☕ AI and your rev org

Prompts matter. July 28, 2026 View Online | Sign Up | Shop Presented By It’s Tuesday. Earnings have some companies looking like high schoolers after landing their first paycheck: Money is coming in, but it’s being spent at an even faster clip. Tesla posted a 26% YoY revenue increase, while Alphabet generated 24%, only for both to be on the outs with investors for being in the red due to AI spending. In today’s edition: The power of custom prompts Bonusly Q&A Can AI supercharge GTM? —Layla Ilchi, Erika Bradbury, Jordyn Grzelewski SALES TECH AI playbook Francis Scialabba As AI automation touches every facet of the sales funnel, more focus is being put on specific AI use cases. In a perfect world, AI tools and agents streamline workflows and simplify tasks, but behind any action is a prompt; many leaders think reps should spend more time curating what they put into AI engines to get the best results. “People that are really good at leveraging the best prompting techniques are producing outsized productivity compared to people that don’t know how to use AI prompts,” said Shankar Ganapathy, founder at Boomerang, an AI-powered intelligence platform. Sticking to the playbook As more companies infuse AI into their tech stacks, CROs and Rev Ops leaders are tasked with helping sales reps get the best out of the technology. While establishing an AI playbook of sorts gives the team a sense of direction, Ganapathy thinks sales reps should feel free to experiment with prompts to see what works best for them as the AI landscape evolves. “We are seeing more and more companies standardize playbooks that are centrally run by the team, so reps can ideate to experiments, but then the moment something is working, it’s taken over by a Rev Ops or a GTM engineer, and it’s deployed as standardized play,” he said. Kuber Sharma, senior director of product marketing at enterprise automation software platform UiPath, says GTM teams should deploy this kind of AI playbook, especially as older generations have had a harder time adopting AI tools. “Salespeople are typically in their profession for a very long time and now we are running into people who’ve been doing the same thing for 20 years, but the way of doing this has changed so much,” Sharma said. “You have to teach the old dog new tricks. Classically you say you can’t teach an old dog new tricks, but having a library really helps that onboarding journey.” Keep reading here for why clean data matters.—LI        Sponsored By Outreach Cloudy with a chance of closed deals How’s the forecast looking in your pipeline? Hard to say? You can see into your pipeline a little more clearly by using an agentic AI revenue platform like Outreach. Outreach helps revenue leaders run tighter forecast calls by turning pipeline signals into clear actions that improve predictability. Tune in to their on-demand webinar featuring Outreach experts to learn: why visibility gaps contribute the most to deal risk, missed targets, and wasted selling time what separates reactive forecasting cultures from proactive, predictable ones how Outreach Forecasting gives teams the confidence and clarity they need to consistently deliver results See if you’ve got clear skies ahead—or if you need to chase away some storm clouds. Forecast with confidence. SALES TECH Rewiring Revenue Illustration: Shannon May, Photos: Unsplash, Adobe Stock Revenue Brew spoke with Bonusly’s senior revenue architect Amani Phipps via email about using AI in the sales org ahead of our latest IRL event. These responses have been edited for length and clarity. What’s the biggest misconception sellers have about AI? The biggest misconception is that AI is already better than it actually is, and that it’s good at basically everything. That shows up as two failure modes I see constantly in change management, when I’m trying to get people across an organization to actually adopt a tool instead of just poking at it. The dangerous one is trusting it too much and turning your brain off. AI often has poor taste and judgment. It’s weak on strategy, because strategy means weighing a pile of variables at once and knowing which ones matter right now, in your specific situation, while that situation keeps shifting under you. It’s strong on deterministic work: clear input, clear output, one right way to get there. The other failure mode is treating it like a finished, all-knowing product instead of what it actually is: a general-purpose tool. Ask Claude, GPT, Perplexity, whatever model you want, to draft an email, and it’ll draft you an email. Ask it to draft that email with real taste, in your voice, with your read on what actually matters in that specific deal, and it can’t, not until you’ve taught it who you are and how your organization thinks. Swap the model and nothing changes. The context is what changes the output. Where do you see the most resistance when teams try to adopt AI into their revenue workflows, and how do you move past it? The resistance breaks into a few areas, but two have come up consistently: trust and change management. Trust is the bigger one day to day. Almost everyone I talk to has felt AI’s presence at work by now, whether that shows up as excitement, dread, amplification, or confusion in work they’re already doing. Read on for how to maintain authentic, human-led relationships.