The Official SaaStr Podcast: SaaS | Founders | Investors

Michael Pryor, Co-Founder & CEO @ Trello, now Head of Trello Product with Atlassian following their recent acquisition.

Kolton Andrus is the Founder & CEO @ Gremlin, the failure as a service startup finds weaknesses in your system before they cause problems.

Dylan Serota, Co-Founder and Chief Strategy Officer @ Terminal, the startup that helps you create world-class technical teams through remote operations as a service.

Rachel Carlson, Co-Founder and CEO @ Guild Education, the leader in education benefits offering the single most scalable solution for preparing the workforce of today for the jobs of tomorrow. 

Sid Sijbrandi, Founder & CEO @ Gitlab, a single application for the entire software development lifecycle.

Jeppe Rindom is the Founder & CEO @ Pleo, the simple spending solution for your company automating expense reports and simplifying company expenses.

In Today’s Episode We Discuss:

• How should founders think about the debate between all remote vs part remote teams? How does life and operations change with each? What are the pros and cons? Is it possible to move between the two overtime?
• What can one do to maintain culture with remote teams? What processes need to be in place to ensure a cohesive and streamlined communication process? What technical architecture needs to be in place? Where are the breakpoints when it comes to communication? How often does one need to do in person off-sites?
• How does being remote or part remote impact fundraising? How do VCs think about this new structure of operations? What is the right way to present it? How does being outside a core tech hub impact one’s ability to raise? How should one run a fundraising process if outside a core hub?  
• How important is it for your team to be near your customers? How does this change according to sector and customer base? How important is it for your team to be near your investors? Does having an exec and sales team in one place and the rest of the team elsewhere work?  

Jason Lemkin

Harry Stebbings

SaaStr

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Rene Yang Stewart, Co-Head and Principal, Vista Equity Partners, and Monica Enand, Founder and CEO, Zapproved discuss growing a company from product market fit to scale. Vista Equity Partners invested in Zapproved in 2017. Hear perspectives from both the investor and founder on growth to scale.

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

How do you manage a sales team when you're at a company with both Free and Freemium Sales-Driven Segments? What about SMB vs. Enterprise Sales? SaaStr CEO Jason Lemkin sits down with Mixmax's Head of Revenue Don Erwin to discuss it all.

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Glassdoor CEO Robert Hohman and Battery Ventures' Neeraj Agrawal  walkthrough Glassdoor's $1.2 Billion story from its launch in 2008 to its 2018 acquisition by Recruit Holdings. Hear about the early days of Glassdoor; tactical lessons on scaling—from building a business model and recruiting an all-star management team to advice on building a compelling, innovative company culture; and learn whyGlassdoor’s $1.2 Billion acquisition is just one milestone in the early innings of the company’s story.

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Krish Subramanian is the Founder & CEO @ Chargebee, the startup that lets you go beyond billing, payments and recurring invoices — to delivering subscription experiences that "wow". To date, Chargebee have “wowed” some of the world’s leading VCs to the tune of $38m including the likes of Insight Venture Partners, Tiger Global, Steadview and Accel Partners. As for Krish, under Krish’s leadership the team has grown to over 300 people and over 5,000 clients making it one of the next generation in truly global SaaS businesses started in India. 

In Today’s Episode We Discuss:

• How Krish made his way into the world of SaaS and came to found one of India’s fastest growing SaaS companies in Chargebee?
• What does Krish mean when he says, “in SaaS, you either sell to one of 2 customer profiles”? How does Krish think about purely serving the SMB market? Does one have to move to enterprise? Does one have to expand the product line to retain customers? How does he think about the mortality rate of SMBs?  
• First, what is continuous customer development? Second, why does Krish believe it is one of the most important things any company must do? What is the process to do it efficiently? Does it have to be in person? What questions reveal the most? How should this data feedback into your product roadmap and pipeline? 
• How does Krish think your customer acquisition and GTM strategy has to change with the movement from SMB to enterprise? What are the biggest challenges in making this transition? How does your customer success and customer support functions change with the move to enterprise? 

Krish’s 60 Second SaaStr:

1. Biggest lessons from working with Lee Fixel?
2. How does one know when is the right time to introduce a new product?
3. What does Krish know now that he wishes he had known at the beginning?

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

Krish Subramanian

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

When is the right time to go upmarket and how do you serve small, medium and large customers in the same company. SaaStr CEO Jason Lemkin sits down with Shopify Plus GM Loren Padelford to discuss.

