The Official SaaStr Podcast: SaaS | Founders | Investors

Kurt Bilafer is the CRO @ WePay, the most complete payments solution for platforms. To date, they have raised close to $75m in VC funding from some of the best in the business including Max Levchin and August Capital just to name a few. As for Kurt himself, prior to WePay he has had experience both in startups and large corporations with his founding of Pilot Software, sold to SAP in 2007, where he spent a further 7 years holding titles such as a Global Vice President of Sales and Director of Strategic Accounts.

In Today’s Episode You Will Learn:

• How did Kurt make his way into the world of SaaS? What were Kurt’s big takeaways from seeing the internal machinations of SAP?
• What is the one metric that guides Kurt’s thinking? How can you calculate your “magic number” for your business? Why must SaaS founders switch from activity based metrics to KPI’s?
• How does Kurt assess scalability and repeatability of revenues? What is a reasonable ratio for sales and marketing expense to revenue?
• Why should SaaS founders focus on the LPI of “time to money”. How can they look to optimize this? How has Kurt seen the enterprise sales cycles change since his time with SAP?
• How does Kurt assess conflict within the sales and marketing teams and customer success and product teams? How can managers look to implement an element of prioritization into what sales teams submit to product teams?

60 Second SaaStr

1. What does Kurt know now that he wishes he had known at the beginning?
2. What is the worst piece of SaaS advice that Kurt commonly hears being given out?
3. What should one look for in their VP of Sales?
4. What mistake does Kurt see most in the world of SaaS?

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

Kurt Bilafer

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

Jens Nylander is the Founder and CEO @ Automile, the startup that makes fleet and asset management much much easier. They have backing from some of the best in the business including Godfather of SaaS himself Jason Lemkin, the wonderful team at Point Nine, Justin Kan and Dawn Capital in London. As for Jens, he really is a serial entrepreneur with past endeavours including creating Sweden’s largest music player and founding Jays, the manufacturer and developer of innovative headphones that went public and is listed on the NASDAQ.

In Today’s Episode You Will Learn:

• How did Jens make his way into the world of SaaS and come to found Automile?
• How does Jens look to build a repeatable scalable sales process with Automile? What are the core infrastructure requirements needed to make the process as automated as possible?
• How does Jens evaluate selling into the SMB market? How does Jens look to optimise the onboarding process to maximise conversion? How does Jens look to minimise churn with a market as potentially unstable as SMB’s?
• Why does Jens prefer technology minded sales teams? What benefits do they bring in terms of process to the sales cycle? What should founders look for in potential new engineering led sales teams?  
• Jens is increasing transparent, posting numerous figures on Twitter, what are the benefits of such transparency? How does that help the team to achieve the wider goal? Are there any cases, such as fundraising or exits, where transparency has negative consequences?

60 Second SaaStr

• What was the hardest element of leaving Europe to go big in the US?
• What does Jens know now that he wishes he had known at the beginning?
• What hires does Jens wish he had made earlier?

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

Jens Nylander

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

Steve Loughlin is a Partner @ Accel in San Francisco, one of the leading funds with prior investments in the likes of Facebook, Dropbox, Atlassian, Slack and many more incredible companies. Prior to Accel, Steve was the CEO and co-founder of RelateIQ, later named SalesforceIQ following the acquisition of the company by Salesforce in 2014 for $390 million. Steve was also president and CEO of Affinity Circles, a professional social network that connected more than 18 million professionals. Steve has also advised or invested in the likes of Palantir Technologies, Addepar, and Roam Analytics.

In Today’s Episode You Will Learn:

• How Steve made his way into the world of SaaS with the founding of RelateIQ and then came to be a Partner at Accel on the other side of the table?
• Why does Steve believe the hardest balance a founder has to consider is the balance between building for the future and building for the present? How can this short to long term dichotomy be considered effectively by the team?
• RelateIQ was early to the AI/ML landscape, what does Steve think they did so right with RelateIQ? Does Steve agree that for an enterprise ML play to be interesting it must fundamentally change the go to market strategy?
• What were the key learnings from working so closely with Marc Benioff on the Salesforce exec team? What is it about the internal structure and operations of Salesforce that make it the massively profitable behemoth that it is today?  
• Having been a founder himself and now a VC, how does Steve look to help founders specifically? Where has Steve found that early stage founders need the most help? Where do VCs proclaim to help the most but really do not at all? 

60 Second SaaStr

1. What is the worst advice Steve often hears being given?
2. What is something that Steve has changed his mind radically on over the last few years?
3. What is Steve’s favourite SaaS reading material?
4. What does Steve 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

Steve Loughlin

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

May Habib is the Founder & CEO @ Qordoba, the best platform for building truly localized products across apps, websites and marketing content. It is the fastest, most scalable way to grow from one market to many. We do also want to say a big congratulations to May for recently raising a fantastic Series with the likes of Upfront Ventures and Rincon Partners leading the round. Prior to founding Qordoba, May was Director of M&A at Mubadala and an investment banker at Lehmann Brothers and Barclays in New York. May has also been named to the 30 Under 30 and CEO of the Year award.

