zenefits (1:19:50) VC’s Role in Narrative (1:22:59) What Do Founders Want From VCs? (1:25:46) Do VCs Increase Success? (1:30:09) Discussing Rippling (1:38:16) Building a Compound Company (1:46:56) Hiring People With a Chip On Their Shoulder (1:49:02) Most Important Job of a CEO (1:51:05) Raised the Next Round (1:54:47) Determining the Valuation (1:58:09) San Francisco   Follow the show: https://twitter.com/cartoonavatars https://www.instagram.com/cartoonavatars/ https://www.tiktok.com/@cartoonavatars   Follow the host: https://twitter.com/loganbartlett   Mixed and edited: Justin Hrabovsky Produced: Andrew Nadeau and Rashad Assir Executive Producer: Josh Machiz Music: Griff Lawson   Links: Sequoia’s Leaked Deck - https://fortune.com/2022/05/25/sequoia-capital-slide-dek-warning-to-founders-downturn/ Zack’s Twitter Battle - https://twitter.com/zachweinberg/status/1527107650911186944?s=20&t=DN_FdiP-WW6rDwmHNkJPTA Parker Conrad Discussing Chip on Their Shoulder - https://techcrunch.com/2021/11/18/parker-conrad-i-like-working-with-people-who-have-a-chip-on-their-shoulder/?guccounter=1&guce_referrer=aHR0cHM6Ly93d3cuZ29vZ2xlLmNvbS8&guce_referrer_sig=AQAAAAqlH6GlRJ8EA-ptL8cD-XPUGeoXNRqKe9l_Qegi--qyyHZQrMTJ8bwlg47vSJ9rkc2eaJlUKyMvb3wA-Rw2PjFYJl5gUwZfO0WPMLF-tRT_lVDYq_uoEnC29d6L45AlVFRTnPJqbCPEJM0_ICBeqES_kZ8t5gUQkVg7BwMKsGs7 Chesa Boudin and San Francisco - https://www.theatlantic.com/ideas/archive/2022/05/chesa-boudin-recall-san-francisco-crime/629907/ Andreessen Horowitz/Flow Carbon - https://www.forbes.com/sites/alexkonrad/2022/05/25/a16z-crypto-record-4th-fund-doubles-down-on-web3-amid-market-crash/?sh=7f704b7f34ff VCs Driving Down Valuation Narrative - https://twitter.com/bgurley/status/1528535418076995584 Executive Producer: Rashad Assir Producer: Leah Clapper Mixing and editing: Justin Hrabovsky Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA 🎥 Subscribe on YouTube: https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=1 Follow on Socials 📸 Instagram - https://www.instagram.com/theloganbartlettshow 📱 X - https://twitter.com/loganbartshow 🎬 Clips on TikTok - https://www.tiktok.com/@theloganbartlettshow About the Show Logan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode of The Logan Bartlett Show, we sit down with the people behind today’s most important startups and extract the tactics, lessons, and frameworks they’ve learned the hard way. Conversations span hiring to GTM, product, growth, fundraising and everything in between - collectively forming the ultimate playbook to make you a better CEO, investor or board member. Tap follow and enable notifications to stay ahead of the game.

Parker Conrad

Co-founder & CEO

Rippling

Sometimes social media works and sometimes it doesn’t. For Matt Epstein, Chief Marketing Officer at Rippling, it is a little bit of both. In 2011, Matt went viral after uploading a Youtube video detailing why Google should hire him. It was also accompanied by a propeller plane with his URL attached, flying over the Google campus. Apparently, Google was not impressed, however, this bold decision ultimately worked in his favor. The video attracted many companies, which eventually led to the beginning of a fast-paced and fulfilling marketing career. In this episode, Matt discusses his unconventional way of attracting Google’s attention and what it was like to pass on other companies in lieu. He talks about how his brashness, which as he puts it, is just a “chip on his shoulder”, attracted the attention of Rippling founder, Parker Conrad. Now, he is along for the ride as he surrounds himself with other like-minded “crazy ones.” Matt also shares his take on why generalists and marketing ops should be “first hires” in SMB and SaaS, and how when you’ve got something to prove in that space it only increases your ambition.  In this episode, we cover:  How Matt’s plea to work for Google went viral - and why he hates social media. (01:48) Matt’s professional evolution from SigFig to employee #1 at Zenefits and his role in garnering the first customers. (08:04) Why Matt recommends generalists and marketing ops as the first hires in the SMB SaaS space - and a deep dive into how a “chip on your shoulder” and insecurity are powerful motivators for success. (17:00) Matt’s decision-making process from applying to Google to passing up on job offers from major tech companies - and Matt reflects on lessons learned at Zenefits. (24:16) How Rippling founder, Parker Conrad, convinced Matt to join the company - and Matt explores the next phase of Rippling’s app ecosystem. (34:26) Matt’s thoughts on Rippling’s recent product launch, marketing their catalog of products, and the challenges of scaling up at a startup. (44:32) A discussion about coping with pressure, why Matt looks for “the crazy ones” when hiring, and why he has no interest in being a founder. (53:26) Links: Connect with MattLinkedIn Email: mepstein@rippling.com Rippling Connect with JoubinTwitter LinkedIn Email: gtmg@kleinerperkins.com  Learn more about Kleiner Perkins

