Manny Medina

Executive Chairman of Outreach, the leading Sales AI platform

Outreach is the leading sales execution platform that helps market-facing teams efficiently create and predictably close more pipeline. From prospecting to deal management to forecasting, our platform leverages automation and artificial intelligence to help revenue leaders increase efficiency and effectiveness of all go-to-market activities and personnel across the revenue cycle. Outreach is the only company to offer sales engagement, revenue intelligence, and revenue operations functionalities in a unified platform. More than 5,500 companies, including Zoom, Siemens, Okta, DocuSign, and McKesson depend on Outreach to power their revenue organizations. Outreach is a privately held company based in Seattle, Washington, with offices worldwide. To learn more, please visit www.outreach.io.

this is the most alarming chart I have seen to date

for Saas, shifting to outcomes is an economic emergency.

I used to think it was a choice for the more enlightened ones

not anymore ...

Sign up at Paid.ai. We help AI Agents get paid!

ByungSun Hwang Ph.D.

The Rule of 40 breaks with AI.

For those who don’t know, the rule of 40 states that your company is healthy if growth rate + profit margin ≥ 40.

Traditional SaaS has got used to 20% profits with costs breaking down at:
- 20% COGS
- 25% S&M
- 25% R&D
- 10% G&A

20% profit + 20% growth = healthy company. 
Easy. 

In the agent world, with all your LLM and tool calls, COGS often goes up to 60%.

BUT NONE OF YOUR OTHER COSTS GO DOWN. 

That’s why AI companies are often looking at -20% profits.  

Those companies must grow at at least 60% YOY durably to be healthy.

Some are seeing that level of growth, but it’s not sustainable with the current level of competition. 

The party has to end sometime.
Something will have to give. 

One area that will change is sales comp. 

I think we’ll see a lot more companies moving sales commissions from % of revenue to % of margins. 

It’s not a new concept. In many industries this is the norm.

Door to door sellers selling encyclopedias or cookware were doing it before. 
And if they gave a discount, it came out of their own pockets. 

Sellers were incentivized by the same metrics that mattered to the business - more deals, bigger deals, and bigger margins.

How are you compensating sellers in the AI era?

I’m hosting a roundtable on this topic soon. DM me to get on the guestlist.

🧲 Uncle! we’re finally hiring a Founding AE Paid
We’ve built double digit millions of qualified pipeline in a month. 
It's just Manoj Ganapathy and I closing
Now we need help! 

🚀 You’ll own the sales motion end-to-end
From strategy to signature. Manoj and I will personally close together with you to make sure you are successful
Our deals are $250K ACV and above. Sold to the full SaaS exec team (CEO, CFO, CRO, CPO, CTO).

You’ll be the person who makes Paid happen inside the world’s best software companies.

🧠 We’re looking for a builder who can sell
We’re not looking for a “closer.” We’re looking for a builder who can sell.

Here’s what that looks like:
Winner: You are competitive. Like to win. All the time. 
Curious: You love untangling complex problems and asking the next question.
Customer-obsessed: You can talk to a CFO about ROI and a CPO about workflow pain.
Technical: You will work closely with our FDE to build what the customer needs and close the deal. Our engineers are sellers 😳 
Strategic: You build internal champions, navigate orgs, and multi-thread
Some Experience: You’ve closed a few $250K–$500K+ enterprise deals in the last 6 months. so you know what's like
Founder energy: You move fast, thrive in ambiguity, and love building. 
High-Agency: You make decisions independently. 

💼 The work
Partner directly with our cofounders (Manoj Ganapathy Raj Dosanjh and I)  to grow the business
Co-Create repeatable sales playbooks as we scale.
Shape the GTM motion — pricing, messaging, and process.

💥 Why Paid
At Paid we sell success - not software, not services - just outcomes!  
It high-stakes work. We don't differentiate between software and services. 
Our customers winning is ALL we care about 

We’re early, ambitious, and moving fast.
This is an opportunity to join at the foundation — massive upside, full agency and autonomy and the empowerment that comes w it..

👉 Let’s Talk
The job is in-person in SF/Bay area. First few weeks in London.

If this is you - DM me.

How do you raise a seed or series A? 

This came up at Slush this week and I wanted to share my 2c.

There is a tactic for seed fundraising that makes it way faster. 

FIRST: Find all the different seed stage VCs that agree with your hypothesis. With your view of the world

There are more seed VCs than stars in the Milky Way. But there’s no magical database. You have to dig in. Trust me though, you’ll get bored before you run out.

