Gusto

Gusto is betting that small businesses need more than another AI assistant. The company’s new product, Gusto Cofounder, is designed to act as a proactive business partner that helps owners manage and grow their companies, drawing inspiration from the traditional mom-and-pop partnership that co-founder and CTOEddie Kimwitnessed growing up. Unlike reactive chatbots, Cofounder can take action across payroll, HR, benefits, scheduling, insurance, and accounting workflows by leveraging data already stored within Gusto. Users interact with the platform through text messages or Slack, while a consent framework ensures access to sensitive payroll and employee data remains tightly controlled. Businesses can grant explicit permissions and gradually increase autonomy as trust is established. The platform also integrates with third-party tools such as Google Workspace, enabling it to gather data, perform calculations, run payroll, and communicate results automatically. Kim said the product was built by a five-person team in just eight weeks using Claude Code, which he believes demonstrates how AI is expanding software creation beyond traditional engineering roles. Looking ahead, Gusto plans to add more integrations and eventually enable customers and developers to share reusable, industry-specific business automations. Learn more from The New Stack around how AI is expanding software creation beyond traditional engineering roles: How AI Is Reshaping Software Engineering: Key Takeaways From DeveloperWeek 2025 AI and the Future of Code: Developers Are Key The Engineer in the AI Age: The Orchestrator and Architect Join our community of newsletter subscribers to stay on top of the news and at the top of your game.

Eddie Kim

Co-founder and CTO

Gusto

This Week in Startups is brought to you by… Vanta. Compliance and security shouldn't be a deal-breaker for startups to win new business. Vanta makes it easy for companies to get a SOC 2 report fast. TWiST listeners can get $1,000 off for a limited time at https://www.vanta.com/twist OpenPhone. Create business phone numbers for you and your team that work through an app on your smartphone or desktop. TWiST listeners can get an extra 20% off any plan for your first 6 months at https://www.openphone.com/twist DevSquad. DevSquad helps startups design better products. If you need UI and UX expertise and don’t want to hire an entire design team, head to http://devsquad.com/startups and book a call. Mention that you are coming from TWiST to get 10% off. * Todays show: Josh Reeves joins Alex Wilhelm to discuss building a product people love (21:11), SMB challenges (23:56), growth strategies (36:47), and more! * Timestamps: (0:00) Josh Reeves joins Alex Wilhelm (2:16) Josh's previous startups and the early days of web development (6:26) Transition to digital solutions and security for small businesses (10:31) Gusto's growth, success metrics, and market penetration (13:38) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist (14:30) Gusto's North Star, marketing strategies, and channel growth (21:11) Building a product people love with good unit economics (22:29) OpenPhone - Get 20% off your first six months at https://www.openphone.com/twist (23:56) Challenges of selling to SMBs and Gusto's product expansion (28:50) Maintaining simplicity in product development (35:18) DevSquad - Visit https://www⁠.devsquad.com/startups, book a call, and mention TWIST for 10% off! (36:47) Ensuring product quality and the role of organic growth in marketing (44:39) Competitive landscape in payroll and HR space (48:54) Gusto's potential fintech ventures and communication styles among founders (56:07) IT spending growth among SMBs and international expansion (1:00:16) Navigating competition and partnerships (1:01:41) Diversification of go-to-market strategies (1:03:31) Financial strategies and thoughts on going public * Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com Check out the TWIST500: https://www.twist500.com * Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp * Follow Josh: X: https://x.com/joshuareeves LinkedIn: https://www.linkedin.com/in/joshuareeves * Follow Alex: X: https://x.com/alex LinkedIn: ⁠https://www.linkedin.com/in/alexwilhelm * Thank you to our partners: (13:38) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist (22:29) OpenPhone - Get 20% off your first six months at https://www.openphone.com/twist (35:18) DevSquad - Visit https://www⁠.devsquad.com/startups⁠, book a call, and mention TWIST for 10% off! * Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland * Check out Jason’s suite of newsletters: https://substack.com/@calacanis * Follow TWiST: Twitter: https://twitter.com/TWiStartups YouTube: https://www.youtube.com/thisweekin Instagram: https://www.instagram.com/thisweekinstartups TikTok: https://www.tiktok.com/@thisweekinstartups Substack: https://twistartups.substack.com * Subscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916

