Aug 23: Cutting deal review time from 90 to 30 minutes
Good morning. Sales leaders are replacing soft coaching with hard structural barriers to force behavioral compliance.
Wiz AVP Michelle Bovee is cutting deal review times from 90 minutes down to 30 by forcing reps to complete a 15-question asynchronous spreadsheet beforehand. If a seller cannot articulate the rationale behind a close date in writing, it triggers instant self-assessment before the meeting even begins.
Today's Sales Plays (22)
Tactical moves operators are running right now, with verbatim source.
outbound
3-T permission-based opener
Open cold calls with one of three Ts (Trigger, Tension, Trust) followed by a specific time-bound permission ask.
Discussing: Opening a cold call without triggering the prospect's default defensive posture.
“You have to have at least one of the three Ts... either a trigger, tension, or trust. And then you need to wrap your permission-based opener by asking for permission.”
MechanismStructure the first 15 seconds using a greeting, exactly one "T" (Trigger: "noticed you opened a new branch", Tension: "need to expand brand awareness quickly", or Trust), and a highly specific permission ask ("Do you have 22 seconds so I can tell you why I called?").
Outcome44% increase in first-time meetings set
CounterpointAsking for a hyper-specific amount of time (22 seconds) pattern-interrupts the standard "do you have a minute" brush-off.
Meet Amanda Long, our newest Pipeline Consultant · Aug 17, 2026
team_and_org
3x Pipeline Virtual Patch Warming
Build virtual territories and warm them with marketing touches until they hit 3x pipeline coverage before assigning them to new hires.
Discussing: New AE ramp times are stretching to six months or more because reps are handed completely cold territories.
“Once I got a patch to a 3x pipeline... I'd cut that patch and I'd start ranking which patches could take my new hires. That would move my ramp time from the theoretical six months... to 90 days.”
MechanismInstead of giving new hires a cold patch, create virtual patches. Direct marketing spend and outreach to these specific accounts to generate touches. Wait until a virtual patch reaches a 3x pipeline-to-quota ratio. Only then, cut the patch and assign it to a newly hired seasoned rep.
OutcomeReduced ramp time from 6 months to 90 days
CounterpointMost orgs assign cold patches on day one and expect reps to build pipeline while learning the product. This shifts pipeline generation to marketing first.
SPOTLIGHT: He Missed Quota 5 Times in 25 Years. Here's the System Behind That.| Mike Carpenter, CEO & Co-Founder @ Xfactor · Aug 20, 2026
forecasting
15-question asynchronous deal review
Require reps to fill out a 15-question spreadsheet before deal reviews to force self-assessment and cut meeting time.
Discussing: Deal review meetings running too long and lacking structured qualification.
“It saves time. So a deal review is in an hour, an hour and a half, but it's actually only 30 minutes. And it's simple questions like, What's the close date of this deal and why that close date?”
MechanismBefore a deal review, reps fill out a spreadsheet with 15 specific questions (e.g., 'What is the close date and why?', 'Who is the economic buyer?', 'When did the POV start and end?'). If a rep cannot articulate the 'why' behind a close date, it forces instant self-assessment before the call.
OutcomeCuts deal review time from 90 minutes to 30 minutes
CounterpointShifts the burden of qualification from the manager interrogating the rep on a call to the rep self-assessing asynchronously.
How to Hire Better Salespeople Than Yourself and Lead Them to Win · Aug 20, 2026
team_and_org
The quit-tomorrow retention test
Ask frontline managers how they would react if a rep quit tomorrow to instantly clarify whether to coach or manage out.
Discussing: Evaluating whether to invest in coaching an underperforming rep or begin managing them out.
“I ask my RDs there if they're on the fence about a rep. I say if they quit tomorrow, what would your call be to me? Would it be? I'm so excited. They're gone. Or would it be shit? We just lost this person.”
MechanismWhen a frontline manager is on the fence about a rep, ask them: 'If this person quit tomorrow, would your call to me be that you are devastated, or excited?' If the answer is devastated, immediately build a retention and recognition plan. If they are excited, start the exit process.
OutcomeInstantly clarifies retention priority
CounterpointBypasses standard performance metrics to measure the rep's actual cultural and operational impact on the frontline manager.
How to Hire Better Salespeople Than Yourself and Lead Them to Win · Aug 20, 2026
discovery
In-meeting calendar lock
Book the next meeting before leaving the room, and use stage-matched content to bridge any unavoidable gaps.
Discussing: Deals are quietly stalling out between meetings because buyers say they will "circle back in a few weeks."
“Ending a meeting without setting the next connection is essentially a sales mortal sin... when the next meeting goes on the calendar before anyone leaves the room, the deal will keep breathing.”
MechanismMake it a hard rule to put the next meeting on the calendar before ending the current call. If the buyer refuses, sustain momentum by sending stage-matched content: proof points and case studies for early stages, or legal and purchasing resources for late stages.
OutcomeSpeaker's word, prevents deals from ghosting.
Counterpoint"Circle back" usually means the buyer is settling into complacency.
EP 138 Building Momentum in Complex Sales with Mike O’Brien and Tom Whelan, Ph.D · Aug 20, 2026
team_and_org
Reverse-question coaching framework
When a rep asks for help on a stalled deal, ask what they have already tried before giving advice.
Discussing: A rep comes to you frustrated by a slump or a stalled deal, looking for you to just give them the answer.
“Generally, my first question is, what have you tried? And, or what do you think? ... it's way better if they can come up with their own solution rather than having somebody tell them.”
MechanismResist the urge to immediately solve the problem. Ask two questions: 'What have you tried?' and 'What do you think?' Force the rep to articulate their past actions and propose their own solution. Only offer your own experience after they have diagnosed the issue themselves.
Outcomespeaker's word, not measured
CounterpointIf you just give the answer and it fails, the rep blames you. Forcing them to self-diagnose builds ownership and confidence.
