Kaitlyn Stephens, CMP, PMP

Went to dinner tonight with 15 GTM leaders in NYC. Here’s a brain dump of learnings: - Email replies are getting worse & worse. Two teams stopped email outreach completely, replacing it with LinkedIn and cold calling - Nooks was shouted out as a great tool for cold calling - Teams getting the best results from cold calling invest in training their teams on scripts, role playing with AI, and role playing with other reps - Video messages work well to follow up after cold calls (shameless plug for Sendspark) - GTM teams want to use more AI, but are inundated with choices (so many new companies!), and poor rep adoption with new tools. - Lots of skeptiscm over how much AI adoption there really is vs what you see on LinkedIn - Also skepticism on whether AI SDRs really work for cold outbound (do they?) - Teams getting good results from AI outreach are using their own data, like conference attendee info, product usage, and historical conversations. They are also keeping humans in the loop (for now) - 1st party data is also more future proof to ensure your outreach will be unique compared to everyone else doing AI outreach - For inbound, Spara is doing cool stuff around qualifying leads and booking meetings with AI. Seems like Intercom’s Finn agent, but 100% focused on sales. Overall, great time! Thanks for hosting {Jon} Studham, David Walker, & Cory Pitt And now it’s late and I’m off to bed… 🥱 but at least I can set my alarm for 8:30am EST instead of 5:30am PST without feeling behind. See ya tomorrow!

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One of the toughest enablement roles? Being the only enablement person in the company. This came up at Sales Enablement Summit Chicago, where Emily FitzPatrick, CPC and Scott Konkol shared their experiences scaling enablement from a team of one to a full-fledged function. And let’s be real, if you’ve been in this position you know it’s not for the faint of heart (or for anyone who enjoys a quiet inbox). One person, tasked with onboarding, training, coaching, content, process optimization, tech stack decisions… and somehow proving impact along the way. No big deal right 😅 If you’re in this boat, here’s what was discussed about what can make or break your success👇 🚩 Trying to fix everything at once When you’re a team of one, your job isn’t to solve every problem overnight. Focus on the biggest revenue blockers first, whether it’s reducing ramp time, fixing messaging gaps or enabling managers to coach better.   🚩 Working in a silo Enablement doesn’t work if it’s just an “extra” function sitting on the sidelines. The best enablement leaders bring sales, CS, and RevOps into the conversation early. The easiest way to earn a seat at the table? Show how enablement moves key business metrics. 🚩 Building programs that don’t match how reps actually sell No one needs another 30-page playbook that never gets opened. If your training and resources don’t reflect real deal cycles and rep workflows, they’ll be ignored. Partner with top-performing sellers to make enablement relevant.   🚩 Tracking effort instead of impact It’s easy to measure how many trainings you ran. But the real question is: Did it change behaviour? The best enablement teams track: - Ramp time reduction - Increased win rates - More multi-threaded deals - Higher quota attainment Scaling enablement isn’t about doing more, it’s about doing what matters. Prioritize ruthlessly, align with revenue goals, and prove your impact. Be sure to give Emily and Scott a follow - they're both awesome (and they’ve been in the trenches). #salesenablement Sales Enablement Collective

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I have some answers... Yesterday Asghar M. and I sat down at Salesforce Tower with Zach Ciliotta-Young, CRO at Slack. We asked the big question from my last post. How do you define success metrics for Slack and build a business case that wins hearts and budgets? My takeaways Slack is becoming our operating system for work. Not another tool to click into, but the layer where HR, CRM, Gong, marketing and approvals all come together. Success lives in the flow of work. Think agents that brief you, chase leads, build canvases, collect forecasts and nudge owners when something stalls. The business case should start simple. Shift spend by consolidating licenses. Then show how Slack improves the ROI of tools we already own. What to measure. 1. Adoption in the flow • % of approvals done in Slack • % of forecast updates submitted via Slack workflows • % of team that never needs to log into system X 2. Cycle and quality gains • Lead response and coverage, including agent handled leads • Time to create exec briefings or event business plans 3. Revenue impact • Pipeline created by agent follow up • Win rate lift when channel knowledge is captured by Channel Expert • Conversion lift on “work objects” surfaced in Slack 4. Cost realignment • Licenses reduced or downgraded because work now happens in Slack • Training and context switching time saved For our world of 90 events a year, the killer demos will be event channels with embedded workflows, canvases that auto-build executive summaries, and an SDR agent that never lets a lead go cold. Zach Ciliotta-Young thanks for the time, we got a lot out of it, I hope the above adequately reflects our conversation. Looking forward to working with Nina Mello to build out the business case. If you've rolled out Slack in an agentic way, what did you track that actually convinced your board? Any metrics I should add to this list? #slack #agenticAI Slack

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It's event season. And we as vendors want to get those prospects talking to us, but remember they have trauma from past events... So stop treating event attendees like Leads. Start treating them like people with trauma. Your prospects haven't forgotten being treated like walking badges to be scanned. They remember every empty promise, every salesperson who talked over them, and every "personalized" follow-up that proved you weren't listening. This isn't just annoying to them, it's a breach of professional trust that makes your brand instantly forgettable in a sea of competition. How I have borken the cycle: 𝗔𝘁 𝘁𝗵𝗲 𝗲𝘃𝗲𝗻𝘁: • Start by asking about THEIR specific challenge • Really listen to their problems vs jumping in with solutions • Ask what would the impact be to the business/them if the problem is solved • Share a takeaway resource they can use tomorrow, whether they buy from you or not    𝗔𝗳𝘁𝗲𝗿 𝘁𝗵𝗲 𝗲𝘃𝗲𝗻𝘁: •  Follow with specific challenge & language they mentioned when they stopped by • Provide content that helps them see how their world would be if they solved their problem • Share assets that highlight how peers/influencers/thought leaders are thinking about the space • Focus on expanding and delivering value, not starting the sales process It's about consistently demonstrating value and respecting their experience. This takes you from "another vendor" into a trusted resource they WANT to engage with long after the conference ends.