A handful of these WILL be into your hypothesis. Probably more than 10.

So find them all.

Be diligent. Dedicate a day a week to finding these people, connecting with them and seeing if they agree with your hypothesis. Develop that relationship. Show them progress. 

This will take a couple months but it will be worth it. And it will save you time later. 

SECOND: Find out where they will take risks. 

There’s 2 types of risk VCs take:
- Those that take market risk - they find amazing technologies and assume that the market will be there. Like a16z. These are great fits to strong technical founders.
- Those that take technical risk - they identify markets that are huge and find founders/technologies that can deliver value for those markets. Like Sutter Hill.

Find the one that is right for you.

Those people will be willing to write you a small check to find out more.

It’s like a game of poker. Show your cards. If they’re interested, they add chips to the pot. 

Your job? 

All you have to do is convince them that you are the right founder for this time for that space. 

Land five believers and one will go all in. That’s how rounds start.

Thanks Slush for an amazing event. It was super energizing to spend time with so many founders of different types and backgrounds, all coming together to help each other and grow the industry.

Shout out to Alexander Schmitt for joining me on the founder’s stage.

We’ve seen a lot of firsts since launching Paid earlier this year. First hires. First office. First customers.

Yesterday was another big first for us - first team day! 

Normally elite teams are locked in delivering alpha.
So asking for a pause to go for an outdoor activity was a big deal.

It was incredible watching the team come together and getting to know everybody outside of the office.

I already knew this team was amazing, but learning more about their backgrounds and what drives them personally was just - wow.

We are small team that punches way above our weight class.

We are hiring for a founding AEs - if you want to be part of this elite team - DM me.

🎯 Great conversation with Camilla Bier at tonight's event Granola 

Two questions really hit home and sparked some candid discussions:

Question 1: 
"How do you evolve from being a founding AE who takes ANY deal just to prove the product works, to actually caring about ACV and deal quality?" 📊

The truth? It's painful but necessary - so as an early AE your move is to get ahead of it. 
In the early days, every logo matters. Every dollar validates your existence. But there's a moment when you realize that ten $10K deals don't scale 
And most take the same effort as one $100K deal 😳 - except the latter actually lets you build a sustainable business. 💡

Question 2: "What happens when you build an SMB motion, hit $10M ARR fast, raise your Series C, and suddenly need to go enterprise?" 🚀

This one got real. Here's what I shared:

When you go from Series A → B → C at breakneck speed, you become what I call a "scale company in a startup's body."

It's like going from eating Cheerios as a 12-year-old to suddenly having a mortgage and three kids in the span of a year. 🥣➡️🏠

Your Series C investors are spreadsheet warriors. They're pattern-matching you against every other company that hit $10M, and they expect enterprise-grade revenue quality. 

But 

your entire DNA - your team, your processes, your product - was built for velocity, not enterprise complexity. 📈

The brutal reality? You can't just "level up" an SMB team to enterprise overnight. 
Different people, different playbook, different everything. 🎭

My advice: Start building your enterprise motion BEFORE you need it. Plant those seeds at Series A. Because trying to transform your go-to-market strategy while hitting aggressive Series C growth targets? That's a recipe for disaster. 🔥

The best companies don't wait for the board to tell them their revenue isn't "high quality" enough. 

They see around the corner and evolve before they're forced to.

Fix it before it's too late. Your future self will thank you

xoxo

The POC is dead. Long live the POV.

The biggest mistake companies make is using proofs of concept to prove their technology works.

Nobody cares if your tech works. Buyers and champions care what it means to THEM. Personally and professionally. Get them promoted? Boost their resume? Elevate their status?

What value will they get? So my advice is to stop proving your tech works. Start proving VALUE - in the shortest possible time

Sales leaders resist POVs because they slow down sales cycles. But done right, POVs can 8X your conversion rates. 

- A normal opportunity goes from S1 to Closed-won at 10-20% conversion rate 
- An opportunity that moves to a POV goes from S1 to Closed-won at 80+% conversion rate 
- 90% of POVs will convert to closed won
- That’s a 70-80% win rate for those who offer POVs vs 10-20% for those who don’t

Yes, your sales cycle lengthens. But you lock competitors out. Most companies won't run multiple POVs. You get in first and close the door behind you.

What if your POV fails?

Well, make sure it doesn’t. 

OBSESS over delivering value. Throw your forward deployed team at it. If you don't, someone else will.

Still no results? Find out WHY (usually team misalignment or tech issues). Communicate it. Reset the POV. Try again. No close-lost, just trying again.