HOW TO DEVELOP THE #1 DIFFERENTIATOR OF GREAT SALESPEOPLE · Aug 17, 2026
team_and_org
Days without leading indicator report
Track the days a rep goes without generating a critical leading indicator to catch slumps before they impact quota.
Discussing: Reps falling behind on pipeline generation but hiding it until the end of the month when it is too late.
“If a rep has gone two days without a proposal, then the director would ping the manager... If a rep has gone five days... the director then sends a note to the manager and the rep.”
MechanismMap your sales cycle to a leading indicator like proposals. For an 8-day cycle: At 2 days without a proposal, Slack the manager. At 5 days, Slack the manager and rep. At 10 days, mandate a calendar meeting with the director, manager, and rep to build a success plan.
OutcomeReps start proactively messaging leadership before the 2-day mark to explain their pipeline.
CounterpointDo not wait for lagging indicators like closed-won; trigger automated leadership interventions based purely on days without a leading indicator.
#601 - How to Build a Sales Team That Manages Itself | Tara DiCristo-Schmitt · Aug 20, 2026
discovery
Cross-functional discovery prep
Prevent technical and product team members from prematurely pitching features by assigning specific conversational lanes in a pre-call document.
Discussing: Bringing SAs, CSMs, or product managers into a discovery call without them interrupting to pitch features.
“Here's the one or two goals of what we're trying to accomplish. Here's the line of questioning... Here's the specific people that I think in this situation will be relevant. And then we get on a call, we talk it through.”
MechanismSend a written readout to the deal team before the call. Outline exactly 1-2 goals for the meeting, the planned line of questioning, and specific role assignments. Explicitly map out scenarios: 'If the conversation goes in X direction, I will take it; if it goes Y direction, Johnny takes the question.' Review this live on a prep call.
OutcomeSpeaker's word; prevents product experts from jumping in with feature pitches and ruining discovery.
CounterpointMost reps just invite SAs to the calendar invite. This requires a written document and a live prep call to enforce conversational boundaries.
Why Great Sellers Hold the Line in Discovery with Stuart Gwynn · Aug 9, 2026
outbound
Morning Cold Call Block
Schedule your daily cold call block between 7 AM and 10 AM when energy is highest and prospects are settling in.
Discussing: Reps struggling with call reluctance and low conversion rates during afternoon dial sessions.
“We know with absolute certainty that the Sellers we work with connect with more prospects, set more meetings, and perform at a higher level in the mornings between 7am and 10am than they do in the afternoons.”
MechanismCommit to a daily cold call block first thing in the morning, specifically between 7:00 AM and 10:00 AM. Do this before checking email or attending internal meetings. The goal is to catch prospects while they are settling in with their coffee, before their day gets derailed by fires.
OutcomeSpeaker notes reps connect with more prospects and set more meetings based on 20 years of live call block data.
CounterpointIndustry studies claiming afternoons are better are flawed; they measure when procrastinating reps finally dial, not actual conversion efficacy.
Is There a Cold Calling Sweet Spot? (Money Monday) · Aug 17, 2026
team_and_org
Embedded forward deployed engineering for edge cases
Embed forward deployed engineers within the GTM team to build lightweight applications that solve deal-breaking edge cases without altering the core product.
Discussing: Losing enterprise deals because the core product meets 90% of requirements but fails on a specific edge case.
“If you don't have FDE moving to go to market and being able to handle edge case requirements, then that's the big miss... to be able to say yes to them is an incredible unlock.”
MechanismEmbed a Forward Deployed Engineering (FDE) function directly within the go-to-market team. When an enterprise prospect has a deal-breaking edge case, the FDE team uses AI to quickly build a complementary, lightweight application that bridges the gap. This allows reps to say yes to custom requirements without derailing the core engineering roadmap.
OutcomeMeaningful improvements in qualified-to-won conversion rates (speaker's word, not measured).
CounterpointSales usually has to beg core engineering for custom features; this gives GTM its own autonomous build capability for deal-closing workarounds.
The Unwritten Rules of CRO Survival | Rick Smolen, CRO @ ShipHero · Aug 23, 2026
team_and_org
The third-person lunch likability test
Bring a third coworker to a candidate lunch to evaluate how the candidate interacts with others.
Discussing: Evaluating the executive presence and likability of a candidate who performs flawlessly on video calls.
“Bring a third person to that lunch. See how they interact with somebody else. You will know in that hour. If that person can hang and be likable and other people want to speak to them, see how they treat the waiter.”
MechanismTake the candidate to an in-person lunch and bring a third coworker along. Observe how the candidate interacts with the third person and the waitstaff, rather than just focusing on you as the hiring manager. This reveals if they can naturally hold a room.
OutcomeReveals true executive presence within an hour
CounterpointCandidates can easily mirror a single hiring manager; adding a third person forces them to manage group dynamics.
How to Hire Better Salespeople Than Yourself and Lead Them to Win · Aug 20, 2026
team_and_org
The Hiring Committee Opt-In
Force the hiring committee to explicitly commit to the extra management burden a non-traditional candidate will require.
Discussing: Evaluating a talented candidate who has a questionable cultural fit or will require high maintenance to succeed.
“I said to the hiring team, I said, you keep in mind, I know we all love this person, but you are going to have to spend an extra amount of energy to make them feel at their very best. And are you guys up for that?”
MechanismBefore extending an offer, tell the hiring team: "I know we all love this person, but you are going to have to spend an extra amount of energy to make them feel at their very best. Are you guys up for that?" Force a verbal opt-in. If the group hesitates, pass.
OutcomeSpeaker notes he has seen groups opt out, saving the team from a bad rhythm fit.
CounterpointWe usually assume if a candidate is talented, the manager alone absorbs the onboarding burden. This distributes the commitment to the whole team.
