Inc - Should You Still Do 1-on-1s in 2025?

So 1-on-1 meetings with your team certainly seem to have gone out of fashion, at least on social media.

The great waste of time, many hard driven founders seem to be saying.

Jensen Huang of Nvidia has 30+ direct reports and apparently no 1-on-1s.   I get it.

But Nvidia was founded in 1993, is doing $140B in revenue a year, dominates its market, and has 29,600 employees.

See also, AirBnB.

When I first started off a first-time CEO, I had never really done 1-on-1s before when I was a VP and a Director before that. My CEOs did 1-on-1s … just not with me.

And I think I missed the point on why. Both of the CEOs I reported to didn’t need one with me.

As a first-time CEO, I started off doing 1-on-1s with all my VPs.  Then about a year in as a first-time CEO I saw a pattern.

This edition of the SaaStr Daily is sponsored in part by Prismatic

Download the guide to learn the key factors that'll help you decide whether building or buying native integrations is the best option for you.

Pricing is more than just a number on a contract — when used thoughtfully, it can become a strategic tool for your SaaS product that can drive product adoption, customer satisfaction, and business growth.

At this year’s SaaStr Annual AI Summit, Akshay Sharma, Head of Pricing and Monetization at Miro, chats with a panel of experts, including Janie Lee, Head of Product at Loom, Alison Harmon, Head of Growth at OpenAI, and Carsten Holm, VP of Pricing and Monetization at Splunk, about their nuanced approach to pricing and monetization.

After going virtual and hybrid during the 2021 era, and moving its HQ to Bozeman Montana when ex-CEO Frank Slootman moved there… and officially leaving the SF Bay (albeit keeping its office in San Mateo) in 2021 … Snowflake is quadrupling down on the SF Bay Area in 2025.

It’s taking over almost 800,000 square feet from Facebook in Menlo Park, the largest lease of the year, per the SF Chronicle.

You can build something great in B2B anywhere today.

But the SF Bay is back in force.

44% of VC funding for SaaS is there now, too.

So Twilio has been on a crazy rollercoaster journey since IPO. It started off with hyper growth, then had a Covid Boost, and then growth radically slowed thereafter.

And now? Growth at Twilio is re-accelerating again. And the stock is up a super impressive 51% this year! 

It’s not the Go-Go Days of years past, but Twilio is back. SaaS is back.

This edition of the SaaStr Daily is sponsored in part by G2

In today’s landscape, AI isn’t just a tool—it’s a business imperative.

Join C-suite execs, including SaaStr CEO and Founder, Jason Lemkin and GTM leaders, as they explore:

• Accelerating your growth with AI
• Exceeding buyer ROI and agility expectations
• Capitalizing on market trends to stay ahead of the competition 

Here are some rough rules:

• You want a VP of Everything (Sales, Marketing, Product, Eng) by about $5m ARR, and ideally, Sales and Marketing well before that. Not all at once, but you can benefit from all of them by then.
• You want to start adding CXOs around $15m-$20m ARR. The CFO is often the last, the CMO often the first “C” level officer.
• Now how does bootstrapping change this? Importantly: not that much in the end, although a lot at first.

Certainly, bootstrapping slows down how many VPs you can hire until and after $1m-$2m ARR.

You probably have to hire them one at a time, a bit slowly.  You may only be able to afford one VP at first, even at $2m-$3m ARR or so.  But after that, if you are growing 50%+ and have 100%+ NRR … you’ve built an engine.  Even if you don’t have quite as much fuel as if you’d raised venture capital.

I’ll share a few of mine:

First, the big, meta financial mistakes:

1. In the first start-up where I was a VP, we as a team voted to sell our company to a company about to IPO for $1 Billion — instead of to Amazon for about $250m. The thing is, the company we sold to went bankrupt and I made nothing.
2. I sold my second start-up to Adobe, left after a year — and the stock went up 10x after I left. Worked out great for my CTO who stayed (proud of him), but if things were structured differently, I would have made nine figures just staying.
3. I had another chance to sell my start-up a company that IPO’d a few years later. Saying No made sense at the time, but in the end, we would have owned $2 Billion of that company, and I owned 20%, so $2B x 20% = well, a lot.

The list is actually longer than this :). These are just the Top 3.

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