Yousuf Khan is a serial CIO, start-up and VC advisor. Most recently Yousuf was the CIO & VP of Customer Success @ Moveworks, the advanced AI built for enterprise providing automatic resolution of IT issues. During his time at the company, they raised over $108m from Lightspeed, ICONIQ, Kleiner, Sapphire and Bain Capital. Pre Moveworks, Yousuf was CIO @ Pure Storage during their period of hypergrowth both as a private and public company. Finally, before Pure, Yousuf’s first role in the valley was with Qualys again as CIO where he owned the entire global IT budget.   

In Today’s Episode We Discuss:

• How Yousuf made his way from the UK to the valley and how that led to his becoming one of the leading CIOs today in the rising prominence of CIOs in enterprise? 
• How open and can transparent can CEOs be with CIOs? Do CIOs know the state of early-stage companies in terms of their cash situation, fundraising etc? Does that ever put them off buying? What is the right tone and temperament to take with those CIOs in the first meetings? How does Yousuf advise founders on quality or quantity of logos in the early days? 
• How does Yousuf advise CEOs approach CIOs when it comes to discounting? Do they make a difference to the buying decision of the CIO really? Should founders offer discounts in exchange for customer testimonials? How can CEOs provide alternative forms of social validity to other CIOs in the ecosystem, other than case studies?  
• How does Yousuf advise founders approach CIOs when it comes to multi-year deals? Does the mindset of the CIO change when the deal is paid upfront? How should the founders position that? When it comes to implementation, how important is time to value in the mind of the CIO? What is the worst thing a founder can do when discussing implementation?    

Yousuf’s 60 Second SaaStr:

1. What separates good from great when it comes to CIOs?
2. What makes the best board members?
3. What are Yousuf’s biggest strengths and weaknesses?

Read the transcript on our blog. 

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

Yousuf Khan

Des Cahill is the Chief Marketing Officer for Oracle CX Cloud Suite, an integrated set of marketing, sales, commerce and service solutions that power customer experience for thousands of leading global brands. Prior to Oracle, Des was the CMO @ Kerio Technologies marketing to over 60,000 SMB customers and 5,000 channel partners. Before Kerio, Des was the CMO @ Ensighten, where he helped grow the customer base from 10 to 100 and revenues from $2M to $14M. Des has also spent time as CEO having founded and grown Habeas Inc from 0 to 450 customers, $9M in revenue and raising 3 rounds of venture financing. 

 In Today’s Episode We Discuss:

• How Des made his way into the world of startups and came to be CMO of Oracle’s CX Cloud suite? 
• Why does Des believe customers are more unpredictable now than ever before? How is their behaviour fundamentally changing? What are some great examples of how Des has seen companies amend to the changing consumer demands?
• How does this change the role of the marketer today? How does this change the prioritisation of customer experience for marketers? What are the challenging elements of this change? How does the role of marketing also integrate with the post-sale and customer success with much of their content being used there?  
• How does Des think about the relationship between marketing and sales teams? What are Des’ biggest tips on how to reduce friction in the handoff from marketing to sales? What works? What does not work? What is the right OKR to measure marketing teams? Does it have to be tied directly to revenue?  

Des’ 60 Second SaaStr:

1. Biggest breakdown in the working of an efficient funnel?
2. Who is killing it in SaaS marketing today and why?
3. Advice in SaaS you commonly hear but disagree with?

Read the full transcript on our blog.

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

Des Cahill

Allie Janoch is the Founder & CEO @ Mapistry, the startup that makes environmental compliance simple. As for Allie, prior to founding Mapistry she started her career in MIT’s Lincoln Lab before joining IQ Engines (acquired by Yahoo). Post acquisition, Allie integrated the technology built at IQ Engines into Flickr search. 

 In Today’s Episode We Discuss:

• How Allie made her way from the world of Yahoo to founding the game changer of environmental compliance in Mapistry? Having had both big company, small startup and founding experience, what would Allie advise new graduates entering the workforce today? 
• What were the biggest mistakes that Allie made when it comes to sales hiring? What were the learnings from those mistakes? How does Allie advise other founders on scaling sales teams? How does Allie think about sales rep payback period? How can one determine the effectiveness of a sales rep when they are engaging in 9-12 month sales cycles?
• How does Allie think about the importance of focus applied to customer segmentation today? How does Allie measure true customer success? NPS? Churn? Product analytics? How does Allie explain the macro market size to VCs when they initially see the small customer segment?  
• Why did Allie start doing their own events with Mapistry? How should startups think about whether events are the right strategy for them or not? How should founders think about resource allocation and budget when it comes to events? How does Allie measure the ROI of events? 

Allie’s 60 Second SaaStr:

1. What does Allie know now that she wishes she had known at the beginning? 
2. What would Allie most like to change about the world of tech and Silicon Valley?
3. What is the biggest challenge for Allie today with Mapistry?

Read the transcript on our blog.

