The Official SaaStr Podcast: SaaS | Founders | Investors

Whitney Bouck is the COO @ HelloSign (now a part of Dropbox). For those that do not know, HelloSign is the company reimagining how you approach your most important business agreements with their award-winning e-Sign solution. As for Whitney, she directly leads the organization's go-to-market efforts, including sales, marketing, business development and customer operations. Whitney is also an advisor to companies funded by the YC Continuity Fund, focusing on enterprise strategy, go-to-market strategy, leadership and execution. If that was not enough, Whitney is also on the board of Ekata, building the global standard in identity verification. Finally, prior to HelloSign Whitney spent close to 5 years at Box where as SVP Global Marketing & GM Enterprise she took on all of marketing globally for Box and was responsible for reshaping the company brand from SMB to enterprise. In Today's Episode We Discuss: How Whitney made her way into the world of SaaS originally with Box and how that led to her coming one of today's leading COOs with HelloSign? What were Whitney's biggest takeaways from seeing the hypergrowth of Box? How did that change her operating mentality? What does truly successful exec leadership look like in Whitney's mind? When is the right time for founders to think about building out their first exec team? What common mistakes do they make in the process? What can founders do to attract seasoned SaaS execs to their early-stage company? What are the questions that suggest an individual has a startup culture to them? What are the indications that they are a "big company" person? What does Whitney believe is the new role of the CIO? What has changed about their tole and what has driven this change? With their coming front and centre in the org, how does that change both the reporting and operating structure of the business? What are the nuances and intricacies of this role that many do not often consider? COO is thrown around as a term today, what does it really mean to Whitney? What does Whitney believe separates good from great when it comes to COOs? When is the right time for founders to start looking for their first COO? What should they look for in their first COO? What is the optimal onboarding process for any new COO? Whitney's 60 Second SaaStr: What does Whitney know now that she wishes she had known at the beginning? What makes for the optimal relationship between COO and CEO? What is the most challenging element of Whitney's role with HelloSign today? 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 Whitney Bouck Ever feel like you can't really connect with prospects or have an organized workflow to get deals closed? Outreach.io, the leading Sales Engagement platform, supports sales reps and their managers by making it simple to humanize and personalize communication at scale; automating the soul-sucking manual work; and dramatically increasing the productivity and efficiency of all revenue-generating teams. You can check them out at outreach.io/saastr to chat with them and receive a free copy of their new book -- Sales Engagement: How The World's Fastest-Growing Companies are Modernizing Sales Through Humanization at Scale.

Our guest today is Pipedrive SVP of Global Sales Tara Bryant. Globalization opens up a world of opportunities for sales growth. We often focus on the positive sides of growth—but what about taking a look at the ugly sides? Even what we could consider "good problems" need preparation, and it starts by understanding your team and your goals, including knowing when and how to recruit members of your team, and building in a way that compliments your growth. Do you need more man-power on the customer facing side, or do you need to bring in new management to keep everything in line? Growth isn't always linear, and the steps to success aren't always one after the other. How do you prioritize and organize to bring the best possible results? This side of success can be scary, but knowing how to prepare can set you up to reach your companies long term growth goals. Missed the session? Here's what Tara talks about: What does the ideal candidate look like? How to hire your core staff really well Enabling salespeople to share learnings 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

Companies that have access to more accurate financial data have the ability to develop seamless exchanges of information, providing consumers with improved ways to manage their finances. But how do companies gain secure access to that data in the first place? Enter the platform company. Hear from Plaid co-founder and CEO, Zach Perret and CNBC's Ari Levy as he walks through his lessons learned building Plaid and how it found itself at the center of the fintech ecosystem. 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 Zach Perret

Former SVP Sales @ PatientPop, Justin Welsh, discusses scaling sales culture sustainably, signs of burnout, communicating with superiors about burnout, and the importance of culture over performance in a team setting.

As a global technology provider powering thousands of SaaS companies, Google is at the forefront of driving exciting and innovative technologies to market. Eyal Manor and Megan Lueders host a fireside chat between Google Cloud and Zenoss, a leader in software-defined IT operations. They discuss the most common and emerging challenges facing SaaS companies today. You'll also learn how leading SaaS companies are able to scale and thrive in this complex, dynamic environment. Join us for this lively discussion between two innovators. Missed the session? Here's what Eyal and Megan talks about: How to develop software faster The emergence of new A.I. services Why the "strongest" conversations need to happen between engineering and marketing 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

