How I Hire with Manny Medina - Co-Founder & CEO @ Paid

Manny Medina scaled Outreach to 1,000+ employees and hundreds of millions in revenue. Now he's throwing out the hiring playbook: "I am never hiring somebody senior again." Learn why he's building Paid with AI first, contractors second, and only hiring juniors who get promoted from within. TIMESTAMPS: 00:00 Introduction & Manny's background with Outreach and Paid 01:31 Why traditional hiring playbooks don't work anymore 03:28 "Never hiring senior talent again" - the controversial stance 04:56 The problem with templated SaaS org structures (SDR → AE → CSM) 07:50 AI first, then contractor, then person framework 09:47 Paid's current structure: 10 engineers, no middle management 11:53 Mission charts vs. org charts approach 15:25 Testing go-to-market strategies with small teams 16:00 How to evaluate contractors like full-time hires 19:15 Contractors who automate themselves = keepers 20:51 Junior talent + fractional advisors model 24:57 London vs. Seattle: Why bigger talent pools don't help 27:44 Finding high-potential junior talent 29:50 The "green line, red line" weekly shipping framework 31:05 Red flags: Aggressive negotiation patterns 34:36 Why "bad breath is better than no breath" thinking is wrong 36:37 Making people successful with constrained freedom 38:25 Weekly demo rituals and organizational consistency 40:17 Spotting and correcting hiring mistakes early 42:36 Key takeaways and final thoughts ABOUT ANDY Andy Mowat has built GTM engines for top companies throughout his career. He led Revenue Operations and Demand Gen at four unicorns, including scaling from $10M to $100M ARR at both Upwork and Culture Amp, and helping guide Box and Carta through IPO scale. With a passion for connecting people, Andy has advised executives on their careers for years and launched Whispered to make searching for executive roles less intimidating. CONNECT WITH ANDY https://www.linkedin.com/in/amowat/ ABOUT HOW I HIRE How I Hire is a podcast in partnership with Whispered and Front Lines where Andy Mowat talks with senior GTM leaders about how they find, vet, attract, and grow exceptional talent. Subscribe for more insights from GTM leaders on building high-performing teams!