The Official SaaStr Podcast: SaaS | Founders | Investors

Jerry Jao is the Founder & CEO @ Retention Science, the startup that brings intelligence to your marketing automation through artificial intelligence that delivers a personalized customer experience, at scale. To date, Jerry has raised over $10m in VC funding with Retention Science from great friends of the show in Forerunner Ventures, Upfront Ventures, Clark Landry, Andy Rankin and more fantastic names. Prior to founding Retention Science, Jerry founded two other e-Commerce marketing technologies and served as Strategic Innovation Officer to Clear Channel Radio. Jerry is also a Guest Lecturer at The Kellogg School of Management and sits on the board of Penango.

In Today's Episode You Will Learn:

• How did Jerry make his way into the world of SaaS with the founding of his first company? What have been the top 3 mistakes that Jerry has made since founding Retention Science?
• With P&G, Unilever and Olay all as enterprise clients, how did Jerry first sell into them as a small startup? What is required to give these large enterprises confidence in buying from startups? What does the perfect case study look like to convert these mega accounts? In the early days is it a quality or quantity of logos game?
• How important is it for the founder to be really actively involved in the sales process to these mega corporations? How does Jerry divide his time now between new and existing customers, as well as team and investor management How does Jerry approach multi-year and prepaid deals with these incumbents? What is the line of reasoning for suggesting prepaid is fair?
• Retention Science have been profitable since 2018, how does Jerry look to balance the mindset of fast growth and profitability? How does Jerry think about payback period for enterprise sales reps with this profitability mindset? How does this affect his thoughts and views on internal asset allocation?

Jerry's 60 Second SaaStr

1. A moment in Jerry's life that has changed the way he thinks?
2. When I say success in SaaS who embodies this to Jerry?
3. What does Jerry know now that he wishes he had known at the beginning?

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

Jerry Jao

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:

• What are the leading indicators that early stage VCs dig deep on to assess the strength of product market fit? What level of traction both in enterprise and SMB would an early stage investor deem exciting enough to pursue? What levels of engagement are sufficient enough to suggest cause for a much larger and increased round?
• How should founders assess sales rep productivity? What can they do to actively shorten the ramp time? How will early stage investors analyse the ramp time? What suggests repeatability of process?
• Why does David believe there is no point focusing on CAC/LTV in the early days? What is the single biggest thing that founders can do to show repeatability of process and revenue as fast as possible?
• What is the most common reason that people miss plan? How must the mindset of the founder switch from extreme frugality to hyper growth scaling? When is the right time for this transition to take place? What are the inherent challenges to this switch?

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

David Skok

If you're looking to simplify file version control, ensure data security and save time while increasing accessibility, Egnyte is the right solution for your business. Egnyte delivers secure content collaboration, compliant data protection and simple infrastructure modernization; all on a single SaaS platform. Founded in 2007, Egnyte is privately held, headquartered in Mountain View, CA and supports thousands of businesses worldwide. For more information, please visit egnyte.com/SaaStr.

MonkeyLearn allows companies to easily analyze text with Machine Learning. Customers like Clearbit and Segment are using MonkeyLearn to turn emails, support tickets, customer feedback, and documents into actionable data. Their platform makes it super easy to classify texts by topic, sentiment or intent or to extract specific data such as keywords, names, and companies. MonkeyLearn makes teams more efficient by automating business processes, getting insights and saving hours of manual text data processing. And if you would like to learn more, head to monkeylearn.com/saastr, that is www. m o n k e y l e a r n .com/saastr. Plus, listeners of the SaaStr podcast will have a very special opportunity to purchase monthly plans for half the price. So, check out MonkeyLearn and start getting more out of your text today.

Dave Kellogg is the CEO @ Host Analytics, the leader in cloud-based enterprise performance management (EPM). Previously, Dave was SVP/GM of Service Cloud at Salesforce and CEO at unstructured big data provider MarkLogic. Before that, Dave was CMO at Business Objects for nearly a decade as the company grew from $30M to over $1B. Dave has also worked in various capacities with the likes of Breeze, GainSight, Tableau and MongoDB and previously sat on the boards of ag tech leader, Granular (acq by DuPont for $300M) and big data leader Aster Data (acquired by Teradata for $325M).

