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 293

Part-Time VPE Sales Recruiting Sales Hiring Scale 293

SaaStr

AUGUST 9, 2023

Ok now that some time has gone by I can reflect a bit more thoughtfully here. My top mistakes as a SaaS founder/CEO: Not convincing the very, very, very best VPE I knew to join as our VPE. I had a great CTO, but I also needed a truly great VPE to scale past $10m ARR and deal with all those issues.

Part-Time VPE 245

Part-Time VPE Sales Recruiting CTO Scale 245

SaaStr

SEPTEMBER 11, 2021

Lately I’ve been working with 5+ SaaS companies all hiring their first VP of Product. That means often it’s not entirely clear who the first VP of Product should report to. A few general learnings: A VP of Product that Reports to CTO / Engineering Rarely Meets With That Many Customers.

Part-Time VPE 318

Part-Time VPE Outsourcing Services CTO Hire CTO 318

SaaStr

SEPTEMBER 26, 2022

Dear SaaStr: 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 $5m ARR, and ideally, Sales and Marketing well before that.

Sales Hiring 277

Sales Hiring Part-Time VPE VPCs (Virtual Private Cloud) Startup 277

SaaStr

OCTOBER 9, 2020

Is usually not really a VP of Sales. I don’t know about you, but I’ve had to recruit a lot of types of folks over the years where my domain knowledge was limited. I’ve had to recruit Ph.Ds. Front-end, mid-end, back-end engineers of all sorts and types. Just pass here, nine times out of ten at least.

Sales Hiring 257

Sales Hiring Part-Time VPE CTO Hire Sales Recruiting 257

SaaStr

DECEMBER 28, 2019

With all that behind you … let me challenge you to 10 SaaS New Year’s Resolutions. 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.

Part-Time VPE 325

Part-Time VPE Sales Hiring Scale Sales Recruiting 325

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. SaaS products get too complex to hack a product roadmap too long. She can be your CTO forever.

Part-Time VPE 286

Part-Time VPE CTO Hire Fractional VPE Sales Recruiting 286

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.

Scale 274

Scale Part-Time VPE CTO Hire Fractional VPE 274

SaaStr

MARCH 24, 2021

But I think the biggest, #1, mistake successful first-time entrepreneurs in SaaS make time and time again these days is they micromanage too long. I see this again and again, and in SaaS, it’s a real lost opportunity. Engineering. And if you don’t have real VPs yet — dude.

Part-Time VPE 318

Part-Time VPE Sales Hiring Sales Recruiting Finance 318

TechEmpower SaaS

AUGUST 7, 2023

Should a startup CTO spend their time programming? Here’s a graphic from Socal CTO that illustrates the roles as they change over time: In its earliest days, a startup’s top need is often to produce a product. Hiring a hands-on lead developer might seem like the right move for an early stage startup. What does the role demand?

CTO Hire 390

CTO Hire New CTO CTO Fractional VPE 390

SaaStr

APRIL 7, 2021

The top SaaS companies grow faster than ever these days. The first type is the kind of management team hired by second+ time founders. Veterans of the SaaS journey. 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.

Part-Time VPE 256

Part-Time VPE Sales Hiring Sales Recruiting CTO Hire 256

SaaStr

NOVEMBER 29, 2020

An organization that has come together voluntarily to take on a mission, at least in part. They’ll revolt when you make a senior or mid-level hire that as a group, they simply cannot suffer one day longer. The three times it happened to me: A very senior engineer that we just HAD to have. Something organic.

Part-Time VPE 284

Part-Time VPE Sales Hiring CTO Hire Scale 284

SaaStr

AUGUST 25, 2023

Hundreds of thousands of experts are telling you how to succeed in SaaS. SaaStr Founder and CEO Jason Lemkin shares the 10 worst pieces of SaaS advice, excuses, and mistakes founders make, and what to do instead You have to understand how venture capital works. No one has time to have coffee with all of those folks.

Part-Time VPE 239

Part-Time VPE Sales Hiring Scale CTO Hire 239

SaaStr

SEPTEMBER 10, 2021

And he made an observation to me that I’d been thinking about for a very long time, but didn’t know how to express. And for the most part, these were incredibly stressful times, when I was very underpaid, overworked, and worked to the bone. Not just being part of something great — but, Being Great.

Part-Time VPE 293

Part-Time VPE CTO Hire AWS New CTO 293

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 306

Sales Hiring Part-Time VPE Venture Capital Fractional VPE 306

SaaStr

JANUARY 22, 2021

As you try to hire up for your SaaS company, you’re going to be faced with a lot of choices and trade-offs. No hire is the perfect package. But there’s one thing I can tell you in SaaS, at least: Almost Everything Except the Product Itself is Sort of the Same at a Given ACV (Annual Contract Value) Level.

Fractional VPE 274

Fractional VPE Sales Hiring Part-Time VPE Engineering 274

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. The traditional SaaS model doesn’t always scale, and not every company has all the bells and whistles to fund marketing, sales, and customer success teams.

Underperforming Technical Team 281

Underperforming Technical Team Enterprise Scale Payments 281

SaaStr

MARCH 6, 2024

So Okta is one of our favorite SaaS and Cloud leaders. Founder CEO Todd McKinnon was VP of Engineering at Salesforce and left to start Okta in the depths of the last downturn. Customer Count Up 8% Year-over-Year to 18,950 It’s hard to find net net customers after $1B ARR. Wow, what an engine at $2.5

Fractional VPE 280

Fractional VPE Part-Time VPE Scale SMB 280

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. Well, this is SaaS. Spend more time with existing customers.

