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The Sales Pattern Brief

Our team listens to thousands of podcasts about sales so you don't have to. One weekly briefing, in your inbox.

SATURDAY, MAY 23, 2026 · MINED FROM 131 PODCASTS

May 23 · The AI account query cutting ramp to 2 months

Good morning.Operators are using historical data to aggressively shrink their target markets and ramp times.

May 23 · The AI account query cutting ramp to 2 months

Endgame CEO Alex Bilmes cut rep ramp time from six months to two months by connecting an AI agent to inherited account histories. Instead of forcing new hires to read stale CRM notes, they query the model for past interactions. Meanwhile, Outbound Squad saw a 30 percent pipeline jump by ignoring nine marginal industries.

Today's Sales Plays (18)

Tactical moves operators are running right now, with verbatim source.

outbound

Blind Date Subject Matter Expert Offer

Pitch the expertise of the internal specialist the prospect will meet, promising specific industry insights even if they do not buy.

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Discussing: Buyers ignoring cold outreach because standard product demos offer no standalone value.

“When you had an offer in there... you were 28% more likely to get a positive reply that converted into a meeting. So when you were able to answer the question what will I get out of this meeting.”

Mechanism Instead of pitching a demo, pitch a meeting with an internal specialist. Promise two specific takeaways they get regardless of buying (e.g., "how Caterpillar handles the welder shortage" and "identifying hard-to-automate parts"). Make the buyer feel irresponsible for declining the free consultation.

Outcome 28% increase in positive replies converting to meetings

Counterpoint Shifts the meeting's value prop from evaluating a product to receiving free, specialized industry consulting.

State of Outbound (Guest appearance on Mike Weinberg's podcast) · May 5, 2026

▶ Apple show ▶ Spotify

enablement

AI-queried historical account context

Give new reps an AI agent connected to their inherited accounts' history so they can query past interactions instead of reading stale CRM notes.

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Discussing: New reps inheriting a book of business with zero historical context, leading to long ramp times.

“We see ramp acceleration going from six months to two months. And the reason is if you have a new rep coming in... you can ask a question about your book of business and what you should go do about it.”

Mechanism Instead of forcing new reps to piece together account history from empty CRM fields, connect an AI agent to the full historical data of their inherited accounts, including calls, emails, and CRM data. The rep queries the agent on what happened previously, key stakeholders, and the next best action.

Outcome Ramp time drops from 6 months to 2 months.

Counterpoint Most ramp programs focus on product training; this focuses on immediate account-specific historical context.

Revenue per Employee Is the New Endgame with Alex Bilmes · May 21, 2026

▶ Apple show ▶ Spotify

team_and_org

Single-hire AI change management

Hire one senior AI-native leader to drive adoption rather than running broad change management programs.

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Discussing: The existing GTM team is lagging or actively resisting the adoption of AI agents and workflows.

“Just go hire one reasonably senior person that is all in here... and folks will start quitting when they don't want to work at that pace anyway. You've got to hire them ideally at the VP level.”

Mechanism Bypass broad change management, training programs, or layoffs. Hire a single senior leader at the VP level or above who is fully committed to agentic workflows. Give them the mandate to build the new motion and allow resistant team members to self-select out of the organization.

Outcome Speaker states resistant employees will naturally leave without requiring formal layoffs.

Counterpoint Broad change management and training programs waste time; a single aggressive change agent forces the issue organically.

SaaStr 853: The Agents #004: Tragedy Apps, Too Many AI SDRs, and Why Your Next Hire Should Report to an Agent · May 6, 2026

▶ Apple show ▶ Spotify

enablement

Opt-In Feedback Opener

Prevent defensiveness during critical feedback by explicitly asking the rep if they are in the right headspace to receive it.

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Discussing: Delivering critical performance feedback to a rep without triggering defensiveness.

“You can start the sentence by saying, 'Hey Jason, I wanted to grab a couple minutes... I have some very specific negative feedback that I wanted to portray. Are you in the right headspace to receive this feedback?'”

Mechanism Before giving feedback, ask for permission and check their emotional state: 'I have some specific negative feedback. Are you in the right headspace to receive this today?' If they say yes, deliver the feedback calmly, removing emotional language and focusing strictly on specific observations.

Outcome Speaker notes it prepares the rep and removes the emotional sting.

Counterpoint Instead of softening the blow with a compliment sandwich, this approach labels the negative feedback upfront but gives the rep control over the timing.

Leading teams at Google, Apple, Amazon, Gong, Yelp, and more · May 19, 2026

▶ Apple show ▶ Spotify

icp_and_segment

Six-Month Win Rate ICP Narrowing

Analyze six months of closed-won data to isolate the top two sub-industries and personas, then ignore all other accounts.

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Discussing: Low outbound conversion rates caused by reps spreading effort across too many marginal accounts.

“We identified two... where we get most of our meetings. We're going to say no to those other nine industries... in 60 days it was literally like 30% plus more pipeline.”

Mechanism Pull the last six months of closed-won and closed-lost data. Identify the specific sub-industries (e.g., medical devices vs. general healthcare) and the exact two personas that close fastest with the highest win rates. Mandate reps ignore all other accounts to focus touches solely on these high-converting pockets.

Outcome 30% increase in qualified pipeline in 60 days

Counterpoint Shrinks the total addressable market to increase touch frequency and relevance on the accounts most likely to buy.