In Today’s Episode You Will Learn:

• How May made her way from North Lebanon to founding one of the hottest early stage SaaS companies on the West Coast?
• May has quadrupled her MRR growth since last year through ‘turning her SDR’s into the smartest people in the space’. What does this mean? How can this be done and replicated? What “SDR best practices did May follow that damaged her?
• May has a unique approach to scaling prospect search, how does this play out Does May agree with Mark Suster with regards to always calling high on customer outbound? Why does May think there is only value in outbound to seriously qualified leads?
• Why does May believe that startups are wrong to think that they have to start at SMB and then move up to enterprise? How can startups immediately start with enterprise? What advice does May have in terms of asking for those big ACV’s as a small startup?
• What advice did May receive during her fundraising that she found particularly jarring? What other than funds does May believe fundraising can be particularly good for? 

60 Second SaaStr

1. What does May know now that she wishes she had known at the beginning?
2. What is May’s favourite SaaS reading material?
3. Hardest moment in the journey with Qordoba?

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

May Habib

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

Nicolas Dessaigne is the Founder & CEO @ Algolia, the most reliable platform for building search into your business. Just last week they raised $53m in funding led by Accel with participation from Jason Lemkin @ SaaStr, Point Nine Capital, AppDynamic’s Jyoti Bansal, Intercom’s Des Traynor and InVision’s Clark Valberg and more incredible investors.

In Today’s Episode You Will Learn:

• How Nicolas made his way to YC and came to found Algolia?
• What are the key things that change when you cross the 10m in ARR milestone? What have been the fundamental learnings in the march to $10m in ARR?
• Jason Lemkin has said before that ‘the first 10 unaffiliated customers you get is the first sign of pre-success’. Does Nicolas agree with him here? When are the first signs of pre-success for Nicolas?
• Does Nicolas agree with Jason that $1m-$2m in ARR is always the hardest for a scaling SaaS startup? Which element did Nicolas find most challenging? How has Nicolas seen himself change and develop as a leader with these inflection points?
• What are the fundamental to building a successful developer community? What have Algolia done to do this so successfully? What mistakes do other startups normally make in their pursuit of this? 

60 Second SaaStr

1. What hires does Nicolas wish he had made earlier?
2. What does success look like for Nicolas with Algolia?
3. What does Nicolas 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

Nicolas Dessaigne

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

Ryan Carson is the Founder & CEO @ Treehouse the startup that teaches you to code and learn the skills needed to launch a new career. They have backing from some of the best investors in the business including the likes of Social Capital, Greylock Partners and then notable individuals such as Reid Hoffman, Josh Elman and Mark Suster just to name a few. As for Ryan, prior to Treehouse he was the creator of famous The Future of Web Apps Conference, showing his unparalleled access to the top tier of West Coast founders. Due to the success of the conference, Ryan later sold the event to another events company.

In Today’s Episode You Will Learn:

• How Ryan made his way into the world of startups and came to found Treehouse?
• How does Ryan think all founders can build a truly diversified pipeline for developer talent? How does Ryan detect the seeds of potential in young engineers? How does he nurture them to grow and fit the desired role?
• How does Ryan approach regrettable and non-regrettable churn? What is the dunning process? Why is it so important to instantly increase retention and reduce churn?
• Does Ryan agree with Jason Lemkin that the hardest element of SaaS scaling is the $1-2m phase? Does Ryan agree with Jason in suggesting that your first 10 unaffiliated customers is the first sign of product market fit?
• Ryan has previously said, ‘as a founder, there is one thing you need, otherwise you will quit’. What is the one thing? Why is it so important?

60 Second SaaStr

1. Why does Ryan know now that he wishes he had known when he started?
2. What is Ryan’s favourite SaaS reading material?
3. Freemium in SaaS: What are the pros and cons?

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 Carson

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

Jeetu Patel is Senior Vice President of Platform and Chief Strategy Officer of Box where he leads the Box Platform organization, driving the strategy of the platform business and developer relations. He also oversees the corporate strategy and development organization for Box. Before joining the company, Patel was General Manager and Chief Executive of EMC's Syncplicity business unit. Prior to EMC, Patel was president of Doculabs, a research and advisory firm focused on collaboration and content management across a range of industries.

In Today’s Episode You Will Learn:

• How Jeetu made his way into the world of SaaS and came to be one of the key executives at Box?
• What are Jeetu’s 3 tips to startup founders looking to build high performing teams? Why does Jeetu believe that team sizes must always remain small? What are the inflection points in team size when dynamics change?
• What does Jeetu argue that founders must pursue really hard problems? What are the benefits of this when hiring new people to the team? How does Jeetu balance between visionary hard problems and unrealistic?
• What does Jeetu mean when he says, ‘do things that do not scale so you can do things that sustainably scale? What are some examples of how this has been done effectively? Where do most startups go wrong in scaling sustainably?