Part-Time VPE 255

Part-Time VPE Sales Hiring Churn Engineering 255

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 I’m going to skip by my life story, and how I grew up as a small child in India, and how the dusty streets influenced my take on unit economics, and SaaS subscription models.

Part-Time VPE 288

Part-Time VPE Technical Cofounder CTO Hire New CTO 288

SaaStr

APRIL 4, 2019

As a global technology provider powering thousands of SaaS companies, Google is at the forefront of driving exciting and innovative technologies to market. You’ll also learn how leading SaaS companies are able to scale and thrive in this complex, dynamic environment. Eyal Manor – VP, Engineering @ Google Cloud.

Cloud 173

Cloud Scale Trends Machine Learning 173

BetterCloud

MAY 7, 2021

Prior to joining BetterCloud as our new VP of engineering, she served as a director of engineering at Twilio. We sat down with Brandon to discuss her vision for engineering at BetterCloud, her approach to building teams, and her advice to young female engineers. I’m a big fan of creating innovation time.

Part-Time VPE 52

Part-Time VPE Engineering Innovation Leadership 52

SaaStr

OCTOBER 24, 2022

Anyone who says the developer market is not strong is behind the times. The developer-led sales motion is different from a typical SaaS sale where you might sell top-down from a sales-led approach, wherein you’re starting with management, and the execution filters down to the wider org. You’ll need to find developers where they are.

Outsourced Development 210

Outsourced Development Underperforming Technical Team Development Part-Time VPE 210

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? But I think for a lot of vertical SaaS, they’ll see impacts when the Q2 numbers come out.

Part-Time VPE 182

Part-Time VPE Sales Hiring Payment Methods SaaS Payments 182

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 185

Investment Technical Review Part-Time VPE Development Team Review 185

Outseta

MAY 8, 2020

Musing after a decade spent building SaaS start-ups By Geoff Roberts 20 min read. Today I can look back across a full decade that’s been spent building SaaS start-ups. I find that refreshing. Exactly 10 years ago today—May 10, 2010—I slinked through office doors that opened to my first day of work at a “real job.”

Part-Time VPE 102

Part-Time VPE Fractional VPE Sales Hiring Underperforming Technical Team 102

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. And—like everything else in the fast-moving SaaS world—pricing is not a once-and-done task.

Sales Hiring 45

Sales Hiring Part-Time VPE CTO Hire Technical Review 45

BetterCloud

NOVEMBER 4, 2021

I’ve lost count of the number of times we’ve said that you can’t secure what you can’t see. But that’s because it’s true—and it’s one of several reasons why experts agree SaaS management platforms (SMPs) are on the rise. There’s still time to join the fun, though. Manjunath Bhat, VP Analyst at Gartner.

Part-Time VPE 52

Part-Time VPE Management Government SaaS 52

BetterCloud

MAY 17, 2021

Being a part of those journeys is the number one driver for why I stay in management. It’sone of the reasons people enjoy working with me;that they know I’m going to give them a good, honest conversation at all times. For me, when I’m assessing good hires, I look for some key things that I think can survive any of those things.

New CTO 52

New CTO Part-Time VPE CTO Coach CTO Hire 52

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 59

Customer Success Part-Time VPE Scale Leadership 59

Sales Hacker

JULY 8, 2019

How to Analyze a SaaS Business Effectively w/ David Skok. Finding Opportunity Through Humility and Curiosity [07:50]. Sam Jacobs: We’ve got a great show for you today–Kim Rose who is the VP of Customer Success and Support at Buildium, one of the fastest growing companies in the Boston area. What You’ll Learn.

Customer Success 66

Customer Success Scale Fractional VPE Part-Time VPE 66

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.

Part-Time CTO 52

Part-Time CTO CTO Technical Review New CTO 52

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). Then, we have this community in SaaS — SaaStr. SaaStr is Turning 10!

Sales Hiring 284

Sales Hiring Part-Time VPE VP of Engineering Sales Recruiting 284

SaaStr

DECEMBER 16, 2023

Dear SaaStr: What Are The Top 10 Things to Know Before Starting a SaaS Company? 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. It takes 7–10 Years in SaaS to Get Anywhere. If you can’t do the time, don’t do the startup.

Part-Time VPE 291

Part-Time VPE CTO Hire Sales Recruiting VPCs (Virtual Private Cloud) 291

SaaStr

JUNE 3, 2021

One fundamental question asked was What Everyone Should Know Before Starting a SaaS Company. More here: If You’re Going to Do a SaaS Start-Up … You Have to Give it 24 Months. but you can’t afford to hire all the people you need to meet their needs. The Cavalry is Coming and here: The SaaS Year of Hell. And Then?—?Reignition.

Part-Time VPE 293

Part-Time VPE VPCs (Virtual Private Cloud) B2C SaaS 293

SaaStr

JUNE 8, 2025

So Rory from Scale, Harry from 20VC and me were back this week on another deep dive on just what’s happening in B2B today: The latest mega raise from Thoma Bravo If OpenAI is eating B2B The MCP threat to SaaS When to Hold and When to Fold as a VC and much more! Skip that part if you want. But the parts after were good.

AI 219

AI Part-Time VPE Venture Capital SaaS 219

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 284

Part-Time VPE Sales Hiring Sales Recruiting Outsourcing Services 284