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

Allie Janoch

Travis Bryant is Partner for Founder Experience @ Redpoint Ventures, the venture fund with a portfolio including the likes of Stripe, Netflix, Zuora, Hashicorp and Juniper Networks just to name a few. As for Travis, prior to joining Redpoint, Travis was head of Customer Growth at Front, after spending 5 years building the global Sales organization at Optimizely, the world’s most popular experimentation platform. During his time at Optimizely, the company grew from from $7 to >$90M in ARR and from 40 to 400 people. Before Optimizely, Travis spent 6 years at Salesforce in a number of sales roles including building the first Platform Sales team.

In Today’s Episode We Discuss:

• How Travis made his way into the world of venture as the first ever Partner for founder experience at Redpoint? What were the 2 biggest lessons Travis took from Salesforce? How transformational is the 12 quarter year for Salesforce?
• Why does Travis believe we need to abolish the title of CRO? Why does it suggest misalignment between customer and vendor from Day 1? What aspects of CRO’s roles is Travis in favour of? What elements is he not in favour of? What does Travis advise founders when it comes to uniting customer facing teams?   
• Why does Travis believe that SaaS has upended the economic model but not the engagement model? How does the engagement model with customer need to shift? What does this do to the structure of the conventional funnel? 
• Why does Travis believe net retention must always be the guiding North Star? How does Travis think about the different steps to customer qualification today and what makes the best SDR’s? What does Travis advise founders when it comes to churn analysis? What questions must you ask? What metrics must you look for? 

Travis’ 60 Second SaaStr:

1. What motto or quote do Travis frequently revert back to?
2. What is the most challenging element of Travis’ role with Redpoint?
3. How should startup operators coming out of larger organizations determine which startup to join? 

Read the transcript on our blog.

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

Travis Bryant

Nicole Alvino, founder of SocialChorus, shares some ‘truth is crazier than fiction stories’ about her time in structured finance at Enron and how she applied what she learned to build a company that has 10 of the Fortune 50 as customers. In your constant effort to grow and win, you’ll get the 5 most important lessons on how to push the envelope just far enough - while keeping your ethics in check.

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

Read the full transcript on our blog.

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.

Find the video and full transcript on our blog.

Sponsor message: Remote and hybrid teams aren't the future of work-- they're the present. Owl Labs is embracing this revolution, and is here to provide remote workers with a virtual seat at the table with the Meeting Owl. Their 360° smart video conferencing camera can recognize and highlight any speaker at the table using an array of 8 microphones. Check it out for yourself at owllabs.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 why Glassdoor’s $1.2 Billion acquisition is just one milestone in the early innings of the company’s story.

Follow SaaStr and our guests on Twitter:

Jason Lemkin

SaaStr

Robert Hohman

Neeraj Agrawal

Sponsor message: Remote and hybrid teams aren't the future of work-- they're the present. Owl Labs is embracing this revolution, and is here to provide remote workers with a virtual seat at the table with the Meeting Owl. Their 360° smart video conferencing camera can recognize and highlight any speaker at the table using an array of 8 microphones. Check it out for yourself at owllabs.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?

Read the transcript on our blog.

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

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 prioritization?

Read the full transcript on our blog.

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

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

Nick Mehta

This episode is sponsored by Owl Labs.

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?

Read the transcript on our blog.

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 

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

Find the video and full transcript on our blog.

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

Remote and hybrid teams aren't the future of work-- they're the present. Owl Labs is embracing this revolution, and is here to provide remote workers with a virtual seat at the table with the Meeting Owl. Their 360° smart video conferencing camera can recognize and highlight any speaker at the table using an array of 8 microphones. Check it out for yourself at owllabs.com!

Dave King is the Head of Marketing at Asana, the work management platform that teams use to stay focused on the goals that grow their business. To date, Asana has raised over $210m from some of the biggest names in tech including Mark Zuckerberg, Peter Thiel, Marc Andreesen, Ben Horowitz, Sean Parker, Ron Conway, Benchmark, Founders Fund and more incredible names. As for Dave, prior to joining Asana, he led the marketing teams at Percolate, Highfive, and Salesforce Community Cloud.

In Today’s Episode We Discuss:

• How did Dave make his way into the world of SaaS and startups? When did he realise his love of marketing SaaS companies?
• What does Dave mean when he says, “we are entering the 3rd wave of marketing”? What were the 1st and 2nd chapters? What does the “3rd wave” of marketing mean for marketers today? How does it change what marketing should be focusing on? How does it change how marketing works with sales and customer success? 
• What does Dave mean when he says, “offsites serve as a crutch for 2 core elements of the marketer's role”? How does Dave advise marketers on crafting their playbook? What are the core questions to ask? Where does Dave see many going wrong here? How does one turn a playbook into a repeatable, measurable process? With channel volatility being so high, is it possible to have a repeatable and predictable process?  
• What are Dave’s biggest observations on what B2B marketers can learn from B2C? How does that change how Dave thinks about new campaigns and community building with Asana today? Who does Dave think has done this particularly well in the world of enterprise? Are there any challenges to trying to carry over B2C into the world of B2B? 