60 Second SaaStr

1. What does Jeetu believe that most around him do not?
2. Fave SaaS reading material?
3. Why businesses will find the rules of the future very different to the rules of the past?

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

Jeetu Patel

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

Laura Bilazarian is the Founder & CEO @ Teamable, the startup that allows you to recruit the best talent from your network. They have raised funding from some stellar investors including the likes of True Ventures and SaaStr. As for Laura, she started out her career on Wall St before making forays into the world of Vietnamese hotel building and being a National Rugby Champion. Laura has also spent time with the likes of Fairmount Partners where she worked on dozens of M&A transactions to large public companies.

In Today’s Episode You Will Learn:

• How did Laura make her way from Wall St to rugby captain to founder of SaaS startup, Teamable?
• Why does Laura believe that “you should always be premium”? What are the benefits to this? How does this affect how Laura views both freemium versions of products and free trials?
• Why does Laura believe that you have to “create an outbound sales culture as early as possible”? Why is this? Does this change according to the differing customer profiles?
• How can SaaS businesses aid in the closing of their clients? What can they do to make this process as seamless and easy as possible? What are the requirements for this process?
• Why does Laura believe there are only ‘2 ways to hire’? What are those 2 ways? What methods of inbound applications must be ignored? How can founders ensure continued quality when hiring at scale?

60 Second SaaStr

1. What does Laura know now that she wishes she had known at the beginning?
2. What is Laura’s fave SaaS reading materials?
3. Competitive advantages of being a female CEO?

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

Laura Bilazarian

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

Mark Suster is Managing Partner at Upfront Ventures which he joined in 2007, having previously worked with Upfront for nearly 8 years as a two-time entrepreneur. Before joining Upfront Mark was Vice President, Product Management at Salesforce.com following its acquisition of Koral, where Mark was Founder and CEO. Prior to Koral, Mark was Founder and CEO of BuildOnline, a European SaaS company that was acquired by SWORD Group. Mark is also the writer of one of my favourite VC blogs, Both Sides Of The Table which is a centre piece to the whole VC community and is a must read for all interested in entrepreneurship and VC.

In Today’s Episode You Will Learn:

• How Mark made his way into the world of startups and came to invest in SaaS with Upfront today?
• What are 4 reasons why startups should prioritise professional services in the early days? Why do most VCs disagree with this? How did Salesforce do this right in their period of hyper-growth?
• How should early stage startups approach the topic of pricing? How can they evaluate whether to call high or low? What are the pros and cons of doing both?
• Mark has previously discussed the importance of finding your champion in the buying process. How can startups determine whether your champion is a decision-maker? What questions can you ask to find this out?
• What changes as a SaaS business scales? What are the key inflection points of company development? How does Mark view the amount B2B startups are raising today? How does Mark evaluate responsible and right spend?

60 Second SaaStr

1. What should your first sales reps be really good at?
2. How has Mark seen early stage SaaS startups go wrong most often?
3. IPO markets, frothy or fantastic?
4. What does Mark know now that he wishes he had known before?

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

Mark Suster

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

Today’s show is centred around The Top 10 VP of Sales Lessons Learned In Scaling To $100M ARR. Leading this conversation is Aaron Ross, author of best selling book, Predictable Revenue, providing the framework for the outbound process & sales team Aaron created for Salesforce.com. During his time at Salesforce as Director of Corporate Development and Acquisitions, Aaron added an extra $100 million in revenue in just a few years. Joining Aaron from the sales perspective we have Andrew Bothwell, VP of Sales @ TalkDesk and Aaron Schilke, VP Enterprise Sales @ Talkdesk, one of the fastest growing SaaS startups today. Providing insight from the other side of the table we have Josh Stein, Partner @ DFJ where his current board responsibilities include Box (NYSE: BOX), Chartbeat, LaunchDarkly, LendKey, SugarCRM, and previous guest with me on SaaStr in Talkdesk. But enough from me so without further ado I am going to hand over the reigns to Aaron Ross.

In Today’s Episode You Will Learn:

• What does Josh Stein believe is the toughest growth stage in SaaS? Which stage separates the men from the boys?
• Why is growing to 100 a case of simple maths? How does this maths affect how you should think about your sales hiring pipeline? How does this maths affect your view of forecasting?
• How do TalkDesk look to build a repeatable and scalable sales process? What have been their major learnings? Where do most startups make mistakes and falter?
• How should VPs of sales approach feedback with their reps? Why has a VP failed if a rep is blindsided by a particular piece of feedback?

 

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

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