The Official SaaStr Podcast: SaaS | Founders | Investors

Dropbox Chief Customer Officer Yamini Rangan draws on 20 years of experience to challenge five common misconceptions about SaaS success. From beating the competition to over (or under) relying on Outbound, she offers a practical perspective on the frameworks that are holding businesses back from reaching their full potential in a changing landscape.   Missed the session? Here’s what Yamini talks about: How to increase the odds of reaching $1B in ARR What is the pull upmarket, why do companies focus their attention there? Common go-to-market myths and lessons. If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin SaaStr  

David Skok is a serial entrepreneur turned VC at Matrix Partners. He founded four companies: Skok Systems, Corporate Software Europe, Watermark Software, and SilverStream Software and did one turnaround with Xionics. Three of the companies he founded went public and one was acquired. Jason Lemkin is the Founder @ SaaStr, the world’s largest SaaS community and leading early-stage SaaS fund with investments in Automile, TalkDesk, Algolia and more. Jason Vandeboom is the Founder of ActiveCampaign, a sales and marketing automation platform that enables small businesses around the world to meaningfully connect and engage with their customers. Since 2013 with their transition to SaaS have grown to more than $50 million in ARR in less than five years, while maintaining profitability. Dave Kellogg is a leading technology executive, independent board member, advisor and angel investor. In his most recent role, Dave was the CEO @ Host Analytics where he quintupled ARR, halved customer acquisition costs and increased net retention rates before selling the company to a private equity sponsor. Fred Shilmover is the CEO and co-founder of InsightSquared, one of Boston’s premiere tech startups paving the way in the sales intelligence space. Throughout the InsightSquared journey, Fred has raised over $25m in VC funding from the likes of DFJ, Bessemer, Salesforce and Atlas Venture. In Today’s Episode We Discuss: Does David Skok believe that ACV should sit at the top of the metrics stack? What are the 4 metrics that fundamentally matter in your business? What can founders do to their pricing model to extract as much value from each customer? How do the very best businesses structure their pricing for value extraction? If ACV increase is a core focus for our startup, should we hire a sales rep solely selling to enterprise? What are the biggest mistakes founders make in this scenario? What can founders do to optimise revenue per lead? How does on need o approach lead targeting according to the individual skills of their reps? Is it best to start at enterprise and work down to SMB or does SMB and work up to enterprise work best? How does the product have to change with the scaling to enterprise? How does the messaging need to change with the scaling to enterprise? How do you need this change to be reflected in your pricing?     What does it truly mean to be an ARR first company? What is the right way for founders to calculate their differing ACVs? What is the right way to present that when pitching VCs? Where do many founders go wrong in how they present and discuss ACVs with investors? 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: Harry Stebbings Jason Lemkin SaaStr David Skok Jason Vandeboom Dave Kellogg Fred Shilmover

Flexport CEO Ryan Petersen will share what he has learned about scaling culture, expanding globally, raising venture capital (or not), and using technology to improve legacy industries.   Missed the session? Here’s what Ryan talks about: How Flexport grew to a multibillion-dollar business. How the company broke into the $2T freight forwarding industry.   If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin SaaStr Ryan Petersen

Sara Varni is the CMO @ Twilio, the company building the future of communications allowing you to engage customers like never before on voice, SMS, WhatsApp or Video. Prior to their IPO in 2016, Twilio had raised over $250m in VC funding from some of the best in venture including USV, Bessemer, Salesforce and Techstars just to name a few. As for Sara, prior to Twilio she spent 10 years with Salesforce in numerous roles including SVP of Marketing for Salesforce’s Sales Cloud and CMO @ Desk.com, among other roles. If that wasn’t enough, Sara is also an advisor @ Anthos Capital. In Today’s Episode We Discuss: How did Sara made her way into the world of SaaS and came to be one of the industry’s leading CMOs with Twilio today? What were Sara’s biggest takeaways from her 10 years at Salesforce seeing the incredible hyper-growth first hand? What does Sara mean when she says, “you have to have a creative plan to get your message to market”? Does Sara really believe that there is a playbook when it comes to marketing? How does Sara determine when to throw the playbook out of the window? What resounding question do you always have to ask yourself when thinking messaging? Messaging is very dependent on the customer being targeted, how does the messaging need to be different when targeting SMB vs enterprise? How does the creative plan to get the message to the target customer change dependent on SMB vs enterprise? Where does Sara see most people go wrong here?    Why does Sara so strongly believe in the power of customer stories? What makes the very best customer stories? What would Sara’s advice be to someone who is wanting to start creating them? Where does Sara see so many people go wrong? What are Sara’s tips for creating this alignment between the marketing team that make the stories and the sales team that sell them? Where are there often points of tension? What does the very commonly used term, “enablement”, really mean to Sara? Does it mean you can hire lower quality candidates and upgrade them? How does Sara distinguish between a stretch VP and a stretch too far? What questions does Sara find most revealing in the interview process?   60 Second SaaStr: What does Sara know now that she wishes she had known at the beginning? Who is crushing it in the world of SaaS marketing today? What is the most common reason for the breakdown of an efficient funnel? 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 Sara Varni

