May 31: The event outbound pivot driving 45% conversion
Good morning. Operators are abandoning generic outreach in favor of highly curated, data-backed executive engagements.
Scale Venture Partners' Craig Rosenberg completely abandoned discovery-call cold outreach, pivoting his entire outbound motion to exclusive data-review events. The shift drove a 45% to 50% conversion rate to advisory meetings, proving that executives will still trade calendar blocks for proprietary insights they cannot find anywhere else.
Today's Sales Plays (16)
Tactical moves operators are running right now, with verbatim source.
outbound
Data-driven event outbound
Stop asking for discovery calls in cold outreach and instead invite prospects to an exclusive event reviewing proprietary data.
Discussing: High CAC and low conversion on standard cold outbound asking for introductory meetings.
“Our outbound back then was only to our events. We didn't try to get a meeting. And it worked amazing because they would get... you get the meetings at the events.”
MechanismMine your product for unique data that competitors cannot emulate. Run outbound campaigns that only ask the prospect to attend an exclusive event to review these specific findings. Do not ask for a meeting in the cold touch. Instead, secure the 1:1 meetings in person at the event.
Outcome45-50% conversion rate to advisory
CounterpointPitching an event attendance rather than a discovery call lowers the friction of the initial cold touch.
Build The World Class Team That Anthropic Won't Steal | Craig Rosenberg, CPO @Scale Venture Partners · May 31, 2026
discovery
The 29-to-1 CFO meeting ratio
Spend 29 minutes of a 30-minute meeting letting the CFO vent, then pitch the benefit in the final minute.
Discussing: Running a 30-minute discovery call with a CFO who is fatigued by feature-heavy sales pitches.
“29 minutes in, I've just been like talking about all my problems... in one minute, she identifies the benefits... I'm like, more information. I was like, yeah, I need that.”
MechanismLet the CFO talk about their problems and challenges for 29 minutes. In the final minute, state the specific business benefit that solves their stated problem, mention your product does this, and casually offer to send more information if they want it.
OutcomeSpeaker's word: CFOs will actively ask to extend the meeting.
CounterpointMost reps rush to pitch features to fill the time; withholding the pitch until the final minute creates pull.
THE SECRETS TO WORKING WITH THE CFO TO GET DEALS DONE · May 27, 2026
icp_and_segment
Buying-Behavior TAM Segmentation
Segment your TAM by buying mechanism—managed contracts vs. unmanaged individual buyers—and deploy different teams and CAC expectations for each.
Discussing: Sizing and attacking a massive TAM where buyers have vastly different purchasing behaviors and unit economics.
“We slice the TAM between what we call is the managed side... and then there's a huge part of the time that we call the unmanaged business... we need different teams to go after those opportunities.”
MechanismSplit the TAM into 'managed' (enterprise buyers signing centralized contracts) and 'unmanaged' (end-users buying individually). Assign dedicated teams to each segment. Set different ROI, CAC payback, and retention expectations based on the segment's specific margin profile, rather than applying a blended average.
Outcome50% YoY growth in new signed enterprise bookings.
CounterpointInstead of just slicing TAM by company size (SMB/Mid-Market/Enterprise), slice it by how the purchase is actually made (centralized contract vs. decentralized individual spend).
Navan CFO Aurélien Nolf on Resource Allocation, IR, and AI in Finance · May 28, 2026
outbound
Peer-matched social proof
Drop mega-brand logos in cold emails and instead name a peer company, a specific champion, and a hard metric.
Discussing: Writing the social proof line in a cold email to a VP or C-level buyer.
“You want to avoid sharing the name of a company that is very unrelated to what the buyer does... The company needs to be similar in size, similar industry, if possible.”
MechanismStop citing massive, unrelated companies (Google, Amazon) just for logo recognition. Instead, name a customer of similar size and industry. Include the specific champion's name ("Siobhan at Shopify") and cite a hard, executive-level metric ("40% lift in ops created" or "$120M in pipeline").
Outcome35-40% increase in reply rates
CounterpointReps default to the most famous logos in their CRM, which alienates buyers who don't share that mega-brand's resources.
#577 - Why Your AI Cold Emails Are Failing (And How to Fix Them) | Jason Bay · May 28, 2026
team_and_org
Marketing Influence Cohort Analysis
Prove marketing ROI to the CFO by comparing win rates and deal sizes of marketing-engaged versus sales-only opportunities.
Discussing: Defending marketing spend to a CFO who believes sales would have closed the deals anyway.
