Pendo

Two failed startups. Zero product-market fit. Then an obsession that built a $200M ARR company. Todd Olson spent a year doing founder-led sales, refused to hire salespeople until $500K ARR, and would not scale until he saw real signs of product-market fit. That obsession paid off - Pendo now generates over $200 million in annual recurring revenue. Todd reveals how he validated product-market fit by tracking installs instead of revenue for an entire year, why raising prices 10x overnight proved PMF was real, and the market validation approach of obsessing over the problem while creating a category nobody was searching for. You will also learn why product-market alignment depends on founder-led sales that surface missing features. Todd built auto-tracking into Pendo so customers did not need developers adding tracking code. Today, Pendo serves 1,400+ customers with about 880 employees and has raised over $479M. 🔑 Key Lessons 📉 Two failures drove product-market fit obsession: Todd's first two startups failed to find fit. After reading "Four Steps to the Epiphany," he obsessed over validating product-market fit at Pendo before scaling anything. 🎯 Track installs, not revenue, to validate product-market fit: For Pendo's first year, Todd only measured installs - putting code in a customer's product - reaching 50 before any paid deal. 🤝 Founder-led sales reveals what is missing from your product: Todd refused to hire salespeople until $500K ARR. Staying in every deal surfaced missing features like surveys that won Pendo's largest customer. 💰 A 10x price increase proves product-market fit is real: Todd raised Pendo's minimum from $99 to $1,000/month overnight. The team panicked, but closed just as many deals. 🛠️ What you refuse to build becomes your differentiator: Todd skipped track events for five years despite every competitor offering them. Auto-tracking became Pendo's key advantage. Chapters Introduction and the Fred Smith quote Starting as a programmer at 14 The dot-com boom and first startup Second startup and failure to find product-market fit Reading Four Steps to the Epiphany Living the Pendo problem at Rally Software Saying no to sessions and track events Getting first 50 installs and first paying customer Founder-led sales to $500K ARR The 10x price increase that proved product-market fit Figuring out the ideal customer profile Lightning round Resources Full show notes: https://saasclub.io/451 Join 5,000+ SaaS founders: https://saasclub.io/email

Todd Olson

Founder & CEO

Pendo

Brought to you by Amplitude—Build better products: https://amplitude.com/ | Lenny’s Job Board—Hire the best product people. Find the best product gigs: https://www.lennysjobs.com/talent | Vanta—Automate compliance. Simplify security: https://vanta.com/lenny — Christine Itwaru is a longtime product operations leader at Pendo and more recently has taken on the larger role of Principal Strategist there. Before leading product ops, Christine spent 12 years in product management. In this episode, we delve into the rapidly growing field of product ops and discover how Christine is part of shaping the role industry-wide. She helps us define the role of product operations, what kind of person would be a good fit for the product ops role, when your company would benefit from product ops, and what red flags to look for if you decide to go down this path.  Find the full transcript here: https://www.lennyspodcast.com/understanding-the-role-of-product-ops-christine-itwaru-pendo/#transcript Where to find Christine Itwaru: • Twitter: https://twitter.com/christineitwaru • LinkedIn: https://www.linkedin.com/in/christineitwaru/ • Website: https://theproductheart.com/ Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • Twitter: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ Referenced: • Ben Williams on Lenny’s Podcast: https://www.podpage.com/lennys-podcast/how-snyk-built-a-product-led-growth-juggernaut-ben-williams-vp-of-product-at-snyk/ • Pendo: https://go.pendo.io/ • Marty Cagan on Lenny’s Podcast: https://www.lennyspodcast.com/the-nature-of-product-marty-cagan-silicon-valley-product-group/ • Salesforce: https://www.salesforce.com/ • Looker: https://www.looker.com/ • Tray: https://tray.io/ • Zapier: https://zapier.com/ • Zendesk: https://www.zendesk.com/ • Casey Winters on Lenny’s Podcast: https://www.lennyspodcast.com/how-to-sell-your-ideas-and-rise-within-your-company-casey-winters-eventbrite/ • Inspired: How to Create Tech Products Customers Love: https://www.amazon.com/INSPIRED-Create-Tech-Products-Customers/dp/1119387507/ • Leaders Eat Last: Why Some Teams Pull Together and Others Don’t: https://www.amazon.com/Leaders-Eat-Last-Together-Others/dp/1591848016/ • The Product-Led Organization: Drive Growth by Putting Product at the Center of Your Customer Experience: https://www.amazon.com/Product-Led-Organization-Putting-Customer-Experience/dp/1119660874 • Product Roadmaps Relaunched: How to Set Direction while Embracing Uncertainty: https://www.amazon.com/Product-Roadmaps-Relaunched-Direction-Uncertainty/dp/149197172X/ • The Product Experience podcast: https://www.mindtheproduct.com/the-product-experience/ • Matilda the Musical: https://www.imdb.com/title/tt3447590/ • Rise on Disney+: https://www.disneyplus.com/movies/rise/6Yv1uRnw2uAJ • Miro: https://miro.com/ • Figma: https://www.figma.com/ • Seismic: https://seismic.com/ • Gong: https://www.gong.io/ In this episode, we cover: (00:00) Christine’s background (02:34) How working with Ben Williams led Christine to Lenny’s Podcast (05:02) The role of product ops in product management (07:31) How 2019 became “the summer of product ops” (11:19) The different ways product ops can assist product teams (15:50) How Pendo used product ops to bring teams together and share data (18:15) Where user research fits in  (22:39) How product ops are being utilized—and not exclusively in B2B companies (24:47) How to convince a product leader that you need product ops (27:41) Why customer experience is the core of a PM’s role (29:47) Who is doing the work of the product ops person before that role is created (31:37) Christine’s response to Casey Winters’s take on ops teams (37:40) Signs your company could benefit from a product ops team (30:56) How a lack of transparency led to Pendo adding product ops (46:11) The line between product ops and product marketing (47:30) Who might be a good fit for a product ops role (53:39) Red flags for product ops roles (that apply to any role)  (54:08) How product teams are structured at Pendo (57:18) Lightning round Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. 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

