Max Freeman

1. Key Themes

Mispriced Talent: Hire Like Billy Beane (Bankers, Low-NPS Sellers, Pedigree Skeptics)

Freeman's central hiring thesis is that resumes mislead and the alpha lives in arbitrage. Ramp hired investment bankers in its early days and now has them running large pieces of the business. Freeman says: "bankers are programmed to work. The concept of a 9 to 5 is completely foreign to these folks." 00:05:19 They also bring "intelligence and… business acumen and a lot of horsepower," and when Ramp had no brand, "being able to call a CFO cold, tell them, hey, I just quit my job at Goldman TMTIP to join this credit card business. That packed a very compelling punch for us." 00:06:06 On sourcing from tech: "You have to treat go-to-market recruiting like Billy Bean. There is so much alpha in finding what companies have grown revenue in a significant way… but have done that despite having a low NPS score." 00:00:00 His reasoning is that sellers at those companies had to create their own demand, navigate complex cycles with weak third-party reviews, and sell at a premium price. The one company he named was Sixth Sense (transcribed "Six cents"): "I'll name one." 00:10:24

Pay Above Market, Demand Multiples of Output

Ramp's SDR economics bet on talent density over cost minimization. Freeman: "We'll pay 2x what a standard SDR is going to make. But guess what? You get to book 40, 50, 60 meetings, which is four to six times what a standard SDR has to book." 00:00:00 The same logic holds for AEs: "Our inside sales reps, our commercial reps, they're taking 10 to 12 calls in a given day… There are some sellers at RAMP that are on 15 plus calls in a given day." 00:08:30

Hiring Diagnostics: Decompose the Number, Reconstruct the Deals

Freeman gives a concrete method for separating true performers from order-takers. "You have to decompose their number. And so, okay, you did 2 million. That's great. How much of it was inbound? How much of it was outbound? How much of it was expansion? How much of it was sourced by your founder?" 00:11:24 He then has candidates "reconstruct them chronologically" and probes losses: "talk to me about a deal that keeps you up at night. Why did you lose it?" 00:11:54 The interview process includes a business case that tests knowledge of Ramp, research on the prospect ("Have you read their 10K?"), and selling fundamentals. The final test is simple: "would I buy a product from this person? If I can't say that with conviction, I'm not going to hire them." 00:13:56

Sales Is an Engineering Problem: OATS and Growth Engineering

Freeman believes outbound has shifted from writing and calling to engineering. "Sales is very much an engineering problem when you break it down. It's a data infrastructure problem. It's a math problem." 00:00:00 In late 2020, Ramp built OATS (outbound automation team), "even before the rise of AI," to automate list scraping, signal detection and email outreach. 00:18:58 Signals included "a new hire, just join the business… I went to the same university as this person. We have overlapping investors on our cap table." 00:19:24 He says the aim is coverage and that the system must be "recursive" with constant A/B testing. 00:21:33 Ramp now has "at least half a dozen engineers that truly obsess over building products for go to market." 00:22:14 The AI-era internal stack includes Ramp Revenue and Inspect (see Operating Insights and Companies).

Choosing a Company: Market, Talent Density, Founders (Not Equity or Title)

Advice to sellers: "thinking about equity, cash and comp is actually the wrong thing to index on. The right thing to index on is the market, the talent density, the business and the founders." 00:14:28 On Ramp's market: "The card business, it's a trillion dollar plus a year market expense. Same thing. Bill payments, multi-trillion dollar a year market. Travel… Banking… So you don't even have to be a good business to find a way to grow." 00:14:57 On a mediocre business: "you're going to go work at a mediocre business that might grow 20, 30% a year. Who cares? You're making the wrong trade." 00:15:26

Sales Compensation and Quota Design by Stage

Early: "I usually advise to do 100% OTE for at least the first two quarters. You just don't know what you don't know." 00:27:54 Founders either blow out a quota and owe multiple six figures, or set an unattainable one that kills confidence. Hire sellers in pairs: "you should never hire one seller or one SDR at a time because the problem is how are you going to benchmark their performance?" 00:29:36 Later stage: "it's existential to over-incentivize new products to get off the ground. And so thinking through 2x to 3x quota retirement for new products." 00:31:48 Early on, focus: "it's so much more valuable to have 20 customers that are raving and thrilled about one single product offering than you in a half-ass way serving six customers on multiple products." 00:31:19