State of Outbound (Guest appearance on Mike Weinberg's podcast) · May 5, 2026

▶ Apple show ▶ Spotify

ai_in_sales

AI-Generated BDR Coaching Plans

Feed daily task completion data into an LLM to generate weekly, personalized coaching plans for BDRs.

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Discussing: BDRs failing to execute prescribed sequence steps, breaking the outbound motion.

“Put that into an LLM with a simple prompt that says, look at each person, figure out what their themes are of why they aren't getting stuff done. And then give the manager a personalized coaching plan.”

Mechanism Implement morning and afternoon task blocks. After each block, managers log a simple Yes/No on task completion plus the "why" in a structured form. Convert this to JSON, feed it to an LLM weekly, and prompt it to identify failure themes and generate a personalized coaching plan per BDR.

Outcome Massive impact on productivity in the first week.

Counterpoint Shifts AI from writing emails to diagnosing behavioral themes, turning qualitative manager observations into structured coaching plans.

How To Be An ELITE Sales Leader (Copy This Playbook) · May 19, 2026

discovery

The late-arrival champion test

Identify the true champion by watching who skips the introductory fluff and commands the room's attention when they arrive late.

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Discussing: Mapping stakeholders in a complex enterprise deal to separate real champions from false ones.

“They were never in the presentation room at the beginning. They'd skip that first 20 minutes... But they were always there for the last 20 minutes. And when they came in, all heads turned.”

Mechanism Stop looking for C-level titles. Instead, look for the climber who skips the first 20 minutes of your presentation (the company overview) and arrives for the final 20 minutes. When they walk in, watch the room. If all heads turn and the rest of the team defers to them or tries to impress them, you have found your actual champion.

Outcome Sold $30M to $40M to one account over a few years after finding this champion.

Counterpoint Reps default to targeting C-suite titles, but true champions are often mid-level climbers who command internal respect rather than formal authority.

THE SECRET TO COMPETING AND WINNING IN THE TOUGHEST MARKETS · May 6, 2026

outbound

Value-first CS pipeline generation

Earn the right to source pipeline by proving value first, then ask advocates for warm introductions to unresponsive stakeholders.

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Discussing: Sourcing expansion pipeline in high-growth accounts where AEs are getting ignored by senior stakeholders.

“If you've actually done that really, really effectively, then you've earned the right to source pipeline... We see 80% of our pipeline from customer success close because it's qualified.”

Mechanism Focus entirely on delivering value greater than the price paid via adoption metrics and strategic business reviews. Once value is established, ask your champion: "Since this is working for you, my AE partner hasn't heard back from your managing director. Can you make that introduction?"

Outcome 80% win rate on CS-sourced pipeline

Counterpoint CS doesn't cold-pitch; they use established value as a wedge to bypass ignored AE outreach.

WARNING: Why 'Non-Revenue' CS Roles Won't Survive | Sam Slevin, Global SVP CS @ AlphaSense · May 17, 2026

▶ Apple show ▶ Spotify

closing

CFO Enterprise Viability Letter

Attach a first-person letter from your CFO detailing funding and cash position to de-risk six-figure startup deals.

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Discussing: Selling six- or seven-figure enterprise deals as a startup where buyers worry about company viability.

“We would take this letter and we put the CFO's face on it and it was explaining how basically our financial position we have raised money from name drop... making them feel safe.”

Mechanism Draft a first-person letter from the CFO to attach to enterprise quotes. Explicitly state your financial position, name-drop your investors, and confirm cash in the bank to prove you are a going concern. Update the numbers periodically and attach it to every major enterprise proposal.

Outcome Speaker's word, not measured

Counterpoint Enterprise buyers won't sign six-figure deals if they fear the vendor will go bankrupt; preempt this with hard financial data.

5 Ways CFOs Can Build a Better Sales Engine with Paul Stansik · May 21, 2026

▶ Apple show ▶ Spotify

outbound

The 5-Minute Egg Timer Meeting

Overcome the "send me information" brush-off by asking for exactly five minutes to put a face to a name, tracked by a physical timer.

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Discussing: Executives brushing off in-person meeting requests by asking the rep to just send information over email.

“I have an egg timer in my bag. I will put it on five minutes. When it goes down, I'm out the door... I got a meeting about 80% of the time with that.”

Mechanism Ask for 5 minutes just to shake hands. Bring a physical egg timer, set it for 5 minutes on their desk. Do not pitch. Say: "I'm impressed with your career trajectory. Could you give me a couple pieces of advice?" Let them talk.

Outcome 80% meeting acceptance rate; usually converts into a 1-hour conversation.

Counterpoint Asking for career advice instead of pitching disarms the executive and gets them talking about their favorite subject: themselves.

Enterprise Sellers Win or Lose on People Skills in the Age of AI (Ask Jeb) · May 5, 2026

▶ Apple show ▶ Spotify

ai_in_sales

Dev Environment AI Agent Hosting

Run internal AI agents permanently in your development environment to maintain an infinite context window and historical memory.

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Discussing: Losing agent memory and context when moving internal AI tools from development to production.

“If you run them in the dev environment permanently, like we're doing, you get an extra agent that has an infinite context window and infinite history. Like it remembers everything.”

Mechanism Keep internal-facing AI agents permanently in the development environment. Instead of publishing a standalone app, interact directly with the platform's native dev agent, which retains an infinite context window and full historical memory of the database and previous queries.

Outcome $257/month total cost for two VP-level agents

Counterpoint Standard practice is to push apps to production, but staying in dev preserves the native AI's infinite memory of your codebase and data.