“being able to compare win rate between those cohorts... our win rate is actually 45% versus 30% when marketing doesn't. Our average deal size is 10K higher. Our sales cycle length is like half.”
MechanismSegment your pipeline into two distinct cohorts: opportunities that had a marketing touchpoint before creation, and those that didn't. Compare the win rate, sales cycle length, and average deal size between the two groups. Use the non-marketing cohort as a control group to prove that marketing engagement actually accelerates velocity and increases ACV.
Outcome45% win rate vs 30%, $10K higher ACV, 50% shorter sales cycle
CounterpointInstead of claiming multi-touch attribution on every deal, isolate the non-marketing cohort as a control group to prove baseline win rates.
The Pressure B2B Marketing Leaders Don’t Talk About Enough · May 28, 2026
discovery
The So-What Champion Test
Test a potential champion by asking them to quantify the financial impact of their pain and offering to build the business case together.
Discussing: Trying to determine if a contact is a true champion willing to fight for budget or just a coach.
“If they don't have it, they're willing to introduce you to the EB. And maybe it's, hey, let's go have a meeting with my boss because they had that answer. And together we can document this.”
MechanismAsk the contact 'So what?' regarding their stated pain. Explain that to get approval, you both need to document the money saved or earned. Ask them to partner on building this business case. If they lack the data, ask them to introduce you to the economic buyer to get it.
OutcomeReveals whether the contact has actual power and influence or is just a coach.
CounterpointReps often accept surface-level pain to check a qualification box; this forces the contact to prove their access and willingness to spend political capital.
The Discipline Behind Nine-Figure Deals with Stuart Gwynn · May 28, 2026
team_and_org
Tenured Rep Deal Strategy 1:1
Retain top-performing enterprise reps by replacing standard metrics reviews with role-playing sessions for crucial customer conversations.
Discussing: Managing a highly tenured, top-performing enterprise rep who doesn't need basic pipeline micromanagement.
“We don't need to pull up M4S, metrics versus S, and go through how many discovery meetings I have... Let's instead spend time where you can actually add the most value and drive the most impact.”
MechanismDrop standard operating rhythm metrics (meeting counts, pipeline generation stats) from the 1:1 agenda. Repurpose the time entirely for role-playing crucial customer conversations or navigating complex internal deal politics. Treat them as a peer for strategy while holding them to the same revenue outcomes.
OutcomeSpeaker cites this management style as a primary reason he remains at the company.
CounterpointManagers often force senior reps through the same pipeline inspection as first-year reps, which degrades trust and wastes time.
The Discipline Behind Nine-Figure Deals with Stuart Gwynn · May 28, 2026
closing
Late-stage intent presentation pivot
Monitor account-level intent for hidden buyers during the trial stage and rebuild your final presentation around their specific search spikes.
Discussing: Mid-to-late stage deals where new, unmapped stakeholders enter the buying committee during demos or trials.
“the CEO was in the database and started bursting on intent. And we saw he searched on cashflow 35 times... build this entire line of presentation around that. And they ended up winning.”
MechanismTrack account-level intent signals for new stakeholders bursting activity on your website. When an unmapped executive spikes on a specific search term (e.g., searching 'cashflow' 35 times), ask your champions why that topic matters to them. Rebuild your final presentation entirely around that specific business problem.
OutcomeWon a deal after 10 straight losses to a competitor
CounterpointReps usually stop prospecting the account once an opportunity is opened; this treats the trial stage as a new prospecting window.
What AI Knows About Your Buyer with Scott Gillum · May 25, 2026
icp_and_segment
The hell no disqualification list
Document the specific attributes of your worst customers and give reps a 'hell no' list of accounts to disqualify immediately.
Discussing: Reps are closing deals that turn into high-churn, high-maintenance nightmare accounts for the post-sales team.
“The hell no list are the attributes of what makes a potential customer a bad one. You might still close it... But if you know that customer is going to be a nightmare long-term... you don't want to get into bed with them.”
MechanismIdentify the traits of your most difficult customers (e.g., requires custom software every six months, berates the team). Compile these into a 'hell no' list. Instruct reps to immediately disqualify any prospect exhibiting these traits during discovery, even if the prospect is willing to buy.
Outcomespeaker's word, not measured
CounterpointSales teams usually focus entirely on who to target; explicitly defining who to reject prevents reps from wasting time on toxic revenue.
Sales Is No Longer A Numbers Game | Tom Stearns & Peter Cleary - 2006 · May 29, 2026
closing
Week-one Q4 closing timeline
Pull custom-paper deals forward to the first week of Q4 to avoid year-end audit scrutiny killing the deal.
