Lessons Redefining a Really Big Category with Coupa (Annual Video + Transcript)

Earlier this year at the 2018 Annual, Coupa Software CEO Rob Bernshteyn sat down with our very own Jason Lemkin to chat about what he’s learned while redefining a big category. To get the full scoop on his observations, insights, and learnings, check out the full session video and transcript below! And in case you haven’t heard, we’re building a completely immersive experience in San Jose for SaaStr Annual 2019! With 3 full days of sessions, featuring over 300 speakers from the best SaaS companies around the world, SaaStr Annual will be filled with actionable thought leadership to help grow your business. Get your tickets to the SaaS show everyone will be talking about! Transcript: Announcer: Please welcome Rob Bernshteyn, Chief Executive Officer and Coupa Value Orchestrator of Coupa Software and Jason Lemkin, founder of SaaStr. Jason Lemkin: Did everyone get lunch? Rob, thanks for joining us. This Continue reading "Lessons Redefining a Really Big Category with Coupa (Annual Video + Transcript)"

Building a Real Unicorn: Tears, Sweat, and Teamwork with Meltwater & Creandum (Europa Video + Transcript)

From bootstrapping a business to building a cohesive culture across continents, our SaaStr Europa 2018 session featuring Meltwater Founder and CEO Jorn Lyseggen in conversation with Creandum’s Carl Fritjofsson covered a wide range of SaaS industry topics and left attendees with loads of helpful insights and advice. Be sure to check out the full session video and transcript below. And don’t miss out when we do it all again — even bigger and better — next June! We’ll have two full days of thought leadership content, networking opportunities, fantastic French food, and fabulous evening events, all in the heart of Paris — snag your Europa 2019 tickets and catch up with us on the other side of the Atlantic next year! Transcript: Carl Fritjofsson: My name is Carl Fritjofsson. I’m a partner with a Swedish venture fund called Creandum. We’re early backers of companies like Spotify and iZettle and a bunch of Continue reading "Building a Real Unicorn: Tears, Sweat, and Teamwork with Meltwater & Creandum (Europa Video + Transcript)"

Smooth Scaling: 3 Female Tech CEOs. Lessons on How to Scale Faster, Better & Farther. (Video + Transcript)

In the below session from Annual 2018, CEOs Jennifer Tejada (PagerDuty), Michel Feaster (Usermind), and Amy Chang (Accompany) discuss the challenges of scaling culture, their biggest career mistakes, and more with humor and candor. It’s definitely worth a watch. And in case you haven’t heard, we’re building a completely immersive experience for SaaStr Annual 2019! With 3 full days of sessions, featuring over 300 speakers from the best SaaS companies around the world, SaaStr Annual will be filled with actionable thought leadership to help grow your business. Get your tickets to the SaaS show everyone will be talking about! Announcer:  Please welcome Jennifer Tejada, CEO of PagerDuty, Michel Feaster, CEO of Usermind, and Amy Chang, founder of Accompany. [applause] Jennifer Tejada: All right, good morning? Audience: Good morning. Jennifer: Wow, are you guys alive? Good morning. Audience: Good morning. Jennifer: Oh, much Continue reading "Smooth Scaling: 3 Female Tech CEOs. Lessons on How to Scale Faster, Better & Farther. (Video + Transcript)"

10 Things I Wish My Board and VCs Had Told Me

1. Power laws are real$1m MRR is when it gets great. No, it doesn’t get any easier then, per se. It never gets truly easier. But you won’t fail after $10m ARR or so if your customers love you. It is different. And you can build something that will trust last once you get there.

2. Just go find the VP you need. You can miss a quarter if need be. No, you can’t miss every quarter. But you aren’t public. You can miss a quarter intentionally once every 6-8 quarters or so if need be to get something bigger done. Focus as CEO on what will move the needle. Go find the VP you really need. I got the VPs of Sales, Product and Marketing I needed. But I should have taken a pause and just found our true VP of Engineering.

