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The Official Saastr Podcast: SaaS | Founders | Investors

The Official Saastr Podcast is the latest and greatest from the world of Saastr, interviewing the most prominent operators and investors to discover their tips, tactics and strategies to attain success in the fiercely competitive world of SaaS. On the side of the operators, we centre around getting from $0 to $100m ARR faster, what it takes to scale successfully and what are the core elements of hiring. As for the investors, we learn what metrics they hone in on when examining SaaS business, what type of metrics excites them and what they look for in SaaS founders.
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Now displaying: September, 2019
Sep 30, 2019

Jeppe Rindom is the Founder & CEO @ Pleo, the simple spending solution for your company automating expense reports and simplifying company expenses. To date, Jeppe has raised over $78m in funding for Pleo from some European favourites of mine in the form of Creandum and Vaestfonden and then also their most recent round led by Stripes Group in NYC. As for Jeppe, prior to founding Pleo he was the CEO @ Nodes, a design and development house that worked with brands including Loreal, BMW and Lego. Before that, Jeppe was the CFO @ Tradeshift where he first hand saw their scaling to 190 countries with offices in 6 different locations. 

In Today’s Episode We Discuss:

  • How did Jeppe make his way into the world of startups and SaaS with his becoming CFO @ Tradeshift? What were his biggest learnings from Tradeshift and how did that impact his operating mentality? What was that a-ha moment for him with Pleo?
  • Why did Jeppe decide to focus on SMBs from Day 1? How does the product build in the early days differ when building for SMB vs enterprise? Why does Jeppe believe that building for SMB makes it easier to build a great culture internally? How does Jeppe think about when is the right time to move into enterprise? What changes?
  • How does Jeppe respond to 3 common concerns VCs have with SMBs:
  1. The price points are so low that it takes huge volume to scale to meaningful revenue?
  2. The mortality rate of SMBs is so high that you are going to always have high churn due to the customer segment?
  3. Serving SMBs in the way that Pleo does is an intensely competitive space, is this a winner-take-all market? How does Jeppe think about competition? 
  • How does Jeppe think about NPS today? How does Jeppe approach the problem of agency when the buyer is not the user? How does Jeppe think about being customer informed but not customer-driven?
  • Pleo has a part-remote work structure, why does Jeppe advocate for this structure in the face of many saying it either has to be remote or not? What has Pleo done to make it work? What tool stack do they have to ensure seamless communication between remote and non-remote? Where are the challenges? What must one always do?
  • How does leadership change for Jesse in the face of scale? How does Jesse think about scaling humanity and the personal touch with the scaling of his leadership? What are the challenges? When do they start to arise? How has raising in the US compared to raising in Europe? What are the core differences? 

Jeppe’s 60 Second SaaStr:

  1. What does Jeppe know now that he wishes he had known at the beginning?
  2. How did raising from the US differ from raising with European investors?
  3. What would Jeppe most like to change about the world of SaaS today?

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

Jeppe Rindom

Sep 26, 2019

Gorgias helps brands automatically respond to basic questions, and track the impact of customer service on sales so support becomes a profit center. Join CEO Romain Lapeyre as he walks you through how to close your first 1000 customers based solely on data.

 

Missed the session? Here’s what Romain talks about:

  • How to build a growth machine
  • How you can tailor onboarding to customers
  • Using data to your advantage

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

Sep 23, 2019

Ryan Bonnici is the CMO @ G2, the company that allows you to get the right software and services for your business with over 897,000 user reviews to help you make smarter buying decisions. As for Ryan, prior to G2 he was Senior Director of Global Marketing at Hubspot where among many other achievements, he scaled HubSpot's marketing-generated sales revenue by 330% year-over-year. Before Hubspot, Ryan was Head of Marketing @ Salesforce (APAC) where he led his team to achieve 227% YoY net-new sales sourced through marketing. Due to his success, Ryan has been named to Forbes’ List of World’s Most Influential CMOs.

