The Official SaaStr Podcast: SaaS | Founders | Investors

Michael Seibel is CEO and a partner at Y Combinator and co-founder of two startups – Justin.tv and Socialcam. He has been a partner at Y Combinator since 2013, advised hundreds of startups, and has been active in promoting diversity efforts among startup founders. Hear his take on the future of work with a decade in learnings from YCombinator.

Missed the session? Here's what Michael talks about:

• How quickly should you hire?
• When is the right time to sell a startup?
• How large a differentiator will investors make in your company?

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Michael Seibel

Peter Yared is the Founder & CEO @ InCountry, the startup that allows you to operate globally with data residency as a service meaning they store your mission-critical data in it's country of origin, without compliance. To date, Peter has raised $8m for InCountry from some of my very favourites including Bloomberg Beta, Felicis, Ray Tonsing @ Caffeinated and CRV just to name a few. Prior to InCountry, Peter founded six and sold 6 enterprise software companies that were acquired by Sun, Citrix, VMware, Oracle, Sprinklr and Prograph. Previously, Peter was also the CTO/CIO of CBS Interactive where he brought CBS into the cloud. At Sun, Peter was the CTO of the Liberty identity consortium that designed SAML 2.

In Today's Episode We Discuss:

• How did Peter make his way into the world of enterprise SaaS with the founding and selling of 6 companies and how did InCountry come about? What is that founding moment?
• Why does Peter feel like it enterprise is really hard again? Why is it no longer to come into large enterprises with a small contract and expand? How does Peter think about enterprise pilots today? Do they really mean anything? What proof points suggest an enterprise is really bought in? What benchmarks should startups bake into the agreements?
• How does Peter think about and approach market sizing today? Why is market risk no longer a risk he is willing to take? Where do many entrepreneurs make mistakes when it comes to market timing? In terms of timing, how should entrepreneurs think about whether to start at SMB and move to enterprise or start enterprise and move to SMB? What are the considerations?
• Why does Peter believe that large orgs are so dysfunctional today? What can founders do to extract the truly special talent out of these large orgs with big pay packets and troves of options? How has Peter found the transition from CTO to CEO this time? What have been some of the challenges? Where has he asked for external help?
• Having built numerous successful remote teams, what have been Peter's biggest learnings in what it takes to successfully build remote teams? Where do many people go wrong? Does it have to be from Day 1? When is the right time to start thinking about this as a startup?

Peter's 60 Second SaaStr:

1. What would Peter most like to change about the world of Silicon Valley and tech?
2. Who is the biggest rockstar in the valley that is less well known?
3. Hire fast, fire fast, agree or disagree?

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

Peter Yared

CRO Erica Ruliffson-Schultz has led New Relic through massive growth, scaling the company's enterprise business 10x since she joined the business pre-IPO. Growing a company's revenues, customer base, team, process, and product doesn't just happen without major work and strategy. Erica will share the five critical steps (and some lessons learned along the way) for scaling in the enterprise.

Missed the session? Here's what Erica talks about:

• How to change up your marketing mix
• How to transition from SMB to enterprise
• Identifying your sweet spot target customers and leveraging your network to access those companies.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Joe Chernov is the VP Marketing @ Pendo, the startup that understands and guides your users allowing you to create products they cannot live without. To date they have raised over $108m in funding from some of the best in SaaS including Meritech, Salesforce, Battery, Spark Capital and Sapphire just to name a few. Prior to Pendo Joe was Chief Marketing Officer at Robin and before that he was the CMO @ InsightSquared where he led the transition from an email-driven leads model to an account-based marketing model. Before InsightSquared, Joe was Head of Content Marketing at Hubspot where he increased blog traffic by more than 1M visits/month and increased leads by 40%. Finally, pre-Hubspot, Joe held VP of Marketing roles at Kinvey and Eloqua.

In Today's Episode We Discuss:

• How Joe made his way into the world of startups and SaaS marketing many years ago? Does Joe really believe in the saying that, "no one really knows what they are doing?" Where are the nuances to it?
• Joe has been CMO and then #2 and alternated between the 2 roles many times, so what the continuous alternating? How does switching from CMO to VP of Marketing prepare you better for each subsequent role? Does Joe agree with the saying that the best in marketing are able to "throw the playbook out of the window"?
• What does Joe mean when he says, "the most powerful mentorship is mentorship from below"? What makes the best #2's just so good? What do they do? What advice would Joe give to a #2 in a role today? What can the individuals do to foster a relationship of deep trust and transparency?
• Having worked at both early and late stage companies, what does Joe believe the early companies can learn from later stage companies? Does installing very severe ops not reduce the creativity of a young company? What does Joe believe that later stage companies can really learn and take from early-stage companies?
• How do the marketing functions differ in both structure and process when comparing early to late stage? What does Joe find to be the biggest challenge within each respective stage? How has Joe seen the content landscape evolve and change radically throughout his career alternating between early and late stage companies?

Joe's 60 Second SaaStr:

1. Who does Joe believe is killing it in SaaS marketing now? Why?
2. ABM, total BS or real meaning to it?
3. If Joe could change one thing about SaaS today, what would it be?

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

Joe Chernov

Hear from Hired's CEO Mehul Patel on how to move from transactional to recurring revenue. Hired is a marketplace that matches tech talent with innovative companies. Hired combines job matching with unbiased career counseling to help people find a job they love. Through Hired, job candidates and companies have transparency into salary offers, competing opportunities and job details.

