Rainbow Unicorns and Other Highlights from Day 2 SaaStr Annual 2018

By Erika Malzberg February 7, 2018

As PagerDuty CEO Jennifer Tejada noted during her panel session today: “SaaStr is a great opportunity for all of us to not have to learn things the hard way.”

In that spirit, day two of SaaStr Annual 2018 continued with SaaS leaders generously sharing their learnings, challenges, best practices, and a few choice words with 10,000+ eager listeners.

Honestly the sessions go so deep and provide so much practical and tactical information that it’s hard to summarize all the insights. So we’ll just let the presenters speak for themselves on topics as varied as crafting the first mile of product, being a CEO, scaling, building a world-class product organization, CIOs as “customer zero,” and keeping your customers happy.

Here is just a sampling of the aha moments we experienced today:

On product development:

“Obsess over the first mile of the product dev experience – it’s woefully neglected (among startups and large companies).” – Scott Belsky, Chief Product Officer, Adobe, @scottbelsky

“When people talk about product they talk about setting the vision, but there’s also this ruthless pragmatism that has to be there or that product will never materialize.” – Jon Aniano, Chief Product Officer, ProsperWorks, @jonaniano

On designing for new users vs power users:

“The shortcut to staying simple is obsessing over new users. Prioritize problems for new users over problems for your power users. Preserve 50% of your time and focus on the new user’s experience (first mile)—not just to keep your product going, but as a way of grounding yourself, and counterbalancing what you begin to believe when you listen to power users all day.” – Scott Belsky, Chief Product Officer, Adobe, @scottbelsky

On founder imposter syndrome:

“Founder imposter syndrome is a very common phenomenon. You turn up to work and you don’t actually know what you’re going to do everyday. You’re out of your depth. It doesn’t go away. If you lean into it, you can make it work for you. When you’re constantly afraid of being called out, you test your ideas more…as long as you’re not paralyzed by it.” – Mike Cannon Brookes, Co-Founder and Co-CEO, Atlassian, @mcannonbrookes

On company values:

“At Atlassian we have the value “Build with heart and balance.” When you build a company, there are a lot of hard decisions you have to make. When I make those hard decisions—or when anyone is making the decision—we consider heart and balance. Think about left and right, consider customer, shareholder, the stock. But also do it with heart. That means do it with passion, lean into it and actually do it. And secondly, do it with some form of caring. Because these hard decisions have impacts on people, so you should think through the impact of that. Don’t take the abstract. When you’re solving people problems, you have to care about people, but you also have to make the right decision by the rest of the company.” – Mike Cannon Brookes, Co-Founder and Co-CEO, Atlassian, @mcannonbrookes

On acquisitions:

“You’ve got to think about both sides of the table and be very conscious of how it’s going to look. Cultural alignment is #1. If that doesn’t fit, it’s going to end badly. Alignment and vision: why are you doing this and what do you hope to achieve out of both sides, what’s in it for both parties. A lot of acquisitions fail because there’s an internal agenda and a deal agenda, and they don’t work together.” – Mike Cannon Brookes, Co-Founder and Co-CEO, Atlassian, @mcannonbrookes

On scaling:

“As much as you can say you’re open, that doesn’t stay when you scale up. How can you stay connected to the people at the company, the product, the customers, and the process as you scale?”- Michael Pryor, CEO & Head of Product, Trello & Atlassian, @michaelpryor

“It’s a very different company every 6 months as you’re scaling. Your leadership style has to change to accommodate the size of your organization.” – Jennifer Tejada, CEO, PagerDuty, @jenntejada

“Growth is like the rings of a tree, and you have to be really conscious of when you’re passing through to the next ring. Up to 20 employees, I made every decision because I had all the information. But now I have to ask myself: Who has the most information to make the decision? And that person needs to be empowered to make the decision.” – Michel Feaster, CEO, Usermind, @MichelFeaster

“You have to understand your sweet spot, why your customers are buying your technology. And, regardless of size of customer, you need to stay true to this core and what problems you are trying to solve. Solve what matters the most to your customers and then, from there, scale.” – Marc Diouane, President, Zuora, @MarcDIOUANE

On workplace culture:

“Culture should have some grit to it: repel the wrong people and attract the right people. It’s got to be defined and crisp.” – Amy Chang, Founder, Accompany, @_amychang

“Culture is not something the leader can delegate. That starts at the top, just like the fish stinks from the head! Demand from the top what kind of culture you expect. Culture is defined by the lowest level of standard you are willing to accept.” – Jennifer Tejada, CEO, PagerDuty, @jenntejada

On building and managing boards:

“I use the board to see around corners. I don’t have time to meet with everyone in the industry. But the members of my board likely do. The service I provide to my board is no surprises. If there’s something controversial that’s going to come up on the next board meeting, I will prepare them ahead of time. Choose wisely. Invest in that relationship. And don’t delegate that core board relationship.” – Amy Chang, Founder, Accompany, @_amychang

