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 279

Scale Part-Time VPE CTO Hire Fractional VPE 279

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 311

Part-Time VPE CTO Hire Fractional VPE Sales Recruiting 311

SaaStr

MARCH 6, 2024

Founder CEO Todd McKinnon was VP of Engineering at Salesforce and left to start Okta in the depths of the last downturn. Seat Contractions Have Brought NRR Down From 120% to 111% While 111% NRR is still quite an engine at this scale, the drop in NRR from seat contractions explains a good chunk of the headwinds Okta has seen. #2.

Fractional VPE 287

Fractional VPE Part-Time VPE Scale SMB 287

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.

Outsourced Development 214

Outsourced Development Underperforming Technical Team Development Part-Time VPE 214

SaaStr

JUNE 1, 2021

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. The issue the SMBs had was, “Well, I’m a 20-person consulting company. It got better.

Part-Time VPE 296

Part-Time VPE Technical Cofounder CTO Hire New CTO 296

SaaStr

JUNE 25, 2019

I started right at the end of 2011, and I started in the role of VP of engineering. The company was 145 people, 40 of which were engineers. We had been still growing in San Francisco, one extra office in Mendoza, and in scaling our company we were finding that customer service was a really big expense for us.

Engineering 184

Engineering Part-Time VPE Sales Hiring Scale 184

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 282

AI Fractional VPE Scale SaaS 282