SaaStr

MARCH 1, 2024

Dear SaaStr: What’s The Number One Challenge for Scale-Up Stage Founders? 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 will need a VP of Product to scale your roadmap.

Scale 274

Scale Part-Time VPE CTO Hire Fractional VPE 274

SaaStr

JUNE 23, 2020

Q: What’s the number one challenge for scale-up founders? 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 will need a VP of Product to scale your roadmap.

Part-Time VPE 302

Part-Time VPE CTO Hire Fractional VPE Sales Recruiting 302

SaaStr

OCTOBER 24, 2022

WorkOS CEO Michael Grinich, Developer Success Manager Betsy Calender, and VP of Developer Experience Zeno Rocha share how to price your product for developers, how to market it to developers, how to how to support them as they scale and use the products. The contract size grows. Doing Business with Developers.

Underperforming Technical Team 210

Underperforming Technical Team Outsourced Development Development Part-Time VPE 210

SaaStr

JUNE 1, 2021

There are rules in starting an enterprise software company. Hire the VP of Marketing, MBA, the VP of Sales, MBA, the VP of Customer, MBA, the VP of Engineering, MBA, and now, the odds of any semblance of survival, let alone success, are vanishingly small at this point. A SaaStr Classic!! It got better.

Part-Time VPE 290

Part-Time VPE Technical Cofounder CTO Hire New CTO 290

SaaStr

MAY 5, 2025

You know what I’m talking about: It’s the VP of Engineering who’s “still evaluating Windsurf and Cursor” but says it’s still a little bit early. The mediocre middle of go-to-market teams is about to be hollowed out, leaving only elite relationship builders and strategic consultants at the top.

AI 270

AI Fractional VPE Scale SaaS 270

SaaStr

JULY 12, 2022

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). You have to create a repeatable process if you’re going to scale up the sales team. They know how to scale. SaaStr is Turning 10! Whatever you do, hire two.

Sales Hiring 284

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

SaaStr

JULY 30, 2020

How does this differ between SMB and enterprise? What are the challenges with enterprise given the long sales cycles? So I went from being a business generalist founder, so prior to that I was in product marketing and product management at VMware, so big enterprise software company. This is in Founding Sales , as a result.

Part-Time VPE 279

Part-Time VPE Sales Recruiting Scale Sales Hiring 279