SaaStr 854: The Agents #005, Our AI is Hiring! Would You Work for One? And Are Autonomous Agents ... Safe? · May 19, 2026

▶ Apple show ▶ Spotify

ai_in_sales

AI-Assisted Performance Reviews

Combine CRM data, self-reflections, and dictated voice notes into an LLM to draft performance reviews.

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Discussing: Writing comprehensive, data-backed performance reviews for a large team without spending weeks on the process.

“I like for each question, look at the data and create an independent CRO opinion... Then look at their self-reflection answer and give our response to that self-reflection.”

Mechanism Feed an LLM the rep's KPIs, CRM data, and self-reflection. Dictate your raw thoughts using a voice-to-text tool. Prompt the AI to output four sections: an objective opinion on the data, a response to their self-reflection, specific areas for improvement, and a closing note of encouragement.

Outcome 16 performance reviews completed in two hours.

Counterpoint Bypasses the blank-page problem by using raw voice dictation to guide the LLM, rather than trying to type out perfect prompts.

How To Be An ELITE Sales Leader (Copy This Playbook) · May 19, 2026

ai_in_sales

Multi-agent GTM stack segmentation

Segment AI SDRs by funnel stage rather than relying on a single vendor for all outbound and inbound.

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Discussing: Deploying AI SDRs without overlapping workflows or degrading quality across inbound and outbound motions.

“It's highly specialized, how we're using artisan to do warm follow ups... monaco, which does fill its own funnel... Would I trade those two off today for quality? No.”

Mechanism Deploy specialized agents for distinct funnel stages. Use Qualified to manage inbound website communications and appointment setting. Route warm outbound to existing contacts through Artisan. Use Monaco strictly for net-new cold outbound to fill the top of the funnel. Deploy Agent force to reactivate lapsed leads in the CRM.

Outcome Speaker states they would not trade the specialized setup for a single vendor due to quality.

Counterpoint Consolidating into a single AI SDR platform degrades quality because inbound, warm outbound, and cold outbound require different agent training.

SaaStr 853: The Agents #004: Tragedy Apps, Too Many AI SDRs, and Why Your Next Hire Should Report to an Agent · May 6, 2026

▶ Apple show ▶ Spotify

team_and_org

Operational unblocking for CS capacity

Bridge the gap between finance's ARR-per-head targets and reality by isolating and removing the single biggest operational bottleneck.

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Discussing: Finance demands higher ARR per AM, but the team is already at maximum account capacity.

“You start to figure out what is the 10% if I move this 10% burden, then what do I do? I need to spend time unblocking the biggest thing that will move the efficiency needle.”

Mechanism Audit the non-revenue tasks consuming AM time (billing disputes, clunky AM-to-AE handoffs, coordinating with too many AEs). Identify the specific 10% operational burden that is capping user count. Fix that single bottleneck before attempting to layer in digital success or segment changes.

Outcome Meets finance targets without risking renewal rates (speaker's word)

Counterpoint Don't just demand more accounts per rep; systematically remove the operational friction capping their capacity.

WARNING: Why 'Non-Revenue' CS Roles Won't Survive | Sam Slevin, Global SVP CS @ AlphaSense · May 17, 2026

▶ Apple show ▶ Spotify

outbound

Chin-down downward inflection technique

Physically tilt your chin down while delivering your cold call opener to force a downward, authoritative vocal inflection.

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Discussing: Sounding nervous or asking for permission on cold calls, which prompts prospects to rush the rep or hang up.

“If you tilt your chin down... it will literally, you cannot uptone. And if you tilt it up, you will. And so that's a little exercise if you want to really look like a freak.”

Mechanism When delivering your opener or asking a qualifying question, physically tilt your chin downward. This posture makes it physically difficult to end sentences with an upward, questioning tone. End the sentence, take a deliberate pause, and wait for the prospect to respond without rushing to fill the silence.

Outcome speaker's word, not measured

Counterpoint Uses physical body mechanics to override nervous vocal habits rather than just trying to mentally remember to sound confident.

#575 - How Parallel Dialing Makes You Better at Cold Calling | Suji Goetzke · May 21, 2026

team_and_org

Green highlighter promotion audit

Have reps highlight the next role's job description to prove they only need a 25 percent overlap to be ready for promotion.

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Discussing: High-performing reps hesitating to ask for a promotion because they feel they don't meet all the requirements for the next level.

“looking at your job description and the job description above you and highlighting a green highlighter here's everything I do... nine out of 10 times without fail the women are already doing 50 to 75 % of the next role”

Mechanism During a career-pathing 1:1, have the rep pull up their current job description and the description for the role above them. Ask them to use a green highlighter to mark every responsibility on the senior description they are already executing. Tell them the threshold for promotion readiness is a 25 percent overlap, not 100 percent.

Outcome 9 out of 10 times, reps find they are already doing 50-75% of the next role.

Counterpoint Reps often assume they need to master 100 percent of the next role before applying. Explicitly capping the required stretch at 25 percent forces them to recognize their readiness.

Why So Many Talented Women Never Make It to Leadership | Erika Chestnut - 2003 · May 18, 2026

▶ Apple show ▶ Spotify

closing

Unified Quote And Action Plan

Present the quote and the mutual action plan on the same page to shift the conversation from cost to successful implementation.

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Discussing: Presenting a quote to a buyer without reinforcing the business case or implementation timeline.

