Empathy As Friction’s Antidote: Lessons From Day 3 At SaaStr Annual 2017

SaaStr Annual: Day 3

“Nobody likes going to customer support.”

That was the fundamental friction that led Zendesk’s CEO and founder Mikkel Svane to ask himself two questions years ago:

Was it possible to create a well designed web-based customer support solution capable of handling millions of tickets? And was it possible for that solution to create a sense of tranquility, rather than frustration, for the customer?

SaaStr 2017 Day 3 Zendesk Mikkel

The answer to both questions? Yes.

Moderated by Devdutt Yellurkar of Charles River Ventures, Zendesk: From Day 0 to Today: The Lessons Learned kicked off Day 3, and Mikkel spoke much about how he worked to build into his team’s DNA an obsession with reducing friction for the customer and for the customer service reps taking care of them.

After the session, I took some time to reflect on the various frictions I’ve felt and heard about while attending SaaStr Annual.

One I felt: passing nearly 20 homeless people during my 3-minute walk to the conference, and knowing that within that time I’d moved from a community where “zero to one” or “one to ten” means dollars... to a community where it means millions of dollars.

One I heard: Jason Lemkin expressed the friction he felt at SaaStr Annual 2016 in wanting to keep the conference tactical and intimate while growing it to an event where CEOs and founders would find value in bringing their teams.

On that, Mr Lemkin, you’ve succeeded. I’ve met so many people this year, and some of the most interesting have been from departments or sectors that likely didn’t have a presence last year.

Among others, I met Michael Kae, a sales development representative for Supplyframe who hadn’t heard of SaaStr until 3 weeks ago but wrote about how exhilarating it was for him; Thalia Castro, a young professionals board member at Sunbeam Family Services who served as a SaaStr Annual volunteer so she could get the chance to network; and Oliver J. Gleeson, a legal consultant who spent three days taking it all in.

I carried these thoughts with me to a session I’ve been looking forward to all week: 7 ½ [Hard] Lessons Learned From My Second SaaS Unicorn.

SaaStr 2017 Day 3 Harry Stebbings

In this session, the incredible Harry Stebbings (left) interviewed David A. Steinberg, of Zeta Global. I was intrigued by this for a few reasons:

1. Because Stebbings is a 20-year-old who has grown his podcast, The Twenty Minute VC, to an average of 300,000 downloads per episode.

2. Because Steinberg co-founded Zeta along with former Apple CEO John Sculley.

For perspective: Sculley had served as Apple’s CEO for ten years before Stebbings had been born.

What a treat this interview was. A seasoned interviewer, Stebbings brought the best out of Steinberg, who shared his insights on everything from the perils of entrepreneurs who try to build brands before the product is ready to this insight on building an intrapreneurial culture:

“You must have the self-confidence as a founder to empower your employees to a level that may make you uncomfortable.”

Again, I found myself thinking about various frictions—between leadership and ego, and in the judgments that often exist between the talent of youth and the wisdom of experience.

From there, I caught the tail-end of a session titled Building a Product Both CIOs and Devs Love, in which April Underwood of Slack shared how she sees Slack Bots advancing their capabilities to the point of being able to answer human business questions, such as, “When did we cross $100M MRR?”

Next, I attended a “Show Me Money” session titled De-Risking Your Startup and found myself fascinated by many points brought up by Leo Polovets of Susa Ventures, a seed-stage venture fund.

After Leo’s talk I watched as Elizabeth Yin of 500 Startups gave some fantastic advice in a session titled 11 Funding Secrets Learned From 1600 Startups.

SaaStr 2017 Day 3 Elizabeth Yin 500 startups

Among those secrets, Yin spoke about creating what she referred to as “forcing functions” to create a sense of urgency and a greater sense of competition among potential early investors.

This included strategic moves like scheduling all of your meetings with potential funders into clusters rather than spacing them out over the course of weeks. In addition, Yin broke down complex startup questions into their easily understood pieces:

SaaStr 2017 Day 3 500 Startups

In the penultimate session of the event, Promise Phelon of TapInfluence blended practical insights with brave authenticity in her featured talk titled Venture-Backed CEO: Lessons Learned Inside and Outside of Silicon Valley.

SaaStr 2017 Day 3 Promise Phelon

Lines like, "Have you all noticed that I'm not a 27-year-old white male from Harvard?" had the audience cheering in approval, while Promise’s sharing of her productivity habits (she writes as soon as she wakes up and she records a 60-second reflection of her day immediately before bed) had the audience scribbling down notes.

In the final session, Sam Altman of Y Combinator served as moderator for a session titled The Best of the Best: YC SaaS Founders.

SaaStr 2017 Day 3 Y Combinator

Left to right: Spenser Skates of Amplitude Analytics; Tracy Young of PlanGrid; Joshua Reeves of Gusto

All speakers had their moments of strength, but Tracy Young cut most eloquently to the heart of topics central to SaaStr Annual.

On building teams as a CEO and founder, she put it like this:

“Founders found the company; it takes a village to build it.”

And nobody in all of SaaStr Annual 2017 spoke with more passion than Tracy did about the importance of having empathy for your customers. She spoke about stepping into a customer’s shoes until their pain points pain you, until you actually begin to pity the ways in which they have to work.

“We know when they get up in the morning, what struggles they have during the day, and what fears they think about before bed.”

For PlanGrid, Zendesk, and many of the other great SaaS companies at this event, reducing friction isn’t merely some exercise in design; it’s empathy in action.


Missed the other recaps? Here’s Day 1 and Day 2.


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