Hey SaaStr Community,

So at least in my experience and orbit, folks in tech have gotten progressively less satisfied and more unhappy the past 18 months or so.

• It’s not layoffs.  Those folks have a reason to be upset, but there really haven’t been many in my ecosystem.  And I’m excluding them.
• It’s not comp.  While many in sales have seen comp declines, overall comp has held up outside of sales, and even in sales many are still paid quite well.
• And importantly — it’s not quality of life.  The vast majority of startups and companies allow a ton of work from home.  And implicitly or explicitly, tolerate or support a lot of side hustles.

Based on many classical ways we measure “quality of life”, it’s much better in fact in tech today than a few years back.

But people are far less happy IMHE than 2019. Even billionaires. You can see billionaire grumpiness all over X / Twitter.

What happened?

My view in so many discussions is simple: many of us lost our sense of purpose the past 18 months.

Working for a startup that’s failing can do that, but it’s more than that.  The free spending of 2021 was fun, but it also led to so much hiring and so much growth that we all thought we were magicians and it was easy.  It wasn’t.  It’s hard.  It’s supposed to be hard.

So look if you’re unhappy today, but have a good job, reflect a bit.  There really are only a few places to find happiness other than inside yourself (which is tough for those of us that are driven). 

My best advice if your job is rewarding is — do more of it.

So perhaps the best management advice you’ll hear again and again is this:

#1.  Never Have a Tough Conversation Over Email

Yes, you probably know this.  As tempting as it may be to avoid conflict, headaches, and hearing things you don’t want to hear — never have a tough “conversation” over email.

And yet, most of us only half listen. And these days, when almost all of us run distributed teams, this advice is ignored again and again. We’re all so used to communicating all day on Zoom and Slack … that why shouldn’t tough news be delivered that way?

Well, the reason is there is almost 100% chance it will be misinterpreted. 

And there’s zero chance to inject any human element into things.

Now, there are a few exceptions. If you have to fire someone for clear issues, email is probably a better way to do it. It makes sure the problematic employee knows for sure the relationship is over.

The bottom line is email “conversations” are ripe to be interpreted in the most negative of ways.  And they can break relationships instantly — that were never intended to be broken.

Be careful.

The fifth edition of SaaStr Europa will feature 2.5 days, and 3,500 B2B/ SaaS Founders, Executives and Investors, coming together to share their learning in the heart of London. 

We’ll once again take over the entire Tobacco Docks for SaaStr Europa 2024, 4-5 of June and bringing the best in SaaS with us. Use our exclusive newsletter code for a discount on tickets.

A few I’m watching:

#1. The Rise of One-and-Done Fundraising as a Vibe

Founders will get back to only planning to raise one round to truly get to product-market fit for real. More startups benefit as the dilution ends up far less, a la Klaviyo, or The Trade Desk, etc.  Yes, both raised more money at the very late stage, but really only needed a round or two to hit scale.

#2. Slower Growth in SaaS is Internalized. For Better or Worse.

The tougher times for many in 2022 and 2023 has led many to internalize slower, more efficient growth. Not just more efficient growth, but slower growth too. We’ve entered a new era of Hyper, Hyper-Growth Startups like OpenAI and … Almost Everyone Else settles for Slower Growth.   I’m not sure this is a net positive.  It’s very hard to build something really big if you aren’t at least growing 40%+ or more when you hit $100m ARR.  So before that, you sort of have to be growing faster to go big.

#3. We Give Up on Hiring, Hiring, Hiring — Not Completely, But in Part.  The Tiny Team Becomes a Vibe.

With fewer and fewer SaaS folks willing to work as hard as before; the average fully-burdened cost of a SaaS employee at $300k; and later-stage capital much harder to get … everyone just focuses on fewer hires. To some extent, this benefits fractional hires, but only at the margin. Folks align at 50 employees at $10m ARR, 100 at $20m ARR, as the New Normal. Fractional both helps and hurts. Folks that need teams to operate, vs. doing a lot of work themselves, become somewhat obsolete.