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Liat Bycel is VP of Customer Engagement @ Airtable, the startup that works like a spreadsheet but gives you the power to organise anything. To date, Airtable has raised over $170m in funding from some of the best in the business including Thrive, Coatue, Founder Collective, CRV and individuals like Patrick Collison, Ashton Kutcher and Raymond Tonsing to name a few. As for Liat, prior to Airtable, she was the Chief Revenue Officer @ Assist. Before Assist, Liat spent 6 years at Twitter where she first hand saw their hyper-growth, managing a team of 40 across New York and SF and also Liat achieved 102% to quota on average every year. Finally before Twitter, Liat was VP of Sales @ Revolution Prep where she led and managed 7 offices. 

 In Today’s Episode We Discuss:

• How Liat made her way into the world of SaaS and came to be VP of Customer Engagement at one of Silicon Valley’s hottest startups in Airtable? 
• What were Liat’s biggest lessons from Twitter on how to hire successfully? What were some of the key takeaways from that experience on how, why and when to fire? Is there ever a right way to do it? How does Liat think about aligning both the personal ambitions of the person with the wider objectives of the company? Why does Liat reject the notion of “hands off leadership?”  
• Companies often worry about whether to go horizontal or vertical, how does Liat personally think about this choice? What does she advise founders as a result? What are the core questions they should ask to determine their strategy? What are the biggest challenges of having such a vertical product? How does it impact messaging and brand? Product roadmap? Pricing?
• How does Liat think about challenging the traditional sales model? How does that challenge the structure of the conventional AE and SDR structure? How does Liat think Airtable is pushing up against the traditional customer success model? How has having children impacted how Liat thinks about operating today? What changes with children? 

Liat’s 60 Second SaaStr:

1. What does Liat know now that she wishes she had known at the beginning of her time with Airtable?
2. What are Liat’s biggest strengths and weaknesses?
3. What are the challenges of prioritisation?

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

Liat Bycel

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

SaaStr CEO Jason Lemkin sits down with Gainsight CEO Nick Mehta to discuss what it means to be a SaaS leader. What are the day-to-day struggles? The fears and the worries and what it means to be "crushing it" 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

SaaStr

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Robert Vis is the Founder & CEO @ MessageBird, the company that allows you to talk to your customers via Voice, SMS and Whatsapp. The company raised a monster $60M Series A from Accel and Atomico with only one prior investor being Y Combinator. As for Robert, prior to MessageBird, he was co-founder and CEO of Zaypay.com which focused on driving mobile payments into 50+ countries, enabling 1.5bln users to pay for virtual goods through their phones (sold to Mobile Interactive Group (MIG). 

In Today’s Episode We Discuss:

• How Robert made his way into the world of startups and SaaS and came to found Messagebird? What was the a-ha moment for him? 
• Why does Robert believe the most important element of being a founder is “thinking big”? How as a founder do you balance between thinking big with investors and then the day to day in the weeds with the team? How does Robert as Europe’s mentality of thinking big today? Have our ambitions exceeded what they have been before? How does being in Benelux change how Robert thinks about global ambitions and growth ambitions?  
• What does Robert mean when he tells founders, “don’t try to scale”? How does Robert think about knowing when a business is ready to scale? Where do many founders go wrong in the preparation for scale phase? What does one need to get in place before scaling?
• Why did Robert wait 6 years before raising any VC money? Why did he decide then was the right time? Once the raise was in, did he feel the pressure of suddenly having a lot of VC funding? How did his mindset to capital allocation change post-raise? How did he see his decision-making process change post raise? How did raising from the US differ from raising in the UK? 

Robert’s 60 Second SaaStr:

1. What does Robert know now that he wishes he had known at the beginning of his time with Messagebird?
2. What keeps Robert up at night? 
3. What are Robert’s strengths and weaknesses? 
4. What advice in SaaS does Robert most often hear that he disagrees with?

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

Robert Vis 

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

David Cummings is the co-founder of the Atlanta Tech Village, Pardot which sold to ExactTarget/Salesforce.com, Hannon Hill,  Rigor, SalesLoft (raised over $75M in capital), Terminus (raised over $25M in capital), and several more. Hear his lessons learned over the years from Pardot to Calendly.

 

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

• How large a role does funding play?
• Matching pricing to value
• How to continuously level up talent

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

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com