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

Kathryn Minshew is the Founder & CEO @ The Muse, named to Forbes’ 30 Under 30 in Media and Inc.’s 15 Women to Watch in Tech. Before founding The Muse, Kathryn worked on vaccines in Rwanda and Malawi with the Clinton Health Access Initiative and was previously at McKinsey. Kathryn has spoken at MIT and Harvard, appeared on The TODAY Show and CNN, and contributes on career and entrepreneurship to the Wall Street Journal and Harvard Business Review.

In Today’s Episode You Will Learn:

• How Kathryn came to found The Muse? What was the a-ha moment for her?
• Why did Kathryn introduce a SaaS business model into the traditionally, transactional model of recruiting? What were the benefits and how did it alter her go to market?
• With no prior sales experience, how did Kathryn find the experience of running the sales team? What were the core takeaways? At what stage should the founder stop selling the product and hire a sales team?
• Why does Kathryn believe you have to make the customer feel slightly uncomfortable to be successful? What did Kathryn look for in her initial sales hires? Why did Kathryn hire 3 reps to start with and not 2, as usually suggested?
• How does Kathryn approach the customer success field at The Muse? When did Kathryn hire her first CS rep? What is Kathryn’s take on CS being involved in the sales process?

1. What does Kathryn know now that she wishes she had known when she started?
2. Biggest mistake SaaS companies are enacting with their recruiting process?
3. Productivity tips and hacks?

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

Kathryn Minshew

Michael Sharkey is CEO & Co-Founder of Autopilot, the startup that allows you to automate customer journeys as simply as drawing on a whiteboard. Autopilot has funding from some of the best investors both in Australia and in SaaS with backing from the likes of Salesforce Ventures and Blackbird Ventures. Prior to founding Autopilot with his two brothers, Michael joined his brother Chris to grow start-up Stayz into a top Australian rental booking site which was acquired by FairFax Digital in 2006 and again by HomeAway for $225M in 2013. Michael also co-founded digital marketing agency Sharkey Media where he helped grow Australian startups. I would love to say a huge thank you to Matt Garratt @ Salesforce Ventures for the intro to Michael today.

In Today’s Episode You Will Learn:

• How did Michael come to co-found Autopilot with his two brothers? What was the a-ha moment for him?
• Why did Michael choose a self service model with Autopilot? How does this model affect their CAC? How does this model alter the outbound marketing strategy?
• How does Michael approach the dilemma of variable or fixed pricing? Has Michael found that the lack of reliability around variable pricing causes customers concern?
• With Michael interest in unit economics, why are we seeing many SaaS startups, Marketo and Eloqua, exiting with losses? What can founders do to adopt the unit economics first mindset? How does this attitude to unit economics affect attitudes to aggressive growth?
• Michael focuses on 100% net retention, what does that process and strategy look like in practice? How does this commitment to 100% retention affect Michael’s management style and work processes?

60 Second SaaStr

1. Biggest mentor to Michael and how it came about?
2. What does Michael know now that he wishes he had known in the beginning?
3. The biggest mistakes SaaS companies make with their email marketing processes?

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

Michael Sharkey

Robert Siegel is a Partner at XSeed Capital, one of the leading seed funds in the valley. At XSeed, Rob specialises on, you guessed it, all things from the wonderful world of SaaS and he sits on the Board of Directors of Cape Productions and Caller Zen. Robert is currently on the faculty at the Stanford Graduate School of Business where he teaches an array of topics that he led to His role as the Co-President Emeritus of Stanford Angels & Entrepreneurs. Prior to joining XSeed, Robert was General Manager of the Video and Software Solutions division for GE Security, with annual revenues of $350 million. Before that, Robert was Co-Founder & Chief Executive Officer of Weave Innovations Inc. (acquired by Kodak). If that was not enough Robert also served in various management roles at Intel Corporation, including an executive position in their Corporate Business Development division, in which he invested capital in startups that were strategically aligned with Intel’s vision. I would also like to say a huge thanks to Tien @ Zuora for the intro to Robert today.

