SaaStr

MAY 22, 2025

Revenue is still recurring in SaaS, of course. The challenge: finding ways to build what customers want today while managing existing obligations. But that playbook is now obsolete. But the rate of change, and the threats from AI, are making the model far tougher than it was just 12 months ago. This isn’t just talk.

AI

SaaStr

JANUARY 27, 2021

Especially the money part. “Give the VP of Sales More Time” This is always terrible advice. If a VP of Sales can’t improve things in one sales cycle or less — she never will. As CEO, you need to find a way. Find a way. “I don’t need a real VP of Marketing … Yet.”

Part-Time VPE

SaaStr

FEBRUARY 1, 2021

That you absolutely, positively, have to only hire “Rockstars” in your startups. A Rockstar engineer really is 10x better than the next tier. And yet … is it worth waiting 6-9 months to hire a VP that’s a true Rockstar, if you’ve struggled to make the hire? It’s true.

Sales Hiring

SaaStr

AUGUST 19, 2021

Q: When should a bootstrapped startup hire a (CFO, COO, CMO)? How can a CEO hire those C-level positions for the first time as a CEO and entrepreneur? Here are some rough rules: You want a VP of Everything (Sales, Marketing, Product, Eng) by about $1m-$2m ARR. You probably have to hire them one at a time, a bit slowly.

Sales Hiring

SaaStr

MARCH 7, 2021

I thought it would be worth drilling down deeper into each of them, and sharing the learnings and mistakes: 1/ Spending less time fixing things, more time recruiting senior folks to own them. No one spends enough time recruiting as it is, after $1m ARR or so. These are all full-time jobs by $1m ARR.

Part-Time VPE

SaaStr

JUNE 23, 2020

In SaaS, it is recruiting your VPs and management team : SaaS products mostly don’t sell themselves. You can hack managing and finding 1–3 reps yourself, but after that, you really need a VP of Sales. You’ll need more than 5–6 core engineers to go big. Q: What’s the number one challenge for scale-up founders?

Part-Time VPE

SaaStr

MARCH 1, 2024

In SaaS, once you have even a few million in ARR, the #1 challenge is recruiting top-tier VPs and building a truly top-tier management team: SaaS products mostly don’t sell themselves. You can hack managing and finding 1–3 reps yourself, but after that, you really need a VP of Sales. She can be your CTO forever.

Scale

SaaStr

APRIL 7, 2021

The first type is the kind of management team hired by second+ time founders. Often folks they convince to once again be a VP of Eng or VP of Sales. But most of us are first-time founders, or close to it. But most of us are first-time founders, or close to it. The director that wants a shot at VP.

Part-Time VPE

SaaStr

SEPTEMBER 24, 2020

You know how everyone says you'll never look and wish you'd kept a bad VP as long as you did? That when you make a mis-hire, you'll always look back and say you should have made a change 3-4 month earlier? A lot of classic SaaStr advice has been how to spot the best potential VPs. When to hire them.

Sales Hiring

SaaStr

DECEMBER 28, 2019

Pick a few that work for you: Get That Key VP Hire Done in Q1. Enough with the excuses for not having hired your real VP of Sales, or that VP of Engineering, or whatever. Hire a real recruiter. Drop other stuff to get this hire done. But anyhow — in January, find a way.

Part-Time VPE

SaaStr

AUGUST 13, 2024

1: Don’t hire a VP (or anyone in the early days) that you aren’t 95% sure is great. Founders between a million and $250M are talking about lowering the bar for hiring because they aren’t sure if the person is great or they’re trying to fill a gap. If you aren’t meeting that many, you aren’t taking hiring seriously.

Sales Hiring

SaaStr

AUGUST 25, 2023

No one has time to have coffee with all of those folks. 2 “Give the VP of Sales more time.” You can’t always expect a great VP of Sales to double sales in 30-60-90 days. They know sales processes, objections, and timings, so they bring in a few deals in the pipe to close faster. Hiring someone too junior.