3. Truly

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The 11 Year Customer

Last week, I met a VP of Sales that had been using EchoSign / Adobe Sign for 11 years.  Her company had been acquired, and the acquirer cancelled the contract, due to a feature gap in the new company’s business process stack.  Lesson #1:  it still hurts!  Even when you haven’t worked there for 6 years. It never feels good to lose a customer 🙁 But Lesson #2 was that Customers for Life isn’t just a tagline.  If that feature gap had been closed, they likely would have been a customer for another 11 years.  “No one wanted to cancel”, she said. 11 years x $50,000 a year = $550,000 CLTV from that first sale in 2007.  Plus, she had recommended the company many times.  Let’s call that a 2x multiplier in Second Order Revenue.  That was a million dollar customer. So what Continue reading "The 11 Year Customer"

Founder to Founder: 10 Toughest Lessons Getting to the First $100m ARR with Cloudflare (Video + Transcript)

What’s it really like to scale a business from a few users to $100m ARR and 7 million users? Michelle Zatlyn, co‑founder and COO of Cloudflare, sits down with Laura Bilazarian, CEO, co‑founder of Teamable, to share her 10 toughest lessons that she learned while scaling Cloudflare into the business it is today. Cloudflare provides a content delivery network, DDoS mitigation, Internet security services and distributed domain name server services by acting as a reverse proxy for websites. From hiring to customer growth and everything in between– this session from SaaStr Annual 2018 is a must-see for all founders. And if you haven’t heard, we’re building a completely immersive experience for SaaStr Annual 2019! With 3 full days of content sessions, featuring over 300 speakers from the best SaaS companies around the world, SaaStr Annual is filled with actionable thought leadership to help grow your business from $0 to $100M ARR. Team packs are back for next year’s
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Why We’re All Ready for a CRO or COO Earlier These Days

I used to think CROs and COOs were made up titles until “Late Stage” or so, and in startups, a bit of a sign of weakness.  Giving away a fancy title to someone that wasn’t really willing to do the work.  I used to think there’s no way a SaaS startup needs a “CRO” or “COO” or other C-level Officers Without a Clear, Single Functional Area to Own Until $40m-50m+ in ARR.

But … like many things … my views have evolved ?

Three trends have fueled the rise of hiring COOs and CROs closer to $10m ARR than $50M ARR:

TalkDesk: Top 10 VP of Sales Lessons Learned Scaling to $100m+ ARR (Video + Transcript)

Aaron Ross of Predictable Revenue hosts a panel on something we CEOs and founders all want to do: scaling the sales to $100m in ARR. He’s joined on the Hypertactical stage with Andrew Bothwell, VP of Inside Sales at TalkDesk, Aaron Schilke, VP of Enterprise Sales at TalkDesk, and Josh Stein, Partner at DFJ Venture Capital to talk about how to achieve that milestone and the often painful transformations a company has to go through to get there. What got to $1m in ARR probably won’t get you to 10, and it certainly won’t get you to 100. How do you let go of people that were great for one stage, but aren’t fit for the next? How should you think about building out your sales process? What do you need to keep in mind when communicating and making your board happy? Why should you start up your outbound marketing Continue reading "TalkDesk: Top 10 VP of Sales Lessons Learned Scaling to $100m+ ARR (Video + Transcript)"

Lucid Software: How 10 Million Freemium Users Built Our Enterprise Sales (Video + Transcript)

How do you successfully transition from a freemium model to serving enterprise clients? For Karl Sun, CEO of Lucid Chart, and Dan Cook, VP Sales of Lucid Chart, they had to build an extremely successful freemium business (with 10 million users!) first as it provided the foundation for the shift to selling to the enterprise. Karl and Dan discuss why they chose a freemium model, how they got to 10 million users, and the different evolutions the company experienced as they moved into enterprise sales. The first evolution was migrating from support to sales. The second was evolving from a digital marketing focus to one that was demand or lead gen. The third was an evolution from end user support to a customer success organization. The fourth was going from an end user product focus to an enterprise product focus. If you want to know more about Lucid Chart’s Continue reading "Lucid Software: How 10 Million Freemium Users Built Our Enterprise Sales (Video + Transcript)"