In Today’s Episode You Will Learn:

• How did Robert make his way into the world of SaaS? What was it about XSeed that made him want to make the transition from operations to VC?
• We have seen many big SaaS exits in the last year with Marketo and Nutanix, does Robert think the time for big SaaS exits has come and gone? Have we moved to a world of consolidation?
• How do companies both large and small need to react to this shift on a strategic level? How does this affect the internal infrastructure of larger companies?
• For smaller startups, how should their attitude to competition change? How does this change Robert’s search process as an investor? How can smaller startups make themselves attractive acquisition targets?
• How does Rob’s view of consolidation affect his excitement for mega returns in SaaS? How does it impact how Rob approaches valuation? How does this change Rob’s expectations of unit economics?

60 Second SaaStr

1. Strategic investors: Good or Bad?
2. What does Rob know now that he wishes he had known when he started?
3. Fave SaaS resource or reading material?
4. Greenfield opportunity in 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

Robert Siegel

David Thompson is CMO at Domo, the company that allows customers to turn data into opportunities. David is a highly accomplished branding expert and recognized leader in demand generation, having served as longtime CMO of WebEx, where he named the company, helped create the cloud-based conferencing category and positioned the company for its IPO and subsequent buyout by Cisco. He also co-founded and served as chief executive officer of Genius.com, a leading SaaS marketing automation company, and he launched the Sales 2.0 Conference.

In Today’s Episode You Will Learn:

• How did David make his way into the world of tech and SaaS pre-bubble? How did the bubble affect how David approached company building going forward?
• What should all SaaS startups consider pre spending big on marketing? What should their core gating factors be? Is it always right to have an internal marketing team?
• What are the must haves and the nice to haves in B2B marketing? Why is Facebook a must have or business branding today?
• How can businesses accurately measure the success of their marketing and branding efforts? Is it all about revenue or is there external reputation metrics to consider?
• On the whole, would David consider successful B2B branding closer to consumer or closer to enterprise marketing? What do the best in the enterprise class do?

60 Second SaaStr

1. What are David’s favourite marketing tools?
2. If David could recommend one book to SaaS founders what would it be?
3. With the martech explosion: are we entering a world of consolidation?

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 Thompson

Daniel Saks is the Co-CEO of AppDirect, which he founded in 2009. AppDirect is the leading commerce platform for selling cloud services and at the firm, Daniel plays a key role in the growth and development of AppDirect, from attracting a leading team, to nurturing relationships with customers and partners. AppDirect has backing from some of the leading investors in the world including the likes of Foundry Group and J.P. Morgan. Prior to AppDirect, Daniel worked at Viant Capital, a boutique tech investment bank.

In Today’s Episode You Will Learn:

• How did Daniel make the move from family business to SaaS founder? How did he get the business off the ground in the early days?
• From working in his family business, what did Daniel observe about the buying patterns of businesses? What makes Daniel believe humans like to buy from humans?
• Is it a problem that many of today’s software vendors lean on direct sales? What are the first steps to create a multi-channel approach? What does it take to support indirect sales channels such as affiliates and resellers?
• What is Daniel’s 4 Step Playbook for optimising the distribution of software? What does it take to move past the early adopter audience into the hands of the wider market?
• Why does Daniel believe that the promise of SaaS is yet to be fully realised? What excites Daniel with the rise of the cloud and the movement away from on-premise?

60 Second SaaStr

1. When is the right time to hire your first customer success rep?
2. What does Daniel know now that he wishes he had known at the beginning?
3. Biggest challenge in the AppDirect journey and how Daniel overcame it?

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

Daniel Saks

Part 2 with David Skok, now David is a serial entrepreneur turned VC at Matrix Partners. He founded four companies: Skok Systems, Corporate Software Europe, Watermark Software, and SilverStream Software and did one turnaround with Xionics. Three of the companies he founded went public and one was acquired. In 2001 David joined Matrix Partners, who had backed his last two startups, as a General Partner. David’s successful exits as an investor at Matrix include: HubSpot, JBoss, AppIQ, Tabblo, Netezza, Diligent Technologies, CloudSwitch, TribeHR, GrabCAD, OpenSpan and Enservio. David currently serves on the boards of Atomist, CloudBees, Digium, Meteor, Namely HR, Salsify, and Zaius. You can also find David’s amazing blog here! Huge thanks to Hardi Meybaum and Jason Lemkin for the intro to David today.