Missed the session? Here's what Mehul talks about:

• How to leverage your company values to drive stability.
• Hiring people, strategically.
• Finding your pricing sweet spot.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin SaaStr Mehul Patel

Dropbox Chief Customer Officer Yamini Rangan draws on 20 years of experience to challenge five common misconceptions about SaaS success. From beating the competition to over (or under) relying on Outbound, she offers a practical perspective on the frameworks that are holding businesses back from reaching their full potential in a changing landscape.

Missed the session? Here's what Yamini talks about:

• How to increase the odds of reaching $1B in ARR
• What is the pull upmarket, why do companies focus their attention there?
• Common go-to-market myths and lessons.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

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.

Jason Lemkin is the Founder @ SaaStr, the world's largest SaaS community and leading early-stage SaaS fund with investments in Automile, TalkDesk, Algolia and more.

Jason Vandeboom is the Founder of ActiveCampaign, a sales and marketing automation platform that enables small businesses around the world to meaningfully connect and engage with their customers. Since 2013 with their transition to SaaS have grown to more than $50 million in ARR in less than five years, while maintaining profitability.

Dave Kellogg is a leading technology executive, independent board member, advisor and angel investor. In his most recent role, Dave was the CEO @ Host Analytics where he quintupled ARR, halved customer acquisition costs and increased net retention rates before selling the company to a private equity sponsor.

Fred Shilmover is the CEO and co-founder of InsightSquared, one of Boston's premiere tech startups paving the way in the sales intelligence space. Throughout the InsightSquared journey, Fred has raised over $25m in VC funding from the likes of DFJ, Bessemer, Salesforce and Atlas Venture.

In Today's Episode We Discuss:

• Does David Skok believe that ACV should sit at the top of the metrics stack? What are the 4 metrics that fundamentally matter in your business? What can founders do to their pricing model to extract as much value from each customer? How do the very best businesses structure their pricing for value extraction?
• If ACV increase is a core focus for our startup, should we hire a sales rep solely selling to enterprise? What are the biggest mistakes founders make in this scenario? What can founders do to optimise revenue per lead? How does on need o approach lead targeting according to the individual skills of their reps?
• Is it best to start at enterprise and work down to SMB or does SMB and work up to enterprise work best? How does the product have to change with the scaling to enterprise? How does the messaging need to change with the scaling to enterprise? How do you need this change to be reflected in your pricing?
• What does it truly mean to be an ARR first company? What is the right way for founders to calculate their differing ACVs? What is the right way to present that when pitching VCs? Where do many founders go wrong in how they present and discuss ACVs with investors?

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:

Harry Stebbings Jason Lemkin SaaStr David Skok Jason Vandeboom Dave Kellogg Fred Shilmover

Flexport CEO Ryan Petersen will share what he has learned about scaling culture, expanding globally, raising venture capital (or not), and using technology to improve legacy industries.

Missed the session? Here's what Ryan talks about:

• How Flexport grew to a multibillion-dollar business.
• How the company broke into the $2T freight forwarding industry.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Ryan Petersen

Sara Varni is the CMO @ Twilio, the company building the future of communications allowing you to engage customers like never before on voice, SMS, WhatsApp or Video. Prior to their IPO in 2016, Twilio had raised over $250m in VC funding from some of the best in venture including USV, Bessemer, Salesforce and Techstars just to name a few. As for Sara, prior to Twilio she spent 10 years with Salesforce in numerous roles including SVP of Marketing for Salesforce's Sales Cloud and CMO @ Desk.com, among other roles. If that wasn't enough, Sara is also an advisor @ Anthos Capital.

In Today's Episode We Discuss:

• How did Sara made her way into the world of SaaS and came to be one of the industry's leading CMOs with Twilio today? What were Sara's biggest takeaways from her 10 years at Salesforce seeing the incredible hyper-growth first hand?
• What does Sara mean when she says, "you have to have a creative plan to get your message to market"? Does Sara really believe that there is a playbook when it comes to marketing? How does Sara determine when to throw the playbook out of the window? What resounding question do you always have to ask yourself when thinking messaging?
• Messaging is very dependent on the customer being targeted, how does the messaging need to be different when targeting SMB vs enterprise? How does the creative plan to get the message to the target customer change dependent on SMB vs enterprise? Where does Sara see most people go wrong here?
• Why does Sara so strongly believe in the power of customer stories? What makes the very best customer stories? What would Sara's advice be to someone who is wanting to start creating them? Where does Sara see so many people go wrong? What are Sara's tips for creating this alignment between the marketing team that make the stories and the sales team that sell them? Where are there often points of tension?
• What does the very commonly used term, "enablement", really mean to Sara? Does it mean you can hire lower quality candidates and upgrade them? How does Sara distinguish between a stretch VP and a stretch too far? What questions does Sara find most revealing in the interview process?

60 Second SaaStr:

1. What does Sara know now that she wishes she had known at the beginning?
2. Who is crushing it in the world of SaaS marketing today?
3. What is the most common reason for the breakdown of an efficient funnel?

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

Sara Varni

It's the employees' market. There are more jobs than there are qualified people to do them. SaaS companies face sustained headwinds in the attracting, cultivating, driving productivity, and retaining talent. Your market competitors are your adversaries, but so is the entrepreneur sitting right next to you whose business is in a completely different sector. Namely CEO Elisa Steele shares practical advice on how to win three key Talentshare battles, which are essential to winning the Marketshare war.

Missed the session? Here's what Elisa talks about:

• How to win Talentshare when the system is stacked against you.
• How to drive synchronization, productivity when your needs are constantly evolving and the talent mix is incredibly fluid and diverse.
• How to use Culture as the lever to maximize the ROI that you get out of the biggest investment your business will ever make.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

SaaStr

Elisa Steele