In Today's Episode You Will Learn:

• Why does Dave believe it is foundational to be an ARR first company? How does Dave think startups can show their ARR first mentality from the first investor meeting? How does this help drive operational efficiency? How does Dave segment ARR into 3 distinct camps?
• Why does Dave argue that SaaS metrics are not nearly as simple as they seem? Which metrics does Dave believe most founders confuse? What metrics will the best VCs pick apart and dig deep on? How can founders respond with accuracy and confidence?
• How does Dave respond to multi-year deals? Under what conditions are they acceptable and not acceptable? How must they be reported in accounting? Where do many startups go wrong when considering multi-year deals? How important is it for them to be pre-paid?
• Why does Dave argue that renewals do not measure customer satisfaction?What is an accurate measurement to determine customer satisfaction? How often should this be conducted? What sample size of customer gives the right amount of data?
• How does Dave approach comp with regards to sales team cross-sell and upsell? Why is it not as black and white as boards often portray? Under which circumstances does Dave believe double comp is justified and not justified? How can you communicate this to your board successfully?

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

Dave Kellogg

If you're looking to simplify file version control, ensure data security and save time while increasing accessibility, Egnyte is the right solution for your business. Egnyte delivers secure content collaboration, compliant data protection and simple infrastructure modernization; all on a single SaaS platform. Founded in 2007, Egnyte is privately held, headquartered in Mountain View, CA and supports thousands of businesses worldwide. For more information, please visit egnyte.com/SaaStr.

Phil Fernandez is a Silicon Valley veteran, with more than 35 years of experience building and leading breakout technology companies. Phil co-founded Marketo in 2006 and led the company as Chairman and CEO for a decade, overseeing its successful IPO and acquisition by Vista Equity Partners. Prior to Marketo, Phil served as president and COO of Epiphany, an enterprise customer relationship management (CRM) software company. Today, Phil is a Venture Partner with Shasta Ventures, the fund with a portfolio including the likes of Nest, eero, Zuora, Canva and many more incredible companies.

In Today's Episode You Will Learn:

• When is the right time to hire your first CRO? Where did Phil make a big mistake in who owns what revenue numbers? What are the traits that make the best CROs? How should they look to work with both sales and marketing to drive efficiency internally?
• Why does Phil believe you must hire the most senior Chief People Officer as soon as you can? What does the role of "Chief People Officer" really embody? How should they look to work with HR internally? Who should they report to? How does this role change with a scaling organisation?
• How has Phil seen the relationship between average contract value and potential for expansion change? What is the correlation between and ongoing services component and both customer NPS and expansion? Where did Phil go wrong with this at Marketo?
• How should emerging SaaS startups today be thinking about technical legacy debt? Why does Phil believe it is never to early to have a Head of Research function? How should this function work with the team to build the latest technology into new products?
• Why did Steve sell Marketo to Vista Equity Partners? What was the thesis and big learnings from that experience? What does Phil mean when he says he did not "watch the clock properly''? How can founders today be proactively thinking about ramp time for sales reps, new product engagement etc.

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

Phil Fernandez

Bill Binch is a leader and expert in the SaaS sales industry, currently CRO @ Pendo.io, the startup that helps you understand and guide your users, creating a product experience they can't live without. They have raised over $58m in VC funding from some of the best in their space with the likes of Battery Ventures, Spark Capital and Salesforce Ventures, all backing them. As for Bill, prior to Pendo, Bill was the Senior Vice President of Global Sales at Marketo for 8 years. He joined when it was a small venture-backed startup with a mission to reinvent marketing automation. It was his sales leadership and expertise that formed a critical component in building Marketo into one of the fastest-growing enterprise software companies in the world, recognized through his being awarded worldwide VP of sales in 2011.

In Today's Episode You Will Learn:

• How Bill made his way into the world of SaaS and came to be employee #18 at Marketo before making the transition to today, as CRO @ Pendo?
• Bill has said before that career paths are for B players. First, what is wrong with the current thinking around career paths? Why does that inherently mean that A players do not align with them? How can one determine when is the right time to step away from the career paths? What characteristics and attributes do those truly special opportunities have?
• Bill has successfully made the transition from transactional business to enterprise business many times, what have been his core learnings on what it takes to make this transition successfully? What are the biggest challenges in making the transition? How does the internal structure of the team change when making this transition?
• What does Bill mean when he says you have to "rig the recruiters"? What incentives can be placed in front of them that ensure you will be a priority for them? On the flip side, what incentives do you have to give the recently on boarded employees to encourage grassroots, word of mouth on the company brand?
• How does the company and sales cycle fundamentally change when moving from $0-1m ARR? What does that mean for the company policy on discounting and pilots? How does the company alter when transitioning from $1-10m in ARR? How can sustainable social validity be built in this stage? How does a company successfully move from $15m-100m in ARR?