The SNL Lesson on Talent and Fit with Lindsay Shookus · Aug 16, 2026
comp_and_quota
Conservative First-Hire AE Quotas
Cap initial AE quotas at $1.5M to attract top talent when transitioning from founder-led sales.
Discussing: Transitioning from founder-led sales to first AEs without a proven track record of rep attainment to sell candidates on.
“you have to start with this conservative like 1.5. And take the hit. If it ended up being too conservative, so what? You had reps that you paid a little bit more money to?”
MechanismSet the initial AE quota at a conservative $1.5M against a $400k OTE (a ~3.75x ratio) instead of pushing for a standard 5x-6x ratio. Accept the lower efficiency margin early on to get top talent in the door. Wait until you have a baseline of multiple reps hitting massive numbers before raising quotas to $3M+.
OutcomeSpeaker's advice to avoid candidates rejecting offers.
CounterpointFounders often try to set 6x ratios immediately based on their own success, which repels experienced talent.
Sales Millionaires Are Back… Wasn't AI Supposed to Destroy This Job?! · Aug 16, 2026
team_and_org
90-Day Win/Loss Anomaly Testing
Dedicate an analyst to find non-obvious win/loss anomalies, test them as measurable rep behaviors for 90 days, and roll out the winners.
Discussing: Sales leadership relies on reps working longer hours to hit numbers instead of finding systemic advantages.
“Her job was to rip through all of our numbers and every activity we did and find anomalies... every 90 days, I'd cross ones off the list that weren't working. And I'd fail those fast.”
MechanismHire a dedicated ops analyst to rip through all sales activity data to find anomalies between winning and losing deals. Turn these anomalies into measurable behaviors. Test these behaviors for 90 days. Kill the ones that fail, and mandate the successful ones across the entire team.
OutcomeMissed quota only 5 times in 25 years
CounterpointReps usually suggest new tactics that are just standard activities with more effort. This forces the use of data-backed anomalies that actually change engagement rules.
SPOTLIGHT: He Missed Quota 5 Times in 25 Years. Here's the System Behind That.| Mike Carpenter, CEO & Co-Founder @ Xfactor · Aug 20, 2026
comp_and_quota
Process-adjusted compensation modeling
Shift from high-commission to higher-base compensation models only after you have a documented sales process that guarantees rep success.
Discussing: Designing compensation plans for early sales hires when transitioning from founder-led sales.
“If you have a system to onboard them and ramp them up quickly... you can start increasing salary and reducing commissions... your cost of sales in that model is a lot higher than it would be if you pay a higher base salary.”
MechanismIf you lack a documented process, use a low-base/high-commission model to minimize risk. Once you build an onboarding system, flip the model: increase base salaries and reduce commission rates. Calculate your target cost of sale per million dollars sold (e.g., 5-20% based on margins) to set the new base.
OutcomeSignificantly lowers overall cost of sales.
CounterpointEntrepreneurs default to high-commission plans to limit risk, but this actually increases the long-term cost of sales once a repeatable process exists.
How to Build a Sales Process Before You Scale Your Team (Ask Jeb) · Aug 19, 2026
discovery
PE mandate AI prompt
Prompt AI to check a PE firm's stance on technology adoption to anticipate top-down build mandates.
Discussing: Pre-call research for a VC or PE-backed account where an in-house build objection is a risk.
“what is Vista Equity Partners posture towards their portcos adopting AI? ... Vista is about as aggressively pro-AI as any PE firm gets. Their posture is not encourage it... but it's a centralized top-down mandate”
MechanismBefore the call, prompt an AI tool: "What is [PE Firm]'s posture towards their portcos adopting [Technology]?" Use the output (e.g., specific platforms or mandates they enforce) to anticipate if you'll be fighting a centralized mandate rather than just a local preference.
Outcomespeaker's word, not measured
CounterpointMost reps research the target company; this researches the holding company's operational mandates to uncover hidden deal blockers.
#600 - Prospect Says “We’re Doing This In-House” You’ll Say… · Aug 18, 2026
discovery
Industry jargon AI prompt
Ask AI what influential CXOs are saying about building in-house to harvest insider jargon.
Discussing: Preparing to handle a build-vs-buy objection without sounding like a defensive vendor.
“the prompt are there CXOs... successful sharing successes or failures publicly What talking points can I glean from them to show that I have CXO voice... One that came up here is the CTO coined a term called vibe debt”
MechanismPrompt AI: "What are the influential voices in the [CXO] community saying about [building X in-house]?" Look for specific jargon in the output. On the call, quote those leaders and use their exact shorthand ("Have you heard of vibe debt?") to sound like an industry insider.
Outcomespeaker's word, not measured
CounterpointInstead of listing vendor-slanted cons, you use the exact shorthand their peers use to describe the pain.
#600 - Prospect Says “We’re Doing This In-House” You’ll Say… · Aug 18, 2026
enablement
Live buyer calls during deal review
When a rep guesses a buyer objection during a pipeline review, call the buyer together right then to find out the truth.
Discussing: Reps making up assumptions about buyer challenges or budget during deal reviews instead of asking the hard questions.
“I'll say, did the buyer say that or did you assume that?... And then I'll often say, you want to call them now? Let's call them together. We'll pick up the phone together.”
MechanismListen for vague assumptions like budget constraints. Ask: "Did the buyer say that or did you assume that?" When they admit they assumed, immediately say, "Let's call them now." Pick up the phone together and ask the buyer the question live to show the rep it is not scary.
OutcomeShows reps it is not scary to ask direct questions and stops them from guessing on future reviews.
CounterpointDo not just tell the rep to ask next time; model the behavior by dialing the prospect live on the review.
#601 - How to Build a Sales Team That Manages Itself | Tara DiCristo-Schmitt · Aug 20, 2026
ai_in_sales
LLM CRM Hallucination Guardrails
Require subject matter experts to map causal links and set probability thresholds before using LLMs to analyze CRM data.