Onboarding Rigor and Leader Involvement

Bootcamps run 60 to 90 days with gated certifications: "You need to complete a disco certification and you need to be excellent. You need to complete a demo certification… If you don't complete them, you don't get turned on in the router. You don't get your accounts." 00:36:44 Reps take their first calls in "two to four weeks." 00:37:35 Freeman insists: "If you're running a big sales team and you're just dependent on enablement, you're going to die. You need your frontline leaders to lean in aggressively." 00:37:46 Ramp schedules by segment: "Our down market sellers, inside sales reps, 60 days. Commercial reps, 90 days. Mid market, four months. Enterprise, five months… strategic enterprise is a six month ramping schedule." 00:41:09

Forecasting, Pipeline Review and Loss Analysis as Culture

Ramp's finance counterpart (Asher) keeps the business "consistently within a 5% delta." 00:45:52 Freeman's lever is accountability: forecast accuracy isn't comped but "it's part of your performance review. It's coming up in one-on-ones." 00:46:18 He eliminated forecast calls as "performative work theater." Pipeline reviews are weekly and focus on at-risk deals and losses. 00:47:16 The key finding: "the majority of the time we're losing to the status quo, which is on us… We did not create enough urgency and you can manufacture urgency as a seller." 00:48:13

Leader as Dual Threat

Freeman: "you've got to be a dual threat. You've got to be able to operate in the clouds… At the same time, you have to be in the trenches with your sellers. Still to this day, I'm making cold calls. I'm sending at least five cold emails every single day." 00:54:33 And: "There's nothing less inspiring as a seller than taking instruction from someone that you don't believe can do the job better than you." 00:55:02

2. Contrarian Perspectives

Go Above Market for SDRs and Hire Bankers

Most founders optimize SDR cost. Freeman pays double and demands 4 to 6x the meetings. Underlying evidence: "We'll pay 2x what a standard SDR is going to make. But guess what? You get to book 40, 50, 60 meetings." 00:00:00 Those bankers (Mike Weber from Citi, Sam Buck from Goldman) "run massive pieces of the business" today. 00:06:34

Hire Sellers From Companies With Bad NPS

Conventional wisdom says to recruit from beloved brands. Freeman says the opposite: sellers who grew revenue at nine-figure scale at low-NPS companies had to "create a lot of your own demand," and that makes them better. 00:09:17 He contrasts this with Ramp, where "we get that 10 to 20 times a month" in unprompted customer praise, and a veteran said "I've never seen this in my 15 years of sales." 00:10:32

Don't Have a Comp Plan Early

Most advice is to set quotas early. Freeman: "I usually advise to not have a comp plan. I usually advise to do 100% OTE for at least the first two quarters." 00:27:54

Verticalize Late, Not Early

"I think companies actually verticalize far too early, especially if you have a huge addressable market, you're in land grab market share mode." The trigger is "3% to 5%" market ownership, when the remaining opportunities become contained. 00:23:24

20x Quota Attainment Means You're Underinvesting

On Eleven Labs' head of sales (Collez, as stated) claiming 20x quota: "if you're that efficient, you're probably leaving money on the table and you need more reps… the old school thought… four to one or five to one. That's too low… anywhere from seven to 12." 00:40:04 He adds some inside sales reps run at "14 to one." 00:40:46

3. Companies Identified

Ramp

Corporate card and spend-management platform expanding into bill pay, travel and banking. Freeman's employer, described as having "the market leading product" and a "talent dense engineering roster that looks more akin to that of a lab, that of a SpaceX." 00:15:26 Customer enthusiasm: "we get that 10 to 20 times a month at Rant." 00:10:32 The title cites $1.7BN ARR. Freeman says "our ambitions are well beyond owning the office of the CFO." 00:52:14