In Today’s Episode You Will Learn:

• What is negative churn? Why is it fundamental for SaaS startups to have a strong grasp of their negative churn?
• How does negative churn affect the pricing axis? What can startups do if they have no alternative product to upsell to?
• To what extent should founders be willing to engage in customisation in order to upsell a product? What are the dangers? What should founders be mindful of?
• To what extent is up sell the responsibility of customer success? Should they have a hand in the sales process? What are the dangers and concerns?
• How important is it for a startup to track their champion with the customer company? Does it matter if your champion leaves? What should you do if so?

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 Skok

David Skok is a serial entrepreneur turned VC at Matrix Partners. He founded four companies: Skok Systems, Corporate Software Europe, Watermark Software, and SilverStream Software and did one turnaround with Xionics. Three of the companies he founded went public and one was acquired. In 2001 David joined Matrix Partners, who had backed his last two startups, as a General Partner. David’s successful exits as an investor at Matrix include: HubSpot, JBoss, AppIQ, Tabblo, Netezza, Diligent Technologies, CloudSwitch, TribeHR, GrabCAD, OpenSpan and Enservio. David currently serves on the boards of Atomist, CloudBees, Digium, Meteor, Namely HR, Salsify, and Zaius. You can also find David’s amazing blog here! Huge thanks to Hardi Meybaum and Jason Lemkin for the intro to David today.

In Today’s Episode You Will Learn:

• How did David make his way into the world of SaaS? What was it about Matrix that made him want to make the transition from operations to VC?
• Why are metrics so important? What role do they play in an organisation? How do good founders respond to questions on not achieving sales targets?
• Why are SaaS businesses immune from being measured on standard financials like GAP financials? What metrics in SaaS really determine the trajectory of the business?
• How can founders examine unit economics to determine whether they have a sustainable SaaS business?
• How does David address sales rep productivity? How much in ARR should they be booking in relation to their annual comp package?

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 Skok

Taro Fukuyama is Founder & CEO @ AnyPerk. Born and raised in Tokyo, Taro is a Y Combinator graduate with AnyPerk and part of the first Japanese team ever to be admitted to YC. He was also named one of Business Insider’s “Silicon Valley 100 Coolest People in Tech Right Now.”Fun fact, Taro co-founded AnyPerk in a Taco Bell car park! What a story! They also have investment from the likes of DCM, YC, Gary Vaynerchuk, previous SaaStr guest Nick Mehta and many more incredible people. I would also like to say a huge thanks to Jason lemkin for the intro to Taro today.

In Today’s Episode You Will Learn:

• How did Taro make his way to San Francisco and come to found AnyPerk?
• As a first time founder, how did Taro look to build out the management team? What were the inherent challenges and what did Taro look for in his core executive?
• What are the 6 questions that will determine whether you have clarity in your organisation? Why is clarity so important to unify the team? What does this clarity allow?
• What are the 5 steps to building a cohesive team? How can CEOs be both vulnerable and authoritative as a leader?
• How should founders approach offsites? What is the necessary preparation? How should they be structured for optimal productivity? What can be done to ensure they produce meaningful outcomes?

60 Second SaaStr

1. Favourite SaaS reading material?
2. What does Taro know now that he wishes he had known at the beginning?
3. The biggest mistake companies make with employee happiness?

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

Taro Fukuyama

Matt MacInnis is the Founder & CEO @ Inkling, the company that brings policies and procedures to life for your desktop workers. The company has backing from some of the best investors in the world with the likes of Sequoia, Felicis and Kapor Capital behind them. As for Matt, prior to Inkling, he spent 7 years at the one and only Apple Inc. I would also like to say a huge thank you to Taro Fukuyama, Founder @ AnyPerk for the intro to Matt.

In Today’s Episode You Will Learn:

• How did Matt make his way into the world of SaaS and Inkling from Apple Inc?
• Does culture in sales really matter? Is it not just about hitting the fucking number? What are the two opposing culture that exist in the world of sales team? Why is missionary always better?
• How can a sales leader instill a competitive element into a missionary sales culture? What are the inherent challenges and how does Matt approach them?
• Is it possible to have a fantastic sales and a fantastic engineering culture? How can the two live under the same roof and what needs to happen to ensure this works?
• In terms of measurement, how can a founder know whether they have a strong culture? What are the signs and indications?