Christine Itwaru

Principal Strategist

Pendo

We've learned Saas companies strive to achieve the T2D3 model. Join Bill Binch, Former EVP Sales, Marketo (currently Operating Partner at Battery Ventures) as he discusses Marketo's success and why the same old playbook needs to be adapted for today. Learn from Bill on how the CEO & CRO relationship shapes this and what new ideas founders need to think through. Full video: https://youtu.be/MS3e6_T5RYs 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

Bill Binch

Operating Partner

Battery VenturesPendoMarketo

To make the leap from HR to sales may seem like a significant obstacle to surmount. For Jennifer Brannigan, CRO at Pendo, it was an easy choice to make. Her decision to pursue her own interests and passion over a high salary set her on a path toward where she is today. And for her, the journey still continues.  As she puts it, her professional roadmap is much like a jungle gym, as it is varied and intriguing. In this episode, Jennifer shares why she transitioned to sales in the midst of an accelerating HR career, and what she learned from her time at NBC Universal and LinkedIn. She also brings a refreshing take as she explains her unconventional subscription to JOMO (the joy of missing out) and provides insight on why she focuses on cultivating potential over check-the-box skillsets. In this episode, we cover: Jennifer’s exciting summer job in Ireland - and why she aspires to embrace JOMO (the joy of missing out). (03:18) A look into the neighborhood Jennifer grew up in, located in South Side, Chicago - and why Joubin thinks she would make a great podcast host. (09:07) How Jennifer’s experience at NBC Universal transferred into her next role - and what she learned from the challenges that came with her position at LinkedIn. (12:56) Jennifer’s perspective on leading LinkedIn’s large-scale layoff and how her HR experience prepared her for that difficult task. (17:54) From LinkedIn to Pendo: Jennifer’s journey towards her role as CRO - and her thoughts on her career trajectory. (21:55) Joubin and Jennifer explore the positive effect that running and exercise have on their mental health. (30:14) More on Jennifer’s path to Pendo: what she looked for in her search and how she spent her first 6 months. (35:15) Pendo’s cross-organizational hiring rubric - and Jennifer’s viewpoint on hiring potential vs success. (43:48) Jennifer uses her own experiences to rank career, money, company, and manager - and she shares her favorite simple habit and one she’d like to develop. (56:44) Links: Connect with JenniferEmail: jen.brannigan@pendo.io Pendo Connect with JoubinTwitter LinkedIn Email: gtmg@kleinerperkins.com  Learn more about Kleiner Perkins