Discussing: RevOps teams are plugging raw LLMs directly into CRM data to find revenue insights.
“If we can't back it up, with running tons of different sum checks about it with certainty, we'll drop it to a 60% probability rating, which means you need to really look at it and test it slowly.”
MechanismDo not let raw LLMs index internal communications or CRM data without a causal AI framework. Require human subject matter experts to map cause-and-effect relationships first. Implement probability ratings for AI outputs. If the system cannot verify an insight with certainty, force the output to display a 60% probability rating.
OutcomePrevents pivoting the business on hallucinated data
CounterpointRaw LLMs generate new code per query without memory, delivering hallucinated insights with absolute certainty. Causal mapping prevents false pivots.
SPOTLIGHT: He Missed Quota 5 Times in 25 Years. Here's the System Behind That.| Mike Carpenter, CEO & Co-Founder @ Xfactor · Aug 20, 2026
enablement
The Anti-Hero Ramp Conversation
Explicitly tell insecure new hires they do not need to carry the room so they stop overcompensating and focus on their core job.
Discussing: A new rep (especially a non-technical rep selling technical products) is overcompensating in meetings to prove their relevance.
“I was trying to insert myself into everything... And it was basically like, we don't need you to carry the room. We hired you to come do this. You'll get a chance to carry the room... but we don't need you to do that right now.”
MechanismPull the rep aside and explicitly remove the pressure to be the hero. Tell them: "We don't need you to carry the room. We hired you to come do this specific job. You'll get a chance to carry the room later, but we don't need you to do that right now."
OutcomeSpeaker notes it removed the pressure and allowed him to just focus on doing his specific job well.
CounterpointManagers usually try to build confidence by hyping the rep up. This builds confidence by lowering the immediate expectations.
The SNL Lesson on Talent and Fit with Lindsay Shookus · Aug 16, 2026
enablement
AI Roleplay for SDR Ramp
Use AI roleplay tools to simulate diverse buyer personas for new reps before their first live calls.
Discussing: Ramping new grads or SDRs who need call practice before hitting the phones.
“if you're a new grad joining a company, how much role playing practice would you have gotten before making your first hundred calls... compared to this thing that is like AI that can give you all the flavors”
MechanismReplace traditional 1:1 manager roleplay with an AI roleplay tool. Have new reps run practice cycles against the AI to experience multiple buyer personas and objections, allowing them to get high-volume practice before their first 100 live calls.
OutcomeFaster cycle time for reps (speaker's observation).
CounterpointTraditional manager roleplay is often one-dimensional and limited by the manager's schedule.
Sales Millionaires Are Back… Wasn't AI Supposed to Destroy This Job?! · Aug 16, 2026
outbound
Late Friday Afternoon Call Block
Run a cold call block on late Friday afternoons to bypass gatekeepers and reach high-level decision makers.
Discussing: Struggling to get past gatekeepers to reach high-level decision makers during standard mid-week business hours.
“I'm a huge fan of late Friday afternoon cold calling blocks because I found that high level decision makers are especially impressed with salespeople who are still grinding it out and working hard on Fridays.”
MechanismBlock out late Friday afternoons for cold calling executives. Gatekeepers have typically logged off early, and the decision makers who are still working are often in a better mood and respect the work ethic of a rep dialing at the end of the week.
OutcomeSpeaker's personal experience, not measured.
CounterpointMost reps abandon Friday afternoons because studies say it's the worst time, leaving an open lane to reach executives directly.
Is There a Cold Calling Sweet Spot? (Money Monday) · Aug 17, 2026
From the Conversations
3x Pipeline Virtual Patch Warming
SPOTLIGHT: He Missed Quota 5 Times in 25 Years. Here's the System Behind That.| Mike Carpenter, CEO & Co-Founder @ Xfactor
Aug 20, 2026 · 29m · 3 quotes pulled
▶ Listen“Once I got a patch to a 3x pipeline... I'd cut that patch and I'd start ranking which patches could take my new hires. That would move my ramp time from the theoretical six months... to 90 days.”
15-question asynchronous deal review
How to Hire Better Salespeople Than Yourself and Lead Them to Win
Aug 20, 2026 · 1h 6m · 3 quotes pulled
▶ Listen“It saves time. So a deal review is in an hour, an hour and a half, but it's actually only 30 minutes. And it's simple questions like, What's the close date of this deal and why that close date?”
30 Minutes to President's Club | No-Nonsense Sales
Days without leading indicator report
#601 - How to Build a Sales Team That Manages Itself | Tara DiCristo-Schmitt
Aug 20, 2026 · 32m · 2 quotes pulled
▶ Listen“If a rep has gone two days without a proposal, then the director would ping the manager... If a rep has gone five days... the director then sends a note to the manager and the rep.”
Sources
▶ ListenOutbound Squad
Meet Amanda Long, our newest Pipeline ConsultantIn this episode, Jason and Amanda Long from Outbound Squad, talk about the daily practice ritual that took her to the top of the leaderboard, how she made it impossible for her manager not to promote her, and how to nail your first front-line leadership role. Check out more free content and get help with outbound at https://outboundsquad.com.