60 Second SaaStr

1. Productivity Tools
2. What does Matt know now that he wishes he had known in the beginning?
3. Biggest mistake most SaaS companies are enacting with their sales process?

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

Matt MacInnis

Whitney Sales is the VP of Sales at TalentIQ, has been involved in bringing products to market and managing high growth sales teams for over a decade. She is the creator of the Sales Method, a strategic framework for launching products, which she used to help three companies earn a place on the Inc 5000 fastest growing companies list. Prior to joining TalentIQ, Whitney held executive positions at Wanelo and SpringAhead and currently serves as a mentor at StartX, Alchemist, and previous guest Acceleprise and a huge thanks to Michael Cardamone @ Acceleprise for the intro to Whitney today.

In Today’s Episode You Will Learn:

• How did Whitney make her way into the world of SaaS and more specifically sales?
• What are the 5 key criteria that founders need to consider before embarking on the sales process?
• How specific and targeted should a customer profile be? How many profiles can they have? What are the best questions to determine the optimal customer segment?
• How can founders identify which buyers are innovators? What tools are best for this? Once discovered, how should founders approach these innovators?
• Founders learn about gaps in customer information from selling. So how close should the integration of content marketing and selling be in the early days?

60 Second SaaStr

1. What are Whitney’s preferred tools for her tech stack?
2. What does Whitney know now that she wishes she had known at the beginning?
3. Does the proliferation of sales tools make it harder or easier?

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 Sales

Ryan Petersen is the Founder and CEO of Flexport, the freight forwarder for the internet age. Flexport recently raised a phenomenal $65m Series B from the likes of Founders Fund, First Round, Felicis, Bloomberg Beta, Yuri Milner, Susa Ventures and more incredible investors. With none other than YC founder Paul Graham stating ‘Ryan has the rare ability to not just satisfy the market but grow it’. Prior to Flexport, Ryan was Founder and CEO of ImportGenius.com, the largest provider of business intelligence to the import-export industry. A huge hand to Chad Byers @ Susa and Jason Lemkin for the intro

In Today’s Episode You Will Learn:

• How did Ryan make her way into the world of SaaS and come to found Flexport?
• How does Ryan view NPS? Why is he so bullish? Why is it the most important metric? What are the downsides to relying on NPS?
• What is the optimal method to structure internal compensation structures? Why is compensation based on NPS and Net not effective and what are the dangers of this?
• How can founders look to implement bottoms up decision making in their organisation? What are the benefits of this and what are the challenges to it’s implementation?
• Ryan is hiring his first VP of Marketing? What should founders look for in their VP of Marketing? Why is now the right time and what challenges has Ryan faced in the process?

60 Second SaaStr

1. Fave SaaS reading material?
2. What does Ryan know now that he wishes he had known when he started?
3. What has been his biggest learning throughout the Flexport journey?

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 Petersen

Josh Reeves is the Founder and CEO @ Gusto. Gusto reimagines payroll, benefits, HR, and personal finance and it is this reimagination that has led to their recent addition to the unicorn club with investors including Google Capital, Kleiner Perkins, Data Collective and General Catalyst, just to name a few. As for Josh, he was selected for the 2012 Forbes 30 Under 30 list. Prior to co-founding Gusto, he was the CEO and co-founder of Unwrap, a SaaS startup which was acquired in 2010, and he began his career as an early employee at Zazzle. I would also like to give a big hand to Jason Lemkin and Phil Libin for the intro to Josh today.

In Today’s Episode You Will Learn:

• HR and Payroll is not sexy so how did Josh make his way into the industry and what was the a-ha moment for Gusto?
• Josh has said before ‘he lives and breathes how a company is built.’ How has Josh looked to grow and develop his own internal organisation at Gusto? How does this vary with stage?
• Josh has hired over 300 people at Gusto, how does he approach the interview process? What is the right way for employers to approach the ‘making offers’ stage?
• How important does Josh feel it is to have an ownership culture and internal entrepreneurialism? How can this environment be fostered and developed?

60 Second SaaStr

1. How employers can ensure new employees have an amazing first day?
2. What does Josh know now that he wishes he had known when he started?
3. The biggest mistake SaaS companies make with their HR and payroll organisation?

