Amanda Kleha is the Chief Customer Officer @ Figma, the startup that allows you to turn ideas into products faster through design, prototyping and feedback gathering, all in one place. To date, Figma have raised over $42m in VC funding from some of the best in the business including Index Ventures, Kleiner Perkins, Greylock Partners and former guests on 20VC, Daniel Gross and Adam Nash. As for Amanda, prior to Figma, she held numerous roles at Zendesk including SVP of Marketing and Sales Strategy. Amanda joined Zendesk as the first marketing hire and over the next 7 years Zendesk grew to over 2,000 employees. Before Zendesk, Amanda worked on the marketing team for Google’s Enterprise SaaS businesses. If that was not enough Amanda is also an advisor at Airtable and Smartling.

In Today’s Episode We Discuss:

• How Amanda made her way into the world of SaaS and came to join Zendesk as their first marketing hire seeing the company scale to over 2,000 over the next 7 years?
• What were some of Amanda’s biggest learnings from seeing Zendesk scale from 12 to 2,000? How does one determine those that can vs cannot grow with the business? What is the sign a stretch VP is a stretch too far? How does Amanda balance between a culture of risk taking but also not accepting failure to easily?     
• How does Amanda like to run the interview process? Why does Amanda like to not show emotion when interviewing a candidate? What are the benefits of this for the brand of your company? What single question does Amanda find most revealing in showing the abilities and character of a candidate in an interview?   
• What does Amanda mean when she says “pricing is made up of 3 components”? Where does Amanda believe most people go wrong with pricing? Is there such thing as no man’s land in SaaS pricing? How does Amanda think the go-to-market has to change with every stage of development? What are the challenges with this?
• How does the structure of decision-making change with scale? What are the inflection points? When does both decision-making and communication tend to break down? What can be done to ensure seamless cross-functional communication across the org? Where do most people fail here?   

Amanda’s 60 Second SaaStr:

1. What does Amanda know now that she wishes she had known when she started in SaaS?
2. Is there such thing as no man’s land in SaaS pricing?
3. How to ensure customer support is strategic and not just reactionary?

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

Amanda Kleha

Anne Raimondi has more than 20 years experience driving growth at startups and building them into nationally recognized brands. She has served as a leader and executive for technology innovators including Zendesk, Survey Monkey, Blue Nile, and eBay. Anne is also a Lecturer in Management at Stanford Graduate School of Business, teaching two popular courses, “Startup Garage” and “POWer: Building the Entrepreneurial Mindset.” She currently serves on the board of directors for SendGrid (NYSE: SEND) and MyHealthTeams. If that was not enough, Anne is also an active angel investor with an incredible portfolio including the likes of Canva, ipsy, and Minted just to name a few.

In Today’s Episode We Discuss:

• How Anne made her way into the world of startups with Zendesk? How did seeing the hyperscaling of Zendesk impact Anne’s operational approach and mindset?
• Does Anne agree that certain individuals are destined for certain stages of company development? What are the leading indicators that one can or cannot scale? What are the inflection points in company growth where process tend to break? What can managers do to provide security in these times of change?   
• Why does Anne believe that everyone should be a product person in SaaS? What are the inherent benefits of this product centricity? How does the element of product centricity change when catering to 2 customers, CIO and consumer? How does Anne advise on this issue of agency?  
• How does Anne approach optimising internal decision-making processes? Where do many leadership teams make mistakes here? What is the right way for leadership teams to communicate their decisions to the wider team? How does Anne approach ensuring cross-functional communication at scale?
• How has Anne seen her style of board membership change over the last 8 years? What has been an inflection point that has changed the way she thinks about what it takes to be a great board member? Who has been the best board member Anne has worked with? What made them so special?  

