Doug Camplejohn
(00:01)
Hello everyone, this is Doug Camplejohn. Welcome to this episode of Revenue Renegades.
This week I’m incredibly excited to be talking with Manny Medina, formerly of Outreach and now with a brand new company, Paid.ai, joining us from London. Welcome, Manny.
Manny
(00:17)
Thank you, Doug. Good to see you.
Doug Camplejohn
(00:19)
Great to see you. I love founding stories and founders. You’ve got a new company. Tell us all about it.
Manny
(00:27)
I did. I came to the realization around $250 million that I am more of a builder than a manager. That coincided with my wife wanting to be closer to Europe. There is so much to do in this new AI agent world that hasn’t even been thought through. I felt it was the right time to agree with the board to find someone else to take over the company and for me to do some big thinking.
When I looked at the problems agent companies have monetizing their agents in a way that makes sense for both margins and customer value, I didn’t find anything out there solving that problem. There are metering, payment, and billing companies, but no one actually solving the problem. Just like with Outreach, that was the beginning of the rabbit hole. As we did more discovery, we found more problems.
Agent companies, including your own, tend to be small and run lean. They use more systems to get things done, and on the back office, no one has thought about how to solve that problem. So we decided to solve it.
Doug Camplejohn
(01:40)
That’s awesome. I love it. I’m very excited about that. By the time this episode comes out, Paid.ai will be in the wild. There’s a ton of noise and excitement around anything agentic right now. What are your thoughts about agent.ai, Crew AI, AgentForce, and all that’s going on?
Manny
(02:18)
They all serve a purpose. The way I see it, agents are now replacing both software and labor. Even if it’s not a full job, it’s at least part of a job, like a role or a function. How agents go to market, how they get billed, and how you turn industry knowledge into agentic behavior is accelerating.
Frameworks like Crew, LangChain, and LlamaIndex make it easy to turn knowledge into agentic behavior and roll it out to customers. Marketplaces allow you to do the same, giving you a go-to-market outcome. For example, there’s Enzo, a marketplace for agents and SMBs. The ability to have an audience ready for your agents is key and magical.
Doug Camplejohn
(03:29)
How do you define an agent? A lot of people seem to be creating if-then statements and calling them agents, but that doesn’t sound like full agentic behavior to me.
Manny
(03:48)
You draw the line at whether an agent can make decisions on its own without human intervention. Some agents may check in with you during execution, but it’s a matter of degree. If an agent has enough freedom to innovate and solve a problem as it sees fit, that’s agentic behavior.
If you have to constantly prompt an assistant, that’s just GPT-ing-there’s nothing magical about that.
Doug Camplejohn
(04:26)
What do you think about the interoperability challenge? It seems like a lot of islands are being created, which could limit opportunities for agents.
Manny
(04:45)
We’re seeing that. There’s an explosion of agents because anyone who can code is jumping in to solve problems. You’ll see a lot of silos and point solutions, just like in SaaS when we started. Eventually, there will be a reckoning about what problems are being solved and how many agents can realistically run in the background.
On the other hand, I’m in the business of making sure agents get paid. We talk to hundreds of agent companies, and the bulk of growth is in vertical agents-healthcare, trucking, supply chain, manufacturing-focused on narrow, repetitive tasks that are error-prone and no one wants to do.
For example, Happy Robot works for brokerages and calls truckers to deliver loads, spinning up thousands of agent instances to negotiate and book deliveries. You see this in healthcare, pharmaceuticals, everywhere-agents solving specific problems.
Doug Camplejohn
(07:14)
I love those examples. Niching down to solve a specific problem is a great way to get started and build from there. Now, Outreach-go ahead.
Manny
(07:31)
The more interesting question is what happens to the companies trying to go horizontal, like AISDRs. Where do they go from here? That’s unclear to me, but you know more about that than I do.