Here’s my 5 steps to win with POVs:

1. Get there first - Speed wins. Close the door on competitors.

2. Study their POV history - What did they pay last time? What worked? What failed? 

3. Find their approval threshold - How much can they spend without CEO/CFO signoff? 
When in doubt charge double the last successful pilot price - everyone leaves money on the table

4. Win fast - All hands on deck. Embed your team. Prove value ASAP.

5. Get the testimonial right after winning the POV - Use it to win your next POV. Rinse and repeat.

Congratulations. You've got a repeatable process for winning customers that STICK.

Go win your first POV.

I'm running a roundtable around selling AI agents next week. DM me for an invite.

There is no more technical moat.

I know that sounds shocking.

But I just spoke with four AI companies today.
All building customer service agents.
All using the exact same technology.

And they’re all thriving.

Why?

Because each one serves a tiny market incredibly well.

One sells to car dealerships.
One to e-learning companies.
One to car washes.
One to healthcare.

They tailor everything — sales, marketing, delivery — to that niche.
They show value in the customer’s own language.

The difference isn’t in the tech.
It’s in how you deliver it.
How deeply you understand the customer problem.
And how clearly you prove it’s solved.

That’s the moat now.
That’s the money.

AI agents are unlocking new and BIGGER budget pools. 

A CEO I just interviewed for the Get Paid podcast told me that for every $1 a company spends on software, they will spend $9-12 on the labor around it - administration, training, implementation, management etc.

Most SaaS companies are used to getting their budgets from the $1 software and tools budget pool. And as they launch their AI agents they are still fishing in that pool - and splitting that $1 with 50 other vendors. 

The new guard of AI natives are playing differently. They are positioning themselves as labor replacement and fishing in the $10 labor pool - and landing deals that are 2-5x higher ACV than their SaaS predecessors. 

If you’re a SaaS sales team selling  in AI, you need to start fishing in the labor pool for much bigger wins.

And to do that, you need to rethink how you do discovery. 

MEDDPICC taught us to find pain, implicate that pain, and position our product as the solution. That worked when we were selling software.

But if you want to get to labor budgets, you need to uncover not just the pain, but how they are solving it right now! Or how they're planning to solve it. In most cases, the answer is - hire someone! 

Hiring or outsourcing is instinct for most buyers. 

Even I caught myself doing this recently. Discussing business gaps with my cofounder Raj, his instinct was to buy or build a tool. Mine? Hire someone to fix it.

"Why are you always hiring people?" he asked.

Good question. My cohort of SaaS founders has been conditioned to solve problems by finding smart people. I was ready to open a $200k role. He was thinking of a $10k AI tool that does the same thing. Same value, wildly different price tag.

So, the labor pool. Here's 3 things SaaS CROs and sales leaders need to do to unlock it:

- Change your discovery to find pain AND how they’re solving pain now, where are those budgets coming from and how large. 

- Implicate the pains and the potential solutions - If you open headcount, or outsource to a BPO, what’s the budget impact this year and next?

- Lean on the zeitgeist - Boards are asking CEOs for agentic strategies. Position yourself as the agentic solution and give your customers something to take back to the board. 

I'm hosting a roundtable discussion on selling AI agents on Thursday. We'll be talking about this among other things. DM me to join!

Six months ago, I posted LLM, tool calls, and other AI Agent features that were upending SaaS economics. 

I said margins were dropping from ~80% to 60%.

I was wrong. 

It's much worse.

Bessemer Venture Partners' State of AI 2025 report just dropped a bombshell: The fastest-growing AI companies are operating at 25% margins.

25% !

The hottest AI startups are running NEGATIVE margins, burning cash to steal your customers.

They use every tool possible to win business.They’re going to undercut your pricing. They’re going to beat you in deals. They’re going to steal your customers.

The old SaaS playbook is dead, and adding credits to seats will not cut it.

Racing to the bottom on price? That's a game you can't win against companies willing to lose money on every deal.

The solution isn't to panic. It's to evolve. Don’t be stuck in race-to-the-bottom pricing with a dozen scrappy AI-natives?

Then you need to figure out to charge for value.

Your pricing model should:
- Make you invulnerable to competition
- Highlight value
- Be proprietary to your solution
- Be mutually beneficial for you and your customers

DM me to join a roundtable I'm hosting on this very issue.

We're rewriting the rules of value-based pricing in the AI era.

Saas seat compression now comes from two places

1- no or low usage. 