60 Second SaaStr?

1. What does Bill know now that he wishes he had known at the beginning?
2. What keeps Bill up at night?
3. What does Bill mean when he says you have to check your ego?

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

Bill Binch

If you're looking to simplify file version control, ensure data security and save time while increasing accessibility, Egnyte is the right solution for your business. Egnyte delivers secure content collaboration, compliant data protection and simple infrastructure modernization; all on a single SaaS platform. Founded in 2007, Egnyte is privately held, headquartered in Mountain View, CA and supports thousands of businesses worldwide. For more information, please visit www.egnyte.com/SaaStr.

Kristina Shen is a Partner @ Bessemer Venture Partners, one of the world's leading venture funds with a portfolio including the likes of Pinterest, Skype, Box, LinkedIn, Yelp and many more incredible companies. As for Kristina, she serves on the boards of DoubleDutch, Glint, Retail Solutions and Zoosk and is also a board observer with RainforestQA, Vidyard, Gainsight and ServiceTitan. Kristina is also one of the best data gurus as the co-author of Bessemer's State of the Cloud 2016 and 2017 and Bessemer 10 Laws of Cloud, which captures the top trends among leading public and private cloud computing and enterprise mobile companies. Due to Kristina's success she has been named to both Forbes and Business Insider's 30 Under 30 in 2014 and 2016, respectively.

In Today's Episode You Will Learn:

• How Kristina made her way into the world of cloud investing and came to be the data guru for much of the cloud landscape?
• What does Kristina fundamentally mean when she states the key question is, is there velocity in this SaaS business? Is velocity just about revenue or ARR growth? How can startups present real velocity with their sales funnel? How can startups present further velocity through their SQL process?
• Why does Kristina believe that "private SaaS multiples are not expensive and we need a new framework"? What makes the existing framework inaccurate? What does this mean for the way Kristina assess ARR multiple and growth rates? How does this framework alter Kristina's perception of the often hailed "Rule of 40"? How does it change with scaling?
• What are the core elements Series A SaaS investors focus on today? With regards to revenue benchmarks for the A round, where do they need you to be both on the low and high end? Where do Series A investors expect startups to be for y/y ARR growth?
• What core metrics are required to successfully raise your Series B in SaaS today? What does Kristina think is the fundamental difference between Series A and B today in SaaS? What can founders do to show repeatability and reliability of revenue streams as they move into the B round?

60 Second SaaStr?

1. What does Kristina know now that he wishes he had known at the beginning?
2. Questions from Jeremy Levine: What would Kristina like her legacy to be as an investor in 20 years time?
3. What keeps Kristina up at night?
4. Is it worse to see an amazing deal and pass on it or to have never seen it at all?

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

Kristina Shen

Jason Lemkin is the Founder @ SaaStr, the world's largest SaaS event with over 20,000 of the world's best SaaS founders and investors attending every year. Jason also invests from SaaStr's debut $70m fund and has made prior investments in the likes of Algolia, TalkDesk, MixMax, Rainforest QA and many more incredible companies.

In Today's Episode You Will Learn:

• How does Jason think founders should approach long sales cycles in the early days? Why does Jason believe that ultimately long sales cycles do not matter? What can the truly great VPs do to impact those long sales cycles?
• How does Jason think founders can tackle lead optimisation with their team? How can founders determine which leads to send to which AEs? What will the effect of this tailored lead distribution be?
• When is the right time for the founder to begin to take a step back from sales? Why does Jason believe that the founder must always be involved in the sales process? How does this look at scale when selling to thousands of customers? How does this mean the founder works with the growing scaling team over time?
• Why does Jason believe that SaaS companies have to raise so much money today? What is the core decision that founders must make when determining how much they need to raise? How should founders approach the topic of cloning? What are the 3 core advantages they have over their clones? What must they be mindful of when being cloned by incumbents?

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

Timo Rein is the Founder & CEO @ Pipedrive, the startup that helps sales people focus on actions that close deals. To date, Timo has raised over $30m from the likes of Atomico, Bessemer Venture Partners, TransferWise Founder Taavet Hinrikus and Andy MCloughlin and has scaled the team to over 330 people across multiple continents. Prior to founding Pipedrive, Timo was a Partner @ Vain & Partners acting in a consultancy role on how to get the best ROI from your sales process and before that was himself a door-to-door salesman with SouthWestern Company selling high ACV products.

