Last week, SureSwift CEO James DeGreef and COO John Austin attended SaaStr Annual, a three-day gathering of Cloud and SaaS Founders, VCs, and Execs in the San Francisco Bay Area. James put together some thoughts on the event, including big takeaways for SaaS founders and operators.

SaaStr 2023

This was my third time attending SaaStr, and it was extra exciting to be able to represent SureSwift this year along with John Austin. I had a great time reconnecting with Bay Area locals in my network, chatting with lots of new faces about the industry, and sharing what’s going on at SureSwift. With so many opportunities to hear from leaders in SaaS about the latest and greatest in strategies, tactics, tooling, and state of the industry, I came away from the week feeling energized and inspired to share a little of what I learned.

There were two overarching themes this year: Getting Back to Work and AI Advances.

Getting Back to Work

Anyone who has been involved in the tech industry for a while knows that the tech/SaaS space has experienced some rapid changes in recent years. At SaaStr, we discussed how the SaaS space had a huge party in 2021 – with super low interest rates, fast growth, and tons of spending – which led to a massive hangover in 2022 and early 2023 that brought us skyrocketing interest rates, a stock market fall, and lower SaaS spending. Now, many early indicators are showing that things are beginning to pick up, but it’s going to be a slow and steady process that will take some time.

Markets are like an escalator on the way up but an elevator on the way down.

Companies are now requiring far more accountability around their teams, work, responsibilities, and results. The tech industry might still have some level of hangover, but the opportunities are there for companies and teams willing to put in the time and build steady results. It’s time to get back to work, working hard, and producing results.

AI Advances

The other big theme this year was the fast-paced progress of artificial intelligence (AI) in various industries, market sectors, and business operations. VCs are keeping significant dry powder for their current portfolios. However, when it comes to making new investments, approximately 80% of their available capital is earmarked specifically for opportunities related to AI.

VCs are seeing co-pilot type opportunities all over the place, and soon we’ll have special purpose Large Language Models (LLMs) for all sorts of needs and tasks. It was interesting to learn about all the various ways AI has huge potential in SaaS businesses, from market understanding, requirements analysis, ROI decision making, UI designs, software development, building test cases and automated test suites, marketing, sales, and customer success automations, and more.

A Few SaaS Considerations

We also took copious notes of SaaS business tactics, growth hacks, new tooling, and new approaches, and these will make their way into our internal SaaS best practice playbooks and into conversations with our growth marketers and customer success teams.

  • Moving from SMB and mid-market to enterprise users: this is a theme for a number of B2B products in our portfolio, which generally focus on product-led growth with a target audience of small and medium sized businesses (SMBs). We see opportunity at SureSwift to focus on mid-market and enterprise spaces. A few excellent SaaStr talks showcased a number of examples and case studies of other SaaS businesses doing this exact thing. It was great to hear about how those companies made the move, including learnings, challenges, scope and sequencing of activities, and more.
  • Many talks on SaaS KPIs, data, and metrics, with David Sacks from Craft Ventures launching the new SaaSGrid product. Craft originally developed the SaaSGrid dashboard for internal use, but is now spinning out a business and making this tool available more broadly. It’s definitely something we’ll be checking out.

Visiting with DuploCloud at SaaStr 2023.

  • I enjoyed the talks on growing and optimizing various parts of your Product-Led Growth (PLG) and Enterprise sales funnels, looking at top, mid, and bottom of funnel tactics, conversion rate improvements, as well as fixing the leaky bucket (churn) and ways to achieve and grow net revenue retention. We also had a great time meeting with the teams at Rocketlane to chat about their solutions for customer onboarding project management, and DuploCloud for DevOps as a service.
  • A number of the SaaS financial KPIs and metrics don’t 100% apply to SureSwift as our model focuses on growing out businesses profitably, rather than rocketship-type outcomes requiring capital as fuel. That said, we heard lots of discussion on CAC to LTV ratio, CAC payback, and other marketing metrics. I really appreciated the discussion on analyzing CAC to LTV by market segment, cohort, and marketing channel – something we can get better at.
  • Having a deep understanding of your business KPIs, metrics, and data, as well as your strategic direction balanced with resource constraints, is critical to making wise SaaS business decisions. It’s something we work hard to achieve at SureSwift, and I’m looking forward to sharing some of the strategies for dialing that metrics-based approach in even more with our product teams.

If you’re into the world of SaaS – whether an operator, acquirer, or both like SureSwift – then SaaStr is a must-attend conference, full stop. I’m so glad we had the opportunity to go, and we’re already looking forward to 2024.