As Satya mentioned, Saas has gotten away charging a lot for a seat with low MAU - monthly active usage.
Well not any more. 
Upon renewal, procurement departments are lopping the bottom 10-20% of users with low MAU. 
That's contraction! 

2- layoffs

The great transformation has began. 
It started with decrease in hiring for entry level jobs (employment for those aged 22-25 declined by nearly 20% this year) 
And it's now spreading to the broader population of white collar jobs

Saas may not be dead, but being on a seat-based monetization sure looks like a road to a grave

time to move to AI agentic pricing - either task based, human replacement based, or outcome based 

pick one
pick quick

A big shift doesn't just improve things - it renders the old way of doing business completely useless.

I had a great conversation with Nicolas Sharp, CEO of Attio, on the Get Paid podcast recently. He used a brilliant analogy.

"Imagine you're building a wooden navy with sail ships. And then suddenly, people are building metal ships that have steam power. It doesn't matter how big your navy was before, it's just completely useless.”

This seismic event is happening right now in the CRM space with the rise of AI.

Listen to the full story on the Get Paid podcast to hear:
- Why the old playbooks are being thrown out
- How Attio built a platform to be "possible and easy", not "possible but difficult”
- The moment they realized their original niche CRM was a trap.

Search “Get Paid with Manny Medina” on YouTube or wherever you get your podcasts!

Your Best SaaS Sellers Are Leaving 80% of the Deal on the Table.

Not because they're bad. Because they're too good at what they've always done.

Hear me out. Here is a classic example:

🔥 Seller demos an AI agent that handles 80% of inquiries.
🔥 Buyer sees it could replace 8-10 FTEs. $800\year value.
🔥 Seller talks about the last purchase and where the budget came from.
🔥 It came from the tools budget, and there is $100K left in that budget.
🔥Closes $75K. Celebrates.

$725K just walked out the door.

🛑 The Problem? Muscle Memory.

Your President's Club winners spent years mastering tools-budget discovery:

🎯 Find the pain in current systems
🎯 Quantify inefficient software costs
🎯 Find similar past transactions
🎯 Close against IT budget

This playbook works. That's why it's killing you.

AI agents don't replace software. 

They replace work.

Stop asking: "What's your software spend?" Start asking: "What's your fully-loaded cost per employee?"

💰 Three Budgets You're Not Touching:

💲 Shadow headcount: Approved roles they can't fill, it lives in CFO's workforce model, not IT budget.

💲 BPO spend: $2M offshore service contracts (not categorized as "software").

💲 Redeployment value: What could 20 freed-up humans accomplish? (Lives nowhere on the P&L).

✅ Here's the Test:
Run your next discovery twice. Once with your tools lens. Once with a labor lens.

Compare the ACVs.
The difference will break your addiction to the tools budget.
The choice is simple:
Close $50K deals against Salesforce licenses.
Or close $500K deals against headcount.

Then think about what you will do with all that extra commission? 😄

I'm hosting a roundtable on Thursday. We'll be talking about how sales changes for AI companies vs traditional SaaS, and what tactics your peers are using to win more deals and get back to growth. 

Want to join? DM me for the link!

our team was consuming $500 of beef jerky per month! 😳

so we decided to buy in bulk and throw in some creatine and share the savings w our customers!

sign up for Paid - get fit!

From building AI agents → to building agent gains.

Creatine? Check.

Jerky? Check.

Lifting belt? Obviously.

Agentic intelligence meets anabolic energy.

Who's in?

Throw back to this gem from Pat Grady earlier this year:

A lot of the companies that are ripping right now have negative gross margins.
That's okay.

If you have negative gross margins because you're chronically underpricing your product, that’s not good.

But you have negative gross margins because you are sub scale and you can see a path toward getting to 60-80% gross margins over time, that's okay.

People are getting a little more reasonable on data privacy. Instead of needing local instances in every European country, for example, you can have a single instance that spans European country.

For enterprise customers, instead of needing dedicated instances per customer because they're worried about their data leaking into somebody else's results, people are now accepting multi-tenancy.

There are lots of different things allowing capacity utilization to go up and COGS per unit to go down.

So, if your gross margins stink today, you might actually be okay as long as you can chart the path to having healthy gross margins over time, which obviously Paid can help you with 😉

Full episode on Youtube or wherever you get your podcasts. Search 'Agent Talk #7: Pat Grady (Sequoia) - What actually works in AI startups'

The SaaS playbook just broke.