▶ ListenTopline
SPOTLIGHT: He Missed Quota 5 Times in 25 Years. Here's the System Behind That.| Mike Carpenter, CEO & Co-Founder @ Xfactor<p>Mike Carpenter — CEO of Xfactor.io, former President of Global Sales at CrowdStrike — didn't win VP of the Year seven out of eight times by outworking everyone. He did it by finding cheat codes in the data everyone else was ignoring.</p> <p>In this episode, he walks through the X-Factor methodology: how he staffed ops teams that were abnormally large by industry standards, how he cut rep ramp time from 18 months to 90 days by warming territories before a new hire ever showed up, and why he thinks most companies running AI on their CRM are getting confident, wrong answers and won't know it until the numbers drop.</p> <p>Mike also shared:<br /> - Why working harder isn't the same as finding an X-Factor<br /> - How he used data to uncover the hidden patterns that drive revenue<br /> - Why static operating plans break down as businesses scale<br /> - How he cut sales ramp time by warming territories before reps entered them<br /> - Why causal AI matters more than simply putting an LLM on your data<br /> - What it takes to build AI that leaders can actually trust</p> <p>Chapters</p> <p>00:00 Intro<br /> 00:33 Meet Mike Carpenter and Xfactor<br /> 04:11 The "X-Factor" mindset that drove 25 years of sales success<br /> 08:18 Why working harder isn't a sustainable competitive advantage<br /> 10:56 The planning problem that inspired Xfactor<br /> 14:57 How AI uncovers hidden revenue opportunities<br /> 18:20 Why MQLs are the wrong metric to optimize<br /> 23:12 The biggest mistake companies make with AI today<br /> 25:52 Where to find Mike and Xfactor<br /> Try Xfactor: xfactor.io/</p>
▶ ListenRevenue Builders
How to Hire Better Salespeople Than Yourself and Lead Them to WinIn this conversation, Michelle Bove breaks down the real mechanics of winning: why likability is underrated, how to hire people better than you, why skip levels work when done transparently, and what it actually costs to prove yourself as a young female leader in cybersecurity.
- ▶ Listen
Revenue Builders
The SNL Lesson on Talent and Fit with Lindsay ShookusIn this Revenue Builders segment, Lindsay Shookus shares lessons from Saturday Night Live on cultural fit, team buy-in, trust, and performance under pressure.
- ▶ Listen
Topline
Sales Millionaires Are Back… Wasn't AI Supposed to Destroy This Job?!<p>Enterprise account executives are now signing for $200,000 salaries, $200,000 variable comp plans, and up to half a million dollars in equity at sign-on. Meanwhile, offer acceptance at the top AI companies sits at 45% and half of the 38,000 startup sales reps in San Francisco and New York have taken a new job in the last two years. In this episode, Sam Jacobs, AJ Bruno, and Asad Zaman go hosts-only on why the sales talent market broke, what QuotaPath's compensation data across more than 1,400 companies says about quota attainment splitting into a barbell, and why Paul Graham calling go-to-market bogus says more about Silicon Valley's blind spot than it does about sales. Plus, where young sellers still get their start, whether a CRO can be great without ever carrying a bag, why go-to-market cannot rescue a company that has lost product-market fit, and what HubSpot's 20% stock drop signals for every SaaS business trying to make the AI transition.</p> <p>Key Takeaways:</p> <p>- The AI buildout has drained the two talent pools it depends on, and compensation is repricing in real time. As Asad Zaman, CEO of STA, described the enterprise AE market: "Enterprise account executives now get paid $200,000 salaries, $200,000 variable comp plans, up to half a million dollars in equity at sign-on. That used to be $150,000 to $175,000 at the top end, just like a year and a bit ago." With 38,000 startup software sellers in San Francisco and New York and a quarter of them changing jobs in the last twelve months, the constraint on AI companies hitting escape velocity is no longer capital, it is people.</p> <p>- The jobs data cuts against the automation narrative. Sam Jacobs, CEO of Pavilion, pointed to the Philippines outsourcing sector, 8% of that country's GDP, where employment in IT and business outsourcing is up 20% to 1.9 million workers and industry revenue is up 30% to $42 billion since the launch of ChatGPT: "I just think, you know, it's Jevons' paradox. It is what happens with every new piece of technology. Everybody thinks the technology is going to wipe everybody out, and instead the economy adapts." Companies are leaner per dollar of revenue and still cannot hire fast enough.</p> <p>- Quota attainment is no longer distributed the way comp plans assume. QuotaPath's first-half numbers put 58% of AEs on track against annual quota versus 55% a year ago, but as AJ Bruno, CEO of QuotaPath, explained, the shape underneath moved: "the standard deviation is way higher this year. Meaning that the winners are going to be winning more … So it's more like a barbell than it is a bell curve." At some AI companies two reps out of ten are closing half the entire number, which breaks the capacity math most sales leaders use to set targets.</p> <p>- For individual sellers, the window matters more than the title. Asad Zaman's advice to reps weighing a step up into leadership: "this is the moment where you can make millions of dollars right now … So don't make silly choices … Become a leader later. Go make money right now." He now benchmarks offers on whether 300% of plan clears a million dollars, and warns that private equity portfolio companies that never gave equity to individual contributors are losing these candidates outright.</p> <p>Connect with the Hosts:</p> <p>Host: Sam Jacobs, CEO at Pavilion - https://www.linkedin.com/in/samfjacobs/<br /> Host: AJ Bruno, CEO at QuotaPath - https://www.linkedin.com/in/ajbruno3/<br /> Host: Asad Zaman, CEO at STA - https://www.linkedin.com/in/azaman1/</p> <p>Topline is more than a YouTube Channel:</p> <p>Subscribe to Topline Newsletter: https://toplinemedia.substack.com/<br /> Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech: https://www.joinpavilion.com/topline-podcast<br /> Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast: https://www.joinpavilion.com/topline-slack</p> <p>Chapters: <br /> 00:00 Three Hosts, Three Topics<br /> 02:19 The Talent Market Has Gone Crazy<br /> 05:42 $200K Base, $200K Variable<br /> 09:00 AI Was Supposed To Kill Sales<br /> 15:16 Go Make A Million Right Now<br /> 16:53 Where Young Sellers Get Their Start<br /> 23:20 Build A University Inside The Company<br /> 31:58 Paul Graham Versus Go-To-Market<br /> 36:22 Why YC Misses Enterprise Software<br /> 40:55 Can A Non-Seller Be A Great CRO?<br /> 44:42 GTM Cannot Fix Product-Market Fit<br /> 49:30 One To Ten To A Hundred<br /> 53:38 Quota Attainment Is A Barbell<br /> 1:02:41 The HubSpot Nightmare<br /> 1:06:05 Falling Back In Love With The Business</p>
