How Founders Are Building the Next Great Startups | Paid.ai, iTruckr & Tenax AI | E2175
Today’s show:
In this TWiST founder triple-shot, Alex digs into the real-world rollout of AI agents: Paid.ai’s Manny Medina explains agent economics and value-based pricing, iTruckr’s Camilo Ramirez shows agents booking loads and coordinating drivers, and Tenax’s Elise Myrans demos computer vision + drones that score a single home’s wildfire/flood risk for smarter underwriting—plus live office-hours on winning enterprise pilots without getting stuck in PoC purgatory.
Timestamps:
(00:00) Brainstorming hacks for sales cycles in regulated industries — castles, moats & alligators!
(03:50) Meet Paid.ai: tracking costs & monetization for AI agents
(04:35) Paid.ai’s Manny Medina on the “year of agents” & early enterprise traction
(09:04) Netsuite - Download the ebook CFO’s Guide to AI and Machine Learning for free at https://www.netsuite.com/twist
(11:06) The tough economics of AI agents vs SaaS — margins squeezed by tokens
(18:20) How Paid.ai gets granular: tracking signals & agent activity with OpenTelemetry
(21:20) Coda - Empower your startup with Coda’s Team plan for free—get 6 months at https://www.Coda.io/twist
(29:16) Enter iTruckr: Camilo Ramirez brings AI dispatch to the freight industry
(31:43) .TECH: Say it without saying it. Head to get.tech/twist or your favorite registrar to get a clean, sharp .tech domain today.
(39:02) Scaling from small fleets to mid-sized trucking companies — lessons from AI Trucker
(55:59) Tenax ai helps homeowners & insurers manage wildfire, flood & climate risk
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Check out the TWIST500: https://www.twist500.com
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Follow Lon:
X: https://x.com/lons
Follow Alex:
X: https://x.com/alex
LinkedIn: https://www.linkedin.com/in/alexwilhelm
Follow Jason:
X: https://twitter.com/Jason
LinkedIn: https://www.linkedin.com/in/jasoncalacanis
Thank you to our partners:
(09:04) Netsuite - Download the ebook CFO’s Guide to AI and Machine Learning for free at https://www.netsuite.com/twist
(21:20) Coda - Empower your startup with Coda’s Team plan for free—get 6 months at https://www.Coda.io/twist
(31:43) .TECH: Say it without saying it. Head to get.tech/twist or your favorite registrar to get a clean, sharp .tech domain today.
Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland
Check out Jason’s suite of newsletters: https://substack.com/@calacanis
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Twitter: https://twitter.com/TWiStartups
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Instagram: https://www.instagram.com/thisweekinstartups
TikTok: https://www.tiktok.com/@thisweekinstartups
Substack: https://twistartups.substack.com
Subscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916
Pricing in the AI Era: From Inputs to Outcomes, with Paid CEO Manny Medina
Former Outreach CEO Manny Medina discusses his new company Paid, which provides billing, pricing and margin management tools for AI companies. He explains why traditional SaaS pricing models don’t work for AI businesses, and breaks down emerging approaches like outcome-based and agent-based pricing. Manny shares why he believes focused AI applications targeting specific workflows will win over broad platforms, while emphasizing that AI companies need better tools to understand their unit economics and capture more value.
Hosted by Pat Grady and Lauren Reeder, Sequoia Capital
Mentioned in this episode:
CPQ: Configure, Price, Quote
Invent and Wander: Book by Jeff Bezos and Walter Isaacson
Foundations of Statistical Natural Language Processing: 1999 book by Chris Manning and Hinrich Schütze that Manny cites as a piece of AI content every AI founder should read. (still in print, companion site here)
The fox and the hedgehog:
Quandri
XBOW
HappyRobot
Owl
Crosby
#151 CEO Outreach, Manny Medina: 10M or Die
Guest: Manny Medina, CEO of Outreach
In its Seattle headquarters, the sales execution platform Outreach has at least one wall covered in AI diagrams and architectural flows. CEO Manny Medina says that’s because he believes “there’s no world in which reps don’t have an assistant the way that coders do.” The AI revolution has also given Manny — who got his M.A. in computer science at Penn — a chance to be more hands-on than your average CEO of a $4 billion company. “I try not to think myself as a CEO,” he says. “I try to think myself as a team member that is doing something useful.”
In this episode, Manny and Joubin discuss northern New Jersey, American opportunity, going to the future, crossing the chasm, jujitsu, Tony Robbins, winning on your own terms, shifting motivations, inspiration through transparency, Moonwalking with Einstein, Lululemon, hands-on CEOs, and “been there, done that.”