Vikas Bhambri is SVP Sales and Customer Experience @ Kustomer, the startup providing Real-time, actionable views of customers with continuous omnichannel conversations and intelligence that automates repetitive, manual tasks. To date they have raised over $113m in financing from some of the best in the business including Tiger Global, Battery Ventures, Boldstart, Canaan, Cisco and Redpoint just to name a few. Prior to Kustomer, Vikas spent over 20 years implementing, consulting, marketing, and selling CRM and ContactCenter solutions with companies like LivePerson and Oracle. In Today's Episode We Discuss: How Vikas made his way into the world of SaaS and came to be at the rocketship that is Kustomer? Why does Vikas believe that a wave of SaaS incumbents are about to be displaced or disrupted? What about the changing tech stacks and infrastructures makes them vulnerable to up and comers? Does this not lead to a consolidatory environment? How does Vikas see the space play out in the coming years when it comes to acquisitions? What have been the dramatic changes that have happened in sales over the last few years? What is the right way for startup founders to address sales rep onboarding? Why is it so crucial to invest in enablement in the early days? How should this enablement be structured? How does this change sales rep payback periods? What is a good payback period? How does Vikas feel about discounting? If accepted, what must the startup ask for in return? How does Vikas think about multi-year deals? When are they good? What sort of terms make them less beneficial for the vendor? How does Vikas think about professional services? What is a good margin for professional services? What ratio of revenue is healthy for professional services to account for? When should one look to hire their first customer success reps? What should they look for in those reps? Vikas' 60 Second SaaStr: What does Vikas know now that he wishes he had known at the beginning? What is his secret to building diverse teams? The sales leader Vikas most respects and admirers and 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

The age-old sales funnel has worked fine for decades…until now. Flaws are being exposed, and a new model is imminent. Why is the sales funnel alone no longer an appropriate way thinking about customers? What will emerge to supplement or replace it? HubSpot CEO Brian Halligan and NEA's Hilarie Koplow-McAdams explore the evolution of the marketing and sales funnel you've been using for decades to generate traffic and convert and leads into customers. Missed the session? Here's what Brian talks about: Why a flywheel instead of a funnel? What does the Grateful Dead have to do with Marketing…? What role do T shaped people play? 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 Brian Halligan

Leah Busque is currently a General Partner at Fuel Capital, an early stage venture fund located in Silicon Valley. She likes to invest across consumer, B2B saas, and technology infrastructure companies at the earliest stages. In 2008 Leah founded TaskRabbit, the leading on-demand service marketplace in the world. She spent nearly a decade involved with the company as CEO and Executive Chairwoman before she sold the company to IKEA in October of 2017. Hear about her takeaways from a product reboot with TaskRabbit. Missed the session? Here's what Leah talks about: What are the lessons learned from a product reboot? When bringing a product to market - what are the BHAGs? How to navigate a product pivot. 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 Leah Busque

Eric Christopher is the Founder and CEO @ Zylo, the software management system built for the cloud pioneering a new standard in software management. To date, Eric has raised over $12m for Zylo from some of the best in the business including Byron @ Bessemer, Salesforce, GGV, Semil @ Haystack and the team at High Alpha. Prior to founding Zylo, Eric was the VP of Sales @ Sprout Social leading the revenue operations for over 11,000 customers. Before Sprout Social he was VP of Sales at Shoutlet, responsible for global direct and channel sales teams and developing and managing strategic relationships. Finally, prior to Shoutlet, Eric spent over 7 years at ExactTarget as a Senior Business Development Manager which is where he met High Alpha's Scott Dorsey. In Today's Episode We Discuss: How Eric made his way into the world of startups and SaaS? What were his biggest takeaways from working with Scott Dorsey @ ExactTarget? What was the founding moment with Zylo? What have been Eric's biggest lessons when it comes to making the transition from founder led sales to sales team? What would we have done differently with the benefit of hindsight? What were the biggest challenges in the process? How does Eric think about the importance of quantity vs quality of logos when acquiring your first few customers? Do big logo brand names really provide social validity or is it over-hyped? How does Eric think about discounting in the early days? What can founders do to really extract the most value from the discount they are giving away? Why does Eric believe that hitting the employee 50 mark is a huge moment for founders and the scaling of the company? What fundamentally changes? What gets harder? What gets easier? How has Eric seen his role evolve with the scaling of the team? How does Eric think about goal and KPI setting with a much larger team? What needs to change? How does one create and retain accountability and ownership at scale? Why does Eric believe that the bar for execution in SaaS in 2019 is so much higher than in 2009? What has changed? How does this make Eric change the way he approaches benchmarking, capital allocation and growth? How did Eric find raising the Series A as a non-Bay area company? Eric's 60 Second SaaStr: What does Eric know now that he wishes he had known at the beginning? What is the toughest role to hire for today? If the money is on the table, take it. Agree or not? 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 Eric Christopher

Michael Seibel, CEO and partner at Y Combinator, shares valuable insights drawn from his decade of experience in the startup world. He emphasizes the importance of aligning hiring with achieving product-market fit, warning against premature scaling. Seibel discusses when to sell a startup and the misconception that raising funds guarantees success. He also highlights best practices for hiring and stresses the need for transparency within teams. Tune in for actionable advice on navigating the tricky waters of early-stage entrepreneurship!