David Hassell is the founder and CEO of 15Five, the leading web-based employee feedback and alignment solution that is transforming the way employees and managers communicate. They have backing from the likes of Matrix Partners, Point Nine Capital and many more leading investors. As for David, he was named "The Most Connected Man You Don't Know in Silicon Valley" by Forbes Magazine, David has also been featured in The New York Times, The Wall Street Journal, Inc., Entrepreneur, Wired, Fast Company, and the Financial Post.

In Today’s Episode You Will Learn:

• How did David made his way into the world of SaaS and came to found 15Five?
• How does David view competition? How should founders view additional competition to their space? What is the right response? Why did David choose such a public and deliberate fight back against one competitive attempt?
• David has said before that is passionate about the meaning and purpose of the business vehicle. What does he mean by this? How does this affect his thinking toward management and organisational structure?
• What are the keys to creating a harmonized, incentivized and happy culture for your business? How scalable is this approach and how has David seen his approach alter and develop with the growth of the company?
• Why did David choose the more bootstrapped funding option over the traditional heavy reliance on VC funding? Which startups is this right for? How can founders know when is the right time to put the pedal to the metal?

60 Second SaaStr

1. David’s fave productivity tools?
2. David’s biggest mentor and how it came about?
3. What does David know now that he wishes he had known at the start?

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

David Hassell

Alex MacCaw is the Founder & CEO @ Clearbit, the startup that is building a suite of business intelligence APIs to help companies find more information on their customers in order to increase sales and reduce fraud. They have backing from some of the best early stage investors including the likes of First Round Capital, SV Angel, Intercom’s Eoghan McCabe, Hubspot’s Dharmesh Shah and many more incredible investors. As for Alex, as well as being a fellow Brit who loves tea, he also worked at the likes of Twitter and Stripe prior to founding Clearbit.

In Today’s Episode You Will Learn:

• How did Alex make his way into the world of SaaS and came to found Clearbit in SF having grown up in the UK?
• Should API driven companies have sales teams? Should they do outbound? What’s the most effective way to generate leads?
• Alex has said before that the trouble is, ‘everyone is treating their customers the same”. What does he mean by this? How do the smart companies differ? How possible is it to address customer specific needs at scale?
• How does this scalability alter when elements like freemium and self service models are added to the equation? How effective have freemium tools been for Alex as a lead gen to on board new customers?
• Why did Alex choose the same pricing structure as the likes of Stripe and Twilio? What was the thought process behind this?

60 Second SaaStr

1. How important is it for SaaS startups to be in SF?
2. What does Alex know now that he wishes he had known when he started?
3. Biggest mentor to Alex and how it came about?
4. Fave SaaS reading material?

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

Alex MacCaw

Ryan Smith is the Founder & CEO @ Qualtrics, an online survey company with 1,200 employees and a valuation of more than $1bn. They have backing from some of the world’s best investors including the likes of Sequoia, Accel and Insight Venture Partners having raised a $150m Series B in 2014. As for Ryan, there are many awesome things, first, he has built Qualtrics from Utah allowing him to gain perspective outside of the traditional tech bubbles, second, he held off on attain VC funding for many years despite the common belief that it is necessary for unicorn growth and finally he has the most incredible work life balance I have seen and if you have not already you must check out this piece on him in Forbes, it really is a must.

In Today’s Episode You Will Learn:

1.) How Ryan made his way into startups and came to found Qualtrics?

2.) Sequoia’s Bryan Schreier states that Ryan’s success is due to running the company on ‘first business principles’. What does he mean by this? How does this affect the way Ryan runs Qualtrics?

3.) Why did Ryan decide to bootstrap the company for such a long time with the likes of Accel and Sequoia looking to invest? What are the benefits of retaining such control? What are the financial requirements to do so?

4.) What makes the best CEO’s? How do they view the internal structure of the company? How do they perceive their role? How do they manage their day and optimise their time?

5.) How does Ryan look to instill ‘radical transparency’ in the organisation? What are the benefits of doing so? Can an organisation ever be too transparent? What are the challenges of such transparency?

David Rodnitzky is founder and CEO of 3Q Digital, a leading digital agency that was acquired by Harte Hanks in 2015. Prior to 3Q Digital, he held senior marketing roles at several Internet companies, including Rentals.com (2000-2001), FindLaw (2001-2004), Adteractive (2004-2006), and Mercantila (2007-2008). David currently serves on advisory boards for several companies, including Marin Software, MediaBoost, Mediacause, and a stealth travel start-up.

In Today’s Episode You Will Learn:

• How did David enter the world of B2B SaaS marketing? What was the entry point for him?
• What really is SaaS marketing? Is it more consumer or B2B like? How does this alter and develop with the growth of the company?
• Before spending heavily on marketing, what gating factors should SaaS founders think heavily about before the big spend? Should this marketing plan be undertaken by an external firm or an internal team?
• What market channels should a SaaS company consider as ‘must haves’ in today’s world, as compared to ‘nice to have’s’? How does David differentiate between the two?
• We are always told if you cannot measure it, do not do it? How can SaaS companies measure the success and effect of their marketing campaigns? What are the key metrics that define success?

