Socks. Doughnuts. Cute Plastic Boats. What I Learned at the SaaStr Annual.

Having tracked this event for years as a startup guy, I finally decided to take the plunge and not only attend for the first time but also sponsor this legendary gathering.

Over 14,000 entrepreneurs, investors and software-as-a-service fanatics made the trek this year to way beyond the land of sustainably sourced pour over coffee and artisanal crafted doughnuts (San Francisco) down to the land Sharks hockey and once the capital of California – San Jose.

Here are my key takeaways from the event this year.

Scale requires a team

Nick Mehta, CEO of Gainsight, remarked in his session that he couldn’t have achieved the rapid growth of his company without a maniacal focus on teams that could execute well and when there were lapses in execution by his team – to fire fast. I met so many founders that were struggling to find key talent to help build their business but a willingness to look at tools to help fill the gaps in their business processes. This seems to be the power of SaaS innovation and business models – tools and platforms can be quickly and easily spun up to actively support the growth of the business and make small teams respond like giants.

Automation is the key to scale

Our team met many founders and execs from early stage ventures that told us they were more open than ever to find tools to give them leverage in the market – particularly in ecommerce, sales planning and marketing analytics. For marketing automation, the focus was to drive more marketing qualified leads and deliver more upfront transparency and disclosure in how they did business as a key competitive differentiator. For Tugboat Logic clients, this upfront effort to convey trust to prospective clients is often manifest in the sales process where enterprises are seeking more information on the security and compliance posture of a potential trading partner. We outline that dynamic in our eBook for startups.

“Failure Is Pretty Likely”

This was one of the memorable refrains from Zendesk founder, Mikkel Svane, who recounted the very up and down journey that his company took, and how at times they ignored their investors and kept to their vision despite a vapor thin bank balance. It’s the tenacity and perseverance of startup founders that often get tested as they constantly assess and reassess their very existence in the market. I shared many stories with founder in the Expo Hall that were already on their second or third pivot as they honed their product/market fit. The great news is that with SaaS based processes, nearly everything can be quickly and accurately measured. This makes monitoring your progress and benchmarking success more transparent for timely decision making. There’s no playbook for this stuff and external benchmarks for your success are still elusive.

Security as a business enabler

We met several startup execs who were spending their Saturdays and evenings responding to vendor assessments. Many wanted to get their life back with a tool and system of record that could enable them to power their sales teams while running the response function off the side of their desk. Our Virtual CISO Platform helps enterprises respond to Vendor Security Questionnaires with one-click that leverages machine learning to automatically read and interpret questions upon upload into our system and then auto-suggest answers drawn from your Tugboat Logic InfoSec system.

Millennial Parents Rule

Despite all the shop talk and commiserating over scaling, surviving and thriving – no tech conference would be complete without some solid swag. What seemed to work best? In no particular order: doughnuts, kids toys, and Tugboat Logic mini rubber tugboats. It would seem that there were a lot of 30-something founders with little kids at home that needed some light-up toys while founders powered down some delish baked treats. The Zendesk swag was epic – with a near “retail” presence and display, their socks, pads, T-shirts, and stickers were very cool and usable!

Under-represented Founders

2019 and 2020 will be the year of the under-represented founder. I met so many amazing entrepreneurs who are driving their idea forward with no safety net, no big Silicon-Valley network, limited funding, a loyal cadre of customers and sheer will of force. Despite the challenges, immigrant founders like myself are so grateful to have the support, mentorship and guidance in a vibrant and supportive community of risk takers at places like SaaStr. See you next year!

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