Firing people is the kindest thing you can do.

Barrett Brooks spent years as COO of ConvertKit, scaling the company past $30M before becoming an executive coach to founders and leaders. He joins hosts Adam Jay and Dale Zwizinski for a conversation about the uncomfortable side of people-first culture.

They get into what most leaders get wrong about kindness, accountability, and the gap between what a company says it values and what it actually rewards.

We discuss:

• Why a "people-first" culture can quietly protect your worst performers
• The real reason firing conversations get avoided, and why that's not kindness
• How to close the gap between stated values and lived behavior
• Building comp plans for intrinsically motivated, creative salespeople
• A simple exercise to learn what actually drives the people on your team

Chapters:
(00:00) Treating coaching like an athlete's craft
(01:29) Talent as a Culture Multiplier
(02:18) The hidden cost of an overly people-first culture
(05:00) "We should have fired more people"
(06:17) Setting boundaries like you would with a toddler
(09:14) The 1% of managers willing to have the hard conversation
(11:28) Where values collided with P&L at Kit
(14:50) What actually builds a winning culture
(18:46) Rebuilding a team after burnout
(25:56) The unsolved psychology of comp plans
(31:55) Monday Morning Move: closing the culture-phrase gap
(38:40) The Craft & Commerce speaker equity story
(41:48) Uncensored Questions

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Most MSP programs don't fail because of bad partners. They fail because nobody built the foundation before trying to scale.

Jon Purcell is the founder of Untapped Channel Strategy and spent 13 years building channel programs inside Apple, VMware, and Workiva. He joins Adam Jay and Dale Zwizinski to break down why so many channel programs look busy on paper while producing almost nothing.

They dig into comp plan misalignment, pricing mistakes, and the expectations that sink MSP programs before they launch.

We discuss:

• Why signing 20 MSP partners on day one guarantees chaos instead of momentum
• How a mismatched comp plan quietly turns reps against your own channel program
• Why Apple's MSP program was built backward, for the vendor instead of the partner
• What it actually means to turn an MSP into a "super user" of your technology
• Why enterprise pricing models break the moment you apply them to MSPs
• The MDF trap that forces partners to spend first and wait to get reimbursed

Chapters:
(00:00) Jon's lawn analogy: why some companies won't buy no matter what

(00:48) The Grumpy Walrus Cloud story: 20 MSP partners, 8% close rate

(02:08) Why companies skip foundations before building MSP programs

(04:09) How comp plans quietly break channel programs

(05:22) Turning MSPs into super users

(10:00) The biggest mistake vendors make in the first 90 days

(13:33) Why Apple's MSP program was broken from day one

(15:54) Why enterprise pricing models don't work for MSPs

(21:33) The MDF trap that breaks channel programs

(24:14) Why leadership still treats MSP programs like a side project

(28:52) Monday Morning Move: audit your MSP program in one week

(34:44) Uncensored Questions: VMware, Broadcom, and ConnectWise

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Every homepage on the internet just added "AI" to it. Anthony Pierri says most of them didn't need to.

Anthony Pierri has looked at more B2B homepages than almost anyone alive. As co-founder of FletchPMM, he's run positioning sprints for 500+ SaaS companies, and this week he sits down with Adam Jay and Dale Zwizinski on the decision every GTM team is dodging right now: is your AI feature making the product you already sell better, or are you quietly becoming a different company? Anthony breaks down why Klaviyo's repositioning worked, why Gong's homepage keeps changing every year, and why founder-led sales collapses the moment you try to scale it. If your traffic dropped after your last rebrand, this episode explains why that might not even be the real problem.

We discuss:

• Why AI features confuse buyers when positioning isn't decided first
• What Klaviyo's repositioning reveals about trading old customers for new ones
• Why creating a new homepage category every year might mean it isn't working
• How founder-led sales narratives fall apart at scale
• The one question every exec team should answer before a rebrand

Chapters:
(00:00) Are your customers really asking for AI agents

(00:50) The Waffleboard Analytics scenario: an AI rebrand gone wrong

(01:42) Why Klaviyo's CRM repositioning was worth the traffic hit

(03:36) The Paramore problem: you don't keep the old fans

(06:50) What happens when founders ignore repositioning advice

(08:20) Does every buyer expect AI built in now

(10:37) HockeyStack's pivot from attribution to AI agents and back

(15:47) Why AI tools still can't out-write a fast human

(19:44) Why founder-led sales narratives collapse at scale

(22:43) The Monday Morning Move homepage exercise

(24:00) Categories, platforms, and the confusion they create

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Your pipeline just dropped 18%, ad spend hasn't moved, and nobody in the room can tell the board why. Sound familiar?