Discussing: Closing a large deal on customer paper with custom terms in the final period of the fiscal year.
“I got to close the books... man, this is just in the gray area... I got to get this booked and bagged in week one of period 12 so all the dust can settle.”
MechanismDo not bring custom-paper deals to your CFO in the final week of Q4. Year-end audit rules eliminate the flexibility that exists in Q1-Q3. Instead, accelerate the timeline to get the deal booked in week one of period 12 so the finance team has time to process non-standard terms.
OutcomeSpeaker's word: prevents the deal from being pushed to Q1.
CounterpointReps often push for end-of-quarter closes, but CFOs have zero flexibility for non-standard terms in the final weeks of Q4 due to audit rules.
THE SECRETS TO WORKING WITH THE CFO TO GET DEALS DONE · May 27, 2026
forecasting
7-Stage Pipeline Reset
Strip the pipeline to seven stages and block 30 minutes daily to execute documented next steps for existing deals.
Discussing: Sub-$5M revenue businesses losing track of active deals and assuming they need more top-of-funnel volume.
“Prospect, meeting booked, qualified, proposal sent, decision pending, closed won, closed lost, that's all you need... you must be able to answer the question, what needs to happen for this prospect to move to the next stage”
MechanismImplement a strict 7-stage pipeline: Prospect, meeting booked, qualified, proposal sent, decision pending, closed won, closed lost. For every prospect, document the exact action required to advance them. Then, block 30 minutes daily dedicated solely to executing those specific next-step tasks.
OutcomeGrew a wealth management consultant from $1.2M to $2.6M in 12 months without net-new prospecting.
CounterpointInstead of adding top-of-funnel volume, freeze net-new prospecting until every existing deal has a documented, binary next step.
The Only Sales System Small Businesses Need Under $5M Year · May 25, 2026
outbound
The blind date meeting offer
Instead of asking for time, pitch the AE's specific expertise and the insights the prospect will gain from the meeting.
Discussing: SDR trying to book a meeting for an AE via cold outreach.
“If you're an SDR setting a meeting for an account executive, I want you to hype them up, talk about their experience, the companies they're working with, what they could expect in that meeting.”
MechanismStop asking for 15 minutes to "learn about their goals." Instead, sell the AE. Hype up the AE's specific industry experience, name the types of companies they are currently consulting with, and explicitly state the insights or transformations the prospect will walk away with from the meeting.
Outcome28% increase in reply rate
CounterpointMost SDRs pitch the product or the company; pitching the AE's expertise turns the discovery call into a valuable consultation.
#577 - Why Your AI Cold Emails Are Failing (And How to Fix Them) | Jason Bay · May 28, 2026
comp_and_quota
Asymmetric commission for complex products
Spike the commission rate on complex products to offset the longer sales cycle risk, without touching the payout for transactional deals.
Discussing: Reps default to selling low-ACV transactional products because complex offerings take too much time and carry higher risk.
“If you disincentivize the deals that are your bread and butter... you'll get less of it. If you give them a larger reward for closing the more complex, more profitable deals, then your argument for why they should be working on those deals gains more validity.”
MechanismCreate an extreme risk/reward imbalance by drastically increasing the commission rate on the complex product (e.g., ten times higher) without reducing the payout on the transactional deals. Pair this with pre-built prospecting lists so reps do not have to source the harder targets themselves.
OutcomeSpeaker pays trainers 10 times higher commission to ensure they sell complex deals despite their primary roles.
CounterpointMost leaders try to force complex sales by cutting commissions on easy products, which just kills baseline revenue.
Jeb Blount on Sales Leadership: Keeping Your Team Focused on the Right Opportunities (Ask Jeb) · May 27, 2026
team_and_org
70-20-10 Resource Allocation
Allocate 70% of resources to the core business, 20% to adjacent safe bets, and 10% to high-risk moonshots to prevent organizational bloat.
Discussing: Allocating headcount and budget across competing initiatives without over-indexing on unproven bets.
“What is very, very typical, is companies doing 100, 100, 100. They just go after everything... you would typically allocate 70% of your resources, your core business.”
MechanismForce rank all investments into three buckets: 70% to the core business with proven unit economics, 20% to adjacent markets or partnerships with balanced risk, and 10% to highly innovative moonshots. Actively kill or delay projects that push the organization into a '100/100/100' spread.
OutcomeAvoids losing sight of what makes money and burning cash on unscalable adjacencies.
CounterpointMost leadership teams agree on funding the core, but fail by refusing to kill pet projects, resulting in a 100/100/100 allocation that dilutes focus.