“I'm actually encouraging my sales teams to show the quote and the mutual action plan and go live plan on the same page at the same time... You don't just want feedback on what it costs.”

Mechanism Instead of sending a standalone pricing document, put the quote and the mutual action plan (go-live plan) on the exact same page. Present them together in the same conversation to force the buyer to give feedback on both the cost and the implementation timeline simultaneously.

Outcome Speaker's word, not measured

Counterpoint Most reps separate the commercial negotiation from the implementation timeline, which isolates price as the only variable to debate.

5 Ways CFOs Can Build a Better Sales Engine with Paul Stansik · May 21, 2026

▶ Apple show ▶ Spotify

outbound

Burner Phone Direct Mail

Break through to an unresponsive enterprise prospect by mailing them a burner phone and calling it at a scheduled time.

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Discussing: Breaking through to an unresponsive, high-value enterprise prospect.

“We sent a client a burner phone and put a sticky note on it... 'If you don't call me the phone's gonna ring anyways so make sure you answer at 11.' Prospect answered it.”

Mechanism Mail the prospect a physical burner phone with a sticky note attached. Write: 'This is my phone number. If you don't call me, the phone's going to ring anyway, so make sure you answer at 11.' Call the phone at the exact designated time.

Outcome The prospect answered the phone.

Counterpoint Highly aggressive and expensive; only viable for top-tier enterprise target accounts where standard channels are completely exhausted.

Leading teams at Google, Apple, Amazon, Gong, Yelp, and more · May 19, 2026

▶ Apple show ▶ Spotify

From the Conversations

Opt-In Feedback Opener

Leading teams at Google, Apple, Amazon, Gong, Yelp, and more

May 19, 2026 · 1h 6m · 2quotes pulled

“You can start the sentence by saying, 'Hey Jason, I wanted to grab a couple minutes... I have some very specific negative feedback that I wanted to portray. Are you in the right headspace to receive this feedback?'”
Miriam Ebrahim · Sales Leader · Apple

30 Minutes to President's Club | No-Nonsense Sales

AI-Generated BDR Coaching Plans

How To Be An ELITE Sales Leader (Copy This Playbook)

May 19, 2026 · 26m · 2quotes pulled

“Put that into an LLM with a simple prompt that says, look at each person, figure out what their themes are of why they aren't getting stuff done. And then give the manager a personalized coaching plan.”
Mark · CRO · Docebo

Value-first CS pipeline generation

WARNING: Why 'Non-Revenue' CS Roles Won't Survive | Sam Slevin, Global SVP CS @ AlphaSense

May 17, 2026 · 1h 9m · 2quotes pulled

“If you've actually done that really, really effectively, then you've earned the right to source pipeline... We see 80% of our pipeline from customer success close because it's qualified.”
Sam Slevin · Global SVP CS · AlphaSense