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

Josh Reeves

Jeff Fernandez is the Co-Founder & CEO @ Grovo, the enterprise learning solution that allows you to educate and empower your employees. At Grovo, Jeff oversees sales, investor relations, and the building of Grovo’s award-winning culture. Prior to founding Grovo in 2010, Jeff served as product manager at Clickable (acquired by Syncapse). From 2006 until 2009, he led business development and sales for Doostang (acquired by Universum Global), an online career networking community. Jeff is also a bit of a rockstar off the field getting the highest honours from Harvard penning his thesis on human performance and then playing semi pro football for the New York Rebels in 2008. I would also like to say a massive thank you to Greg Sands @ Costanoa Venture Capital for the intro to Jeff today.

In Today’s Episode You Will Learn:

• How Jeff came to found Grovo? What was the a-ha moment for him?
• Jeff is renowned to ‘lead from the heart’. What are the advantages of this as a CEO? How does this affect the company, the culture? What are the inherent challenges?
• Question from Greg Sands: Jeff likes to ‘work the sales floor’, how does that work? What does Jeff actually do? What have been Jeff’s observations having seen the sales floor up close?
• How does Jeff look to structure the compensation for his sales team? How does this vary with time and stage?
• What does Jeff mean when he says ‘sometimes you have to go slow to go fast’? How does that play out in his management style?

60 Second SaaStr

1. Jeff’s biggest productivity tips?
2. Biggest challenge for Jeff in being CEO @ Grovo?
3. What does Jeff 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

Jeff Fernandez

Sangram Vajre is the Co-Founder & CMO at Terminus, the leading account-based marketing platform. Prior to Terminus, Sangram was the Head of Marketing @ Pardo, prior to it’s acquisition by Salesforce. Sangram is also the brains behind the marvel that is Flip My Funnel which challenges the status quo of traditional B2B marketing practices and transform how B2B marketers approached driving revenue in their organization. You might remember in a recent episode Tim Kopp @ Hyde Park Ventures cited Sangram and his revolutionary approach with Flip My Funnel as one to watch. If that was not enough, Sangram is also the author of "Account-Based Marketing For Dummies".

In Today’s Episode You Will Learn:

• How Sangram came to found Flip My Funnel and Terminus? What was the a-ha moment and origin story for Sangram?
• Why does Sangram believe the funnel needs to be reinvented? Where are the inefficiencies? What can be done to optimise the funnel and what are the steps to do so?
• How did Sangram establish such a strong brand in the B2B space on a shoe-string budget in such a short space of time? What tactics can be done to exert your authority over a domain?
• How does Sangram look to create an ownership culture of internal entrepreneurs at Terminus? Why is it so important to try and hire people who know more than you?
• Why did Sangram decide to hire a customer success rep before any other function? What did he look for in his first CS person? What does Sangram thinks is fundamental to being successful at CS?

60 Second SaaStr

1. Biggest learning from founding and scaling Terminus?
2. Sangram’s Favourite 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

Sangram Vajre

Matt Murphy is a Managing Director @ Menlo Ventures where he focuses on multi-stage investments across cloud infrastructure and AI-first SaaS applications. Since joining Menlo, Matt has led investments in Heap Analytics, Usermind, and Veriflow. Previously, Matt was a General Partner at Kleiner Perkins for over 15 years.  Matt was also an observer at Google (from initial investment to IPO), launched the iFund in ’08 (a collaborative initiative with Apple to build the defining applications on the iOS platform), and led KPCB’s investments in AutoNavi (Nasdaq: AMAP, 2010) and Aerohive Networks (Nasdaq: HIVE, 2014). Before joining KPCB, Matt worked at semiconductor startup Netboost (acquired by Intel) and prior to that at Sun Microsystems.

In Today’s Episode You Will Learn:

• How Matt made his way into the world of VC and enterprise investing? What were his biggest takeaways from working alongside John Doerr @ Kleiner Perkins?
• How is the enterprise investing landscape changing? What fundamental shifts have we seen and what have been the dominant repercussions of this?
• Nakul Mandan stated that ‘we would see the 2nd wave of consumerisation of enterprise through business model’. Does Matt agree with this and what key trends is Matt most excited about in SaaS?
• How does Matt look to evaluate early stage SaaS valuations? What are people fundamentally misvaluing and how should the topic be approached?
• Is it harder now for SaaS companies to raise than ever before? What metrics does Matt look for in a Series A investment opportunity?  