Jennifer Brannigan

CRO

Pendo

Joe Chernov is the VP Marketing @ Pendo, the startup that understands and guides your users allowing you to create products they cannot live without. To date they have raised over $108m in funding from some of the best in SaaS including Meritech, Salesforce, Battery, Spark Capital and Sapphire just to name a few. Prior to Pendo Joe was Chief Marketing Officer at Robin and before that he was the CMO @ InsightSquared where he led the transition from an email-driven leads model to an account-based marketing model. Before InsightSquared, Joe was Head of Content Marketing at Hubspot where he increased blog traffic by more than 1M visits/month and increased leads by 40%. Finally, pre-Hubspot, Joe held VP of Marketing roles at Kinvey and Eloqua. In Today's Episode We Discuss: How Joe made his way into the world of startups and SaaS marketing many years ago? Does Joe really believe in the saying that, "no one really knows what they are doing?" Where are the nuances to it? Joe has been CMO and then #2 and alternated between the 2 roles many times, so what the continuous alternating? How does switching from CMO to VP of Marketing prepare you better for each subsequent role? Does Joe agree with the saying that the best in marketing are able to "throw the playbook out of the window"? What does Joe mean when he says, "the most powerful mentorship is mentorship from below"? What makes the best #2's just so good? What do they do? What advice would Joe give to a #2 in a role today? What can the individuals do to foster a relationship of deep trust and transparency? Having worked at both early and late stage companies, what does Joe believe the early companies can learn from later stage companies? Does installing very severe ops not reduce the creativity of a young company? What does Joe believe that later stage companies can really learn and take from early-stage companies? How do the marketing functions differ in both structure and process when comparing early to late stage? What does Joe find to be the biggest challenge within each respective stage? How has Joe seen the content landscape evolve and change radically throughout his career alternating between early and late stage companies? Joe's 60 Second SaaStr: Who does Joe believe is killing it in SaaS marketing now? Why? ABM, total BS or real meaning to it? If Joe could change one thing about SaaS today, what would it be? 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 Joe Chernov

Joe Chernov

VP of Marketing

PendoRobin Powered

Joe Chernov is the Chief Marketing Officer at Robin, the startup that simplifies scheduling, visibility and management of meeting rooms, desks and people in your workplace. To date, Robin have raised over £9m in funding from some of our dear friends in the form of BoldStart, Accomplice and FirstMark, just to name a few. As for Joe, prior to Robin he was the CMO @ Insight Squared where he led the transition from an email-driven leads model to an account-based marketing model that's tightly coupled with sales. Before InsightSquared, Joe was Head of Content Marketing at Hubspot where he increased blog traffic by more than 1M visits/month and increased leads by 40%. Finally, pre-Hubspot, Joe held VP of Marketing roles at Kinvey and Eloqua. In Today's Episode We Discuss: How Joe made his way into the world of startups and SaaS marketing many years ago? What was Joe's missed founding story and how does that affect his thinking today? Does Joe believe that ABM is a paradigm shift in the way we approach marketing or another word for high ACV target sales? How can founders determine whether they have the right business, pricing and hiring strategy that will align with an ABM strategy? Is it the right decision to focus squarely on ABM? How should it play into your overall marketing portfolio? Why does Joe believe we have seen a massive rise in SaaS conferences? How can a startup determine whether the conference strategy is the right strategy for them? Where does Joe see many startups going wrong when selecting this approach? Why does Joe believe you have to get comfortable with losing money in conferences? What are the determinants or leading indicators of a successful conference? What is the ideal composition in terms of attendance? Why does Joe believe that marketing should be held accountable to a number that is directly tied to revenue? Why does Joe believe that Head of Sales and Head of Marketing should not be separate functions? What is it that leads Joe's thinking when saying, sales and marketing are overlapping functions? What are the commonalities of the truly special CMOs? When is the right time to really consider adding the CMO to your exec team? What is the ideal relationship between the CMO and the CEO? What is the one question that will largely determine the strength of a potential CMO? Joe's 60 Second SaaStr: What does Joe know now that he wishes he had known at the beginning? Who does Joe believe is killing it in SaaS today and why? Advice Joe often hears in the world of SaaS that he actively disagrees with? 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 Joe Chernov