▶ ListenMental Selling: The Sales Performance Podcast
EP 138 Building Momentum in Complex Sales with Mike O’Brien and Tom Whelan, Ph.D<p>Why do promising complex sales deals suddenly lose momentum and go nowhere?</p><p>In this first of a two-part series adapted from a webinar, <a href="https://www.linkedin.com/in/execleadership/">Mike O’Brien</a>, Executive Vice President of Sales at <a href="https://www.integritysolutions.com/">Integrity Solutions</a>, and <a href="https://www.linkedin.com/in/whelant/">Tom Whelan, Ph.D.</a>, Director of Corporate Research at <a href="https://trainingindustry.com/">Training Industry, Inc.</a>, examine the common breakdowns that cause promising sales opportunities to stall.</p><p>They discuss why sellers can mistake a responsive, enthusiastic contact for someone with real decision making influence, and how that mistake can leave them restarting the sales process when the right stakeholders finally enter the conversation. Mike and Tom also explore why leading with product features can make even a polished sales conversation irrelevant to the buyer, and why sellers need to connect capabilities directly to business problems and desired outcomes. Finally, they unpack one of the quietest threats to a complex sale: losing momentum between meetings when next steps and commitments are unclear.</p><p><strong>In this episode, you’ll learn:</strong></p><ul><li><strong>Finding the Right Decision Makers:</strong> Why a responsive, enthusiastic contact may not have real influence, and how relying on one champion can stall a deal.</li><li><strong>Selling Outcomes Over Features:</strong> How connecting solutions to real business problems makes sales conversations more relevant to buyers.</li><li><strong>Maintaining Sales Momentum:</strong> Why clear next steps and consistent engagement keep complex deals from quietly stalling.</li><li><strong>Navigating Buyer Complexity:</strong> How internal alignment, procurement, and ROI questions can extend the buying process.</li><li><strong>Building the Right Sales Skills:</strong> Why sellers need deliberate practice to build the skills required to manage complex opportunities.<p></p></li></ul><p><strong>Resources</strong>:</p><ul><li>Mike O'Brien’s LinkedIn: <a href="https://www.linkedin.com/in/execleadership/">https://www.linkedin.com/in/execleadership/</a> </li><li>Learn more about Integrity Solutions: <a href="https://www.integritysolutions.com/">https://www.integritysolutions.com/</a> </li><li>Tom Whelan, Ph.D.’s LinkedIn: <a href="https://www.linkedin.com/in/whelant/">https://www.linkedin.com/in/whelant/</a> </li><li>Learn more about Training Industry, Inc.: <a href="https://trainingindustry.com/">https://trainingindustry.com/</a> <p></p></li></ul><p><strong>Jump into the conversation:</strong><br>(00:00) Meet Mike O’Brien and Dr. Tom Whelan</p><p>(01:58) Five common breakdowns in complex sales</p><p>(05:10) Why sellers connect with the wrong people</p><p>(08:22) What research reveals about stalled deals</p><p>(12:02) Getting access to the right decision makers</p><p>(14:55) Why buyers care about outcomes over features</p><p>(17:32) The proof and evidence buyers actually want</p><p>(19:49) How sales momentum gets lost between meetings</p><p>(22:20) Navigating longer buying cycles and buyer barriers</p>
▶ ListenThe Best of the Brutal Truth about B2B Sales & Selling - The show focuses on the enterprise Sales Process
HOW TO DEVELOP THE #1 DIFFERENTIATOR OF GREAT SALESPEOPLE<p>Here is a FAQ Video on the Courses: <a href= "https://youtu.be/0F7imrzjXWs">https://youtu.be/0F7imrzjXWs</a></p> <p>Here is a deep dive into which course is best for you: <a href= "https://youtu.be/JM_jgS8M-iU">https://youtu.be/JM_jgS8M-iU</a></p> <p><a href= "http://www.b2brevenue.com/">https://www.b2bRevenue.com</a> - Get Your Free E-Book on How Companies make Decisions.</p> <p>FAQ:</p> <ul> <li>1 YEAR ACCESS, PAY MONTHLY OR ANNUALLY NOT A SUBSCRIPTION</li> <li>OFFICE HOURS EVERY<span class= "Apple-converted-space"> </span> OTHER WEEK VIA ZOOM. 1 HOUR GROUP Q&A.</li> <li>UNLIMITED 1-ON-1'S<span class= "Apple-converted-space"> </span> ARE FREE AS LONG AS THEY CAN BE SHARED IN THE COURSE. 1-ON-1 ARE</li> <li>FULL ACCESS ON DAY ONE - NOTHING IS GATED OR TIME RELEASED.</li> <li>ALL CONTENT IS VIDEO BASED AND SELF PACED</li> <li>I RECOMMEND TAKE COURSE ONCE WITHOUT NOTES OR APPLYING IT SO YOU UNDERSTAND THE BIG PICTURE FIRST. THEN TAKE AND APPLY IT STEP BY STEP.</li> <li>YOU START WHEN YOU WANT AND GO AS FAST OR SLOW AS NEEDED.</li> </ul> <p> </p> <p>Email me additional questions: <a href= "mailto:[email protected]">[email protected]</a></p> <p> </p> <p> </p> <p>— SAMPLE EMAIL TO EXPENSE THE COURSE</p> <p>MGR,</p> <p> </p> <p>I have been listening to the brutal truth about sales podcast for X months and it speaks to the issues we face.</p> <p> </p> <p>They currently offer a course that includes video instruction, group Q&A and One-on-One coaching. I'm committed to my own personal development and</p> <p>would like your help in expensing the course.</p> <p> </p> <p>It would pay for itself if I closed only one new deal of $X value.</p> <p> </p> <p>Please let me know by Friday if I can move forward with this 1 year course.</p> <p> </p> <p>Thanks,</p> <p>ME</p> <p>Here are some student interviews from the courses:<span class= "Apple-converted-space"> </span></p> <p><span class="Apple-converted-space"> </span></p> <p> </p> <p>————————————————————————————————————</p> <p>Audible 30 day Free Trial:</p> <p><a href= "http://www.audibletrial.com/BrutalTruth">http://www.audibletrial.com/BrutalTruth</a></p> <p> </p>