Josh Reeves

Co-Founder & CEO

Gusto

Josh Reeves has built Gusto into a nearly $10B company with over $500M in ARR, serving small businesses. In our conversation, Josh delves into Gusto’s 13-year journey, sharing insights on how they achieved product-market fit by initially targeting a very narrow niche. He also highlights the tactics they’ve used to build an intentional culture of humility and helpfulness, along with lessons he’s learned in hiring executives. We also explore the future of Gusto and the opportunities that lie ahead for the business. (00:00) Intro (00:36) Early Days and Product Market Fit (01:02) Building a Scalable Business (01:41) Gusto's Core Offerings and Customer Focus (02:51) Challenges and Strategies in Payroll (05:40) Expanding Gusto's Reach (10:11) Customer Feedback and Product Development (23:03) Hiring and Company Culture (29:23) Values and Leadership at Gusto (37:14) Sustaining Passion and Long-Term Vision (43:27) Balancing Growth and Sustainability (46:29) Balancing Competition and Kindness in Startups (46:38) The Importance of Team Collaboration (47:47) Navigating Feedback: Kindness vs. Niceness (48:25) Hiring for Ambition and Humility (49:57) Aligning Company Values with Success (53:11) Work-Life Integration at Gusto (56:11) Building a Long-Term Oriented Business (57:15) Mentorship and Learning from Other Founders (01:00:09) Structuring and Scaling Product Teams (01:06:16) Organizational Design and Leadership (01:08:31) Hiring Executives and Internal Growth (01:13:13) The Journey of Rebranding to Gusto (01:21:05) The Role of a CEO in a Growing Company (01:28:39) Fundraising and Investor Relations (01:33:14) Future Goals and Impact of Gusto (01:35:48) 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.

Josh Reeves

Co-Founder & CEO

Gusto

SaaStr 727: High-Velocity Techniques to Maximize Sales with Gusto's CRO and Head of Go-to-Market Tolithia Kornweibel, CRO, and Jamie Edwards, Head of Go-to-Market Operations and Tools, share how Gusto maximizes revenue so that you can do the same. Together they share the high-velocity techniques they use to maximize sales, including: Sell to SMBs Use round-robin to assign accounts, but you're not sure if it's optimal Are stuck in a world of geographic territories Spend a lot of time manually building territories -------------------------------------------------------------------------------------------- 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 Get more when Northwest Registered Agent starts your business. They'll form your company fast and stand up your entire business identity in minutes. That means business free domain, business email, website, hosting, address, mail scanning, business phone app, all within minutes. Visit https://www.northwestregisteredagent.com/saastr to get a 60 percent discount on your next LLC.

Tolithia Kornweibel

CRO

Gusto

Jamie Edwards

Head of Go-to-Market Operations and Tools

Gusto

Hello and welcome back to Equity, TechCrunch's venture capital focused podcast where we unpack the numbers and nuance behind the headlines. Today we have something a bit different for you. In light of the never-ending Musk-Twitter saga, and news that the new social media CEO had cut its corporate communications staff to the bone -- and then some. So to get more perspective on the role that a corporate comms team plays in both startups and public companies alike, we wrangled two folks who have just that experience set: Kelly Boynton, senior director of communications at Gusto Keyana Corliss, until recently the head of global communications and PR at Databricks The pair discussed the role that comms plays in companies both internally and externally, and why it deserves a seat at the decision-making table. Given the media furor surrounding Musk himself, you can imagine that we had a lot to talk about. Oh, and Keyana has a podcast that Alex was a guest on, in case you want to hear more from her! Regular service returns tomorrow! Equity drops at 7 a.m. PT every Monday and Wednesday, and at 6 a.m. PT on Fridays, so subscribe to us on Apple Podcasts, Overcast, Spotify and all the casts. TechCrunch also has a great show on crypto, a show that interviews founders, one that details how our stories come together, and more! 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

Kelly Boynton

Senior Director of Communications

Gusto

Keyana Corliss

Head of Global Communications and PR

Databricks

The foremost topic on every founder's mind right now: how to weather the ups-and-downs of an unpredictable economy. Gusto, has swerved with every economic curve since its founding 10 years ago. But throughout it all, Gusto has defined valuation differently—in terms of the value it provides to customers vs the value it extracts. In this talk, Gusto CEO and founder Josh Reeves can speak to how Gusto has weathered the ups-and-downs of the economy—and why aligned success models (what's good for the customer = what's good for society = what's good for your business) are so important, especially now. Josh can share the specific business decisions Gusto has had to make with this approach, particularly over the past few years and today. Full video: https://youtu.be/TuJnbPG3Tmk 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

Josh Reeves

Co-Founder & CEO

Gusto

To celebrate 10 years of SaaStr, we're revisiting some classic podcast episodes. Up today: a 2016 interview with Harry Stebbings and Gusto Co-Founder and CEO Josh Reeves. At the time of this interview, Gusto had 350 employees serving 40,000 customers. Today, it's grown to more than 2,000 employees serving over 200,000 businesses. 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

Josh Reeves

Co-Founder & CEO

Gusto

About Fredick “Flee” Lee Fredrick "Flee" Lee is the CSO at Gusto, the platform that helps 100,000+ small businesses nationwide pay, insure, and provide benefits for their teams. Flee has more than 15 years of experience leading global information security and privacy efforts at large financial services companies and technology startups, most recently as Square's head of information security. He previously held senior security and privacy roles at Bank of America, NetSuite, and Twilio. Links Referenced:  LinkedIn: https://www.linkedin.com/in/fredrickdlee/

Fredrick Lee

CSO

Gusto

Gusto's Lexi Reese walks you through scaling high performance teams. Is trust earned or given? How do you communicate for impact? This podcast is an excerpt from Lexi's session at SaaStr Scale. You can find the full video and transcript on our blog: https://www.saastr.com/high-performance-teams/