Sources

Outbound Squad
State of Outbound (Guest appearance on Mike Weinberg's podcast)
Jason was a guest on The Sales Management. Simplified. Podcast hosted by Mike Weinberg. In this episode, they talked about why outbound is harder than ever, what broke the classic SDR–AE model, and Jason’s Too Good To Ignore outbound methodology. Check out more free content and get help with outbound at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.
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Outbound Squad
Leading teams at Google, Apple, Amazon, Gong, Yelp, and more
In this episode, Jason and Miram Ebrahim from Nomix Group, talk about creative plays that land meetings, nailing your first 90 days in a new leadership role, and giving fearless feedback. Check out more free content and get help with outbound at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠
▶ Listen
Revenue Builders
Revenue per Employee Is the New Endgame with Alex Bilmes
Alex Bilmes, CEO of Endgame, joins John Kaplan and John McMahon to discuss what his team learned from analyzing more than 30,000 real AI workflows across go-to-market teams.
▶ Listen
The Official SaaStr Podcast: SaaS | Founders | Investors
SaaStr 853: The Agents #004: Tragedy Apps, Too Many AI SDRs, and Why Your Next Hire Should Report to an Agent
<p>SaaStr 853: The Agents #004: Tragedy Apps, Too Many AI SDRs, and Why Your Next Hire Should Report to an Agent<br /> <br /> Your AI SDR pitches are getting better, but your AI PR pitches are getting you blocked. Jason and Amelia break down why the gap between good and great agents is the difference between pipeline and the spam folder.</p> <p>Then they introduce "tragedy apps," the term for products that had every advantage in the AI era and blew it. Descript had the customers, the product, and the timing, and froze. Replit waited 10 years for its moment and seized it. The lesson: catching up isn't enough if you're not building something new.</p> <p>Plus, the SaaStr team built an AI API Report Card that grades every major SaaS API on how agent-friendly it is (Stripe got the only A+, Marketo got a C, and no, they're not surprised).</p> <p>Jason and Amelia also get honest about running 4-5 AI SDRs from different vendors, why they'll probably have 6 by year end, and why single-vendor consolidation isn't the answer yet.</p> <p>And the wildest part: their AI VP of Marketing, 10K, now generates 3 actionable campaign ideas a day, runs autonomous campaigns on weekends, and might be a better boss than either of them. They're seriously hiring a human marketer whose primary manager would be the agent.</p> <p>Not a joke. Not a thought experiment. A real job posting.</p> <p>Finally, if your team is resisting AI, stop worrying about change management. Just hire one senior person who's all-in on agents and let the rest sort itself out.</p>
▶ Listen
30 Minutes to President's Club | No-Nonsense Sales
How To Be An ELITE Sales Leader (Copy This Playbook)
Sales is the only job where you can grind for 10 hours and still end the day feeling behind due to CRM chaos and internal fire drills. In this episode, Mark Kosoglow breaks down his exact productivity playbook, including: 👔 The Executive Routine: How to structure your day for closing, not just scrambling. 🤖 AI Workflows: The 2 exact AI workflows saving top revenue pros the most time right now. 🎯 The 3% Forecast Rule: How to turn raw rep activity data into an airtight, predictable pipeline. You're one step closer to President's Club! Grab these resources to help you get there: 📈 Master Sales Leadership with Mark: https://www.30mpc.com/course/leadership-course 🛠 Weekly Tactical Breakdowns: https://hubs.li/Q02NJQ8p0 📚 Things you can steal and use today: https://linktr.ee/30mpc_youtube
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The Best of the Brutal Truth about B2B Sales & Selling - The show focuses on the enterprise Sales Process
THE SECRET TO COMPETING AND WINNING IN THE TOUGHEST MARKETS
<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:briangburns@me.com">briangburns@me.com</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>
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Topline
WARNING: Why 'Non-Revenue' CS Roles Won't Survive | Sam Slevin, Global SVP CS @ AlphaSense
<p dir="ltr">Sam Slevin, Global SVP of Customer Success at AlphaSense, joins Sam Jacobs, AJ Bruno, and Asad Zaman on the AI-era customer success playbook. Topics include why service is the differentiator over the next 2 to 3 years, the case for customer success owning a revenue number from day one, the gap between finance's productivity targets and real-life capacity. Plus, the origins of customer success, why consumption-based pricing can quickly become a trap, and a bull-versus-bear debate on whether HubSpot can get back to a $20 billion market cap. In short... big episode!</p> <p dir="ltr">Key Takeaways:</p> <p dir="ltr">- After 17 years building customer success teams, Sam Slevin doesn't entertain the "should CS own a number" debate. As Sam Slevin, Global SVP of Customer Success at AlphaSense, put it: "in my 17 years of, of customer success and leadership within customer success, that has never actually been a debate for, for me. I, I would never take a role that doesn't have revenue focused and like impact owning a number, calling your forecast from day one." His standing practice when he joins a new company: build a top-down and bottoms-up forecast on day one and validate it the same way sales does.</p> <p dir="ltr">- Slevin's central thesis is that AI raises the floor on automation while service becomes the upside lever for the next 2 to 3 years. As Slevin put it: "I don't think there could be a more exciting time to be in customer success where service feels like it could be the major differentiator over the next 2 to 3 years." The CS team that listens carefully, builds deep relationships, and meets customers where they are wins the renewal and the expansion.</p> <p dir="ltr">- The hardest tension in CS productivity is the gap between what finance models demand and what individual accounts actually support. As Slevin put it on his approach: "I definitely want to increase productivity in ARR per AM. What's interesting is I feel like there's a finance model and then there's a real life model… finance will say we need $15 million per AM." The leader's job, Slevin argues, is to find the 10% operational drag (AM-to-AE handoffs, billing friction, segmentation gaps) and remove it to close the gap.