SaaStr

MAY 3, 2025

Dear SaaStr: From 0 to $10m ARR, At What Point Do We Start Hiring and Whom? From 0 t o $ 10M ARR, the hiring roadmap is critical because every hire has a disproportionate impact on your trajectory. Marketing : Likely no VP of Marketing yet either — unless. I Hired My VP of Marketing at $20k MRR.

Sales Hiring 237

Sales Hiring Part-Time VPE CTO Hire Scale 237

SaaStr

MARCH 7, 2021

These are all full-time jobs by $1m ARR. Fixing it yourself becomes the biggest time sink and excuse for not hiring there is. You end up spending all your time backfilling roles you should have hired. And even worse, you often sort of give up trying to make the hire. And hire against it. More here.

Part-Time VPE 293

Part-Time VPE Sales Recruiting Sales Hiring Scale 293

SaaStr

OCTOBER 25, 2023

For part one of this Ask Me Anything session, Jason covers everything you need to know about hiring your first VP of Sales, what he really thinks about AI, what the future of lead generation in 2024 looks like, and much more. Q: Should Product Marketing Work for Product or Marketing? There is no silver bullet.

Scale 284

Scale Sales Hiring Sales Recruiting AI 284

Chart Mogul

MARCH 9, 2020

An early entrant to the SaaS field, the company has pioneered a number of fields that are now commonplace in the industry — content marketing, the transparent startups movement, and remote work. Joel had what he calls “an honest conversation” with Buffer’s CTO Dan. Established in 2010, Buffer hardly needs an introduction.

Payment Solutions 113

Payment Solutions Payment Features Payments Social Media 113

Upscope

JANUARY 5, 2020

If you position around "time saved" you lose money Jason Cohen has built and sold several companies and is the Founder and CTO of WP Engine. He perfectly explains a situation in which you can 8X your price if you avoid positioning around "time saved" and instead focus on growth. Summary of how to 8X your price.

Strategy 128

Strategy Marketing Sales Hiring Engineering 128

Outseta

NOVEMBER 19, 2019

Marketing Consultant As a marketing consultant , I’ve played roles ranging from strategic advisor to independent contributor to interim head of marketing. Full-time Head of Marketing I’ve been hired to lead marketing teams at four companies in a full-time capacity now.

Sales Hiring 50

Sales Hiring CTO Coach CTO Hire Underperforming Technical Team 50

Chart Mogul

MARCH 9, 2020

An early entrant to the SaaS field, the company has pioneered a number of fields that are now commonplace in the industry — content marketing, the transparent startups movement, and remote work. Joel had what he calls “an honest conversation” with Buffer’s CTO Dan. Established in 2010, Buffer hardly needs an introduction.

Payment Solutions 52

Payment Solutions Payment Features Outsourcing Services Payments 52