Part-Time VPE

SaaStr

JUNE 11, 2019

And that’s really good when you’re scaling part of the team that looks like yourself. So if you’re an engineer and you need more engineers, having a network of engineers is an awesome thing. You don’t know where to find them. You guys are awesome. You don’t know how to interview them.

Merchant Services

SaaStr

NOVEMBER 12, 2020

you don't know what to do: 1/ Spend more time w/existing customers. 2/ Hire 1 great VP. Those are good times indeed. But there will be times when almost all of just not only struggle … but are just sort of out of ideas. The revenue recurs. Spend more time with existing customers.

Part-Time VPE

SaaStr

JULY 6, 2020

Just go find the VP you need. Go find the VP you really need. I got the VPs of Sales, Product and Marketing I needed. I got the VPs of Sales, Product and Marketing I needed. But I should have taken a pause and just found our true VP of Engineering. You can miss a quarter if need be.

Part-Time VPE

SaaStr

JULY 30, 2024

Okta’s VP of Engineering, Monica Bajaj, and Senior Director of Platform Product Marketing, Priya Ramamurthi, share Okta’s playbook to PLG, developer experience, and Enterprise ARR. Adopt At the time of adoption, the user starts to feel confident about the product. Let’s start with product-led growth (PLG).

Underperforming Technical Team

SaaStr

DECEMBER 18, 2020

Todd McKinnon, CEO of Okta, for the first time joined us at a SaaStr event, SaaStr Scale 2020. Customers believed in the early days — but many investors and potential hires often didn’t. But VCs and many potential hires thought the space was too small and simple in the early days. That is was “just a widget.”

Part-Time VPE

SaaStr

JUNE 23, 2019

And that’s really good when you’re scaling part of the team that looks like yourself. So if you’re an engineer and you need more engineers, having a network of engineers is an awesome thing. You don’t know where to find them. You guys are awesome. You don’t know how to interview them.

Merchant Services

SaaStr

JUNE 1, 2021

As part of the run up to 2021 SaaStr Annual in the SF Bay Area Sep 27-29 , we’re taking a look back at some of our favorite classic sessions. (And This is the revenue growth for HubSpot leading up to the IPO. You’ll find out tomorrow. And grab the best deal ever on 2021 Annual tickets here ). It’s been fine.

Part-Time VPE

SaaStr

JUNE 28, 2020

” In this episode of the SaaStr podcast, Aileen and SaaStr Founder Jason Lemkin take a deep dive on how Aileen finds deals, her tips for a winning pitch, and the state of VC in 2020. 347: Ready to hire your first VP Sales? You can see the full video here , and read the podcast transcript below. But haven’t done it before?

Part-Time VPE

SaaStr

OCTOBER 24, 2022

Anyone who says the developer market is not strong is behind the times. It might even be months later that a VP of Engineering or a CTO or CFO realizes that they’re built on a new platform. The opposite is also true if all those details are frustrating to deal with, like poor documentation or slow loading times.

Outsourced Development

SaaStr

JULY 8, 2020

We’ll have some time. It sounds minor or technical, but if you want to due diligence on a human being, I get to do it a few 100 times a year. I used it in kind of my breakfast pre warm-up, the crazy times we’re in. From Satya from Homebrew, we just heard that seed’s at an all time high.

Investment

SaaStr

OCTOBER 14, 2019

My #1 suggestion is this — try to have every single employee that can materially influence revenue have a variable revenue component. Your VP Marketing sure better have her comp plan tied to the leads or opportunity commits that make the plan work. But if the plan is blown out, she shares in the extra revenue.

Sales Hiring

Sales Hacker

NOVEMBER 16, 2023

The insight behind how implementing buying committee playbooks increased revenue 270%, doubled win rates, and shrank forecasted misses at Stytch. Failure to do this will result in faulty forecasts, wasted time and effort, and missed targets. Examples: Software Engineer, Product Manager, or Account Executive.Sales Enablement Manager.

Part-Time VPE

OpenView Labs

JUNE 23, 2021

It’s a great time to be a founder. Let’s qualify that statement: It’s a great time to be a founder of a revenue-generating, venture-funded company. These are optimistic times. A founder, on the other hand, has deep institutional knowledge, and many times only they know what they know.