—EB        Sponsored By Outreach Can you see clearly now? If your pipeline is looking a little blurry, then Outreach has something that could help. Outreach Forecasting helps you see where your period is trending so you can spot gaps sooner. Watch their on-demand webinar to learn more about why visibility gaps are such a big deal. REVENUE STRATEGY & LEADERSHIP Supercharge my GTM Jim Hilbert Jim Hilbert, chief revenue officer of agentic AI studio Freehand, is no stranger to the CRO role, having headed up revenue multiple times over his decades-long career in the B2B SaaS world. Thanks to AI, the last few years have brought some of the most consequential changes to go-to-market organizations he’s seen. “More so than ever for me, I have this thing on my shoulder: ‘Jim, you’ve got to go faster on AI,’” Hilbert told Morning Brew. “I’ve just hired three sellers in the last month, which normally would have taken me six months, [and] in two weeks they were able to get on the phone and start having conversations with customers, just by going through the onboarding that we built through AI…That’s a huge change.” Freehand (formerly Pando) launched in February. The San Francisco-based startup uses AI to automate supply chain spending and procurement. With AI dramatically speeding up the pace at which the revenue organization operates, Freehand recently launched a growth expansion team and is eyeing new geographies and markets beyond freight. Freehand says it’s already working with Fortune 500 clients, and can cut manual procurement and sourcing work by up to half and reduce reconciliation and accounts payable cycle times by up to 90%. “Our go-to-market is very focused on very, very large strategic enterprises,” Hilbert said. “With AI, this year I’m also starting to go down into the lower enterprise mid-market space and really getting focused on having more logos as well as just the largest brands on the globe.” This conversation has been edited for length and clarity. How have AI and automation changed your job? It’s mostly just given me productivity gains to-date. All the things that I would work with my sales or rev ops teams on, they’re now using AI to get better dashboards for me. We can focus more on the different segments, whether it’s SMB, mid-market, enterprise, strategic, what’s working, what’s not working, do analysis of the [total addressable market] better than we’ve ever had before. Keep reading here for Hilbert’s take on retaining employees.—JG        active pipeline Stat: 9%. That is the low end of how much Verizon expects to grow its free cash flow after inking a $1 billion fiber deal with Google. (Reuters) Quote: “In AMC’s entire 106-year history, there has never been a quarter like this one.”—AMC CEO Adam Aron during the company’s latest earnings call (Yahoo Finance) Read: The creator economy has a new middle class. (Bloomberg) Comin’ down the pipe: Can’t get any real visibility into your pipeline? Outreach Forecasting can help. Check out their on-demand webinar to see how they can help you forecast with confidence and clarity.* *A message from our sponsor. Inside 260 Sample Sale’s new store concept (Retail Brew) Founders Assaf and Ariel Azani told Retail Brew about the cult-favorite sample sales’ rebranding into a permanent boutique known as Store260. Three IT strategies for implementing AI hiring tools (IT Brew) As employers turn to AI tools to sift through a flood of résumés and find qualified candidates for IT jobs, many are designing “knockout criteria” to help determine who gets an interview. Aetna’s CMO on the plan to win back providers’ trust (Healthcare Brew) Health insurers are eager to regain patients’ and providers’ trust, but they have a long road ahead. Share the Brew Share the Brew, watch your referral count climb, and unlock brag-worthy swag. Your friends get smarter. You get rewarded. Win-win. Your referral count: 0 Click to Share Or copy & paste your referral link to others: revenuebrew.com/r/?kid=953893c8 Level up your career with these resources from our sponsors! Are your AI tools all sprawled out? Deploy purpose-built AI agents instead What separates good companies from great ones starts long before the exit. Subscribe to Founder Brew today. Written by Layla Ilchi, Erika Bradbury, and Jordyn Grzelewski Was this email forwarded to you? Sign up here. Get smarter in just 5 minutes Business News: Morning Brew Tech & AI News: Tech Brew Markets News: Brew Markets Real Estate News: The Playbook Money & Career: Bossy Take The Brew to work Marketing Brew CFO Brew HR Brew IT Brew Retail Brew Healthcare Brew Founder Brew Interested in podcasts? Check out ours here. ADVERTISE//CAREERS//SHOP//FAQ Update your email preferences or unsubscribe here. View our privacy policy here. Copyright © 2026 Morning Brew Inc. All rights reserved. 22 W 19th St, 4th Floor, New York, NY 10011