Tiller takeaways from the 2022 SaaStr Annual Conference

Chantelle Little
October 28, 2022
5 min read
Picture of Tiller team members at 2022 SaaStr Annual Conference

Six members of our team recently took a field trip to the 2022 SaaStr Annual Conference in the San Francisco Bay Area. SaaStr is known as the world’s #1 gathering of SaaS and cloud founders, venture capitalists, and executives. It’s a few days packed with sessions and endless opportunities to network and learn. And learn we did.

Why take Tiller to SaaStr?

We specialize in helping software companies achieve business goals. What better way to learn more about our customers than spending a few days with 10,000+ of them all at once?
Our sales and account management team were sponges, networking with fellow attendees and soaking up insights from SaaS legends like Stripe, Drift, HubSpot, and many more. We even got to meet one of our customers in person for the first time!

We came back with piles of notes and debriefed as a team. Here are just a few of our favourite highlights from the 2022 SaaStr Annual Conference.

Photo of a 2022 SaaStr conference session

Focus on people over product

We talk about this a lot at Tiller, but it’s important to be reminded every now and again. Whether you’re building an app or designing a website, you must keep users top-of-mind. This applies to the initial build, but also the iterations and optimizations. Here are a few tips:

  • Put user needs ahead of your own – when they win, you win
  • Make sure all teams have a customer-first mindset – strategists, designers, sales, everyone
  • Solve for real problems – if users don’t have a problem, they won’t need your solution
  • Be meticulous in your craft – errors may seem small to you but how-stoppers for users
  • Make improvements with urgency and focus – real people depend on the experience you create
  • Seek feedback as often as possible – be proactive in your search for improvement
  • Eliminate friction fast – spot issues, get feedback, and iterate as fast as possible

Sales isn’t slimy

The most effective sales pitch we heard during the conference was: “I want you to spend a ton of money on my product so that we can help you make a lot more of it”.

It’s simple but powerful. B2B software companies can become so focused on winning on price that they underestimate their value, set low prices, and negatively influence the perception of the brand. After all, when was the last time you bought a 99-cent coffee and expected it to taste like Starbucks? The lower the price, the less you expect. Instead of leading with low prices, lead with high value. The price will often take care of itself. And customers don’t mind the sales process when their business’ pain is solved at the end of it.

You don’t grow by climbing a ladder

Growth isn’t linear. It’s more like climbing all over a jungle gym than climbing up a ladder. It’s driven by watching peers face challenges and find solutions. By testing a hypothesis and pivoting quickly when it fails. The best growth comes from moments (or weeks or months or years) of discomfort. The perseverance required in times of change and transition will increase your capacity for the future.

It takes grit to build something meaningful

We attended a particularly insightful session with the co-founders of HubSpot, Dharmesh Shah and Brian Halligan. They explained that it took 10 years of work before they were really proud of their product. No wonder so many tech startups fail after just a few years in. Tech founders and investors can’t expect every startup to immediately take off one year in. More often it takes years of hard work and problem-solving, day in and day out, before you finally start to experience success.

One of the ways Shah and Halligan kept at it was to write two blog posts per week about the company. This played a huge role in the early growth of the company because it forced them to think deeply about their business every single week. It was a lot of hard work and took time they probably didn’t have, but they learned a lot about themselves and their product along the way. The best part? Some of the blog posts written 15 years ago are still driving leads today – proof that content marketing is well worth the investment.

Face-to-face collaboration still matters

We’ve proven this to be true within our own team, but it’s still fascinating to see the research to prove it. While great creativity can occur anywhere, the most creativity and collaboration happens when people get in a physical room together. And creativity ultimately creates more value for customers.

  • 74% of GenZ employees work most effectively when they have face-to-face time with their coworkers (Remote Work & Compensation Pulse Survey)
  • 20% more ideas are generated through “in-real-life” meetings than through Zoom (Stanford Research)
  • Creativity increases a company’s growth by 12% (McKinsey Research)

Partnerships fuel growth

Finding the right partners can help businesses focus on meaningful strategies and expand revenue potential. It’s helpful to look at partnerships with long-term goals in mind. Find partners who can grow with you, not just get you to the next milestone. In three short days at SaaStr, we identified 15 partnership opportunities, and we’ve been building the relationships ever since.

Culture can’t be copied

Skills and qualifications are important, but great company culture is what really sets you up for success. Change happens often – new products, new leadership, shifts in the market, and more. Your team will be a lot more willing to experience the discomfort of growth if you’ve created a safe, positive place for it to happen.

Photo of Tiller team members at SaaStr conference

In summary

We had a great time at SaaStr. We bonded together as a team and identified ways to grow as individuals and as an organization. We gathered specific insights to share with our clients to help drive their businesses forward. We may have also collected a fair bit of swag, a list of potential partners, and a long list of ideal customers… All in all, we returned to Calgary energized about our future and the opportunity we have to help B2B software succeed.

Chantelle Little
Chantelle founded Tiller in 2008, with a vision to build out a digital agency that would help companies express their brands and grow their revenues. She’s grown Tiller from a tiny one-woman-shop into a thriving agency with clients all around the world. Naturally curious about the world around her, Chantelle is constantly focused on learning, growing and broadening her perspective so she can better partner with Tiller clients across industries. She’s also especially passionate about getting to know Tiller’s team members on a personal level, and then helping them grow professionally inside of the company. On Chantelle’s expansive list of other interests, you’ll find real estate, coffee, golf, more coffee, seeking out and trying new restaurants, and winding down the day with something to read. All of which helps her get up the next morning and do it all again.

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