▶ ListenSales Gravy: Jeb Blount
How to Build a Sales Process Before You Scale Your Team (Ask Jeb)<p><strong>If you are still the only person selling at your company, the worst thing you can do is start hiring before you have a documented process for people to follow. </strong></p><p>In this Ask Jeb, Jeb Blount answers two questions on scaling a sales team the right way, one from Yemi, who is building his first team from scratch, and one from Ramesh, who is trying to figure out how to budget for sales pay and support in a B2B healthcare business.</p><p>Jeb walks through the three stages every founder hits when they try to grow a team: the solo seller, the roller coaster, and the building phase, including the $45,000 mistake he made this year by skipping straight to hiring without a process in place. He also breaks down how to think about compensation, why a lower base and higher commission actually raises your cost of sale, and how to calculate what a new sale should cost you as your business grows.</p><p>What You'll Learn:</p><ul><li>Why documenting your sales process before you scale protects you from expensive turnover</li><li>The three phases every founder cycles through when growing a sales team, and which is the most dangerous one</li><li>Why you have to block time outside of peak selling hours to build out your system instead of waiting until you are desperate</li><li>How bringing in a sales leader to document the process, separate from the founder's own instincts, speeds up the process</li><li>How to calculate cost of sale in and use it to guide your compensation strategy</li><li>Why a low base salary and high commission structure can actually lower your true cost of sale</li><li>Why your margin should determine how much you can afford to pay in commission</li><li>How support staff and infrastructure spending shift as a company grows past its early scrappy stage</li></ul><p>-</p><p><a href="http://salesgravy.com/ask" rel="nofollow">Submit</a> your question: <a href="http://salesgravy.com/ask" rel="nofollow">salesgravy.com/ask</a></p><p><a href="https://a.co/d/00b8wZYQ" rel="nofollow">Purchase</a> Jeb Blount's new book: <a href="https://a.co/d/00b8wZYQ" rel="nofollow">90 Days to Level Up Your Sales Skills</a></p><p>Grab your tickets for <a href="https://outboundconference.com/" rel="nofollow">OutBound Conference</a></p><p><a href="https://www.linkedin.com/in/jebblounthttps://www.linkedin.com/in/jebblount" rel="nofollow">Follow</a> Jeb Blount on <a href="https://www.linkedin.com/in/jebblount" rel="nofollow">LinkedIn</a></p><br/><br/>Our Sponsors:<br/>* Go to https://OmahaSteaks.com and use promo code BEEF at checkout for $35 off. Minimum purchase may apply.<br/><br/><br/>Advertising Inquiries: <a href='https://redcircle.com/brands'>https://redcircle.com/brands</a><br/><br/>Privacy & Opt-Out: <a href='https://redcircle.com/privacy'>https://redcircle.com/privacy</a>
▶ Listen30 Minutes to President's Club | No-Nonsense Sales
#600 - Prospect Says “We’re Doing This In-House” You’ll Say…Jen Allen-Knuth and Nick Cegelski break down exactly what to do when a prospect tells you, “We’re going to build this in-house.” Instead of immediately defending your solution, you’ll learn how to build trust, uncover the beliefs behind their decision, and guide them toward seeing the risks of DIY for themselves. You’ll learn to: 🔎 Seek to understand before you sell: Uncover why they want to build, how far along they are, who’s involved, and what they’re already worried about before trying to change their mind. 🤝 Help them succeed with DIY first: Lower their defenses by advising them on resources, technology, success metrics, and even peer introductions before you ever pitch against the in-house option. ⚖️ Make build vs. buy impossible to ignore: Surface the hidden costs, maintenance, employee adoption, and cross-functional buy-in of building internally, then contrast those pitfalls directly with what your solution handles for them. -- You’re one step closer to President’s Club!: 💼 Selling to the C-Suite Course: https://hubs.li/Q04thbhX0 🏋 30MPC Training: https://www.30mpc.com/course/team-training 🛠 Weekly Newsletter: https://hubs.li/Q02NJQ8p0 📚 Things you can steal and use today: https://linktr.ee/30mpc_youtube
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30 Minutes to President's Club | No-Nonsense Sales
#601 - How to Build a Sales Team That Manages Itself | Tara DiCristo-SchmittTara DiCristo-Schmitt breaks down the tactical sales leadership systems she uses to build predictable pipeline, coach reps, and create a culture of accountability. Learn how to inspect rep calendars, run better pipeline reviews, and catch performance problems before they hit quota. 📅 Eliminate calendar white space: Review reps’ calendars weekly and build two weeks ahead with net-new meetings, referrals, target accounts, and prospecting blocks so cancellations don't kill pipeline. 📊 Track “Days Without” key activities: Identify the leading indicator that drives revenue, then track how many days reps go without it to trigger coaching before performance slips. 🔍 Make pipeline reviews teach discovery: Ask the same qualification questions every week so reps learn exactly what they need to uncover from buyers and stop filling gaps with assumptions. You're one step closer to President's Club! 📱 Connect with Tara on LinkedIn! 🏋 30MPC Training 🛠 Weekly Tactical Breakdowns 📚 Things you can steal and use today
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Revenue Builders
Why Great Sellers Hold the Line in Discovery with Stuart GwynnIn this Revenue Builders minisode, Stuart Gwynn of MongoDB explains why the best sellers slow down in discovery, hold the line with the customer, and use disciplined qualification to determine whether a problem is real, urgent, and worth solving.