Anne’s 60 Second SaaStr:

1. What does Anne know now that she wishes she had known at the beginning?
2. The right way for founders to view competition?
3. What would Anne most like to change in 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

Anne Raimondi

Jason VandeBoom is the Founder and CEO of ActiveCampaign, a sales and marketing automation platform that enables small businesses around the world to meaningfully connect and engage with their customers. Jason founded the company in 2003 and under Jason's leadership, ActiveCampaign has flourished from a successful but small company and then in 2013, they transition to SaaS, since they have grown to more than $50 million in ARR in less than five years, while still maintaining profitability and its culture. They have also only raised a single $20m PE round to accelerate their growth, making them a market leader in terms of funds raised/ARR generated.  

In Today’s Episode We Discuss:

• How Jason made his way into the world of SaaS and came to found ActiveCampaign?
• Why is Jason so bullish that “SMB first, works”? What are the inherent benefits from starting at SMB? How does it affect product feedback? How does it affect how you build and scale your team? How does one start to layer in market and enterprise over time? Why does it give you additional leverage?  
• What does Jason think is the right way to scale your sales team> Why does one not need funding to scale sales teams? When does Jason believe is the right time to hire your first VP of Sales? What were the biggest mistakes that Jason made in the scaling of his sales team? Why should hire 3 reps to start at one time?  
• How does Jason view the current fundraising environment? Why does Jason believe that “no one cares if you get funding”? Why does Jason believe there is a fear around needing fast growth? Who is to blame for this? How should founders in the messy middle feel when seeing large fundraises in the media?
• Why does Jason believe that all leaders need to be consuming all feedback? How does Jason consume feedback on a daily basis? What metrics and elements does he look for in this assessment? How has Jason’s role changed over the 16-year CEOship? Does it get easier over time in Jason’s mind? What has been the biggest challenge?

Jason’s 60 Second SaaStr:

1. What does Jason know now that he wishes he had known at the beginning?
2. No man’s land of SaaS pricing, exist or a myth?
3. Multi-year deals, all they are cracked up to be or overrated?

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

Jason VandeBoom

Ryan Barretto is the SVP of Global Sales at Sprout Social, a leading provider of social media engagement, advocacy and analytics solutions for business. To date they have raised over $111m in funding from the likes of NEA, Goldman Sachs and their very recently announced $40m Series D led by Future Fund.  At Sprout Social Ryan oversees both the Sales and Customer Success organizations. Prior to Sprout, he was the VP of Global Sales at Pardot–a Salesforce company. At Pardot, Ryan's team tripled revenue growth in two years, making Pardot one of Salesforce's fastest growing businesses and during his 10 year tenure at Salesforce he saw the company grow from $180m to $7.5Bn.

In Today’s Episode We Discuss:

• How Ryan made his way into the world of SaaS with Salesforce over 13 years ago? What were some of Ryan’s biggest takeaways from seeing Salesforce scale from $180m to $7.5Bn?
• Why does Ryan think that it is lazy to believe that you have to pick a market and you can’t have them all? How can one approach the element of very different messaging being required for SMB vs enterprise? How can one do both? How does that change the structure of the team? How can one build a product with the simplicity of SMB and functionality of enterprise?  
• When it comes to winning the market, what does Ryan mean when he says, “boring is better than sexy”? What are the 4 elements all founders must consider when pricing their SaaS product? Where does Ryan see many go wrong with pricing? When serving SMB, how can one provide enterprise quality customer support? How does Ryan feel about customisation? What number justifies it?  
• Why does Ryan believe that being good at sales won’t make you a great sales leader? What is needed to make the transition? What can sales reps do to learn and bridge that gap? What has worked for Ryan in the past? Where has Ryan seen many go wrong here? What 3 elements does Ryan look for in al additions to the team?
• What is the number 1 issue that is preventing people building truly diverse teams? How can we change our job descriptions to make the more inclusive? How can we expand our candidate pool to include more diverse people than usual? What can leaders do to build environments of inclusion where people can really bring their full selves to work?

Ryan’s 60 Second SaaStr:

1. What does Ryan know now that he wishes he had known at the beginning?
2. Sales rep productivity, what is good to Ryan?
3. What motto or quote does Ryan frequently revert back to? 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 Barretto