Navan CFO Aurélien Nolf on Resource Allocation, IR, and AI in Finance · May 28, 2026
team_and_org
The slighted third GTM hire
Target the third-in-line leaders at mega-cap companies who were passed over for promotion to build your GTM team.
Discussing: Competing for GTM leadership talent against AI giants offering massive equity and $400K+ OTEs.
“Then there's a person who was third in line in Anthropic and did not get the job... bro, you're third, so fuck them and come over here and go build a big company.”
MechanismInstead of trying to match the compensation of top-tier AI companies, recruit the person who was third in line at those companies and didn't get the top job, or a leader whose last two startups failed. Offer them the top seat and a chance to prove themselves with heavy commission upside.
OutcomeSpeaker's word, not measured
CounterpointOptimizes for chip-on-the-shoulder motivation rather than purely financial upside.
Build The World Class Team That Anthropic Won't Steal | Craig Rosenberg, CPO @Scale Venture Partners · May 31, 2026
icp_and_segment
Macro-driven ICP redirection
Track macro capital flows to identify newly funded sectors, then explicitly redirect your team's prospecting lists away from dry markets.
Discussing: A macro market shift kills your primary buyer's budget, but reps keep calling them out of habit.
“We're in a marketplace where all of a sudden the banks are flushed. They got tons of money. Sports has got no money... Why don't we go where the money is?”
MechanismTrack macro capital flows via daily financial news to find sectors receiving sudden funding. Explicitly dictate the new target list to the reps and explain the reasoning behind the shift. Do not expect reps to spot the trend or self-correct away from their legacy accounts.
OutcomeShifted from sports to banks early in the pandemic; banks carried the business through the downturn.
CounterpointReps are naturally myopic and will keep calling a dead ICP out of habit; leaders must dictate the pivot.
Jeb Blount on Sales Leadership: Keeping Your Team Focused on the Right Opportunities (Ask Jeb) · May 27, 2026
From the Conversations
Data-driven event outbound
Build The World Class Team That Anthropic Won't Steal | Craig Rosenberg, CPO @Scale Venture Partners
May 31, 2026 · 1h 6m · 2 quotes pulled
▶ Listen“Our outbound back then was only to our events. We didn't try to get a meeting. And it worked amazing because they would get... you get the meetings at the events.”
The 29-to-1 CFO meeting ratio
THE SECRETS TO WORKING WITH THE CFO TO GET DEALS DONE
May 27, 2026 · 51m · 2 quotes pulled
▶ Listen“29 minutes in, I've just been like talking about all my problems... in one minute, she identifies the benefits... I'm like, more information. I was like, yeah, I need that.”
Buying-Behavior TAM Segmentation
Navan CFO Aurélien Nolf on Resource Allocation, IR, and AI in Finance
May 28, 2026 · 49m · 2 quotes pulled
▶ Listen“We slice the TAM between what we call is the managed side... and then there's a huge part of the time that we call the unmanaged business... we need different teams to go after those opportunities.”
Sources
▶ ListenTopline
Build The World Class Team That Anthropic Won't Steal | Craig Rosenberg, CPO @Scale Venture Partners<p>Craig Rosenberg, Chief Platform Officer at Scale Venture Partners and co-founder of Topo, joins AJ Bruno and Asad Zaman to take on the question every founder is wrestling with: can you still build a world-class sales team when OpenAI and Anthropic are handing individual contributors $10 million equity packages? Craig argues you do not have to compete head-on, then lays out the hiring profile to chase instead, the quota-to-comp discipline that keeps packages sane, and why founder brand has become the most reliable pipeline play left as CAC keeps climbing. Topics include enterprise AE compensation, where private equity is still winning the GTM talent war, the Topo playbook for events and data-as-moat, and a bull-versus-bear debate on whether Gong goes public in the next 36 months. Plus, a Quiz Pro Quo on the real customer counts behind Salesforce, HubSpot, and ZoomInfo.</p> <p>Key Takeaways:</p> <p>- Rather than try to outbid OpenAI and Anthropic for talent, build your own farm system and develop people into the role. As Craig Rosenberg, Chief Platform Officer at Scale Venture Partners, put it: "You have to change your hiring profile to a unique profile that's unique to your business, but then you gotta coach 'em up."