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Sales Gravy: Jeb Blount
Is There a Cold Calling Sweet Spot? (Money Monday)<p>It’s the never-ending task that most people push off as long as they can. But knowing the best day of the week, even the best time of day to make cold calls, is a sales skill itself. Jeb Blount tackles one of the most common questions salespeople ask him and discusses the oversaturation of internet studies that all contradict each other on the best times to pick up the phone. If the smartest teams in the business can’t agree on a set time, is there really even a best time to cold call? The trainers at Sales Gravy, backed by years of experience and measurable data, all overwhelmingly agree that there is.</p><p><br></p><p>📖 Purchase Jeb Blount's book, <a href="https://a.co/d/0hneYtLq" rel="nofollow">90 Days to Level Up Your Sales Skills</a></p><p>🎲 Learn more about the <a href="https://outboundconference.com/" rel="nofollow">OutBound Conference</a></p><p>🖋️ Download our <a href="https://salesgravy.com/resource/dial-sheet/" rel="nofollow">Free Fanatical Prospecting Call Tracker</a></p><p>🔗 <a href="https://www.linkedin.com/company/salesgravy/" rel="nofollow">Follow us on LinkedIn!</a></p><br/><br/>Our Sponsors:<br/>* Go to https://OmahaSteaks.com and use promo code BEEF at checkout for $35 off. Minimum purchase may apply.<br/><br/><br/>Advertising Inquiries: <a href='https://redcircle.com/brands'>https://redcircle.com/brands</a><br/><br/>Privacy & Opt-Out: <a href='https://redcircle.com/privacy'>https://redcircle.com/privacy</a>
- ▶ Listen
Topline
The Unwritten Rules of CRO Survival | Rick Smolen, CRO @ ShipHero<p>The Unwritten Rules of CRO Survival | Rick Smolen, CRO @ ShipHero</p> <p>Rick Smolen, CRO of ShipHero and sales advisor to Riverwood Capital's portfolio of more than 2 dozen enterprise software companies, joins Sam Jacobs, AJ Bruno, and Asad Zaman to argue that AI is leverage rather than a shortcut. Topics include why AI note-takers quietly degrade seller performance, why ShipHero has not raised a single quota despite real AI investment, and why the leading AI companies keep hiring classic enterprise CROs. Plus Rick's scorecard for judging revenue leadership beyond the number, an honest conversation about getting fired, and a bull case for HubSpot. In short... big episode!</p> <p>Key Takeaways:</p> <p>- AI widens the gap between the best and worst sellers instead of lifting everyone, and Rick Smolen, CRO at ShipHero, frames it in financial terms: "It's like debt... debt is leverage. It can make performance exceptionally good, or it can bankrupt you." His prediction is that the strongest performers get 10x better while the weakest become "unmistakable and hard to hide."<br /> - Outsourcing note-taking to an AI tool costs sellers the exact signal that closes enterprise deals. As Rick put it: "the computer can't capture the tone, can't capture the nuance, can't capture the content." His warning to any rep who treats it as time saved: "when a seller is going to say, oh cool, I don't have to do note-taking anymore, like their performance is going to go backwards."<br /> - The 3-to-5x rep productivity story does not survive contact with an enterprise sales cycle. Despite meaningful AI investment and measurable conversion-rate gains, Rick reports that at ShipHero "we have not raised quotas on anybody on the team," adding that "I don't believe that if I was to double somebody's quota that I give them any chance to be successful."<br /> - The AI-native companies scaling fastest are staffing go-to-market with the most traditional enterprise leaders available. Asad Zaman, CEO at STA, walks through the CRO hires at OpenAI, Cursor, Factory, and Anthropic and lands on the pattern: "we're back to like, let's just hire John McMahon's disciples and let them run at the market."</p> <p>Connect with the Hosts & Guests:</p> <p>Host: Sam Jacobs, CEO at Pavilion - https://www.linkedin.com/in/samfjacobs/<br /> Host: AJ Bruno, CEO at QuotaPath - https://www.linkedin.com/in/ajbruno3/<br /> Host: Asad Zaman, CEO at STA - https://www.linkedin.com/in/azaman1/<br /> Guest: Rick Smolen, CRO at ShipHero - https://www.linkedin.com/in/ricksmolen/</p> <p>Topline is more than a YouTube Channel:</p> <p>Subscribe to Topline Newsletter: https://toplinemedia.substack.com/<br /> Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech: https://www.joinpavilion.com/topline-podcast<br /> Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast: <a href= "https://www.joinpavilion.com/topline-slack">https://www.joinpavilion.com/topline-slack</a></p> <p>Chapters: <br /> 00:00 Introducing Rick Smolen<br /> 02:37 AI Is Not Good Or Bad<br /> 05:19 The AI Slop Email Mystery<br /> 08:25 AI Note-Takers And Lost Nuance<br /> 12:01 The Best Get Better, The Rest Worse<br /> 15:24 The Soft Part Of Enterprise Sales<br /> 18:24 Can Reps Be 5x More Productive?<br /> 23:09 Have Quotas Gone Up At ShipHero?<br /> 26:48 Why AI Firms Hire Classic CROs<br /> 30:48 What Is Driving Pipeline Now<br /> 49:37 Leadership In A Confused World<br /> 56:44 Should A CRO Jump Ship?<br /> 59:35 Have A Plan, Not Excuses<br /> 1:06:08 Bulls And Bears: HubSpot<br /> 1:09:32 Vibe-Coded Demos And FDE Teams</p>
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