Tas Bober, founder of The Scroll Lab, joins Adam and Dale to make the case that conversion rate might be the most overrated number in B2B marketing. They get into why she questions the board before she questions the page, the three buckets she uses to measure what's actually happening before a form ever gets filled out, and the real client numbers behind it, including a buried FAQ that lifted purchases 265% and a landing page rebuild that took meetings booked from 0.13% to 3.16%.

They discuss:

• Why questioning the board's assumptions comes before touching the page
• The three buckets of measurement: pre-conversion, conversion, post-conversion
• How a buried FAQ lifted one client's purchases by 265%
• Why 76 touchpoints, not one landing page, decide most B2B deals
• How to test attribution without cutting your whole budget blind

Chapters:
(00:00) Why tabbed blocks are killing your conversions

(00:41) The Blissful Sugar Metrics scenario: pipeline down 18%

(01:45) Question the board before you question the page

(04:04) Why buyers need 76 touchpoints before they'll convert

(05:01) The three buckets: pre-conversion, conversion, post-conversion

(06:59) The Snagit FAQ that lifted purchases 265%

(09:31) Why 85% of B2B buyers decide before your website matters

(11:44) The dating analogy for why B2B still hides everything

(21:58) Consumption vs. conversion: why the form fill isn't the finish line

(31:21) How to test attribution without guessing

(35:18) Monday Morning Move: audit your highest-spend landing page this week

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A deal slips, the VP pulls the call recordings, and the postmortem always ends the same way: "take better notes." Woody Klemetson says that's never once fixed anything.

Woody Klemetson, Founder and CEO of AskElephant, ran sales teams for over a decade before building the AI layer he wished he'd had. Adam and Dale put him in the hot seat with a real deal-slippage scenario, and Woody breaks down why the actual failure point is almost always shitty discovery, not bad notes. They get into BANT versus DICTATE, why reps stay quiet instead of asking leadership for help, the line every revenue team building with AI needs to hear, and why most companies buy tools for themselves instead of their reps.

We discuss:

• Why postmortems and "take better notes" never fix a slipping deal
• The real difference between engagement signals and BANT checkboxes
• Why reps stay quiet instead of asking leadership for help
• How AskElephant's memory graph rethinks CRM data and AI forecasting
• The Monday Morning Move for running a deal review that actually works

Chapters:
(00:00) Introduction
(02:03) Why "take better notes" never fixes anything
(03:46) 99% of deals die from bad discovery
(05:21) Why BANT is dead
(07:58) The cost of reps not asking for help
(11:00) The 8x8 morning huddle system
(15:43) Standing out when every AI pitch sounds the same
(18:38) Is AI making sales reps think less
(28:23) The telephone game killing million-dollar decisions
(34:21) Why AskElephant built a memory graph instead of a data table
(36:24) Monday Morning Move: rebuild your deal reviews around why
(40:14) Uncensored Questions

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Your top rep is closing 3x quota. Your median rep isn't. The dashboards, the KPIs, the coaching sessions: none of it explains why.

Jack Siney is a 7x entrepreneur with 5 exits and co-founder of FrontRace, an activity intelligence platform built to answer a question most sales leaders can't: why do two reps with the same training, same territory, and same tools produce completely different results?

Jack joins Adam and Dale to break down the "20 small things" framework: the order, timing, and tone behind every deal that CRMs were never built to capture, and why he's telling companies to slow down on AI until their data and process are actually in order.