In this episode, we cover:
Leaving Ecuador for the US (02:21)
Would Manny do it all again? (07:45)
Finding product-market fit (10:09)
Scaling, scarcity, and stability (14:41)
AI-assisted sales reps (18:59)
Winner takes most (24:20)
Placing long-term bets (26:42)
Imposter syndrome and chips on your shoulder (32:59)
“Ten million or die” (35:15)
Irrational forces (42:33)
Manny’s weekly internal emails (44:17)
Memorizing names and making sacrifices (48:00)
Personal and professional goals (52:23)
“All the other jobs were taken” (56:53)
Do-overs (01:00:18)
Bad and good startup advice (01:03:24)
Who Outreach is hiring and what “grit” means to Manny (01:05:58)
Links:
Connect with MannyLinkedIn
Connect with JoubinTwitter
LinkedIn
Email: grit@kleinerperkins.com
Learn more about Kleiner Perkins
This episode was edited by Eric Johnson from LightningPod.fm
SaaStr 292: Most Downloaded Founder Episode of 2019 with Manny Medina, Founder & CEO @ Outreach
This interview originally aired as Episode 229 on April 29, 2019.
Manny Medina is the Founder & CEO @ Outreach, the market leading sales engagement platform that turns your team into a revenue driving machine. To date, Manny has raised over $114m in funding from some great people including friends of the show in the form of Alex Clayton @ Spark, Mayfield, Trinity Ventures and DFJ Growth, just to name a few. Prior to founding Outreach, Manny spent 7 years with Microsoft where he ran the Latin America and Canada business development group for Microsoft's emerging mobile division, representing $50M of yearly revenue. Befofe that Manny was a Senior Product Manager @ Amazon where he engineered the compensation system for Amazon Associates and Web-Services which accounts for 15% of Amazon's traffic.
In Today's Episode We Discuss:
How Manny made his way to found the leader in sales engagement from product management at Amazon and Business Development @ Microsoft.
How does Manny fundamentally approach managing top of funnel? What are the 2 big dangers of not managing it aggressively? What can be done to ensure not only full but high quality top of funnel?
Why does Manny believe it is so important to track pipeline coverage as one of your core metrics? What does good look like when it comes to pipeline coverage? How does this change if you are creating vs in an existing market? How does Manny think about specialisation within the sales function? Why are SDR's 99% of the time not able to carry leads to completion?
How does Manny think about quota construction today? Does Manny err on the side of setting high to be ambitious or setting low to increase confidence? How can managers really empower their reps to be aggressive in hitting their quota and exceeding it? How does Manny think about resource allocation on the individual rep level? What is sufficient? What is excessive?
Does Manny believe that the founder should always be responsible for selling their product at one moment in time? How did Manny sell the first $1m in ARR simply through walking the streets of SOMA and selling door-to-door? What were his biggest lessons from doing this? Why does Manny believe that you should not have a VP before $5m?
60 Second SaaStr:
What does Manny know now that he wishes he had known in the beginning?
What does the future of sales prospecting look like to Manny?
What would Manny like to change about the world of SaaS today?
Read the transcript on our blog.
If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:
Jason Lemkin
Harry Stebbings
SaaStr
Manny Medina
SaaStr 229: The 2 Most Important Numbers For Your SaaS Business, Why You Should Not Have VPs Until $5m in Revenue & How To Manage Top Of Funnel Efficiently But Aggressively with Manny Medina, Founder & CEO @ Outreach
Manny Medina is the Founder & CEO @ Outreach, the market leading sales engagement platform that turns your team into a revenue driving machine. To date, Manny has raised over $114m in funding from some great people including friends of the show in the form of Alex Clayton @ Spark, Mayfield, Trinity Ventures and DFJ Growth, just to name a few. Prior to founding Outreach, Manny spent 7 years with Microsoft where he ran the Latin America and Canada business development group for Microsoft's emerging mobile division, representing $50M of yearly revenue. Befofe that Manny was a Senior Product Manager @ Amazon where he engineered the compensation system for Amazon Associates and Web-Services which accounts for 15% of Amazon's traffic.
In Today's Episode We Discuss:
How Manny made his way to found the leader in sales engagement from product management at Amazon and Business Development @ Microsoft?
How does Manny fundamentally approach managing top of funnel? What are the 2 big dangers of not managing it aggressively? What can be done to ensure not only full but high quality top of funnel?
Why does Manny believe it is so important to track pipeline coverage as one of your core metrics? What does good look like when it comes to pipeline coverage? How does this change if you are creating vs in an existing market? How does Manny think about specialisation within the sales function? Why are SDR's 99% of the time not able to carry leads to completion?
How does Manny think about quota construction today? Does Manny err on the side of setting high to be ambitious or setting low to increase confidence? How can managers really empower their reps to be aggressive in hitting their quota and exceeding it? How does Manny think about resource allocation on the individual rep level? What is sufficient? What is excessive?
Does Manny believe that the founder should always be responsible for selling their product at one moment in time? How did Manny sell the first $1m in ARR simply through walking the streets of SOMA and selling door-to-door? What were his biggest lessons from doing this? Why does Manny believe that you should not have a VP before $5m?
60 Second SaaStr:
What does Manny know now that he wishes he had known in the beginning?
What does the future of sales prospecting look like to Manny?
What would Manny like to change about the world of SaaS today?
Read the full transcript on our blog.
If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:
Jason Lemkin
Harry Stebbings
SaaStr
Manny Medina