Key Learnings from SaaStr Annual 2023

by Egan Montgomery - Director of Go-To-Market
Picture of Director of Go-to-Market, Egan Montgomery, with High Alpha logo.

High Alpha hit the road last week to participate in the much-anticipated SaaStr Annual 2023. We engaged in thought-provoking discussions, soaked up industry insights, and had the pleasure of connecting with some of the brightest minds in the SaaS community. 

We’re excited to return to our Indianapolis-based HQ with newfound connections, ideas, and inspiration. We wanted to share our key takeaways with you while they’re still fresh in our minds.

#1: You’re Measuring Marketing Success The Wrong Way

In today’s SaaS world, efficiency is the talk of the town. Investors certainly still value growth (a lot). But growth expectations may have come down slightly in exchange for much higher expectations around efficiency. 

Meanwhile, as fundraising markets have tightened and customer acquisition costs have gone up, marketers and sellers are being asked to do more with less. 

Alex Rosemblat, Chief Marketing Officer at Datadog gave an excellent session about Datadog’s pursuit of efficiency. The presentation was loaded with ideas, but two of the key themes were around measurement. 

  1. Measure down funnel conversion activity: In other words, stop putting weight into top of funnel metrics like cost per lead. Startups should be measuring outcomes by late stage sales opportunities and customers. Focus on metrics like cost per opportunity and cost per customer, and segment your as much as possible by product line, sales geography, and customer segment.
  2. Do your cost accounting on an account basis (not leads): In other words, we should be looking at costs and results at the account or company level, not at the person or lead level.

Alex’s advice is an excellent guideline to measure efficient growth because it removes superfluous and potentially misleading information like cost per lead and cost per click. Instead, it focuses on the account metrics that matter. 

#2: Put Executive Offices Where It’s Noisy

While at SaaStr, I heard a great story from a former Salesforce leadership team member. He told me that Marc Benioff at Salesforce would make sure his office was close to the SDR/BDR team. Why would Marc do this? BDRs and sales teams are an organization’s most direct connection to the market. The learning generated from calling, emailing, and demo-ing, to prospective customers is important information that can inform key elements of the GTM and product direction of a company. 

This was so important to Benioff that he actually sat the BDRs near his own office. 

This is an amazing insight that highlights the importance of staying very close to the market (literally and figuratively). Founders and executives should consider sitting in “noisy” places in the office, such as near SDRs, sales, or customer success teams. Distributed teams should explore systems and processes to simulate this phenomenon or risk falling behind competitors who bias towards in-person work. 

#3: Stop Overthinking Your Launches

Figma is famous for waiting several years to launch their product. It’s hard to argue with anything Figma did given they were acquired by Adobe last year for $20B. However, one Figma employee said the company’s Founder, Dylan Field, wishes they had launched earlier. In fact, she indicated it’s one of his biggest regrets.

The desire to make something perfect, whether that be a product, blog, campaign, or deck, is a temptation we must always resist. Software innovations are not forged within the walls of an office, but rather in the harsh yet rewarding wilderness that is the market. 

Founders and team members alike should bias towards launching as opposed to waiting. There will always be undotted “I”s and uncrossed “T”s. At least at first. Let the market react. Learn. Then regroup. 

Final Thoughts

As we conclude our journey at SaaStr Annual 2023, we carry with us not only the memories but also a renewed sense of community and connection. To everyone who shared a conversation with us, presented on stage, attended our event, we thank you. 

We are already counting down the days until Saastr 2024!