In Today's Episode You Will Learn:

• How Timo made his way into the world of SMB CRM with the founding of Pipedrive from the days of being a door-to-door salesman of high ACV products?
• Why did Timo choose to go global with Pipedrive from day 1? What are the benefits of founders having this global mindset from the start? What are Timo's biggest learnings in terms of acquiring customers globally early on? What worked? What did not work? How did Timo think about pricing on an individual country perspective? What are the challenges with this?
• Having raised from both US and UK VCs, how does fundraising differ when comparing Europe to the US? If Timo had to say the West Coast, East Coast and European VCs each had one area they focus, what would that area be? What are the challenges with these inherent focus points? What advice would Timo have for foreign founders looking to make it big in the US?
• How does Timo look to manage a team so spread across the globe? What are the core challenges of this? What works? What does not work? What functions can be split up by geography? What must remain in one location? Now at 300 people, how does Pipedrive ensure for the same values fit when hiring at scale?
• Many VCs say with such low ACV and such high churn, the SMB market is too difficult. How does Timo respond to this? How does Timo think about ensuring the continuous refilling of top of funnel? How does Timo think about acquiring such small customers in a cost efficient manner?

60 Second SaaStr?

1. What does Pipedrive look like at $100m ARR?
2. What keeps Timo up at night?
3. Who is Timo's favourite angel investor?
4. What does Timo know now that he wishes he had known at the beginning?

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

Timo Rein

Jason Lemkin is the Founder @ SaaStr, the world's largest SaaS event with over 20,000 of the world's best SaaS founders and investors attending every year. Jason also invests from SaaStr's debut $70m fund and has made prior investments in the likes of Algolia, TalkDesk, MixMax, Rainforest QA and many more incredible companies.

In Today's Episode You Will Learn:

• When is the right time to hire your first sales rep? What characteristics must those sales have? Why does Jason believe it is impossible to poach a rockstar from another fast scaling startup? Should you then hire the stretch VP or the more experienced, potentially burnt out exec?
• How does Jason think about aligning compensation to company objectives? Within the company, which functions serve as the best test areas for variable compensation? What must you be wary of when installing a system of variable compensation?
• When is a stretch VP a stretch too far? What must a stretch Head of Sales have done to make him ready? What must a VP of Product done before to make him ready? What resources can you build around stretch VPs to provide them with additional support?
• How does Jason think about the first time you spend to acquire customers? Why does Jason suggest just trying to make $1 for every $1 you spend? Why is it crucial to think of your marketing spend on a blended basis? How can you create alignment between the marketing teams number and the cadence of sales?

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 Lee is the Founder & CEO @ ProsperWorks, the #1 recommended CRM for G Suite. To date, ProsperWorks have raised over $85m in VC funding from the likes of True Ventures, Norwest, GV, Bloomberg Beta and more incredible names. As for Jon, prior to ProsperWorks, he started in investment banking at Merrill Lynch before moving to run a large operations team at Yahoo. Jon then founded Bazaar Advertising Solutions, a business self funded from a Palo Alto apartment that Jon scaled into a highly profitable $47m business in less than 2 years. Jon then sold Bazaar to Epic Media in 2006. Following the acquisition, Jon founded DNA Games, the number one casino simulation game on Facebook with more than 20 million players, ultimately acquired by Zynga in May 2011.

In Today's Episode You Will Learn:

• How Jon made his way into the world of CRM having successfully founded and sold 2 prior business in the lead gen and gaming space? Why does Jon believe building a SaaS business is very much like building a gaming business?
• How does on think about the scaling of company culture with the scaling of headcount? Where does Jon see the inflection points where this culture starts to break down? What does Jon mean when he suggests "the importance of a culture of innovation"?
• Why does Jon believe it is so important to insert a culture of risk into the organisation? How does this risk mindset differ and look across different segments of the business? How does Jon aim to create a culture of risk and ambition without a fear of failure and not hitting targets?
• Why does Jon think it is always better to start in SMB and move to enterprise? How does this decision change how one thinks about product roadmap? How does this change how one approaches traction building ahead of fundraising? What should one look to learn from rapid iteration and testing before moving to the enterprise market?

60 Second SaaStr?

1. What does Jon know now that he wishes he had known at the beginning?
2. What keeps Jon up at night?
3. What is Jon's favourite SaaS reading material?

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 Lee