<br /> - A resume from a hot AI lab is not a guarantee of success at your company. As Craig Rosenberg noted, "The person that is going to do well at Anthropic may not do well at Series B," so hire for the stage and the hunger rather than the logo.<br /> - On compensation, Craig anchors the package to the role's real value: "you pay for what your wedge costs… if you feel like you have to pay $10 million, then you have a huge problem and you gotta go back to the drawing board." If the number runs away from you, the model is broken.<br /> - With CAC climbing and most channels breaking down, founder brand has become the highest-leverage pipeline play. As Craig Rosenberg said, "The value of building a founder brand, when you look at the data, it's amazing," pointing to gains in both pipeline and deal size.</p> <p>Connect with the Hosts & Guests:</p> <p>Host: AJ Bruno, CEO at QuotaPath - https://www.linkedin.com/in/ajbruno3/<br /> Host: Asad Zaman, CEO at Sales Talent Agency - https://www.linkedin.com/in/azaman1/<br /> Guest: Craig Rosenberg, Chief Platform Officer at Scale Venture Partners - https://www.linkedin.com/in/craigrosenberg/</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 Introducing Craig Rosenberg<br /> 02:34 Can Anyone Out-Hire The AI Labs?<br /> 04:33 Why Craig Isn't Worried<br /> 06:52 Enterprise AE Comp Is Climbing<br /> 08:21 Founders Overpay For Star CROs<br /> 10:53 Why AI Reps Struggle At Series B<br /> 14:00 Hire The Slighted CRO<br /> 14:42 Quota-To-Comp And Attainment<br /> 18:45 Can AI Labs Sustain Growth?<br /> 22:20 Where PE Still Wins GTM Talent<br /> 27:17 Major Runs Reshape GTM<br /> 32:36 The Topo GTM Playbook<br /> 37:55 Quiz Pro Quo<br /> 47:45 Founder Brand And Rising CAC<br /> 58:42 Bulls and Bears</p>
▶ ListenThe Best of the Brutal Truth about B2B Sales & Selling - The show focuses on the enterprise Sales Process
THE SECRETS TO WORKING WITH THE CFO TO GET DEALS DONE<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> <p> </p> <p> </p>
▶ ListenRun the Numbers
Navan CFO Aurélien Nolf on Resource Allocation, IR, and AI in Finance<p>In this episode of Run the Numbers, CJ sits down with Aurélien Nolf, CFO of Navan, to unpack how to pre-align before budgeting, how to think about portfolio construction inside a company, when to fund or kill internal bets, how IR is becoming more connected to FP&A, and where AI actually works inside finance teams.</p><p>—</p><p>SPONSORS:</p><p>Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at<a href="https://www.rillet.com/cj"> <u>https://www.rillet.com/cj</u></a></p><p>EY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at <a href="https://www.ey.com/techstartups"><u>https://www.ey.com/techstartups</u></a></p><p>SpendHound is a SaaS spend management platform built for finance and procurement teams that want visibility and leverage in every deal. By tracking all your software, benchmarking pricing across thousands of vendors, and surfacing contracts and renewals, SpendHound helps you stop overpaying and negotiate with confidence. Trusted by teams at ZoomInfo and Hootsuite. Get started at <a href="https://www.spendhound.com/cj"><u>https://www.spendhound.com/cj</u></a></p><p>Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at <a href="https://www.brex.com/metrics"><u>https://www.brex.com/metrics</u></a></p><p>Aleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at <a href="https://www.getaleph.com/run"><u>https://www.getaleph.com/run</u></a></p><p>RightRev is an automated revenue recognition platform built for teams that have outgrown spreadsheets and billing tool workarounds. It handles high-volume subscriptions, usage-based contracts, and mid-cycle upgrades, so you can scale without scrambling at month-end. For RevRec that keeps your books clean, visit <a href="https://www.rightrev.com/CJ"><u>https://www.rightrev.com/CJ</u></a></p><p>—</p><p>LINKS: </p><p>Mostly Talent: <a href="https://mostlymetrics.typeform.com/to/cLTxtAsN"><u>https://mostlymetrics.typeform.com/to/cLTxtAsN</u></a></p><p>Guest: <a href="https://www.linkedin.com/in/aureliennolf5b716412/"><u>https://www.linkedin.com/in/aureliennolf5b716412/</u></a></p><p>Company: <a href="https://navan.com/"><u>https://navan.com/</u></a></p><p>CJ: <a href="https://www.linkedin.com/in/cj-gustafson-13140948/"><u>https://www.linkedin.com/in/cj-gustafson-13140948/</u></a></p><p>Mostly metrics: <a href="https://www.mostlymetrics.com"><u>https://www.mostlymetrics.com</u></a></p><p>—</p><p>TIMESTAMPS:</p><p>0:00 