We discuss:

• Why CRM dashboards and activity data can't explain performance variance between reps
• The "20 small things": the micro-behaviors in order, timing, and tone that separate top and bottom performers
• Why coaching fails when the documented sales process doesn't match what top reps actually do
• How activity intelligence surfaces what to stop doing before it surfaces what to start doing
• Why AI implementations fail on bad data, and what "getting your house in order" actually means first

Chapters:

(00:00) Introduction: the magic is in your company data

(03:19) The 20 small things nobody measures

(06:09) Manager vs. leader: leading people, not numbers

(10:09) Order and timing: why "when" matters more than "what"

(15:30) Common sense isn't common: the data behind the instinct

(21:42) Why FrontRace: a layer on top, not a rip-and-replace

(23:29) AI hallucination, drift, and the metric engine

(26:07) Normalizing messy data across HubSpot, Airtable, and more

(28:33) Why the same behavior wins for one rep and loses for another

(30:36) The Monday Morning Move: find the unexplained gap

(32:30) Uncensored Questions

(43:56) Dream vacation destination

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Sixty-five GTM leaders. Tents in the Montana wilderness. No pitches, no name tags, no one asking what anyone does for a living. This is Arcadia, the leadership gathering Jason Yarborough built with his wife and co-founder Sam after years of watching partnerships get treated as an afterthought everywhere he worked. Three years in, they finally let us behind the curtain.

Jason walks us through why the whole event is built around trust instead of transactions, how the programming has quietly flipped from almost all go-to-market content to nearly all personal development, and the four blunt questions he asks every partner when a channel stalls out.

We also get into where AI is genuinely earning its keep in partnerships (it's not where you'd guess), why he thinks imposter syndrome is really just self-sabotage wearing a different name, and what it takes to run a company with your spouse without ever fighting about it. Sam joins near the end to talk about what three years of watching leaders show up and disconnect has taught her about trust.

If your partner team only hears from sales when there's a lead to hand off, you'll want to hear how Jason fixed that.

We discuss:

• Why partnerships still isn't treated as a native GTM function
• The four questions that turn around a stalled partner channel
• Where AI actually helps in partner identification and enablement, and where it doesn't
• Building a trust-first community instead of a pitch-first conference

Chapters
(00:00) Introduction

(12:50) The anti-conference conference

(13:36) The community before the content

(17:22) Three years of programming: from all-GTM to all-personal

(21:27) Vetting who gets into a 65-person room

(26:12) Imposter syndrome is just self-sabotage

(27:32) Why partnerships still isn't a native GTM function

(28:30) Where AI actually helps in the partner channel

(30:18) Running Arcadia (and a family) with his wife

(35:21) The science behind why this actually works

(35:50) Uncensored questions: dream vacations and decompressing after Arcadia

(39:59) Monday morning move: the four questions that reinvigorate a partner channel

(41:27) Sam on trust, and what's next for Arcadia

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We put Dawn Stallwood in the hot seat with a real crisis: a $1.8M contract that fell apart 11 days after signing because the sales deck promised things the paperwork didn't back up. Almost three decades as in-house counsel, a law partner, and a notary taught her how to spot the gap between what gets said and what gets signed, and she's built an entire career around closing it.

We get into why she calls herself a Chief Integrity Officer, how to apologize without admitting fault, and why vulnerability might be the most underused negotiating tactic in sales. We also press her on AI in the sales funnel, and on the founder dependency trap that quietly tanks a business right before an exit.

If your org treats integrity as a value on the wall instead of an operating principle, this one's for you.

We discuss:

• Crisis management and the art of apologizing without admitting fault
• Vulnerability as a trust-building and negotiating tool
• AI's role and risk in authentic sales outreach
• Founder dependency and succession planning before an exit

Chapters
(00:00) Introduction

(01:56) The Art of the Apology in a Crisis

(05:09) What a Chief Integrity Officer Actually Does

(08:30) Vulnerability as a Negotiating Tactic

(13:15) Building a Culture Brave Enough for Hard Conversations

(18:27) AI, Authenticity, and the Sales Funnel

(21:12) Succession Planning and the Founder Dependency Trap

(25:47) Navigating Equity, Earnouts, and Exit Conversations

(27:29) Monday Morning Move: The Contract Gap Analysis

(32:46) Uncensored Questions: Hard Truths and Lessons Learned