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