Preview and intro</p><p>1:21 Welcome and guest intro</p><p>3:06 100-mile ultramarathon at Lake Tahoe</p><p>4:47 Resource allocation lessons from EA</p><p>6:41 Bucketing bets: proven, intuition, moonshots</p><p>7:43 Pre-alignment before budgeting</p><p>9:58 The 70/20/10 framework</p><p>10:35 Sponsors — Rillet | EY | SpendHound</p><p>13:51 The common trap: chasing everything</p><p>16:16 Lyft: $1B burning to $1B profitable</p><p>18:11 Killing projects without crushing morale</p><p>19:24 TAM as the planning foundation</p><p>20:57 Navan's TAM: managed vs. unmanaged</p><p>22:15 Sponsors — Brex | Aleph | RightRev</p><p>25:48 Why go after the unmanaged segment</p><p>28:24 Not all TAM dollars are equal</p><p>29:26 How IR is evolving</p><p>30:45 Why FP&A and IR belong together</p><p>31:54 Metrics: disclose vs. guide</p><p>34:04 Use internal metrics externally</p><p>35:12 Communicating bad news to the market</p><p>39:22 Earnings prep: the black book</p><p>40:04 AI in finance: can't vibe code compliance</p><p>41:31 Ava handles 55% of interactions</p><p>43:08 AI ROI: same framework as anything else</p><p>44:02 Why finance hasn't had its AI moment</p><p>44:46 Lightning round</p><p>44:56 Screwed up: wrong investor meeting</p><p>45:23 Sunday planning ritual</p><p>46:42 Advice to younger self</p><p>47:29 Finance software stack</p><p>48:34 Craziest expense: curtains at the hotel laundry</p><p>49:17 Credits</p>
▶ ListenSales Gravy: Jeb Blount
Jeb Blount on Sales Leadership: Keeping Your Team Focused on the Right Opportunities (Ask Jeb)<p>When the market shifts, your salespeople won't shift with it on their own. That's your job as a sales leader. In this episode of Ask Jeb on the Sales Gravy Podcast, Jeb Blount takes questions from two sales leaders navigating some of the most common and costly team management challenges in sales: how to redirect high performers when market conditions change, and how to get a small team to stop chasing easy transactional deals and start closing high-value complex ones.</p><p>Jeb draws on real experience, including a story from the early days of the pandemic when one of his top performers kept prospecting into a dead market. His answer was simple: go where the money is. But making that shift happen at the team level takes leadership, market awareness, and consistent communication. The second question tackles compensation design, product confidence, and how to use success stories to shift your team's mindset from the path of least resistance to the deals that actually move the needle.</p><p>In This Episode:</p><ul><li>Why salespeople won't naturally redirect their targeting when market conditions shift</li><li>How sales leaders can stay ahead of market trends to point their teams in the right direction</li><li>Why salespeople default to easy deals and what drives that behavior</li><li>How to fix the risk-reward structure without cutting incentives on bread-and-butter business</li><li>Building product confidence so your team can go toe-to-toe with complex buyers</li><li>Using success stories to motivate teams toward higher-value opportunities</li></ul><p><br></p><p>Perfect For:</p><ul><li>Sales leaders managing teams through market shifts or economic uncertainty</li><li>Sales managers with reps who avoid complex or longer-cycle deals</li><li>Anyone building or restructuring a sales compensation plan</li></ul><p><br></p><p>Jeb Blount is the author of Fanatical Prospecting, Objections, Sales EQ, and more than a dozen other bestselling sales books. He is the founder of Sales Gravy and one of the most sought-after sales trainers and speakers in the world.</p><p>Have a question for Jeb? Submit it at <a href="http://salesgravy.com/ask" rel="nofollow">salesgravy.com/ask</a></p><p>Get your tickets to OutBound Conference: <a href="http://outboundconference.com" rel="nofollow">outboundconference.com</a></p><p>Get your copy of Jeb's new book: <a href="https://a.co/d/0hneYtLq" rel="nofollow">90 Days to Level Up Your Sales Skills</a></p><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
#577 - Why Your AI Cold Emails Are Failing (And How to Fix Them) | Jason BayYour cold outreach reply rates are completely flatlining because of AI slop. In this episode, Jason Bay breaks down how to: 🎯 Flip your sales funnel into a "martini glass" to go deep on fewer accounts. 🤖 Break through the AI noise by prioritizing messaging precision over mindless volume. 👔 Disqualify 90% of your weak pipeline so you only target high-intent prospects. - - You're one step closer to President's Club! 📈 Cold Email Course: https://hubs.li/Q04j3r9V0 🛠 Cold Email Data Report: https://hubs.li/Q04j3GHJ0 🛠 Weekly Tactical Breakdowns: https://hubs.li/Q02NJQ8p0 📚 Things you can steal and use today: https://linktr.ee/30mpc_youtube