Lexi Reese

COO

Gusto

Tomer London is the Co-Founder @ Gusto, the people platform for small businesses providing one place to run payroll, manage benefits, and support your team. To date, Tomer and the team have raised over $520M with Gusto from some of the industry's leading investors including General Catalyst, CapitalG, Kleiner Perkins, T Rowe, Fidelity and more and then individuals including Shopify Founder Tobias Luttke, Sam Altman, Max Levchin, Matt Mullenweg, Kevin Hartz and Elad Gil to name a few. Prior to Gusto, Tomer did a PHD in Electrical Engineering at Stanford and before that was Founder and CEO @ Vizmo, mobile self-service technologies for enterprise to try to fix customer care. In Today's Episode You Will Learn: 1.) How Tomer made his way from creating inventory management software for his Father's small business in Israel to Stanford and founding the unicorn that is Gusto? 2.) Why does Tomer believe that most founders approach fundraising with the wrong mindset today? What does he mean when he says, "fundraising = creating change"? What is the "values motivation alignment"? How can founders use it to help them select the right investor for them? Why should you add investors just as you would new team members? 3.) Having raised over $200M in the latest financing, how does Tomer think about when is the right time to pour fuel on the fire and go big? Is it a fundamentally different mindset when you have so much cash thrown on you? What would Tomer advise founders with suddenly expanded budgets? With 111 investors on the Gusto cap table, what would Tomer advise founders when it comes to cap table management? 4.) What have been Tomer's biggest learnings when it comes to building a delightful product at scale across different segments? How important does Tomer feel time to delight from the UX perspective is? How does Tomer think about testing levels of user delight? NPS? Product analytics? How does Tomer think about the balance between product development and going all out for scaling? 5.) How has Tomer seen himself change and evolve as a leader of the last 5 years? What elements has he found super challenging to come to grips with? Where does Tomer believe he has a superpower on the flip side? Question from Laela @ CapitalG, what specifically did you do to create the culture that you did in the early days? Items Mentioned In Today's Show: Tomer's Fave Book: No Room for Small Dreams: Courage, Imagination and the Making of Modern Israel As always you can follow Harry, The Twenty Minute VC and Tomer on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Tomer London

Co-Founder

Gusto

Lexi Reese is the Chief Customer Experience Officer at unicorn startup, Gusto and is one of the top female executives in Silicon Valley. Lexi's passion for serving customers was sparked by her early career in microfinance as a public policy advocate with ACCION International—giving loans to people living in poverty to start their own ventures. She later worked at Google for eight years, most recently serving as Vice President of Programmatic Sales and Strategy globally. Lexi also started the Cambridge AdWords team for Google's small business organization. Now at Gusto, Lexi ensures that Gusto is continuously going above and beyond to serve all customers. In Today's Episode You Will Learn: How did Lexi make her way from the world of Google and Facebook to SaaS with Gusto? What were the biggest takeaways from spending 8 years at Google and seeing the immense hyper-growth there? How has Lexi applied those learnings to Gusto today? How does Lexi look to put the 'customer first' thesis into practice? What does this look like in reality and from day 1? How can one maintain such high levels of customer service with an ever increasing customer base? How can one insert elements of repeatability to make this easier? Question from Hunter Walk: How do you fundamentally measure customer satisfaction? What benchmarks do you calibrate against to consider success? 60 Second SaaStr What does Lexi know now that she wishes she had known in the beginning? Most challenging aspect of Lexi's role? Question from Tien @ Zuora: How do you look to avoid the hype culture that pervades the valley? 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

Lexi Reese

COO

Gusto

Josh Reeves is the Founder and CEO @ Gusto. Gusto reimagines payroll, benefits, HR, and personal finance and it is this reimagination that has led to their recent addition to the unicorn club with investors including Google Capital, Kleiner Perkins, Data Collective and General Catalyst, just to name a few. As for Josh, he was selected for the 2012 Forbes 30 Under 30 list. Prior to co-founding Gusto, he was the CEO and co-founder of Unwrap, a SaaS startup which was acquired in 2010, and he began his career as an early employee at Zazzle. I would also like to give a big hand to Jason Lemkin and Phil Libin for the intro to Josh today. In Today's Episode You Will Learn: HR and Payroll is not sexy so how did Josh make his way into the industry and what was the a-ha moment for Gusto? Josh has said before 'he lives and breathes how a company is built.' How has Josh looked to grow and develop his own internal organisation at Gusto? How does this vary with stage? Josh has hired over 300 people at Gusto, how does he approach the interview process? What is the right way for employers to approach the 'making offers' stage? How important does Josh feel it is to have an ownership culture and internal entrepreneurialism? How can this environment be fostered and developed? 60 Second SaaStr How employers can ensure new employees have an amazing first day? What does Josh know now that he wishes he had known when he started? The biggest mistake SaaS companies make with their HR and payroll organisation? 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 Josh Reeves

Joshua Reeves

Founder & CEO

Gusto