Doug Camplejohn
(07:47)
Let’s talk about that. Speaking of explosions, I can’t count how many AISDRs have been funded recently. What are your thoughts on AISDRs specifically, and in general, which categories of work are most susceptible to agents taking over?
Manny
(08:08)
AISDRs are still a bit in copilot mode. When you let them run amok, they’re not great at scale yet. Having run Outreach, our job was to create engagement between a rep and someone they want to engage with. Engagement is fundamentally human, though there’s some math to it.
That doesn’t mean you have to brute force it or spam people. We always advocated doing research and ensuring relevance in outreach. Personalization isn’t as important as relevance. People care that you’re starting a new company or have specific needs, not that you live in California.
I wish there was more of that in the AISDR world-using true research and A/B testing, putting people in cohorts, figuring out what works, and scaling that. That’s the next step.
Doug Camplejohn
(10:13)
Let’s switch to Outreach. Pioneer in the space, helped many sales teams become more productive, but also used as a spam cannon. Marc Kosoglow, your former VP of sales, now head of Operator, describes it as paying for the sins of the past. How do you create something more narrow?
You built a general-purpose tool that got used in various ways. Can you talk about the different approaches and how you see Outreach evolving?
Manny
(10:56)
At the beginning, our job was to lower the friction for a rep trying to educate the market. A rep is taking innovation to the market and telling the world about it. If something is well known, marketing is enough. If it’s not, someone has to make others aware.
We aimed to make communication simple and easy. Without LLMs, we guided people with information and education, finding heuristics around what works. We got good at educating users about observational experiments-true A/B testing.
If you want to penetrate an account, don’t just spam Doug, but reach out to his team, find insights, and use that to break in. It’s about finding information others don’t know and surprising them in a pleasant way.
The future is to continue that mission across the funnel-helping people close deals faster, expand, and understand the funnel using LLMs. Our unique point of view is that we came from sales engagement and own the channel of human-to-human communication about something new.
Doug Camplejohn
(13:45)
Speaking of AI, I remember back in 2020 you were talking about AI before it was cool. I think Kaia was the AI assistant you had. Tell me about the vision behind that and its evolution.
Manny
(14:05)
One of my favorite people, Mike Maples, says founders live in the future and try to bring it forward. Abby Abishek, our VP of Engineering, showed me that technology could understand a customer conversation and, within four microseconds, recommend the right answer or information to a rep in real time.
That was the aha moment: the future is one where the computer tells you what to say. Once you see that, you can’t unsee it. Kaia was born from the obsession to bring that future forward.
Doug Camplejohn
(15:40)
It felt like Kaia made a huge splash, and what you describe still feels cutting edge. I’m surprised I haven’t heard more about it from others. Did it blend into the Outreach product, or what happened?
Manny
(16:06)
One thing about category creation is that you also need to own the category, not just create it. You have to be out there telling stories and owning the space.
You may not have heard more about Kaia because it was good enough for most people to record conversations and analyze them afterward. Kaia took off in regulated industries where what the rep said was critical, and where reps were overloaded with new products.
Those were the two strong use cases: changing behavior at the point of conversation, not after. We didn’t put enough emphasis on owning the category of live conversational intelligence.
Doug Camplejohn
(17:59)
When you describe it, it feels like having the ultimate SE on the call. Let’s talk about market positioning. There were multiple massive companies that sprang up around Outreach, like Clari, SalesLoft, and Gong. When I got to Salesforce, the leadership was unaware of most of them.
Manny
(18:37)
I remember you got them to invest in us. That was funny-you precipitated a meeting where everyone was deciding whether to buy or build.
Doug Camplejohn
(18:50)
I didn’t make a lot of friends at Salesforce for investing in Outreach, especially with the high-velocity sales team, but that’s a story for another day.
Manny
(19:02)
Can’t wait.
Doug Camplejohn
(19:03)
Tell me about that dynamic. It seemed like you all had your own swim lanes-Clari in forecasting, Gong in conversation intelligence, Outreach in sales engagement. Then you all started expanding. Messaging now seems very similar between the three. How does Outreach compare, and where do you see the future?