- SaaS companies added just 30% net new ARR in 2024-25 (Jamin Ball)
- Growth crashed from 36% to 12% (Aventis Advisors)

Billions of dollars are stuck in SaaS no man’s land.

The only way out is to get back to growth.

The good news is that you're already sitting on the solution.

You have a treasure trove of workflow data and operating procedures. 

The companies winning right now are already turning that knowledge - procedures, data, and policies - into AI agents. 

But most are still figuring out how to sell them. And most are getting it wrong.

Here’s 3 ways I’m seeing SaaS companies package their AI products, ranked from worst to best:

🚩OPTION 1: The "mega seat"
Bundle AI into existing seats at a premium.

It sounds safe, but it’s not.

Procurement is already cutting 10-20% of low-usage seats. Layoffs mean fewer buyers. You're fighting seat compression with... more seats? Bigger seats? 

Procurement will tell you to give them the more premium seat for the same price as the last seat if you want to maintain the contract value. 

Congratulations you got yourself a flat renewal! Yay! 

👍🏽 OPTION 2: Seat + credits
Attach AI credits to seats.

Simple to understand. Allows you to start demonstrating value without rocking the boat.

But not so simple to adopt.
How do you retrain customers to use new AI features? 
You have to put work here - otherwise a pure agentic company will convince your champion that you were built 15 years ago and no longer relevant.

This is a great way to get started down the path to … 

🚀OPTION 3: Launch a new product
Package your AI into a brand new product.

Look at Intercom and Fin. Matillion and Maia. Salesforce and Agentforce.

This approach wins because:
- You own the new category before competitors wake up - this category is for you to lose
- Customers pay for results, not seats
- Sales cycles collapse - no one argues with ROI
- You escape the compression death spiral 

The companies already making this shift are pulling ahead. 

The rest are still debating seat pricing while their ARR bleeds out.

I'm hosting a closed-door roundtable with SaaS leaders navigating this exact transition. DM me for an invite.

“You don't buy enterprise software, you inject it into your corporate veins.”

Quote of the week courtesy of Dave Kellogg on the latest episode of Get Paid.

In markets with high switching costs, like a lot of enterprise software, land grab strategies make sense.

But in markets where customers can switch providers with a click, giving away your product for free doesn't build a moat, it just burns cash.

“If you’re in a market with high switching costs, grab share, because you’re going to get something for it downstream.”

Listen to the full episode for more great insights into AI pricing, FDEs, sales commission structures, hiring AI natives vs SaaS veterans and tons more.

Search “Get Paid with Manny Medina” on Youtube or wherever you get your podcasts.

Love when a legend like Nick Mehta drops tactical gold

Board Member: Gainsight, F5 (NASDAQ: FFIV), Pubmatic (NASDAQ: PUBM)

How do you run client meals that people actually look forward to?

I've led hundreds of customer lunches and dinners over the years. As Erica Mansfield Robin Merritt Emily Wilkes Kat Leong Lauren Olerich know well, I have a very particular (or as some might say, "high maintenance") approach to making sure guests have a special experience.

As a note to myself, this is a partial list of my event eccentricities:

1. Topical Theme: Something attendees are already thinking about.
2. Goldilocks Zone: For one discussion, 20 is too big. But 8 RSVPs mean 5 might show. I've found 14 signed up is perfect.
3. Reply to RSVP: For intimate settings, having to click on a site and fill out a form reduces attendance.
4. Reminder: A second email with who's coming so far has a big effect on reg (social proof).
5. Day-Before Email: Get folks in the right state of mind with an agenda and prep info.
6. Real Private Room: There are so many fake private rooms out there. I've seen ones where a curtain divides the room from the restaurant. Make sure it's truly isolated.
7. Cozy Size: Nothing kills a vibe more than a 40 person room with 10 in it.
8. Turn It Down: Tell the server to cut the music in the room when dinner begins.
9. Mingle: Allocate 30 min before dinner for folks to meet each other.
10. Assigned Seats: Not always required but good way to make sure people meet each other.
11. One Convo: Jeffersonian dinners are special.
12. Active Moderation: Make sure everyone gets a chance to speak.
13. End On Time: Nothing worse than customers feeling like they can't leave.
14. Checkout: Final question - e.g., "one word to describe what you learned today but you can't repeat someone else's word?"
15. Thank You Email: Right after with a summary and contact info.
16. Team: None of it is possible without an epic team like the folks I listed above.

What have you learned about running small customer meals?

it's the Friday after Thanksgiving 

possibly the least productive non-holiday day in the year 

enjoy

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