In Today’s Episode We Discuss:

  • How Ryan made his way into the world of SaaS from Sydney, Australia and came to be one of the world’s leading CMOs with G2 today? What were Ryan’s biggest takeaways from his time at Salesforce? How did it change his mindset?
  • What are the core differences when comparing marketing functions at the likes of Salesforce to smaller companies like G2? What can they learn from each other? Where does Ryan sit on whether marketing is an art or a science today? How did Ryan turn a $6,000 initiative at Hubspot into a product that generated $64m net revs?
  • What have been Ryan’s biggest lessons in what it takes to acquire the best talent? How does Ryan build candidate pipe? What works most effectively? How does Ryan structure and run the process? What core questions does Ryan ask and find most revealing of the individual’s character? What does Ryan love to see in a candidate? 
  • Does Ryan agree that marketing teams should always be held directly accountable to a number tied to revenue? What type of CMO would Ryan bucket himself as; demand gen or brand? How does Ryan think about the relationship between the two? 

Ryan’s 60 Second SaaStr:

  1. What does Ryan know now that he wishes he had known at the beginning of his career in marketing? 
  2. What is the biggest BS that Ryan often hears in the world of marketing?
  3. Which marketing leader does Ryan most respect and admire and why?

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

Ryan Bonnici

Sep 19, 2019

SaaS is about creating long-term value for your customer, and being compensated appropriately for that value as a business. Learn actionable monetization tips from a Product/Growth operator turned VC.

 

Missed the session? Here’s what Naomi  talks about:

  • How to avoid underpricing your product
  • Fitting your businesses’ product to the market

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

Sep 16, 2019

Janine Pelosi is the CMO @ Zoom, the next-generation enterprise phone system. Prior to their very successful IPO, Zoom raised funding from some of the best in the business including Sequoia, Emergence Capital, Horizons Ventures and 2 of my favourites in the form of Matt Ocko @ Data Collective and Dan Scheinman. As for Janine before joining Zoom, she spent 11 years at Cisco where among many incredible achievements she led worldwide demand gen for WebEx and led their worldwide digital marketing team with a $25M annual budget. 

In Today’s Episode We Discuss:

  • How Janine made her way into the world of SaaS and came to be one of the leading CMOs today with Zoom?
  • How has the role of the CMO changed over the last 5 years? Would Janine agree with Jason Lemkin that “the role of the CMO is to execute the vision of the CEO”? What makes Janine and Eric’s relationship so successful? What makes Eric the special leader that he is? How does the changing power of the CMO affect their relationship with the CEO?   
  • When is the right time for startups to hire their first CMO? What should they look for in that ideal candidate? What should they have in place in terms of infrastructure, prior to hiring the candidate? What does the right onboarding process look like for a CMO? Where does Janine see many going wrong when hiring their first CMO? 
  • How does Janine look to create alignment between sales and marketing? Why does Janine not believe in having the labels of “MQLs and SQLs”? How does Janine look to reduce the friction when handing off between marketing and sales? What are the common causes? How are we seeing marketing also blend with customer success?

Janine’s 60 Second SaaStr:

  1. What does Janine know now that she wishes she had known at the start of her time at Zoom?
  2. Who does Janine most respect in the world of marketing today? Why?
  3. What would Janine most like to change about the world of SaaS today? 

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

Janine Pelosi

Sep 12, 2019

Matt Schatz is SVP of Sales at WPEngine, responsible for defining and executing the global sales strategy. Matt has nearly two decades of senior leadership experience in sales and customer growth, specifically for technology companies with customers around the world including Bazaarvoice, CityVoice and Rackspace.

 

Missed the session? Here’s what Matt  talks about:

  • Getting your “first story”
  • What is a lucky lead and how does that turn into predictable growth
  • Building trust across time zones

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

Sep 9, 2019

Allison Pickens is the COO @ Gainsight, the company that provides everything you need to turn your customers into your biggest growth engine. To date Gainsight have raised over $184m from some of the world’s best VCs in the form of Lightspeed, Bessemer, Insight Venture Partners, Battery Ventures and Salesforce Ventures just to name a few. As for Allison, in her 5 years at Gainsight her list of achievements in endless from running all functions that drive value for Gainsight customers, now a 150 person team, to building out the corporate development function to being the right hand to the CEO. Allison is also an Entrepreneur-In-Residence at Bessemer Venture Partners and sits on the board of RainforestQA. Before Gainsight, Allison started her career in NYC with stints at Bain and The Boston Consulting Group.