Manny
(19:46)
I can’t comment on current messaging since I haven’t been an executive for a while, but there are strong points of differentiation. Outreach has a unique point of view.
All these companies’ founders were friends, and we tried to make it a good business for all. Over time, Clari needed a smoother entry and bought a sequencing product to help growth and position as a platform.
The real competitor was Gong, especially as we developed real-time conversational intelligence. Gong needed to become stickier and justify its pricing as more competitors entered the market.
Eventually, you have to own a record that matters to management, not just live in workflows. That’s what we all realized. CRM data now gets dumped into Snowflake or Databricks, and activity happens elsewhere, leaving a gap for a new system of record. For us, it’s about understanding buyer activity. The market is still undefined, and Salesforce is trying to become a system of record with new offerings.
Manny
(23:08)
I don’t know where this ends, but you have to own a record to be viable.
Doug Camplejohn
(23:11)
I remember saying to Mark that Clari, Gong, and Outreach are all $100M+ companies trying to relegate Salesforce to a dumb backend database. No one’s ripping out Salesforce yet, but its value is shifting.
Manny
(23:50)
Clari positions itself as running Outreach or a shadow CRM, but the reality is everyone wants to run it as a proper system of record. You try to avoid fighting Salesforce directly, but forecasting should have been Salesforce’s business all along. I’m surprised that didn’t happen sooner.
Doug Camplejohn
(24:49)
That was my business at Salesforce. I have tremendous respect for Marc and the team-they’re brilliant at sales, marketing, and corporate development. But there’s so much technical debt. Simple features like inline editing took years to ship.
Manny
(25:49)
We bought Canopy, a forecasting product, and integrated it. That led us to sell to advanced users who wanted to do magical things. Forecasting has an opportunity to be redefined from scratch. Every CRO wants to find the most likely forecast and apply their own wisdom, but that doesn’t exist yet. With LLMs and new technology, someone should be able to build it.
Doug Camplejohn
(27:09)
Natural language is the interface of the future. If you could capture the conversations a CRO has with their team or board, you could type in questions and get answers.
Manny
(27:31)
Exactly. Many questions are “what ifs” that require heavy AI-both LLMs and data analysis. That’s the future, and I hope someone builds it.
Doug Camplejohn
(27:59)
Let’s talk about that. Kaia in 2020 was pre-ChatGPT and still innovative, but now everything has AI as a seasoning. Looking forward, how do you see AI reshaping the sales funnel, CRO role, and go-to-market?
Manny
(28:33)
AI will make the job of a salesperson much more scientific and less about gut feel. Buyers will have more knowledge than ever before.
Manny
(29:03)
Young reps will have AI tools at their disposal, which will separate those who are comfortable with AI from those who aren’t. I don’t do any writing without running it through AI tools now.
Doug Camplejohn
(37:18)
That’s awesome.
Manny
(37:19)
It’s about having a strong ethos around non-negotiables and giving people the space to succeed.
Doug Camplejohn
(37:31)
Someone once told me the CEO’s job is MVP-money, vision, and people. I almost think of those in reverse: people, vision, money. Anytime I feel overwhelmed, I focus on those three.
Manny
(37:58)
You’ve raised a lot of capital, and in Silicon Valley, raising money isn’t the hardest part. The hardest part is finding and keeping the right people. Vision is set once or twice a year. The real challenge is alignment-having the right people working on the right things in the most aligned way.
Doug Camplejohn
(38:55)
Speed of execution is critical. If one person on a rowing team is out of sync, the whole thing falls apart. It’s about having the right people and ensuring everyone knows their role.
Manny
(39:21)
If you read “The Boys in the Boat,” they picked up big, strong kids who couldn’t synchronize their oars. Once they did, they won medals. It’s a great book about alignment.
