How to win in the Agent Economy w. Outreach's $4B founder, Manny Medina

Jun 26, 2025

Manny Medina, co-founder and CEO of Paid.ai and former CEO of Outreach, transformed the sales engagement sector. In this conversation, he dives into the agent economy, revealing how AI can enhance rather than just automate tasks. Manny highlights the shift toward outcome-based pricing for market relevance and emphasizes the importance of genuine human connections, even in an AI-driven world. He also discusses the 'one box' revolution and encourages leaders to prioritize emotional engagement over quantifiable metrics to foster loyalty.

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ADVICE

Obsess Over Seller Experience

Focus deeply on the seller's experience, especially for pipeline generation roles like SDRs.
Ensure users love your product, even if the job is hard or unpleasant.

ANECDOTE

Sales Lessons Learned From Customers

Manny learned sales by listening to sales pros and adapting their best practices to Outreach.
Key lessons included leaving value on the table and the necessity of pipeline generation at the rep level.

ADVICE

In-Person Meetings Build Trust

Always meet customers in person to build rapport and gather insights.
Taking detailed notes during conversations increases trust and allows deeper questioning.

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Manny Medina built Outreach from $0 to $4B+.

He created the sales engagement category by riding the SaaS wave from 2014 - 2024.

Now he's on the cutting edge of a new wave: The Agent Economy.

While most of us are in the fog of AI war, Manny has inspiring clarity on what this new world will look like, why, and how to win in it.

That’s what we cover in this episode. If you care about winning with AI, it's a must-listen.

What you'll learn in our conversation:

* How to compete when every feature can be copied by AI in minutes

* The "one box" revolution and what it means for AI

* The "rent experience, hire hunger" framework for agent-era teams

* Why agents need to think, suggest, and act (not just automate)

* How the best leaders will adapt to this new paradigm

* How to demo right in the agent economy (not just slapping AI on your homepage)

My take-aways from our talk:

1️⃣ We're in software's 3rd Act, Outcomes.

Act 1: Systems of record. Act 2: Workflows. Act 3: Outcomes. In this new world, you need to deliver "receipts not dashboards". This has ramifications throughout your org structure.

2️⃣ "Love is not a metric".

Love is not a metric. It's a feeling. It's the words they use. It's when an SDR tells you, "you'll have to pry Outreach out of my cold, dead, hands." The best leaders optimize for love and don't stop until they get there.

3️⃣ "If you're worried about TAM, you haven't found your edge yet"

Every leader has a choice: sell to everyone, and be relevant to no one, or take a stand and actually break through. In this 3rd wave, the winners will be the leaders courageous enough to take a stand and be truly different, even if there's no "TAM" to back it up.

4️⃣ Build backwards from customer success, not forward from features

"What does the customer want? They want a meeting in the least amount of time. They don't want 12 steps. They want one step. Matter of fact, they want zero steps." Winners don't retrofit the human to the technology. They start with the outcome, and work backwards.

Full Interview: https://www.peersignal.org/podcast

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