Matt Epstein

CMO

Rippling

Parker Conrad is the Founder and CEO @ Rippling, the employee management platform allowing you to manage your employees' payroll, benefits, devices and more—in one place. To date, Parker has raised over $197M for Rippling from the likes of Founders Fund, Kleiner Perkins, Initialized, Bedrock, Greenoaks and Coatue. Prior to founding Rippling, Parker was the Co-Founder and CEO @ Zenefits and if that was not enough, Parker is also a prominent angel having invested in the likes of Census, Pulley and then also AgentSync and TrueNorth, alongside 20VC Fund. In Today's Episode with Parker Conrad You Will Learn: 1.) How did Parker make his way into the world of technology and startups? What was the founding a-ha moment for Parker with Rippling? How did his journey with Zenefits change or alter his leadership style today with Rippling? 2.) Why does Parker believe that the conventional advice of focus, focus, focus is BS? What does Parker mean when he states, "The Compound Startup"? How does the approach of the compound startup differ from traditional approaches of product and company building? What are the core benefits of using the compound startup approach? 3.) How does Parker think about providing sufficient product quality with an increasing breadth of product offering, entailed within a compound startup? In what way does pricing differ when comparing compound startups to traditional startups? How can compound startups optimise their pricing on a bundle basis? What has Slack and Microsoft taught us about this? 4.) Why does Parker disagree with the conventional analogy of the VC <> founder relationship being a marriage? Why does Parker refer to it more as a "General Contractor" relationship for a house? What can founders do to sufficiently protect themselves from overarching VCs? What can VCs do to be the very best partners to the founders they work with? 5.) How does Parker evaluate his relationship to money today? How has it changed over time? What does Parker know now that he wishes he had known at the start of his founding of Rippling? What have been Parker's biggest lessons on talent acquisition? Why did Parker decide to bring on a COO when he did? How has it changed his role? Item's Mentioned In Today's Episode with Parker Conrad Parker's Favourite Book: Matilda by Roald Dahl As always you can follow Harry and The Twenty Minute VC on Twitter here!

Parker Conrad

Co-founder & CEO

Rippling

Parker Conrad is the Founder & CEO @ Rippling, the startup that gives you back your time from payroll to employee computers, Rippling makes it unbelievably easy to manage your company's HR and IT - in one system. To date Parker has raised over $59m in funding from some of the best in the business including Mamoon @ Kleiner Perkins, Garry Tan @ Initialized, Justin Kan, SV Angel and Y Combinator, just to name a few. As for Parker, prior to founding Rippling, he was the Founder & CEO @ Zenefits, the startup he built from $0 to $60m in ARR in just 3 years. Before that he co-founded Sigfig where he grew assets on the platform to over $35Bn across 500k users. In Today's Episode We Discuss: How Parker made his way into the world of startups and SaaS, came to found Zenefits and what was that a-ha moment for the founding of his most recent company, Rippling? What does Parker do with regards to operational scaling that is unconventional but works? Why does Parker believe it is fundamentally better to wait for as long as possible before hiring customer support? Why should engineers also be doing customer support? Why should your engineers be heavily involved in the customer support hiring process? What are the benefits of this? How can one prevent their customer support team from being a wall of protection for the product and eng team? How can you ensure seamless collaboration and communication flow between product and customer support? Stripe last week recently announced their 5th office would be… "remote", so how does Parker feel about the building of remote teams? What are the most important things when establishing your first remote team? What do you look for in those hires? What can be done to ensure a greater feeling of community and closeness despite the distance? What have been some of the biggest challenges for Parker in building out the remote team? Parker has been a CEO with 3 different companies now and so how has he seen his style and approach change over the years? What has Parker found the hardest to get good at? When advising founders on fundraising, what advice does he give? How can founders know when is the right time to raise? How should they look to build relationships with investors between raises? 60 Second SaaStr: What does Parker know now that he wishes he had known in the beginning? What one thing would Parker like to change about tech and Silicon Valley? Biggest mentor and what has Parker learned from them? Read the full transcript on our blog. If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Parker Conrad

Parker Conrad

Co-founder & CEO

Rippling

Matt MacInnis is the Founder & CEO @ Inkling, the company that brings policies and procedures to life for your desktop workers. The company has backing from some of the best investors in the world with the likes of Sequoia, Felicis and Kapor Capital behind them. As for Matt, prior to Inkling, he spent 7 years at the one and only Apple Inc. I would also like to say a huge thank you to Taro Fukuyama, Founder @ AnyPerk for the intro to Matt. In Today's Episode You Will Learn: How did Matt make his way into the world of SaaS and Inkling from Apple Inc? Does culture in sales really matter? Is it not just about hitting the fucking number? What are the two opposing culture that exist in the world of sales team? Why is missionary always better? How can a sales leader instill a competitive element into a missionary sales culture? What are the inherent challenges and how does Matt approach them? Is it possible to have a fantastic sales and a fantastic engineering culture? How can the two live under the same roof and what needs to happen to ensure this works? In terms of measurement, how can a founder know whether they have a strong culture? What are the signs and indications? 60 Second SaaStr Productivity Tools What does Matt know now that he wishes he had known in the beginning? Biggest mistake most SaaS companies are enacting with their sales process? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Matt MacInnis

Matt MacInnis

COO

RipplingInkling