And much more here 

So sometimes steady and even is the right path. SproutSocial is one of those. Founded back in 2010, it’s had steady growth to $100m ARR, IPO’d quietly in 2019, then hit $200m, and grown 30%+ annually every year since.

That’s compounded to $360m in ARR today, and a market cap of $3.4 Billion, so about 9x ARR.  Far better than the average public SaaS company.  Sometimes, the committed but measured approach is the best one.

Let’s start with one important learning: angry customers usually aren’t lost customers. If they’ve already decided to leave you for another vendor, they generally just go dark instead.

So you still have a shot not just to save them and keep them, but turn it around.

A few basic thoughts:

1. Have the CEO talk to them — and if possible, make a commitment to fixing one issue (even if small). This isn’t magic. But customers do appreciate talking to the CEO. Especially if she or he commits to solving at least one big headache.  This is 100x better than the CEO hiding from the issues.
2. Let them vent. The customer isn’t always right. But the fault is always yours. Sometimes, they just need to be heard.
3. Share your product roadmap 1-on-1 with them, at least 1–2 times a year. This gives them a chance to provide input.  And also, even if they are unhappy, is shows maybe there’s enough coming down the road that it’s not quite worth the effort to really work on switching.
4. Give them your mobile phone number. A classic tactic to show you care. Salesforce used to put custom physical “hotlines” in the offices of their largest customers. You picked it up, it connected you directly and immediately to top-tier customer success.
5. Invite them to your VIP customer advisory board, if they are a Top 10 customer. This engages them more. It’s almost always appreciated.
6. Go visit them in person (if you can). Now that we are returning to in-persons meetings, go get on a jet (vaccinated) and go meet them. This almost always saves an angry customer and restores some trust.

 So I thought the toughest times for venture would be behind us now.  In 2022, we were in free fall, with public market caps falling like a knife, and the IPO markets frozen. 

And 2023 was the year of the Work Out in venture.  Bridge rounds slowed down, and VCs acknowledged a lot of portfolio companies just weren’t going to make it. 

It got real in 2023, and that realness got normalized.  The drama mostly was behind us.  And public SaaS stocks in many cases did really, really well in 2023.

So shouldn’t 2024 at least be better for venture?

So I thought.

But the reality is I’m a bit more worried the venture drama in 2024 will be bigger than 2023. Why? Four core reasons.

Mark Roberge, SaaStr fan-favorite and Co-Founder and Managing Director of Stage 2 Capital brought together some of the top CROs in SaaS during the SaaStr Annual to share some of their greatest learnings and pivotal moments leading some of the Cloud 100 SaaS companies. 

Dini Mehta, former CRO at Lattice, Kate Ahlering, CRO at Calendly, and Mark Wayland, CRO at Box, share their stories and offer advice to founders on:

• How do you define and refine an ICP?
• Can you start and stop a PLG motion? 
• What should you look for in an Enterprise rep vs. a Mid-Market rep? 
• How do you diagnose and solve churn? 
• How should you handle presenting challenges to your C-suite team when you’ve just joined the company? 

• SaaStr 719: What's New at WordPress with Matt Mullenweg, CEO of Automattic and Co-Founder of WordPress. Hosted by Jason Lemkin, Founder and CEO at SaaStr

• SaaStr 718: Predictions for Venture, IPOs and the State of SaaS in 2024 with SaaStr CEO and Founder Jason Lemkin and Harry Stebbings, Founder and Host of the 20 Minute VC         

• SaaStr 717: How Enterprise Companies are Buying AI (or Not) with ContextualAI, Anthropic, Glean, and Unusual Ventures

Listen on Apple Podcast, Spotify or Google Podcasts

Literally some of the worst senior-ish sales and marketers I have ever worked with are selling books or courses or both

You've been warned

The biggest mistake you can make as a founder when you hire your first

VP of Sales is stepping out of sales

I see this again, and again

It only works with the very best VPs of Sales

Every other first VP of Sales needs you doing at least half of

what you were doing before

You think it's

the competition

The funding drama

Those lost key deals

That rough quarter

You think those are what wear you down

But it's the internal battles that do the real damage

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