Tom Tunguz is General Partner @ 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 Tom, he joined Redpoint in 2008 and has since led investments in Kustomer, Looker, Expensify and Gremlin all prior guests on the show I hasten to add. He is also the co-author of Winning with Data: exploring the cultural changes big data brings to business. Tom has also been named on the Forbes Midas Brink list. Before joining Redpoint, Tomasz was the product manager for Google’s AdSense social-media products and AdSense internationalization.

In Today’s Episode We Discuss:

• How Tom made his way from creating software with his father in Brazil to being GP and forefront figure in the SaaS investment community as a GP at Redpoint today?
• Annual contracts: To what extent do annual contracts dominate today? How does this differ when comparing enterprise to SMB? Why does Tom think in the early days one should be wary of signing too many multi-year contracts? What are the dangers there? How does Tom think about calculating churn when it comes to multi-year contracts?
• What were the findings on what good looks like when it comes to logo retention? How does this differ when comparing SMB to enterprise? What were the commonalities of leading indicators of churn? Is it fair to always surmise that when serving SMB one will always have a higher rate of churn? What is the right way to conduct a churn analysis?
• Assisted vs unassisted: What does Tom believe are the leading benchmarks for both? How does this differ when comparing SMB to enterprise? How does the impact of a salesperson change the conversion rate? What time frame from SAL to closed lead suggests product market fit? What one question must all founders be asking in the sales process?
• How does Tom think about constructing comp plans the right way today? How should comp plans differ when comparing AEs to customer success? Where should the responsibility for upsell lie, customer success or sales? Should sales commission be paid on renewals?  

Tom’s 60 Second SaaStr:

1. What does Tom know now that he wishes he had known at the beginning?
2. What is Tom’s favourite book and why?
3. What is Tom’s most recent investment and why did he say yes?

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

Tom Tunguz

Nick Mehta is the CEO @ Gainsight, the #1 customer success platform for corporate services, turning your customers into your best growth engine. To date Gainsight have raised over $156m from some of the world’s best VCs in the form of Lightspeed, Bessemer, Insight Venture Partners, Battery Ventures and Salesforce Ventures. As for Nick, prior to Gainsight he was the CEO @ LiveOffice where he grew cloud archiving ARR from $2m in 2008 to $25m in 2011 and drove and negotiated the acquisition by Symantec for $115m in cash. Before LiveOffice Nick was Senior Director of Product Management @ Symantec where he led $378 MM market-leading email archiving / security businesses managing over 180 people across 3 continents. I do also have to say a huge thank you to both Byron Deeter and Jason Lemkin for the intro to Nick over two years ago.

In Today’s Episode We Discuss:

• How Nick made his way into the world of SaaS and came to lead the charge in the category creation of customer success as CEO with Gainsight? What were some of his big lessons from being CEO at 2 companies during 2 macro market crashes?
• What does Nick mean when he says, “customer success will fail if it is just a role and not a strategy?” What can the leader and CEO do to imbue this company wide approach to customer success? What tangible actions are on offer? What works? Where do many make mistakes?
• Nick has previously said, “burying customer success undel sales does not work”. Why does this have such a high rate of failure? What should the optimal sales to customer success relationship look like? What does Nick mean when he says, “product is to customer success what marketing is to sales”. How should product and customer success work together?
• Why does Nick believe the mythology of the “A player” when business building is fundamentally dangerous? What can leaders and CEOs proactively do to ensure a diverse and differentiated talent pipeline? What question does Nick find most revealing in terms of one’s character and potential? Where do many go wrong in building and scaling their teams in SaaS?
• Why does Nick push back against the “hire fast and fire fast” thesis? What are the negative consequences of it? Why is it short-sighted and premature in many cases? What does Nick suggest for individuals struggling to find their optimal role within an organisation? How much time does one give someone struggling to find their role?

Nick’s 60 Second SaaStr:

1. Who must fundamentally own the renewal, sales or customer success?
2. What Nick know now that he wishes he had known at the beginning?
3. What would Nick most like to change in the world of SaaS?
4. Most surprising action that has moved the needle for a company in terms of retention?

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

Nick Mehta

In Today’s Episode We Discuss:

• David Skok: General Partner @ Matrix Partners: Why does David believe that all good products have at least one variable pricing axis? How can founders determine which variable they should choose for their product? What are the pros and cons?
• Chetan Puttagunta: General Partner @ Benchmark: Why does Chetan believe we have seen a strong decline in the per seat pricing model? What are the major drawbacks of it? What are we seeing replace it? What has Chetan seen work well amongst his portfolio?     
• Mark Suster: General Partner @ Upfront Ventures: What were Mark’s two biggest lessons on pricing from seeing the hyper-growth of Salesforce first hand? WHat does Mark advise founders when it comes to price anchoring and discounting? How does Mark view the sale of professional services with this in mind?
• Amanda Kleha: Chief Customer Officer @ Figma: What were Amanda’s biggest learnings from running the Zendesk pricing playbook? What does Amanda mean when she says that successful pricing is broke up into 3 separate product features?   
• Brad Birnbaum: Founder & CEO @ Kustomer:Why does Brad push back on the common suggestion of a “no man’s land in SaaS pricing”? Why is innovation in pricing actually detrimental to sales in most cases?
• Guy Podjarney, Founder & CEO @ Snyk: How does Guy think about having a large enough base to test pricing strategies? How does Guy think about the balance between freemium and paid? Does one have to come first?

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

Bridget Gleason is VP of Sales @ Logz.io, the startup that uses predictive analytics and machine learning to provide monitoring, troubleshooting and security. To date, Logz have raised over $45m in funding from the likes of Openview, 83North and Vintage just to name a few. As for Bridget, she has the most incredible track record. Before Logz, Bridget was VP of Corporate Sales @ Sumo Logic where she drove ARR up by a record 237%. Prior to SumoLogic, Bridget was VP of Sales @ YesWare where she increased MRR per rep by 450%. Finally before YesWare, she was VP of Sales @ Engine Yard, where she tripled monthly recurring revenue, over course of 3+ year tenure, in 3 key leadership roles.

In Today’s Episode We Discuss:

• How Bridget made her way into the world of sales and became the sales leader she is today, having started in the world of marketing?
• Having led and scaled numerous sales teams, does Bridget agree the best sales reps are outgoing and extroverted? How does the successful profile of a sales rep depend on (1) whether you are selling to SMB or enterprise? (2) The stage of the company? How can one stress test the character type of the candidate pre-hire in the interview stage?     
• Does Bridget believe that sales reps really are as coin operated as many suggest? Why is that potentially an unfair position to take? How does Bridget think about structuring the right comp plans for her team? What other methods of incentivisation does Bridget believe works equally as efficiently?    
• Does Bridget believe that you should pay sales rep commissions on services revenue? Should one pay the same or lower commissions on renewals? Should multi-year deals be paid upfront? How does one structure commissions for the sales team with that in mind?  
• When does Bridget believe is the right time to hire (1) your first sales reps? (2) Your first VP of Sales? Why does Bridget believe that 70% of VP of Sales positions do not work out in the first 9 months? What can founders do to increase the likelihood of success within their VP of Sales role? Where do many go wrong?  

Bridget’s 60 Second SaaStr:

1. What does Bridget know now that she wishes she had known when she started in SaaS?
2. SDR’s are the most important function in the sales process, agree or not and why?
3. Sales training, what works? What does not?

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

Bridget Gleason