Doug Camplejohn
(39:55)
That’s on my reading list now. Thank you.
Manny
(39:58)
It’s an amazing book.
Doug Camplejohn
(40:01)
You’ve had an interesting life journey, growing up in Ecuador and going to Harvard. Thank you for not mentioning Harvard right away.
Manny
(40:12)
They tell you not to bring it up, so I try not to. Hopefully people forget about it and we can move on.
Doug Camplejohn
(40:22)
What’s the joke-if you’re a CrossFit vegan who went to Harvard, what do you talk about first?
Manny
(40:27)
That’s amazing.
Doug Camplejohn
(40:30)
How has your personal journey influenced your leadership philosophy?
Manny
(40:43)
My leadership philosophy doesn’t come from school. The hardest thing in leadership is the loneliness of decision-making. Most decisions are locked in your brain, and there are few people you can confide in. At school, they tell you the path you choose is hard, and if you don’t like it, do something else.
I try to make it suck less by finding people who give me energy. My wife is my partner in that. Debriefing with her over a bottle of wine is important to me.
One of the most impactful moments was a fireside chat with Satya Nadella. He told me that life is path-dependent; you are here because of all your choices. Your journey is shaped by your decisions and their outcomes. Even now, I make choices based on what I learned at Outreach, and before that, at Microsoft and Amazon.
As learners, we’re always looking for new paths and applying what we learn.
Doug Camplejohn
(43:18)
That’s a perfect note to finish on. A few wrap-up questions: AI is touching every part of our lives. If you could automate one personal task forever with AI, what would it be?
Manny
(43:42)
Scheduling. There hasn’t been a true EA yet. I love Fixer, Blockit, Calendly, but nothing can manage a CEO’s calendar across multiple time zones with last-minute changes. I wish that existed.
Doug Camplejohn
(44:02)
What’s something you’re passionate about that might surprise people?
Manny
(44:07)
I love grilling with a passion. My favorite weekend is firing up the coals and grilling meat. The sound of sizzling and checking on a bone-in ribeye lowers my blood pressure and makes me a better man.
Doug Camplejohn
(44:34)
Are you a Traeger guy? What’s your grill of choice?
Manny
(44:38)
There’s a grill for every occasion. My favorite is cooking with live fire. I had a Memphis grill in the U.S. that burned pellets and reached 600°F for searing and smoky flavor. I also love Argentinian grills with wood and coals you can move up and down. During COVID, I had a custom smoker built in Oklahoma-it’s my most precious item.
Doug Camplejohn
(45:20)
I’ll have to visit you in London for some barbecue. Maybe Manny’s third business will be barbecue.
Manny
(45:22)
My brisket is legendary. If I wasn’t doing this, I’d apprentice at a smokehouse and open my own.
Doug Camplejohn
(45:43)
There’s a Chef’s Table series about barbecue, right?
Manny
(45:47)
Yes! Watch it all the way through. I love it.
Doug Camplejohn
(45:58)
What’s one thing you can’t live without in your daily routine?
Manny
(45:58)
I use Perplexity for everything. It’s such a better experience, and I’m addicted to it. I wouldn’t know what to do without it.
Doug Camplejohn
(46:12)
Five years ago, I couldn’t imagine someone upending Google, but now everything starts with Perplexity for me.
Manny
(46:23)
Exactly. I go straight to Perplexity for everything. There’s always a positive surprise, and I’m addicted to that dopamine hit.
Doug Camplejohn
(46:45)
How can listeners stay in touch with you and help with Paid?
Manny
(46:50)
If you’re building an agent company or AI agent, come to Paid and sign up for the beta list. I’ll get back to you personally if you mention Doug Camplejohn from Outreach.
Doug Camplejohn
(47:06)
Manny, always a pleasure seeing you. You look great. I’m glad London is working out for you, and thank you for taking the time.
Manny
(47:10)
Thank you, Doug. That was great.
