Lessons from SaaStr

February 08, 2018 Payments
By Owen Linderholm, Senior Content Strategist
By Owen Linderholm, Senior Content Strategist

The annual SaaStr conference is taking place right now in San Francisco. One of the tag lines for it is  ‘learn and scale together’ and it boasts over 10,000 SaaS founders, CEOs, executives and employees in attendance. That number feels low when walking the halls. Day One was an immense crush and lines for everything were huge. Despite that the mood has been extremely positive and intense conversations are taking place everywhere. Tons of sales deals are taking place in the hallways. Sessions are packed. The acronym ARR has been abused like never before…

One theme of the conference is a deliberate focus on diversity and inclusion. So much so that 60% of the speakers are women and minorities. That’s a huge and noticeable change from typical tech conferences. Current thinking suggests that greater diversity results in smarter decision-making and the sessions and panels have mostly been very high quality – a correlation perhaps. 

We thought we would bring you some of the highlights we observed during the first two days from the sessions.

The following are snippets of advice that stood out among the lengthy sessions and interviews. They are either direct quotes or paraphrases of the advice that these leaders had to offer.

Phil Fernandez – Cofounder, Marketo

Do not outsource HR – bring it in-house ASAP. It’s a global fight for talent and workplace culture, and trust is incredibly important. Hire a very senior HR person as soon as you can.

Charge (money) from day one. Providing some service or products for free has consequences you can’t anticipate. Sales gets sloppy. It translates directly into churn. Build some pricing into everything.

You need world-class sales enablement. That doesn’t mean salesforce administration. Often salesforce admin drives revenue operations and it should be the other way around. Build revenue and sales enablement around the business and then have that drive the tools.

Stuart Butterfield, founder and CEO, Slack

There’s a big difference in [all aspects of] the company from 50 to 60, 80 to 320 to over 1000 (people)

The critical factor for success is team performance (versus performance of individuals)

Marcus Ryu –  co-founder, Guidewire

One thing that is unique to an entrepreneur is the opportunity to hit the pin of demand on the head at exactly the right angle.

We decided we were going to be the company that asks the most (in looking for customers). More opportunities means more success.

It takes patience. Everything will be harder than you anticipate and nowadays people want results immediately. That can’t work for everyone. You need patience.

Tracy Eiler, CMO InsideView

How do you see the other point of view – argue against yourself. When you bat the other side and come up with what could go wrong you polish things so much. Red teaming is a great skill. [ed note: red teaming is deliberately playing the opposition team as a way to evaluate strategies].

Jennifer Tejada, CEO PagerDuty

It’s a different company every six months while scaling. Leadership style has to change to accommodate the evolution. Figure out which decisions you have to be involved in vs. which which you can delegate.

Culture starts at the top like a fish stinks from the head. Demand from the top the culture you expect. Culture is defined by the lowest level of behavior you are willing to accept.

One of dumbest things I did – we had a disruption – half of the cloud was down – so I went into the incident war room and just said ‘pick up the pace’ as if they weren’t already working flat out and understood the issues far better than I. It’s now referred to as the CEO ‘swoop and poop’. You need to have empathy and respect.

Amy Chang, Founder and CEO Accompany

Hiring decisions and culture are interrelated – be clear on what you will hire and fire for. Culture should repel the wrong people and attract the right people.

You need to acknowledge when someone does something well – give it an order of magnitude more than you think. Be specific. I think about who I need to appreciate every Sunday and send that email.

Michel Feaster, CEO Usermind

I made every mistake you can make. After we raised our first round we felt pressure to hire fast and hired without understanding. Now we never scale anything until the first thing is working. We had team issues, process issues, architecture issues, coding issues. I almost killed my own company by being too aggressive to grow fast.

Scott Heimes, CMO SendGrid

Only 80% of WANTED email reaches the intended recipient. Deliverability is really complex. It impacts reach, conversion, opportunity, etc.

[Referring to headline creation] Three words wins out ( it converts better than any other combo). Use buzzwords very carefully. Do not use hashtags. [The actual words] yesterday and tomorrow convert better than today. Remember your purpose and make it clear.

About the author


Owen Linderholm, Senior Content Strategist

Owen Linderholm is Senior Content Strategist at WePay. He has previously held content and editorial roles at Yahoo, Microsoft, IDG and the BBC.

More blog posts by Owen Linderholm