Joe Chernov

VP of Marketing

PendoRobin Powered

Bill Binch is a leader and expert in the SaaS sales industry, currently CRO @ Pendo.io, the startup that helps you understand and guide your users, creating a product experience they can't live without. They have raised over $58m in VC funding from some of the best in their space with the likes of Battery Ventures, Spark Capital and Salesforce Ventures, all backing them. As for Bill, prior to Pendo, Bill was the Senior Vice President of Global Sales at Marketo for 8 years. He joined when it was a small venture-backed startup with a mission to reinvent marketing automation. It was his sales leadership and expertise that formed a critical component in building Marketo into one of the fastest-growing enterprise software companies in the world, recognized through his being awarded worldwide VP of sales in 2011. In Today's Episode You Will Learn: How Bill made his way into the world of SaaS and came to be employee #18 at Marketo before making the transition to today, as CRO @ Pendo? Bill has said before that career paths are for B players. First, what is wrong with the current thinking around career paths? Why does that inherently mean that A players do not align with them? How can one determine when is the right time to step away from the career paths? What characteristics and attributes do those truly special opportunities have? Bill has successfully made the transition from transactional business to enterprise business many times, what have been his core learnings on what it takes to make this transition successfully? What are the biggest challenges in making the transition? How does the internal structure of the team change when making this transition? What does Bill mean when he says you have to "rig the recruiters"? What incentives can be placed in front of them that ensure you will be a priority for them? On the flip side, what incentives do you have to give the recently on boarded employees to encourage grassroots, word of mouth on the company brand? How does the company and sales cycle fundamentally change when moving from $0-1m ARR? What does that mean for the company policy on discounting and pilots? How does the company alter when transitioning from $1-10m in ARR? How can sustainable social validity be built in this stage? How does a company successfully move from $15m-100m in ARR? 60 Second SaaStr? What does Bill know now that he wishes he had known at the beginning? What keeps Bill up at night? What does Bill mean when he says you have to check your ego? 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 Bill Binch If you're looking to simplify file version control, ensure data security and save time while increasing accessibility, Egnyte is the right solution for your business. Egnyte delivers secure content collaboration, compliant data protection and simple infrastructure modernization; all on a single SaaS platform. Founded in 2007, Egnyte is privately held, headquartered in Mountain View, CA and supports thousands of businesses worldwide. For more information, please visit www.egnyte.com/SaaStr.

Bill Binch

Operating Partner

Battery VenturesPendoMarketo

Todd Olson is the Founder & CEO @ Pendo, the startup that allows you to capture all user behaviour, gather feedback and then provide contextual support. They have raised over $30m in VC funding from some of the very best in the business including Neeraj @ Battery Ventures, Megan @ Spark and Matt @ Salesforce Ventures just to name a few. As for Todd, prior to Pendo he held various different roles in product as well as co-founding 2 prior startups. In Today's Episode You Will Learn: How did Todd make his way into the world of SaaS and come to found Pendo? Why does Todd believe that there is inherent tension between customer success and product teams? How has this changed from sales and marketing team tension? What does Todd suggest to mitigate this tension? How does Todd evaluate his hiring process? At what stage does one become a specialist vs a jack of all trades? Why does Todd always believe that you should hire ahead of where you are? Todd has previously said that 'money is not all the same'. How does Todd look to select his investors? What value adds are most desired for Todd? What do the best investors do that make them so? 60 Second SaaStr What does Todd know now that he wishes he had known in the beginning? What is Todd's favourite SaaS reading material: Mattermark Daily, Tom Tunguz Creating a startup culture for adults? 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 Todd Olson

Todd Olson

Founder & CEO

Pendo

Bill Binch is a leader and expert in the SaaS sales industry. Bill was the senior vice president of worldwide sales at marketo for 8 years and he joined when it was a small venture backed startup with a mission to reinvent marketing automation, it was his sales leadership and expertise that formed a critical component in building Marketo into one of the fastest growing enterprise software companies in the world. Recognized through his being awarded worldwide VP of sales in 2011. In today's show with Bill we discuss: What were Bill's biggest takeaways from his time scaling the sales organisation at Marketo?? Why did Bill find it enticing selling to sales and marketers with Marketo? How can startups go about approaching the topic of the sales cycle? What does the right cadence look like? How can sales leaders look to establish a quota that is achievable and confident? Why is it about deal frequency not dollar size? How can we optimise the hiring process for sales professionals? What are the benefits to over hiring? Is this sustainable in a downturn? Does Bill agree that customer success will be the new sales, as Nick Mehta stated? In a round we call the 60 Second Saastr, we also hear: SaaS tools that Bill could not live without? Creating your own scorecard? What does Bill know now that he wished he had known at the beggining 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 Bill Binch

Bill Binch

Operating Partner

Battery VenturesPendoMarketo