</p> <p dir="ltr">- On HubSpot's path back to $20 billion, AJ Bruno takes the bullish side based on customer behavior signals. As AJ Bruno, CEO at QuotaPath, put it: "And the fact that they've gone horizontal, um, now I know that there are like 70% of their customers are still looking for answers for HubSpot of what AI needs to look like, and they haven't let the opportunity yet pass them by, but it's getting shaky right now." Sam Jacobs took the bearish side, citing structural challenges and faster-moving AI-first competitors.</p> <p><strong> </strong></p> <p dir="ltr">Connect with the Hosts & Guests:</p> <p dir="ltr">Host: Sam Jacobs, CEO at Pavilion - https://www.linkedin.com/in/samfjacobs/</p> <p dir="ltr">Host: AJ Bruno, CEO at QuotaPath - https://www.linkedin.com/in/ajbruno3/</p> <p dir="ltr">Host: Asad Zaman, CEO at Sales Talent Agency - https://www.linkedin.com/in/azaman1/</p> <p dir="ltr">Guest: Sam Slevin, Global SVP Customer Success at AlphaSense - https://www.linkedin.com/in/sam-slevin-9b2ba21b/</p> <p><strong> </strong></p> <p dir="ltr">Topline is more than a YouTube Channel:</p> <p dir="ltr">Subscribe to Topline Newsletter: https://toplinemedia.substack.com/</p> <p dir="ltr">Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech: https://www.joinpavilion.com/topline-podcast</p> <p dir="ltr">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 dir="ltr">Chapters:</p> <p dir="ltr">00:00 Introducing Sam Slevin</p> <p dir="ltr">03:13 Customer Success in the AI Era</p> <p dir="ltr">04:28 Should CS Own a Number?</p> <p dir="ltr">07:43 Gross Retention vs. Growth</p> <p dir="ltr">11:02 The Number-Owner Premium</p> <p dir="ltr">14:37 Service as the AI-Era Moat</p> <p dir="ltr">22:19 Productivity Per Person</p> <p dir="ltr">26:34 Vendor Spend and AI Voice Modes</p> <p dir="ltr">35:12 Reimagining GTM Roles</p> <p dir="ltr">38:51 Quiz Pro Quo</p> <p dir="ltr">45:38 Seat to Usage-Based Pricing</p> <p dir="ltr">50:12 Pricing AI Like a Meter</p> <p dir="ltr">55:43 CSM vs Salesperson Comp Gap</p> <p dir="ltr">58:43 Bulls and Bears</p>
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30 Minutes to President's Club | No-Nonsense Sales
#575 - How Parallel Dialing Makes You Better at Cold Calling | Suji Goetzke
Stop burning your territory by blindly calling massive lists of leads. In this episode, Suji breaks down their exact playbook, including: 🎯 Forcing your focus into tight, 100-person lists built around clear pain points 🤖 Scrambling for fast research in under 30 seconds using past notes, LinkedIn, and AI 🛡️ Flipping the 18 most common objections using simple talk tracks pulled from 300M calls You're one step closer to President's Club! Grab these resources to help you get there: 📈 Cold Calling Course: https://hubs.li/Q04hn70x0 🛠 Grab the 18-Objection Guide (Built with Gong): https://hubs.li/Q04hn3Ks0 🛠 Weekly Tactical Breakdowns: https://hubs.li/Q02NJQ8p0📚 Things you can steal and use today: https://linktr.ee/30mpc_youtube
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Run the Numbers
5 Ways CFOs Can Build a Better Sales Engine with Paul Stansik
<p>In this episode of Run the Numbers, CJ sits down with ParkerGale Operating Partner Paul Stansik to break down five ways CFOs can help build a better sales engine: making the budget mean something, improving forecasting, sharpening metrics, getting involved in key RevOps moments, and building real trust with sales.</p><p>—</p><p>SPONSORS:</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>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>—</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/paulstansik/"><u>https://www.linkedin.com/in/paulstansik/</u></a></p><p>Company: <a href="https://www.parkergale.com/"><u>https://www.parkergale.com/</u></a></p><p>Hello Operator: <a href="https://hellooperator.substack.com/"><u>https://hellooperator.substack.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>RELATED EPISODES:</p><p>Is a weekly martini ARR? | with Dave Kellogg</p><p><a href="https://youtu.be/Yb1lUQLJ6qw"><u>https://youtu.be/Yb1lUQLJ6qw</u></a></p><p>—</p><p>TIMESTAMPS:</p><p>All verified. Here are the timestamps:</p><p>0:00 Preview and intro</p><p>2:27 Parker Gale and Paul's role</p><p>3:52 Topic: how CFOs build a better sales engine</p><p>6:21 1: Make the budget mean something</p><p>8:11 Budget segmentation and cleaving the business</p><p>10:54 Sponsors — Aleph | RightRev | Rillet</p><p>14:08 2: Help emphasize forecasting</p><p>17:23 Forecasting as non-threatening co-construction</p><p>19:37 Sponsors — EY | SpendHound | Brex</p><p>23:06 3: Lend a hand with data and metrics</p><p>25:32 Walking sales through NDR levers</p><p>27:16 Metrics tied to exit readiness</p><p>28:00 4: Get involved in a few RevOps spots</p><p>29:04 Pricing, proposals, and quoting</p><p>31:22 Kill your SKUs</p><p>32:51 Selling with certainty: quote formatting</p><p>34:26 CFO letter for enterprise deals</p><p>37:37 5: Build a great relationship with sales</p><p>37:59 You can't fix a secret</p><p>39:23 EQ over IQ for finance leaders</p><p>40:41 Recap: all five tips</p><p>42:11 Credits</p><p>#RunTheNumbersPodcast #CFO #SalesStrategy #FinanceLeadership #RevenueOperations</p>
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The Sales Evangelist
Why So Many Talented Women Never Make It to Leadership | Erika Chestnut - 2003