▶ ListenGTM Live
The Pressure B2B Marketing Leaders Don’t Talk About Enough<p>You can't be a great marketer if your nervous system is stuck in survival mode.</p><p>If you're a marketing leader, you know the feeling. The 12AM Slack from the CEO. The “where's-the-pipeline?” question that never goes away. The low-grade anxiety running underneath every campaign, every board deck, every quarter. </p><p>In this episode, Carolyn and Amber connect the inner game to the measurement problem. The anxiety marketers carry isn't a personal failing. It's the tax you pay for being judged by numbers that miss your real contribution: shaping how the market perceives you, long before anyone fills out a form.</p><p>And here's what nobody in GTM is actually talking about: you cannot build the future you want while your body is locked in defending the present. Your brain chemistry doesn't know the difference between the meeting you're dreading and the one that's already over — it reacts the same way to both. And when you live in that state, you can't create. You can only react.</p><p>What this episode covers:</p><ul><li>The breakthroughs from both Amber and Carolyn’s recent vacations</li></ul><ul><li>Why so many B2B marketers are operating from low-grade panic, and why it’s costing them their best work</li></ul><ul><li>How belief and brain chemistry shape what you're able to create, and why you have to embody the outcome before it shows up</li></ul><ul><li>Why marketing's real job is shaping brand perception in-market, and why traditional KPIs can't see that work</li></ul><ul><li>How to use zero-party data — what customers tell you directly — to inform the customer journey instead of guessing from last-touch behavior</li></ul><ul><li>Three books that reshaped how Carolyn thinks about wealth, awareness, and building a future you can't yet see: Happy Pocket Full of Money, The Power of Awareness, and Dr. Joe Dispenza's Becoming Supernatural</li></ul><p><br></p><p>If you're a marketing leader tired of doing your best work from a place of panic, and tired of watching it disappear into numbers that can't measure it, this one's for you.</p><p>-----------------------------------------------------</p><p>Want answers now?</p><p>🔎 The fastest way to understand how marketing is driving pipeline and revenue → All your data, connected, so you can see what’s working and what to do next.</p><p><a href="https://www.passetto.com/book-a-call"><u>[Get your full pipeline & revenue breakdown in 2 weeks]</u></a></p><p>-----------------------------------------------------</p><p>Not ready for that yet?</p><p>🎯 Understand why it’s been so hard to see what’s working → We’ll show you where your visibility breaks and why your current KPIs can’t answer these questions.</p><p><a href="https://www.passetto.com/working-session"><u>[Apply for a 1-hour marketing KPI assessment]</u></a></p><p>-----------------------------------------------------</p>
▶ ListenRevenue Builders
The Discipline Behind Nine-Figure Deals with Stuart GwynnStuart Gwynn, a top-performing enterprise seller at MongoDB, joins John Kaplan and John McMahon to unpack what separates disciplined enterprise execution from deal chasing.
▶ ListenMake It Happen Mondays - B2B Sales Talk with John Barrows
What AI Knows About Your Buyer with Scott Gillum<p>AI already knows your buyer better than most sales reps do. The question is — what are you going to do about it?</p><p>In this episode, John is joined by Scott Gillum, author of The Hidden Buyer Journey, to unpack seven years of research on how buyers actually make decisions — and why our sales and marketing tools are barely scratching the surface of what's possible. From personality profiling and corporate culture mapping to the death of the sales stage, this conversation goes deep on what it really takes to sell in a world where the buyer is more informed, more protected, and more machine-assisted than ever before.</p><p>If you're serious about staying relevant as a sales professional in an AI-first world, this one's a must-listen.</p><p>Want to make sure you're equipped before the market moves on without you? Visit www.jbarrows.com and learn how you can <strong>Make It Happen.