Dave’s 60 Second SaaStr:

1. What does Dave know now that he wishes he had known at the beginning of his career in marketing? 
2. Biggest breakdown in the working of an efficient funnel?
3. A moment in Dave’s life that has served as an inflection point and changed the way he thinks? 

Read the transcript on our blog.

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

Dave King

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?

Read the transcript on our blog.

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

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?

Read the full transcript on our blog.

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

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, Menlo Ventures Partner Naomi Ionita.

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

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

This podcast is an excerpt of Naomi’s session at SaaStr Annual 2019. You can watch the full video on our website.

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

Naomi Ionita

Today's sponsor: Traditional customer beta testing can't keep up with the speed of Agile or the demands of continuous delivery. Centercode's approach to real-world Delta Testing fuels product and engineering teams with actionable quality and UX insights before every new release. Visit Centercode.com to learn more.

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? 

Read the full transcript on our blog.

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

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

This podcast is an excerpt of Matt’s session at SaaStr Annual 2019. You can watch the full session on our blog.

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

WP Engine

Today's sponsor: Traditional customer beta testing can't keep up with the speed of Agile or the demands of continuous delivery. Centercode's approach to real-world Delta Testing fuels product and engineering teams with actionable quality and UX insights before every new release. Visit Centercode.com to learn more.

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?

Read the full transcript on our blog.

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

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?

Read the full transcript on our blog.

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

Tom Bogan, CEO of Adaptive Insights, a Workday company, will review the key principles to building a successful SaaS company. From team to vision to metrics to funding and more, these principles provide the framework for high-growth, high performing SaaS companies.

How can you develop a winning culture? How can you set aggressive but realistic goals? What’s needed to build the right team in SaaS today?

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

• The important maxims about team building
• Insights on fundraising and why you might not want to always raise at the highest valuation
• Personal stories from his time building Adaptive Insights

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

Whitney Bouck is the COO @ HelloSign (now a part of Dropbox). For those that do not know, HelloSign is the company reimagining how you approach your most important business agreements with their award-winning e-Sign solution. As for Whitney, she directly leads the organization's go-to-market efforts, including sales, marketing, business development and customer operations. Whitney is also an advisor to companies funded by the YC Continuity Fund, focusing on enterprise strategy, go-to-market strategy, leadership and execution. If that was not enough, Whitney is also on the board of Ekata, building the global standard in identity verification. Finally, prior to HelloSign Whitney spent close to 5 years at Box where as SVP Global Marketing & GM Enterprise she took on all of marketing globally for Box and was responsible for reshaping the company brand from SMB to enterprise. 

In Today’s Episode We Discuss:

• How Whitney made her way into the world of SaaS originally with Box and how that led to her coming one of today’s leading COOs with HelloSign? What were Whitney’s biggest takeaways from seeing the hypergrowth of Box? How did that change her operating mentality?
• What does truly successful exec leadership look like in Whitney’s mind? When is the right time for founders to think about building out their first exec team? What common mistakes do they make in the process? What can founders do to attract seasoned SaaS execs to their early-stage company? What are the questions that suggest an individual has a startup culture to them? What are the indications that they are a “big company” person?  
• What does Whitney believe is the new role of the CIO? What has changed about their tole and what has driven this change? With their coming front and centre in the org, how does that change both the reporting and operating structure of the business? What are the nuances and intricacies of this role that many do not often consider? 
• COO is thrown around as a term today, what does it really mean to Whitney? What does Whitney believe separates good from great when it comes to COOs? When is the right time for founders to start looking for their first COO? What should they look for in their first COO? What is the optimal onboarding process for any new COO? 

Whitney’s 60 Second SaaStr:

1. What does Whitney know now that she wishes she had known at the beginning?
2. What makes for the optimal relationship between COO and CEO?  
3. What is the most challenging element of Whitney’s role with HelloSign today?

Read the full transcript on our blog.

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 Bouck

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.

Our guest today is Pipedrive SVP of Global Sales Tara Bryant.

Globalization opens up a world of opportunities for sales growth. We often focus on the positive sides of growth—but what about taking a look at the ugly sides? Even what we could consider “good problems” need preparation, and it starts by understanding your team and your goals, including knowing when and how to recruit members of your team, and building in a way that compliments your growth. Do you need more man-power on the customer facing side, or do you need to bring in new management to keep everything in line? Growth isn’t always linear, and the steps to success aren’t always one after the other. How do you prioritize and organize to bring the best possible results? This side of success can be scary, but knowing how to prepare can set you up to reach your companies long term growth goals.

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

• What does the ideal candidate look like?
• How to hire your core staff really well
• Enabling salespeople to share learnings

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

Companies that have access to more accurate financial data have the ability to develop seamless exchanges of information, providing consumers with improved ways to manage their finances. But how do companies gain secure access to that data in the first place? Enter the platform company. Hear from Plaid co-founder and CEO, Zach Perret and CNBC's Ari Levy as he walks through his lessons learned building Plaid and how it found itself at the center of the fintech ecosystem.

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

Zach Perret