Ramp Revenue

Ramp's internal revenue operating system that automates pre-call research. "A 90 seconds to perform your pre-call research" versus 15 to 30 minutes manually; it "bridges the talent gap" between average and great sellers. 00:50:57 He is open to productizing it: "I can certainly see a time when we take these other products to market." 00:52:14

Inspect (Ramp's internal coding agent)

"Inspect is Ramp's internal coding agent in Harness. It feels as though I have an engineer and a sales engineer in my pocket." Sellers use it to build "bespoke custom demos" and analyze customer configurations. 00:58:26

Ramp Router

Mentioned as an existing Ramp product, alongside the possibility of releasing more internal tools. 00:52:14

Sixth Sense (garbled "Six cents")

Named as an example of a company with a low NPS but strong revenue growth, producing sellers Freeman wants. "I'll name one." 00:10:24

Crosby

AI law firm, sponsor of the episode. It "combines AI, some of the best engineers in the world, from companies like Ramp and Stripe and some of the best attorneys in the world from top ten law firms," returning red lines in under four hours. Customers include Cognition, Ramp and Clay. 00:01:46

OneMind

GTM "superhumans" product used by HubSpot, Alteryx and ZoomInfo to "qualify buyers, ride along with sales reps and coach customers." 00:02:41

Framer

AI website builder trusted by "Perplexity and Miro." 00:03:59

Profound

Freeman is trying to recruit Charlie DeMuth from there every six months. 00:59:54

Clay

Freeman's top candidate pick is Becca Lindquist "from Clay." 00:59:29

Eleven Labs

Cited as having a head of sales who claimed 20x quota attainment. 00:40:04

Snowflake and MongoDB

Examples of the "old school" 4:1 or 5:1 quota ratio and of services-led customer success: "while that might work for Snowflake, I don't think it's the right decision for us at Ramp." 00:44:24, 00:44:24

Oracle, Workday, SAP

Cited as companies that verticalized sales "moderately well" after owning large market share. 00:23:53

Deel and Revolut

Hosts note they productized internal tools (performance management software) into external products. 00:52:14

Harvey, Nagora, Astralore (as transcribed)

The host argues enterprise deployment is hard and that a new entrant won't easily unseat Harvey and Nagora, "who spent two years kissing the ass." 00:53:07

Twilio, Uber

Used by the host as a hypothetical for separating real sales credit from happenstance. 00:11:24

Capital One

Eric and Kareem "had already built and sold a business to Capital One." 00:16:41

KKR

Cited as an example of the signal data (a new debt sponsor) that Ramp Revenue surfaces. 00:51:27

4. People Identified

SVP of Sales at Ramp. Started as a mid-market AE at a prior company (the host cites Namely), "quit my job to become an SDR all over again at ramp." 00:14:57 Built OATS and Ramp Revenue, still cold emails daily, and is credited by Ramp's CEO with the revenue build.

Eric Glyman

Ramp co-founder and CEO. Freeman: "my boss was effectively Eric… I'm seeing him in sales conversations… it felt like I earned 50 MBAs in a nine month period." 00:56:03

Karim Atiyeh (transcribed "Kareem")

Ramp co-founder. Freeman credits him with early engineering resources for OATS: "I give a lot of credit to Kareem early on with providing engineering resources." 00:18:18 Along with Eric, "had already built and sold a business to Capital One." 00:16:41

Colin

Freeman's boss at Ramp, who "has taken companies public. He's sold businesses." 00:56:30

Mike Weber

Pulled from Citi; "runs a massive piece of the business." 00:06:34

Sam Buck

Came from Goldman; "runs a massive piece of the business." 00:06:34

Asher

Ramp's finance counterpart who built forecasting systems keeping the business "consistently within a 5% delta." 00:45:52

Dave Schneider

Investor and mentor. Freeman: "I'm super grateful that I get to call Dave Schneider a friend and a mentor." 00:56:30 His line: "there's three categories of performance in sales. One, you are God. Two, I don't know yet. Or three, you're fucking fired." 00:00:00