On building a great product team:

“Tremendously important in a product manager candidate is customer empathy, the ability to see the world through your customers eyes and know what makes them tick.” – Cheryl Chavez, Former Group VP of Product Management/UX, Marketo

“I focus on hiring for the role in front of me and trusting that, as a leader i will be able to help that individual to grow as the organization grows.” – Jen Taylor, CP, Cloudflare

On moving upmarket:

“When you move upmarket, you want to maintain some of that simplicity in the portfolio but round that out with more APIs, more controls, and more fine-grained accessibility to the controls. How do you bring in those complementary portfolios and skill sets to round out the offerings? You need to help reorient the team to think about the customer differently, broadening the aperture.” – Jen Taylor, CP, Cloudflare

“When you have gotten yourself to product market fit in SMB space, you’ve created a consumer product essentially. There’s amazing focus on the user. When you go upmarket, consumer product management doesn’t work anymore. What that means is that you care equally as much about the buyer, the seller, and the end-user. Enabling the sales team to say yes. Allowing the buyer to validate the product. These are things that become super important when you go upmarket.” – Jon Aniano, Chief Product Officer, ProsperWorks, @jonaniano

“When we moved upmarket, it came with a lot of different challenges: buyers were different, complexity around MSA, product fit, etc. You have to rethink the entire company processes. At every plateau, if you’re successful in solving the problem, you’ll get another year of fast scale and growth.” – Marc Diouane, President, Zuora, @MarcDIOUANE

On using your own product:

“We are the petri dish, the sandbox to test or use our own products. This does 3 things: 1) we can give real feedback to our engineering team right away. 2) they get to see it in a real live production environment, how it works upstream and downstream. 3) we write white papers about the experience of using our own product which sales uses to talk to their customers. In this way, IT, engineering, and sales all come together.” – Sheila Jordan, CIO, Symantec, @SheilaJordan90

“When you believe in your own product—which you should, because you shouldn’t be at the company if you don’t—part of that is to use your product to as great extent as possible. Being customer zero is really important. You should be the first and best referenceable customer. You how your products fit into the reference architectures that we’re all building today, how your products work with other products.” – Paul Chapman, CIO, Box, @PaulChapmanBox

“There’s a certain humility that comes with being the CIO at a tech company where everyone who works there, all the engineering folks, run circles around you technically. Using your own product, and loving and relishing and operating with your own product, is a way to professionally connect with the rest of the company, to connect with the rest of the company.” – Wendy Pfieffer, CIO, Nutanix, @WendyMPfieffer

“Building real expertise in all the products you use requires an investment. It’s part of your DNA to invest in providing feedback early on.” – Alvina Antar, CIO, Zuora, @alvinaantar

On the “first time right” metric:

“A metric that I track is “first-time right”. When a product is delivered to me from any vendor, I track if it’s right the first time. That’s a report card on the engineering organization, the QA org, etc. But also a report on my team, how we invest and use.” – Wendy Pfieffer, CIO, Nutanix, @WendyMPfieffer

On the challenges of growing from $1M to $100M ARR:

“It’s hard at $1M. It’s hard at $10M. And at $100M. It’s always hard. The biggest challenge is when you have to let go of something that you love and that you’re good at. It can be hard to make that pivot. It’s personal.” – Yvonne Wassenaar, CEO, Airware, @ytechdata

“Every day you have to think about reinventing yourself, and do an iteration around processes or the organization. There’s no smooth ride.” – Marc Diouane, President, Zuora, @MarcDIOUANE

“It’s not always easy. It’s not usually easy. But that’s how great companies are built, that’s how you pioneer a new market or disrupt an existing one.”- Craig Hanson, General Partner, NextWorld Capital, @craigalanhanson

“People will make or break your business. The people are creating the problem or creating success. People are the key.” – Marc Diouane, President, Zuora, @MarcDIOUANE

“The narrower and the smaller you start, the better. It’s much more fun to grow your vision then to shrink it because it was too broad to begin with.”- Godard Abel – Co-Founder & Executive Chairman / G2, @godardabel

On pivoting:

“People talk about pivots like they’re black and white: ‘Did you make a pivot or did you not?’ There are some pivots that are black and white, like you’re either in hardware or you’re not. You make the decision and be done with it. But the other type of pivot may not be as severe. You’re not throwing the baby out with the bathwater, just expanding into new areas.” – Yvonne Wassenaar, CEO, Airware, @ytechdata

On customer happiness:

“If you can figure out how to get the financial quantification of customer satisfaction, you have a better chance of improving it and a better chance of driving growth.” – Tom Hale, President, SurveyMonkey, @tomeghale

When you’re done processing all this golden content and ready for more insights on taking your SaaS business to the next level, download our free guide from ZEO Co-Founder and CEO Tien Tzuo, The Climb: How to Build a Billion Dollar Run Rate.