60 Second SaaStr

1. Matt's Fave SaaS reading material?
2. What are the greenfield opportunities in SaaS today?
3. What was Matt's biggest takeaway from working with John Doerr @ Kleiner Perkins?

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

Matt Murphy

Brandon Bruce is the Co-Founder and COO @ Cirrus Insight, the plugin for Gmail and Outlook that automatically updates Salesforce as you work. Cirrus is a bootstrapped startup with triple-digit yearly growth since it's founding 4 years ago and has grown from 2 co-founders in 2011 to a team of 55 people today. And I have to say a huge thanks to Aaron Ross, Author @ Predictable Revenue for the intro to Brandon today. Likewise, if you want to join me and Jason for mojitos at SaaStr Annual 2017 and also want an incredible 20% off ticket prices, then all you have to do is click here!

In Today’s Episode You Will Learn:

• How did Brandon make his way into the world of SaaS and come to found Cirrus Insight?
• What does Brandon mean he says he likes to take the road less travelled in Sales? What have been his learnings from his interactions on the front line of sales? How has it changed how he approaches sales?
• How are Cirrus so efficient at events in terms of getting more leads, meeting and sales? What is the strategy going into events? How can we optimise this?
• Speaking of events in general there, how does Brandon look to define prospect and buyer personas? How important is this for events? How narrow and specific do these personas have to be?
• Brandon has stated before in the importance of learning and doing manual before automatic with the future in mind. What do he mean by this and how does it affect his roadmap and thought process to the future going forward?

60 Second SaaStr

1. Favourite SaaS reading material?
2. What does Brandon know now that he wish he had known at the beginning?
3. The biggest challenge of running Cirrus and how Brandon looks to combat it?

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

Brandon Bruce

John Barrows is essentially the Godfather of Sales. We often have VPs of Sales from tech titans on the show but who trains those VPs and sales reps to be the best in the world at sales? That is where John Barrows comes in, with clients including Dropbox, Box, Marketo, Twilio and many more, John has amassed a wealth of knowledge and experience allowing him to provide the most proactive sales tips and strategies to optimise the sales process. If you have not checked out his blog, that really is a must and can be found here.

In Today’s Episode You Will Learn:

• How did John make his way into the world of SaaS and more specifically sales optimisation?
• How has John seen the sales landscape evolve? What has been the effect of the segmentation of roles pioneered by Salesforce?
• What will be the catalyst that causes teams to shift from current sales methods and teams to AI replacing the sales team? What does this depend on?
• How does John view the integration of sales and marketing? How does the rise of ABM change this?
• How can sales reps perfect the balance of being direct and being rude? How important is a summary email? What is the optimal structure and how should sales reps follow up on summary emails?

60 Second SaaStr

1. The most common question asked to John by VPs of Sales?
2. What are the benefits of Top Down prospecting?
3. Do execs need structure?

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

John Barrows

John Gleeson is VP of Customer Success @ Affinio where John was employee #1. 2 years and a half years later, John is the VP of Customer Success following their Series A and has seen the team expand to over 40 people and have offices in New York, Toronto, Halifax and Ireland. John has written a special blog post just for SaaStr listeners today outlining his ultimate guide to customer success reading, it is my go to guide for customer success.

In Today’s Episode You Will Learn:

• How did John make his way into the world of SaaS and more specifically customer success?
• John has previously described customer success as ‘The Analogue of Sales’, what does he mean by this? How does it affect the way he views customer success
• How does John view the role of sales vs customer success in large accounts? How do they partner to drive expansion?
• How customer success managers be truly productive at the enterprise level? How can they measure their success with this productivity increase?
• Moving downstream, why does John believe the $2m benchmark per CSM is the hardest phase? What skills do you need to be successful at this stage? With so many accounts, is it possible to be proactive?

60 Second SaaStr

1. The biggest mistake most companies make when it comes to customer success?
2. Most common questions asked by CSM leaders?
3. Measuring customer success?

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

John Gleeson