The Latest from SaaStr: Cutting Off Your Long Tail: When Is It Worth It?

So I think the second SaaS app I ever purchased was LivePerson.  The first was Salesforce, to get our CRM going (today, we would likely have gone with HubSpot). 

And the second was LivePerson, to handle chat and support.

Back in the day, it was a magical app.  It tracked tickets, shared personas, and provided analytics.  All in the Cloud!

I fell so in love with support automation, when I invested, I did a ton in support, from Talkdesk (first VC), to Front, to Gorgias (#1 e-commerce contact center) to MaestroQA and more.

But the space is competitive, and LivePerson didn’t keep up, even as the product suite did more and more.  While today they are still at a stunning $480m in ARR … they aren’t growing any longer.  In fact, they shrunk 1% last quarter, and are losing money.

As a tough result, their market cap is $335m.  Less than 1x ARR.

A cautionary tale of being innovative, but over time … not keeping up.

Most startup founders create companies to grow them. While all organizations are different, one core truth remains — Everything changes. This is true in life and business. 

If you don’t want your company defeated by change, you need to adapt your Go-To-Market strategy at every stage of growth.

Managing Partner of CIPIO Partners, Rolan Dennert, shares how companies need to readjust and rethink GTM fit — and even product market fit — from time to time. 

CIPIO Partners is a pan-European growth equity firm and early growth investor, primarily in software and software-enabled models. 

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

Secureframe makes it easy to get SOC 2 compliant. With guided workflows and one-click integrations, the entire process is automated.

Not every leader is created equally. A bad experience with a revenue operations leader might taint your view of the position at all future companies, but that would be a mistake, as CRO Confidential podcast host Sam Blond learned first-hand. 

In this week’s CRO Confidential episode, Blond talks to one of the best revenue operations leaders on the planet, Cherishma Shah, where she shares insights into the Rev Ops role, why your startup might need one, and how to maximize impact with this powerhouse position. 

Shah is the Senior Vice President of Go-To-Market Strategy, Operations, and Enablement at Guild Education and formerly held the same role at Brex, working alongside Blond. 

Now that we have much larger spaces for SaaStr Annual 2023 in SF Bay Area and Europa 2023 in London, we’ve been able to run a new initiative: building an Executive Briefing Center, and letting our top sponsors do their own meet-ups and even mini-events in our Executive Briefing Center. 

The benefit was getting all of the vibe and infrastructure of Annual for your own mini-event for 20-100.  It turned out to work really well.

Mutiny, G2, Google Cloud, WorkOS, and other leaders took advantage to various degrees in 2022, so we’re upgrading and enhancing this for SaaStr Europa 2023 and Annual 2023.  Read more about Mutiny’s 100 CMO meet-up at SaaStr Annual here.

So folks in general are under more pressure to hit numbers and the plan than just a few quarters ago, and at bigger startups, that brings up a question in so many investor meetings and board meetings I attend at $30m+ ARR:

Should we cut off our long tail?  It just takes up so much time and resources, and just isn’t generating much revenue anymore.

What I mean is, in the early days, everyone is excited about your Free users, your single-seat customers, and the little guys. But later … that fades:

I remember the first time I worked directly for a CEO.  I’d reported to leaders before, and a VP before, but never the CEO.

It was also my first start-up job.  The start-up I joined had about 60 people and just one office, a big shared office like a fishbowl.  My desk was in there.  In one big open office in the center of the company sat the CEO, the President, the Controller, and as of my first day … me.  The four of us in that fishbowl.

It was quite a way to begin your first start-up job.  By being in that office with the CEO and President, almost every time the “door closed” for a conversation, I was in it.  I always asked if they wanted me to step out, but they almost always wanted me to stay.  I guess if it was a conversation they didn’t want me involved in, they could have met down the hall or in a conference room or at Starbucks or wherever.

A few months ago we rolled out a new, weekly, free open AMA with some of our most popular SaaStr speakers of the past few years.  Anyone can join, and they are live each Wednesday at 10am PST, and we save at least 20 minutes for open Q+A.  We do a mix of CEO, CXOs, and top VCs,

Our past and future speakers include:

• Tomasz Tunguz, Venture Capitalist
• David Kellogg
• Tracy Young, CEO and co-founder of TigerEye and $800m PlanGrid
• Sameer Dholakia, Bessemer Venture Partners
• Jeff Richards and TIffany Luck, GGV Capital
• Jessica Bartos, Salesforce Ventures
• Ashley Kramer, CMO Gitalb
• CEO, Hugo
• Head of HubSpot Ventures
• Jason Eubanks, CRO, Harness
• and tons more!

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

Learn how to bring payments in-house without taking on extra costs and risks and create a better payment experience.

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