60 Second SaaStr

1. Biggest mistake current SaaS companies are currently enacting with their marketing?
2. Favourite marketing resources and tools?
3. What does David 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

David Rodnitzsky

Steve Garrity is COO and founder of Hearsay Systems the leading advisor-client engagement solution for the financial services industry. Hearsay have backing from the likes of Sequoia, NEA, Kleiner Perkins Partner, Mike Abbott and Path Founder, Dave Morin. Before founding Hearsay, Steve worked as an engineer at Microsoft Corporation in Seattle is a graduate of Stanford University with a BS and MS in Computer Science. While at Stanford, he was selected as a Mayfield Fellow in the Stanford Technology Ventures Program. During which, he joined Fortify Software as a product manager. Steve is also an investor in, and advisor to a number of Silicon Valley start-ups.

In Today’s Episode You Will Learn:

• How did Steve made his way into the world of SaaS from the world of Microsoft?
• How does Steve approach the management around his engineering team? How does Steve balance management of engineers while still allowing creativity? Are there dangers of giving engineers freedom?
• Is it possible to have both a happy engineering and sales? How does Steve look to harmonise the team? Is it not contra popular theory to have different cultures for different segments of the team?
• Why does Steve believe that executive coaching is an almost universal requirement? How does Steve justify that to the board?

60 Second SaaStr

1. Steve’s Biggest Productivity tools?
2. What does Steve now know that he wishes he had known at the start?
3. The biggest mistake SaaS companies are enacting with their social media strategies?

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 Garrity

Peter Reinhardt is the Founder and CEO @ Segment, the startup that allows you to collect all of your customer data and send it anywhere and they count some of the biggest and best companies in the world as customers including the likes of Reuters, HotelTonight, New Relic and Atlassian. They do not only have some of the world’s leading customers but some of the world’s best investors with the likes of Accel, Thrive and Kleiner Perkins participating in their latest $27m Series B. I would like to say a huge thanks to Grant Miller @ Replicated for the intro to Peter today.

In Today’s Episode You Will Learn:

• How did Peter make his way into the world of SaaS and come to found Segment?
• How does Peter define product market fit? Does he agree with Justin Kan in stating that it is when you get the first 10 customers that are unaffiliated?
• Why does Peter believe product market fit suffers when related to Job’s idea of the reality distortion field? What is so damaging and what should founders look to avoid?
• How do technical and non-technical co-founders differ in their approach to product market fit? How do their expectations, desires and reactions alter to differing levels of uptake?
• How did Peter navigate the process of scaling prices with time? Was he nervous when doing so? What does Peter advise founders when attempting significant price increases?

60 Second SaaStr

1. What were the biggest takeaways from YC?
2. What does Peter know now that he wishes he had known at the beginning?
3. The biggest challenge in building out the team?
4. Favourite SaaS resource or reading material?

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

Peter Reinhardt

Seth Besmertnik is the Co-Founder & CEO @ Conductor, the company that boasts the biggest customer list in their category including more than 500 Fortune and Internet Retailer 500 brands like Under Armour, Citi and FedEx with their web presence management and SEO. With this incredible success, the company has been ranked 13th fastest growing software company in the US and the 3rd Best Place To Work in NYC. They have also raised funding over $60m from some of the best investors on the east coast in the form of Matrix Partners and FirstMark Capital just to name a few. I would like to say a huge thanks to Fayez @ Bluecore for the intro to Seth today.  

In Today’s Episode You Will Learn:

• How did Seth make his way into the world of SaaS? What was the a-ha moment for Conductor?
• What does Seth mean when he says, ‘B2B companies need to build a weapon in their marketing’? How does this look in his approach? How does this differ according to differing startup budgets?
• Previously, Meaghan Eisenberg @ MongoDB has said ‘the largest lift you are going to see is from your site’. Does Seth agree with this? How should we prioritise the site? What are the fundamentals to consider in terms of optimising conversion?
• With the proliferation of content today, to what extent should B2B companies look to alternative platforms such as  Snapchat, Youtube and Instagram for content differentiation? What are the fundamentals to consider with platform diversification?
• How does Seth suggest creating a culture of content creation in previously segmented cultures? How can this be done with actionable strategies to encourage non-marketing professionals to produce content?

60 Second SaaStr

1. What does Seth know now that he wishes he had known before?
2. Biggest advice on content creation for B2B SaaS companies?
3. Fave SaaS reading material?
4. Being a CEO vs Being a Founder

Jason Lemkin

Harry Stebbings

SaaStr

Seth Besmertnik