It’s the employees’ market. There are more jobs than there are qualified people to do them. SaaS companies face sustained headwinds in the attracting, cultivating, driving productivity, and retaining talent. Your market competitors are your adversaries, but so is the entrepreneur sitting right next to you whose business is in a completely different sector. Namely CEO Elisa Steele shares practical advice on how to win three key Talentshare battles, which are essential to winning the Marketshare war. Missed the session? Here’s what Elisa talks about: How to win Talentshare when the system is stacked against you. How to drive synchronization, productivity when your needs are constantly evolving and the talent mix is incredibly fluid and diverse. How to use Culture as the lever to maximize the ROI that you get out of the biggest investment your business will ever make. If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin SaaStr Elisa Steele

Dave Kellogg is a leading technology executive, independent board member, advisor and angel investor. In his most recent role, Dave was the CEO @ Host Analytics where he quintupled ARR, halved customer acquisition costs and increased net retention rates before selling the company to a private equity sponsor. Before that Dave was SVP/GM of Service Cloud @ Salesforce where he led the $500m line of business for customer service applications. Finally pre-Salesforce, Dave was CEO @ MarkLogic where he grew the team from 40 to 240 and revenues from $0 to an $80m revenue run rate. If that was not enough, Dave currently or has previously sat on the boards of Nuxeo, Alation, Aster Data and Granular. In Today’s Episode We Discuss: How did Dave make his way into the world of SaaS over 20 years ago? How did seeing the boom and bust of the dot com and 2008 affect Dave’s operating mentality? What were his biggest lessons from being in the Sequoia boardroom when they presented “RIP good time”? How does Dave think about when is the right time to raise? How does Dave advise founders on how much is the right amount to raise? Does Dave agree that if the money is on the table founding teams should take it? Why does Dave believe 99% of companies die? The first step in being acquired by a PE house is “making the book”, what goes into “making the book”? Who is involved? How long does it take? What are the clear differences between a good book and a bad book? How should execs think about making exciting enough go-forward plans for it to be attractive to buyers but also realistic enough that they can hit it in the acquisition process?   How does the selection for who receives the book look? Who decides this? What is the fundamental aim in the distribution of the book to many parties at the same time? What does Dave know now about the world of PE that he wishes he had known at the beginning? IOI’s is the next step, what are they? How do they set up the process from there? How do management meetings with potential PE acquiring firms compare to founders meeting VCs in the early days? How many meetings is normal to have in this process? How long do they last? What does Dave believe is crucial to achieve in these in person meetings? How much of a role does price play in selecting the ultimate acquiror? How much of a role does their brand and reputation play? 60 Second SaaStr: What does Dave know about the process that he wishes he had known at the beginning? The biggest misconception about the world of PE and acquisitions? Burn rate is a function of the personality of the CEO? Agree or disagree? Why? 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 Dave Kellogg

Brex Co-Founder and CEO Henrique Dubugras will talk about what he's learned building the fastest-growing B2B company. Henrique started his first company at 16 and has now built two successful companies from nothing. Learn what he did differently the second time around and the specific decisions he made to drive growth among B2B companies with Brex.   Missed the session? Here’s what Henrique talks about: How Brex grew from a few basic functionalities to a corporation Growing from $0 to $2B in ARR in less than two years. If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin SaaStr Henrique Dubugras

Amit Bendov, Founder and CEO of Gong.io, shares insights from his journey in SaaS, emphasizing the importance of validating ideas through customer conversations. He discusses pricing strategies, including the right time to introduce charges and the balance between customer expectations and actual payments. Amit also explores the complexities of sales technology and the essential roles within sales organizations. He underscores resilience in entrepreneurship and the significance of connection in building a brand.

Join Molly Ford, Salesforce Global Equality Programs Senior Director, and Leyla Seka, Salesforce VP of Mobile for actionable advice they have applied on their own journey. Here are their lessons learned on driving change in gender equality, equal pay and racial equality within Salesforce. Missed the session? Here’s what Molly and Leyla talk about: Building a community of allies and allyship How to drive equality What you can be doing as an employee to help drive the culture you want If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin SaaStr Molly Ford Leyla Seka  

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