Crafty CTO

JUNE 10, 2025

First, my book of business on the fractional CTO side of things filled up completely, reducing available writing time. 2023-02-20 John Seely Brown, former director of Xerox PARC, has helpful advice—from April 2000! Thinking back on it, I see two causes.

AI 40

AI Artificial Intelligence ChatGPT CTO Hire 40

SaaStr

MAY 20, 2020

Their competitor bought them out in April 2000, couldn’t IPO, and was bankrupt by August. He joined StubHub as CTO, but didn’t get nearly as much equity as the other CTO — because he “wasn’t committed enough.” If your customers love your product now, hire reps.

CTO Hire 355

CTO Hire New CTO CTO Airlines 355

SaaStr

APRIL 4, 2019

Megan Leuders: So a great example of that is when we’re selling to a large financial institution and we do sell to kind of the Global 2000. Megan Leuders: And when you were talking to CEOs and CTOs today, what do you believe is the biggest technology challenge that they are facing as a SaaS company? Large enterprise customers.

Cloud 173

Cloud Scale Trends Artificial Intelligence 173

SaaStr

NOVEMBER 13, 2020

I just came out of Stripe, I just came out of Datadog, I came out of Fastly, I’m an engineer, I love the guy that was the CTO of Fastly who [inaudible 00:08:34] making it up. Just like a whole bunch of people said, “I’ll never hire remote.” And all of a sudden they’re like, “I guess, I could hire remote.”

Sales Recruiting 219

Sales Recruiting Development Team Review Technical Review Sales Hiring 219

SaaStr

MAY 16, 2021

But what they don’t have is a good enough founding team: Sometimes, if the prospective founder isn’t super technical, then the CTO/VPE isn’t really great. They’ve got a rent-a-CTO. Or sometimes they are great, but the team members are just not great enough for their new C-level roles (CEO, CTO, CMO, CSO, CBO, C?O).

Part-Time VPE 260

Part-Time VPE CTO Hire New CTO CTO 260

SaaStr

APRIL 18, 2019

” And actually Chris today 17 years later he’s actually still running that business at Oracle, but a lot of our other families so he joined us at the BigMachines in 2000 to run our European business. Tim Handorf you can see there, joined me at BigMachines in 2000. He’s still with us today, now running ThreeKit.

Sales Recruiting 231

Sales Recruiting VP of Engineering Scale SaaS Payments 231

Hull

JANUARY 22, 2019

These roles are filled by engineers that roll up to the CMO/COO (not CTO) as part of a growth team. By 2000, cookie-based A/B testing on web birthed the "Conversion Rate Optimization" industry. Same process, different medium. It is operations => rules-based growth. Take a look at our active job posts.

SaaS Payments 77

SaaS Payments Technical Advisors Engineering Payment Solutions 77