Part-Time VPE

SaaStr

APRIL 4, 2019

They wanted real-time results. And so we actually had to make some major adjustments and look for an alternative way to deliver the software which clearly meant that we needed to move to the cloud full-time. Traditionally we’ve been around since 2005 and traditionally have been a software on-prem business. How can you automate?

Cloud

OpenView Labs

OCTOBER 11, 2019

Pricing is an incredibly important part of any SaaS product’s go-to-market strategy. At Hired, we started out with a transactional model that was—at the time—a super disruptive approach and one of our key differentiators. At Hired , we help top R&D, engineering, and tech talent find jobs they love.

Sales Hiring

Outseta

MAY 8, 2020

I find that refreshing. Beyond just being smart, I’ve routinely come across people in tech that are tenacious, objective, and have high emotional intelligence—so much so that I often find myself thinking, “It’s too bad so many of these smart people are building email marketing software!”

Part-Time VPE

Intercom, Inc.

FEBRUARY 28, 2019

In his spare time, he also hosts his own growth-focused podcast, called The Growth TL;DR. Short on time? I’m really excited to be on your podcast; it’s one of the ones I listen to all the time. I joined HubSpot at a very interesting time when we were about 300 people globally, way back in 2013.

Part-Time VPE

ChurnZero

NOVEMBER 24, 2020

Acquisition gets all the glory while Customer Success gets relegated the part of the unsung hero.”. As a former Customer Success executive and current SaaS business advisor to founders, revenue, and customer leaders, Anna brings a refreshingly candid perspective to the table on how to get a seat at it. OK, ready for some tough love?

Customer Success

BetterCloud

MARCH 3, 2021

He’s held executive-level engineering positions at companies such as Intel, McAfee, and SendGrid. Before joining BetterCloud, he served as a VP of engineering at Twilio. At the same time, this is an area that has been underserved from a technological solution set. It’s easy to say, “Well, let’s just go build things.”

Part-Time CTO

SaaStr

JULY 12, 2022

As part of that, we wanted to look back at some of our most iconic content and sessions. One of the first what How to Hire a Great VP of Sales at the New York Enterprise Tech Meet-Up (thank you to John Lehr and Work-Bench for setting this up). Make the revenue recur, I’m interested. SaaStr is Turning 10!

Sales Hiring

SaaStr

DECEMBER 16, 2023

A mediocre tech team, a part-time CTO, or even just a decent CTO just doesn’t get you there. Wait until you find a great partner here. Finally you have great customers and traction — but you can’t afford to hire all the people you need to meet their needs. If you can’t do the time, don’t do the startup.

Part-Time VPE

SaaStr

JUNE 3, 2021

but you can’t afford to hire all the people you need to meet their needs. If you can’t do the time, don’t do the startup. You have to love, or at least commit to, recruiting constantly. You have to hire so many functions in SaaS?—?VPS, VPS, VPM, VPP, VPCS, VPE, etc. You will have a Year From Hell here.

Part-Time VPE

SaaStr

MAY 3, 2021

And if your team knows how to spend it, correctly — find a way to get them the capital they need to grow even faster than plan. And importantly, you need to spend more time with your existing customers (vs. But even if you’ve hired the world’s best VP of Sales … you can’t opt out of sales entirely.

Part-Time VPE

SaaStr

FEBRUARY 2, 2021

That’s the power of compounding SaaS revenue. But it turns out, the hardest part isn’t the Magic and the Impossible. The hardest part is this phase: the Possible, But Painful. If your VPE, or head of marketing, or someone key quits — you’re almost dead. At least, hire 2 VPs at a time.

Scale

SaaStr

FEBRUARY 13, 2021

The good thing about SaaS is the revenue recurs. I wrote a piece some time ago here, a person favorite, about Our Year of Hell. When a bad hire at a key time, and some confusion on strategy, led us to our worst year ever on a Year-over-Year growth rate basis. At least some times. At least at some small scale.

Part-Time VPE