Impressions/Lessons from SaaStr 23

3 min readNov 29, 2023

I had a fantastic time at SaaStr this year. These points are based on my personal observations, so they are mostly anecdotal.


  • Prevailing consensus is that AI will play a significant role in every application, although many are unsure about its precise integration into the tech stack. Jason Sacks highlighted three potential winners:
  1. Established infrastructure providers — probably eventually owned by big tech.
  2. Co-Pilots: co-pilot for professional job categories to help people do their job better.
  3. Pre-AI SaaS supercharged by adding AI functionality such as APIs (ie Notion autocompleting tasks). Startups with access to proprietary data that incumbents lack will win.
  • Sessions on metrics and benchmarking drew substantial attendance. People need context to their data and help figuring out what metrics to cascade to their teams. People want to know the story behind their data, get help on which metrics to share with their teams, and be able to track multiple metrics all at once.
  • Craft Ventures reported an 80% failure rate from Seed to Series A among startups.


  • Unlike the previous year (SaaStr 22) with ten competitors in each category, this year saw about three.
  • Smaller Series A B2B companies initially succeeded with free trials but faced growing challenges in larger markets. While attracting innovators and early adopters remained relatively steady, it was much harder attracting late majority and laggards in 23.
  • New dashboard tools are continually emerging. This growth is not exclusive to incumbents such as Domo or Tableau; the total addressable market for visualization keeps expanding.
  • The word “embedded” was everywhere, highlighting that users are becoming overwhelmed by the multitude of standalone software choices. They want to avoid constant screen switching. However, it wasn’t clear how the actual mechanics of integrating these tools into transactional systems like CRM, ERP, and other point of records actually works.
  • Sales reps are improving. Even non-technical BDRs effectively articulated their product offerings.

Tip: Visit exhibitors later in the day when traffic lightens to reverse pitch.


  • This is where I found the most value: book a few days ahead of the conference since these slots fill up fast. They’re usually group meetings or one-on-ones.

Tip: You can check the Braindate kiosk and ask to join full sessions.

Bootstrap/Raise Capital/Venture Debt:

  • People had a lot to say about bootstrapping vs raising capital. These topics often overshadowed discussions about actual products.

Tip: Very few will offer good insights but everyone has an opinion about fundraising.


  • Great place to start chatting and then follow-up. Stay until the last call.
  • Founders complained the most about not having teams aligned to their vision.

Tip: Most of the parties are on the SaaStr event page. You can also go around the booths and ask sponsors.

Practice Your Pitch and Refine Your Value Proposition:

  • Gauge reactions and determine what aspects resonate and what doesn’t. Practice different versions of your pitch and gauge reactions. Being in person really helps evaluate emotional reactions.
  • Ask executives directly if the solutions address genuine pain points in their daily operations. Gain insights into the severity of the problems they face.

Meetings with Your Team:

  • There’s something about the collaborative energy of meeting with your team and brainstorming in the conference environment.

Other Tips and Tricks:

  • Attend the most interesting sessions and stay after to chat with attendees. It’s an effective way to blend theoretical knowledge with practical insights.
  • Waiting in line for food trucks is the stupidest waste of time. There are sandwiches everywhere.
  • Swap phone number with those you want to stay in touch with. Many people feel overwhelmed by email and LinkedIn, so give the people you care about a call.