Chris Degnan

Referenced for "you can't do more than seven" meetings and for the view that customer success should be paid professional services. Freeman: "I love Degnan too." 00:34:01

Chad Peters

Legendary sales leader who said young people don't want to work. Freeman: "He's a beast." 00:34:01

Becca Lindquist

Clay sales leader; Freeman would hire her. 00:59:29

Charlie DeMuth

Enterprise frontline leader at Profound: "He's an animal. And I've been trying. Every six months, I try and bring him in." 00:59:29

Mark

SVP of Sales at Profound, named as the person Freeman hopes won't hear he's poaching. 00:59:54

Collez

Head of sales at Eleven Labs who claimed 20x quota attainment. 00:40:04

Alex

Ramp enterprise seller who said he'd never received unprompted customer praise like this in "15 years of sales." 00:10:55

Scott

Ramp enterprise team member, "number one right now," used as an example of a candidate who researched the team. 00:43:13

Susan (hypothetical)

Used as the example stakeholder (VP of procurement) a seller asks a champion to bring into a call. 00:25:32

Will

Ramp executive Freeman operates toe-to-toe with, alongside Eric and Colin. 00:54:33

Seth Godin

Referenced for "purple cow": being different is sometimes being better. 00:58:06

John Sculley

Referenced for the Apple "sell flavored water" line, used as a framing for not wasting a career on weak products. 00:16:09

Harry Stebbings

Host of 20VC. Used to listen to his podcast as an SDR and reach out to guests. 01:04:18

5. Operating Insights

Build the Early Sales Team in Pairs

"You should never hire one seller or one SDR at a time because… how are you going to benchmark their performance?" A 10 to 20% delta between two peers means investigate structural advantages (pipeline, product knowledge, motivation); an outlier gap means shed the weaker one. 00:29:36, 00:30:14

Use a Seller-Friendly Founder Test and a Champion Test

Test an early-stage company by asking whether the technical co-founder will give engineering resources. 00:18:18 Test a buyer by asking them to bring their boss to the next call as a "give to get": "Is Harry going to bring Susan into the call? Okay, great. You may have a champion." 00:25:32

Compress Cycles With Qualification, Not Discounting

"The best way to compress sales cycles is qualifying with more rigor": influence plus 12-month commitment. 00:24:35 On pricing, if the buyer raises it after call one, "that's usually a bad sign. It's not a sophisticated buyer." Up market, "co-author business value assessments" and total cost of ownership so "you could circumvent any pricing concessions." 00:27:09

Spot Great Hires in Onboarding by Their Questions

"There is a direct correlation in onboarding with sellers that are annoying and sellers that are not… constantly asking questions 24 seven. They're very thoughtful." Quiet reps, or those asking what "any AI bot or Notion bot can answer," are a weak signal. 00:41:37 Freeman reserves at least 10 minutes in interviews for candidate questions. 00:42:31

Review Calls Personally and Cull the Meetings

Freeman estimates 70/30 impressed versus below-standard first calls and personally reviews Gong calls of new and tenured reps. 00:39:06 He replaced forecast calls with a weekly pipeline review focused only on at-risk deals, because "every hour matters." 00:47:16

6. Overlooked Insights

Pre-Call Research Is a Talent-Gap Equalizer

Freeman noted in passing that Ramp Revenue "bridges the talent gap": an exceptional seller notices "KKR just came in… this random person that isn't even in finance or accounting happened to use Ramp at a previous company," while "an average seller might neglect all of that." 00:50:57 The implication is that AI tooling can raise the floor of the entire team and turn saved minutes into "extra selling days… which allows us to over time increase quotas." This quantifies productivity as a quota lever, not just a cost saving.

Brand Spend Shows Up as Sales Capacity, Not Attribution

Freeman said brand "is hard to truly attribute this in the data" but acts as "a surround sound for our outbound SDR team" and gives sellers experiences (sporting events, "our bill pay musical," bespoke dinners) to invite prospects to, which he says is "directly correlated" with cycle times and expansion. 00:49:53 The overlooked point is that brand investment functions as a sales-engagement asset, not merely top-of-funnel awareness.