The Official SaaStr Podcast: SaaS | Founders | Investors

This interview originally aired as Episode 229 on April 29, 2019.

Manny Medina is the Founder & CEO @ Outreach, the market leading sales engagement platform that turns your team into a revenue driving machine. To date, Manny has raised over $114m in funding from some great people including friends of the show in the form of Alex Clayton @ Spark, Mayfield, Trinity Ventures and DFJ Growth, just to name a few. Prior to founding Outreach, Manny spent 7 years with Microsoft where he ran the Latin America and Canada business development group for Microsoft’s emerging mobile division, representing $50M of yearly revenue. Befofe that Manny was a Senior Product Manager @ Amazon where he engineered the compensation system for Amazon Associates and Web-Services which accounts for 15% of Amazon's traffic. 

In Today’s Episode We Discuss:

• How Manny made his way to found the leader in sales engagement from product management at Amazon and Business Development @ Microsoft.
• How does Manny fundamentally approach managing top of funnel? What are the 2 big dangers of not managing it aggressively? What can be done to ensure not only full but high quality top of funnel? 
• Why does Manny believe it is so important to track pipeline coverage as one of your core metrics? What does good look like when it comes to pipeline coverage? How does this change if you are creating vs in an existing market? How does Manny think about specialisation within the sales function? Why are SDR’s 99% of the time not able to carry leads to completion? 
• How does Manny think about quota construction today? Does Manny err on the side of setting high to be ambitious or setting low to increase confidence? How can managers really empower their reps to be aggressive in hitting their quota and exceeding it? How does Manny think about resource allocation on the individual rep level? What is sufficient? What is excessive?
• Does Manny believe that the founder should always be responsible for selling their product at one moment in time? How did Manny sell the first $1m in ARR simply through walking the streets of SOMA and selling door-to-door? What were his biggest lessons from doing this?  Why does Manny believe that you should not have a VP before $5m? 

60 Second SaaStr:

1. What does Manny know now that he wishes he had known in the beginning?
2. What does the future of sales prospecting look like to Manny?
3. What would Manny like to change about the world of SaaS 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

Harry Stebbings

SaaStr

Manny Medina

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Lucidchart has been recognized as one of the most mature Product Lead Growth business models in the market, driving over 700,000 registrations per month, combined with a hyper-efficient B2B business model. It didn’t happen by accident. It happened through experimentation: from extensive A/B testing (with over 500 marketing tests completed in 2018), to testing crazy brand videos (which have garnered over 200 million views and was named the only ad campaign that truly mattered in 2018 by Adweek), to constant iteration and expansion of the business model.

Experimental marketing brings together the science and art of marketing, allowing for creativity that drives results. It’s an essential skill in the toolkit of the modern marketer, and one that’s easy to get started with, no matter your company scale.


Key Takeaways:

- Discover how to start or extend your marketing experimentation.
- Learn how marketing experimentation can apply across funnels, brands, and business models.
- Get tips on how to build a culture of experimentation that fosters creativity and drives business results.

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

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?

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

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Salesloft CEO Kyle Porter, Zoom Head of Sales Ops Hilary Headlee and Fireeye VP of WW Sales Christina Foley share the seven tips and tricks to getting more revenue per AE.

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

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?

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

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Kevin Egan, Slack's VP of North American Sales and Dannie Herzberg, Slack's Director of Sales as discuss their strategies for going from Freemium to Enterprise at Slack.

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

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?

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

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

Hear about Adyen’s journey from a Dutch payments startup to a global public company with more than 15 offices around the world working with large global companies like Facebook, Spotify, Uber and Microsoft. Roelant shares lessons from the company’s own global growth path and will be giving practical tips for companies who are thinking about expanding their business globally. Roelant is joined by Felicis Ventures Founder, Aydin Senkut, who shares the commonalities he sees in successful companies...starting with culture.

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

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 organisations determine which startup to join? 

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

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com

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.

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cloud.substack.com