</strong></p><p><strong>What You’ll Learn</strong></p><ul><li>Why corporate culture predicts deal velocity better than any sales methodology</li><li>How to use personality profiling tools to adapt your style to any buyer</li><li>Why 85% of the people who actually influence your deals aren't in your CRM</li><li>The one thing AI still can't replicate — and why it's your biggest competitive advantage</li><li>Why Return on Effort (ROE) is replacing ROI as the real measure of AI in sales</li></ul><br/><p><strong>Scott Gillum</strong> is the Founder and CEO of Carbon Design. Prior to founding Carbon Design, he was the President of the Washington, DC office for gyro (a Dentsu agency), the world’s largest B2B agency.</p><p>His career follows the pipeline. Starting at the bottom closing deals as a sales rep. Then as a management consultant after graduate school, helping clients build and capture demand for sales and marketing channels. Advertising broadened his knowledge and experience in building brands and creating awareness.</p><p>Along the way, he’s been the head of marketing for an Inc. 500 company, and an interim CMO for a Fortune 500 company. Today, Scott helps clients improve the effectiveness of their marketing efforts up and down the funnel. From transitioning to digital to finding new ways to communicate, connect, and motivate audiences.</p><p>Scott’s a member of the Gartner for Marketing Leaders Council and he writes a regular column for MediaPost on business marketing. He’s articles have appeared in leading publications such as Forbes, Fortune, Adage, the Huffington Post and he has contributed to various books on marketing. Additionally, his work on sales and marketing integration was made into a Harvard Business School Case Study and is taught at leading business schools across the nation.</p><p>Website: <u><a href="https://carbondesign.com/scott-gillum/" rel="noopener noreferrer" target="_blank">https://carbondesign.com/scott-gillum/</a></u></p><p>LinkedIn: <u><a href="https://www.linkedin.com/in/scottgillum/" rel="noopener noreferrer" target="_blank">https://www.linkedin.com/in/scottgillum/</a></u></p><p><strong>John Barrows</strong> is a sales trainer, speaker, and founder of JB Sales with over 25 years of experience in the industry. He has made hundreds of cold calls a week, led startups to acquisition, and trained high-performing teams at companies like Salesforce, LinkedIn, Amazon, and Okta. Through JB Sales, John focuses on practical sales execution—helping reps fill pipeline, close deals, and build trust with buyers in today’s AI-driven sales environment.</p><p><strong>Connect with John Barrows:</strong></p><p>LinkedIn: <u><a href="https://www.linkedin.com/in/johnbarrows/" rel="noopener noreferrer" target="_blank">https://www.linkedin.com/in/johnbarrows/</a></u> <a href="https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqbnBBemdVT2pBZ1dhY0szYzlzOGUzYURaekEtUXxBQ3Jtc0trNkZEWVBuS3dOOWZaZ0pZVFNrOGtNNHpuNjZWdGx0aVBhX2dNODRTdjVKVG1tS0xnRlJXWk5WOUpVdzk1YzQ1R3ZoTFhRZ3pxeFFibXU5WnFlVGJtVXl5dDUzM1JqdnkwRGRMaC05VTZ2YmNFLTFiSQ&q=https%3A%2F%2Fwww.linkedin.com%2Fin%2Fjohnbarrows%2F&v=bULevYtP1Ds" rel="noopener noreferrer" target="_blank"> </a></p><p>Instagram: <u><a href="https://www.instagram.com/johnmbarrows/" rel="noopener noreferrer" target="_blank">https://www.instagram.com/johnmbarrows/</a></u></p><p>TikTok: <u><a href="https://www.tiktok.com/@johnmbarrows" rel="noopener noreferrer" target="_blank">https://www.tiktok.com/@johnmbarrows</a></u></p><p>Check out John's Membership:<a href="https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqbGZxSnNVNDNhZU1zTGlfUHNWX19ZemtTLTM3QXxBQ3Jtc0tuY0sxajVtV1ZsdW5TMGtlV2tWTmNDTGVtUUZ6a1J6VmlMVi1DdU5uQ1cwRjRqdjF2ZlVqcXFveUtBWkp1WnZXSEZqQzA1TnJUclAxRVZWNm9fRjFxSlllYjdoTEd1VHFUUEFJbDdCSkR4SEU4TVgzTQ&q=https%3A%2F%2Fgo.jbarrows.com%2Fpages%2Findividual-membership%3Fref%3D3edab1&v=bULevYtP1Ds" rel="noopener noreferrer" target="_blank"> </a><u><a href="https://go.jbarrows.com/" rel="noopener noreferrer" target="_blank">https://go.jbarrows.com/</a></u></p><p>Join John's Newsletter: <u><a href="https://www.jbarrows.com/newsletter" rel="noopener noreferrer" target="_blank">https://www.jbarrows.com/newsletter</a></u></p>
▶ ListenThe Sales Evangelist
Sales Is No Longer A Numbers Game | Tom Stearns & Peter Cleary - 2006<p>show notes</p>
▶ ListenThe Salesman.com Podcast
The Only Sales System Small Businesses Need Under $5M Year
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