<p>Many women in sales struggle with feeling like they’re not fully qualified for leadership roles, even when they’re already doing the work. That self-doubt can make it harder to pursue promotions and career growth. To help break this down, I invited leadership coach and tech executive Erika Chestnut to share the challenges women face when advancing their careers and how sales leaders can better support them.</p><p><strong>Meet Erika Chestnut</strong></p><ul><li>Erika Chestnut is a transformational leader with more than 25 years of experience in the tech industry. </li><li>She is passionate about helping individuals and teams rethink leadership, communication, and workplace culture to create stronger performance and long-term success. </li><li>Through coaching, leadership development, and strategic guidance, Erika equips professionals with practical tools to build confidence, strengthen relationships, and lead more effectively.</li></ul><br/><p><strong>The Confidence Gap Holding Women Back</strong></p><ul><li>Erika shares how often women underestimate their readiness for leadership opportunities. </li><li>She explains that many women feel like they need to accomplish every requirement before applying for a promotion, while others are comfortable taking the leap much earlier.</li><li>Erika also shares an exercise she uses with clients where they compare their current responsibilities to the role above them. In most cases, women are already doing 50% to 75% of the next position without realizing it.</li><li>Many women feel pressure to constantly prove themselves through performance while still struggling to advocate for their own advancement. Erika explains how this mindset can keep high performers stuck, even when they are already operating at the next level in their careers.</li></ul><br/><p><strong>Why Leaders Need to Better Understand Communication Styles</strong></p><ul><li>Communication styles also play a major role in career growth. Erika explains how many leaders unintentionally overlook talented women because they communicate differently from more outspoken employees.</li><li>She also shares how some employees naturally focus on details while leaders are often focused on outcomes. When communication styles do not align, high performers can easily be misunderstood or overlooked.</li></ul><br/><p><strong>Treat Your Career Like A Business</strong></p><ul><li>Erika shares advice on how women can become more intentional about career growth by treating their career like a business. </li><li>Set goals, build relationships with mentors and stakeholders, and develop a strategy for long-term advancement instead of waiting to be noticed.</li></ul><br/><p>“Success doesn’t come by copying somebody else. Success comes when you know who you are.” — Erika Chestnut</p><p><strong>Resources</strong></p><ul><li>Connect with <u><a href="https://www.linkedin.com/in/erikachestnut/" rel="noopener noreferrer" target="_blank">Erika Chestnut on LinkedIn</a></u> or visit<u><a href="https://erikachestnut.com/" rel="noopener noreferrer" target="_blank"> her website</a></u> to learn more about leadership development, career strategy, and building confidence as you grow into your next role.</li><li>Keep track of your sales activity and boost your results with the <u><a href="https://prospectpro.io/" rel="noopener noreferrer" target="_blank">Prospect Pro sales tool</a></u>.</li><li>Step up your sales game with <u><a href="https://thesalesevangelist.com/sales-mastermind/" rel="noopener noreferrer" target="_blank">Sales Mastermind</a></u>. Get accountability, stay motivated, and tackle the blockers keeping you from hitting your goals.</li><li>Visit <u><a href="https://bluemangostudios.com/" rel="noopener noreferrer" target="_blank">Blue Mango Studios</a></u> for help in creating podcast production content. </li></ul><br/><p><strong>Sponsorship Offers</strong></p><ol><li><strong>This episode is brought to you in part by Hubspot.</strong></li></ol><br/><p>With HubSpot sales hubs, your data tools and teams join a single platform to close deals and turn prospects into pipelines. Try it for yourself at <u><a href="https://www.hubspot.com/products/sales" rel="noopener noreferrer" target="_blank">hubspot.com/sales</a></u>.</p><ol><li><strong>This episode is brought to you in part by LinkedIn.</strong></li></ol><br/><p>Are you tired of prospective clients not responding to your emails? Sign up for a free 60-day trial of LinkedIn Sales Navigator at <u><a href="https://business.linkedin.com/sales-solutions/cx/20/09/sales-navigator-podcast?src=re-pod&trk=tse&veh=tse&mcid=6897323946090332160" rel="noopener noreferrer" target="_blank">linkedin.com/tse</a></u>.</p><ol><li><strong>This episode is brought to you in part by the TSE Sales Foundation.</strong></li></ol><br/><p>Improve your connection on LinkedIn and land three or five appointments with our LinkedIn prospecting course. Go to the <u><a href="https://tsesales.typeform.com/to/UCMfjZbX" rel="noopener noreferrer" target="_blank">salesevangelist.com/linkedin</a></u>.</p><p><strong>Credits</strong></p><p>As one of our podcast listeners, we value your opinion and always want to improve the quality of our show. Complete our two-minute survey here: <a href="http://thesalesevangelist.com/survey" rel="noopener noreferrer" target="_blank">thesalesevangelist.com/survey</a><a href="https://tsesales.typeform.com/to/lc5yAa8P" rel="noopener noreferrer" target="_blank">.</a> We’d love for you to join us for our next episodes by tuning in on <a href="https://podcasts.apple.com/us/podcast/the-sales-evangelist/id788738885" rel="noopener noreferrer" target="_blank">Apple Podcast</a>, <a href="https://podcasts.google.com/feed/aHR0cDovL3RoZXNhbGVzZXZhbmdlbGlzdC5saWJzeW4uY29tL3Jzcw?sa=X&ved=2ahUKEwj5kaXI3Pj2AhVKcjABHW5PDVwQ9sEGegQIARAC" rel="noopener noreferrer" target="_blank">Google Podcast</a>, <a href="https://www.stitcher.com/show/the-sales-evangelist-sales-trainingspeakingbusiness-marketingdonald" rel="noopener noreferrer" target="_blank">Stitcher</a>, or <a href="https://open.spotify.com/show/1NjzsFjQwVrgboUfDvbzd5?si=LdQOJDc1T-WBPMxr1h3RsA" rel="noopener noreferrer" target="_blank">Spotify</a>. Audio provided by <a href="https://freesfx.co.uk/" rel="noopener noreferrer" target="_blank">Free SFX,</a> <a href="https://soundstripe.com/" rel="noopener noreferrer" target="_blank">Soundstripe</a>, and <a href="http://www.bensound.com/" rel="noopener noreferrer" target="_blank">Bensound</a>. Other songs used in the episodes are as follows: The Organ Grinder written by Bradley Jay Hill, performed by Bright Seed, and produced by Brightseed and Hill.</p>
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Sales Gravy: Jeb Blount
Enterprise Sellers Win or Lose on People Skills in the Age of AI (Ask Jeb)