In Today’s Episode We Discuss:

  • How Allison made her way into the world of SaaS with Gainsight from her start in finance at Bain in New York?
  • What does a strategic plan really mean to Allison? What is included in it? How should it be structured? In terms of ambition, how does one set ambitious enough plans to be a stretch but not a stretch too far? How does one tie their strategic plan to their financial plan? What is the right way to communicate this throughout the organisation?   
  • Why does Allison believe product marketing and customer success are the new sales and marketing? What have been Allison’s biggest lessons on how to effectively measure adoption? Who is accountable to this number? CS or product management? Does Allison believe that marketing needs to be held accountable to a number directly tied to revenue? 
  • How does Allsion respond to the common negative of “services revenue”? What is an acceptable ratio of services to software revenue? How can one approach setting up a services team for scale? Why is having such a great CS team actually bad for product development in the long run? How can one mitigate this?

Allison’s 60 Second SaaStr:

  1. What does Allison know now that she wishes she had known at the beginning of her time with Gainsight?
  2. How often should CS check in with their customers? What does that look like? 
  3. If on a tight budget, how should one staff a CS team?

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

Allison Picken

Sep 5, 2019

Building a company made up of distributed teams presents a plethora of complex challenges that can derail productivity and impact employee retention. But with it comes immense benefits and competitive advantages such as the diversification of ideas, speedier product development, and representation in important regions and time zones. Come and hear about the typical pitfalls (and how to avoid them) from Pat Poels, an executive with over seven years under his belt leading Eventbrite’s now 300+ strong engineering team that sits across North America, South America, and Europe

 

Missed the session? Here’s what Pat  talks about:

  • Engineering your own luck
  • How to build an engineering team

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

Sep 2, 2019

Jon Herstein is the Chief Customer Officer at Box, the company that provides one platform for secure content management, workflow and collaboration. Prior to their IPO, Box had raised funding from some of the best in the business including Andreesen Horowitz, Bessemer, DST, Emergence and Meritech, just to name a few. As for Jon, prior to being Chief Customer Officer at Box, he was Senior VP of Customer Success, responsible for all post-sales services Box provides from implementation to user adoption and more. Before Box, Jon spent 4 years as VP of Professional Services at NetSuite and prior to that, close to 8 years as Senior Director of professional services at Informatica.

In Today’s Episode We Discuss:

  • How did Jon make his way into the world of SaaS and come to be one of the leading figures in the rising tide of the customer success movement?
  • What does Jon mean when he says, “you have to constantly bring your customers to the forefront of your employees minds”? For non-customer facing roles, what can one do to give them that perspective? Does it work to ensure every function spends time in customer support? What is challenging about that? What can be done in the onboarding phase to ensure the individual has the most empathy for the customer, regardless of function?  
  • For those in CS, what is the right communication cadence to check in with their accounts? What should the agenda look like? What outcomes should they drive towards? Should they be involved in the upsell process? How does Jon think about post-mortems on churned clients? How do they structure them? What lost client stands out to Jon and what would he have done differently to retain them?
  • From Jon’s experience seeing Box in hyperscaling, at what stages do SaaS orgs start to break down? Why does Jon think that is? What can be done to proactively try and mitigate this? How does Jon think about the structuring of roles and responsibilities with scale? What does this done well look like? Where do many people go wrong here?  

Jon’s 60 Second SaaStr:

  1. What does Jon know now that he wishes he had known at the beginning of his time with Box?
  2. What motto or quote does Jon frequently revert back to?
  3. What is the most challenging element of Jon’s role with Box today?

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

Jon Herstein

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.

 

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