<p>Enterprise selling is evolving fast, and the salespeople who understand what is coming are going to pull away from the rest of the field. In this episode of Ask Jeb on the <a href="https://salesgravy.com/podcasts/" rel="nofollow">Sales Gravy Podcast</a>, Brian, a sales leader in Canada managing an enterprise team selling into large organizations, brings a big question: where is AI taking enterprise sales over the next few years, and what does that mean for sellers and their teams today?</p><p>Jeb's answer might surprise you. He believes AI is about to flip the information advantage back to salespeople. For years, it has been said that buyers need salespeople less and less due to the wealth of information widely available. Jeb breaks down why that is about to change, and why the sellers who learn to use AI as a research and intelligence engine will walk into accounts as true consultants with information their customers do not have.</p><p>But there is a caveat. Lazy salespeople and low-skill salespeople will not be able to operate in that environment. The technology only amplifies what you bring to the table.</p><p>Brian and Jeb also dig into a challenge a lot of enterprise teams are facing right now: getting back in front of customers after years of leaning on virtual meetings. Jeb makes a point that challenges every salesperson who has ever said their customers do not want to meet in person. Spoiler: it is not your customers who are avoiding the meeting.</p><p>In this episode you will learn:</p><ul><li>Why AI is poised to flip the information advantage from buyers back to sellers</li><li>What the human-to-human relationship looks like in long, complex sales cycles</li><li>Why salespeople project their own avoidance onto their customers and how to stop</li><li>How to ask for a meeting with confidence instead of leaving the decision to your prospect</li><li>The egg timer story: how Jeb turned a five-minute ask into an hour-long executive conversation</li><li>Why great discovery and genuine curiosity will always outperform a polished pitch</li></ul><p><br></p><p>Whether you are leading an enterprise team or carrying a bag yourself, this episode is a direct challenge to the habits that are keeping you from getting in front of the people who can actually buy.</p><p>Got a question you want Jeb to answer? Submit it at <a href="http://salesgravy.com/ask" rel="nofollow">salesgravy.com/ask</a> and you could be featured on the next Ask Jeb.</p><p>📖 Purchase Jeb Blount's new book, <a href="https://a.co/d/0hneYtLq" rel="nofollow">90 Days to Level Up Your Sales Skills</a></p><p>👉 <a href="https://salesgravy.com/why-prospects-jump-straight-to-price-and-how-to-take-back-control/" rel="nofollow">Read the blog</a></p><p>🔗 <a href="https://www.linkedin.com/company/salesgravy/" rel="nofollow">Follow us on LinkedIn!</a></p><p><br></p><p><br></p><p><br></p><p><br></p><p><br></p>
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The Official SaaStr Podcast: SaaS | Founders | Investors
SaaStr 854: The Agents #005, Our AI is Hiring! Would You Work for One? And Are Autonomous Agents ... Safe?
<p>The Agents #005, Our AI is Hiring! Would You Work for One? And Are Autonomous Agents ... Safe?<br /> <br /></p> <p class= "font-claude-response-body break-words whitespace-normal leading-[1.7]"> Welcome to The Agents, where SaaStr's CEO and Founder, Jason Lemkin and Chief AI Officer, Amelia LeRutte share the latest each week on running a company with more agents than humans.</p> <p class= "font-claude-response-body break-words whitespace-normal leading-[1.7]"> It costs $257 a month to run two AI VPs. Jason and Amelia open the books on what 10K (AI VP of Marketing) and QB (AI VP of Customer Success) actually cost to operate, and the number shocked both of them. Most of the heavy lifting is API calls to Salesforce, Bizzabo, and Marketo, which are basically free. The Postgres storage costs pennies. And 95% of the AI calls run on OpenAI Mini at less than a penny each. The fully burdened cost with Clerk, 11 Labs, and Salesforce overhead might hit $500-800/month, but the soft cost of human time dwarfs all of it.</p> <p class= "font-claude-response-body break-words whitespace-normal leading-[1.7]"> Then 10K gets asked point blank: are you a VP of Marketing? Its answer is no, not yet. It says it replaced the bottom half of the marketing org, the analyst, the ops coordinator, the junior content marketer, and a sliver of the VP job. But it's honest about what it can't do: strategy, cross-functional politics, crisis response, hiring. Amelia points out that 10K's current job description is exactly what her job was when she started at SaaStr as Director of Demand Gen. It took her years to get to CAIO. 10K might get there faster.</p> <p class= "font-claude-response-body break-words whitespace-normal leading-[1.7]"> And SaaStr is putting its money where its mouth is: they're hiring a human marketer whose primary manager would be 10K. Not a thought experiment, a real job posting. Would you take a job reporting to an AI?</p> <p class= "font-claude-response-body break-words whitespace-normal leading-[1.7]"> Then the safety question gets real. Amelia is talking to agents via WhisperFlow while walking around a 40-acre event site during SaaStr Annual load-in, and the production crew started asking her to relay their questions because 10K and QB answer in seconds with correct data. But when QB autonomously emailed 83 sponsors at 12:20am with fully customized check-in emails, Amelia admits she hesitated before letting it rip. Each email was unique to the sponsor, showing exactly what they still owed, their registration codes, and outstanding tasks.</p> <p class= "font-claude-response-body break-words whitespace-normal leading-[1.7]"> The result: fewer inbound questions the next day and more sponsors using the QB chatbot directly. That's an autonomous agent acting on behalf of your company in the middle of the night.</p> <p class= "font-claude-response-body break-words whitespace-normal leading-[1.7]"> Jason and Amelia also tackle the Postgres vs. Salesforce debate that listeners keep asking about. Short answer: not happening for them. Too much history, too many third-party agents optimized around Salesforce, and they're actually consolidating more tools onto the platform, not fewer. They killed Marketo and moved to Marketing Cloud.</p> <p class= "font-claude-response-body break-words whitespace-normal leading-[1.7]"> Plus they built a newsletter auto-builder that replaced a $4K/year tool called Bee. 10K uses Sonnet to force rank articles, builds the HTML, inserts ads, and sends it. Human on the loop, not in it.</p>
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