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Two killer product marketing roles just opened up— and I can personally vouch for both hiring managers. ⭐ Planning Center | Product Marketing Manager Chris Elliott is building a values-led team in the church tech space. They need a T- or π-shaped PMM who can lead go-to-market for 4–6 products and bring depth in content or demand gen. → PLG / No sales team to support. → Sabbaticals, every-other-Fridays off, and 95% health coverage. → Remote first with team meetups in Carlsbad, CA. I’m doing an AI workshop with Chris and his team at the end of the month, and they’re incredibly thoughtful in the way they approach their work. 💡 --- ⭐ MoEngage | Lead Product Marketing Manager, North America Aditya Vempaty says this one comes with the keys to the GTM engine. Messaging, launches, sales alignment, campaign input—you’ll lead the charge, not just “support” the team. → Strong emphasis on storytelling and cross-functional collaboration → Deep customer + sales integration, not just decks and docs → Remote-friendly (bonus if you’re in SF) Aditya helped me shape our latest brand-demand survey strategy—and his take on GTM and leadership is 🔥. 📎 Full JDs are in the comments!

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Event satisfaction just dropped 8% and it’s not attendees leaving..... ... it’s your tech stack fragmenting the experience. According to Forrester’s Q1 2025 “State of B2B Events” survey, 46% of large orgs juggle six or more disconnected event platforms (and only 20% actually integrate them into their marketing ecosystem). Attendees today expect seamless, personalized interactions from registration to follow-up. When your tools don’t share data, every touchpoint feels disjointed, and your ROI remains a mystery. The cure? Consolidate. Prioritize data orchestration over feature overload. Streamline your stack so one unified platform powers registration, engagement tracking, on-site services, and post-event analytics. The result: happier attendees, clearer insights, and measurable ROI. #EventMarketing #MarTech #B2BEvents #TechIntegration #ROI

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Run events like ops. Track them like pipeline. If you’re still talking about events like they’re special one-offs or fluffy brand plays... especially in Saas... you’re missing it. They’re programs. They’re part of your GTM motion. They should earn their spot in the pipeline. Treat them like it. 👏 👏 #MarketingForTech #GTMStrategy #EventTech #NotJustLogistics

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Two things are happening in GTM right now that keep bringing me back to the relationship between practitioner communities and products: 1️⃣ AI features add a depth to product design that makes proximity & deep empathy for your end user's needs more critical than ever. It's one thing to make a slick UX based on understanding the task that someone is trying to accomplish- it's another to understand how AI could change the user's relationship with their work, intuitively handle tasks that would previously have gone to the user, and create products that show up as teammates vs interfaces. The empathy & expertise needed to deliver powerful and intuitive AI products can't come from an ivory tower. Great product teams will spend more time with their user communities and find the AI power users to imagine & spec out what's next in their domain. 2️⃣ The breadth & pace of innovation has made it impossible to own every aspect of solution development- companies have to go to market with partners, and the communities of entrepreneurial, passionate & professional partner leaders are thriving. Partnership Leaders, Ultimate Partner®, and Baptie & Company- these communities are rising to meet the critical moment in the market. Repeatable playbooks to make successful partnerships, resources and mentorship- the exchange of ideas across the network of GTM experts has never been more vital. I'm grateful to Asher Mathew, Vince Menzione and Rod Baptie and so many others for pouring so much of themselves into building community. I'm extremely appreciative of AI + partnership experts like Joe Estes, Munish Khetrapal, Abhishek Reddy, and Stuart Francis engaging with WorkSpan to design next gen AI Teammates. Partnership leaders have always been some of the most creative and entrepreneurial people in GTM. The best ones are already bringing AI into their practice. Partnerships will never be the same.

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💨 Last month I had the pleasure of chatting with the Marketing AI Pulse Community here in Atlanta. (Ok, technically, it was in Peachtree Corners - my ITP self feels the need to point that out 🧭 - still, you get my point!) ✨AI is rapidly changing not only the way software is built and serviced, but the very way it's bought and sold. (See our Buyer Behavior Report for further validation: https://lnkd.in/e2FabENn) Three things I’m seeing from my perch here at G2: 1️⃣ Buyers want real-time answers. They’re not hanging out in long discovery cycles anymore. They’re getting to a shortlist fast—much faster than the “old” way of buying and selling. 2️⃣ They want validated information, not vendor claims. Real customer experiences matter more than polished messaging. People are actively searching for proof from peers before they make a decision. 3️⃣ The buying cycle is shrinking. Especially with AI. Buyers don’t just want to hear that it exists—they want to know how it integrates and how they can start using it immediately. ROI isn’t a future promise anymore; it’s an expectation. Thanks to Aby Varma for having me out! Always a good day when you get to sit next to Sangram Vajre! 😄

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AbM iS DeAd 🤣 Stop it. If anything is true, it's that we're seeing ABM evolve. From a marketing project into a strategic GTM lever. Uniting GTM teams around a specific GTM goals. • Upsells • Cross-sells • Retention • Enterprise expansion • Vertical expansion • Horizontal expansion • Partner expansion • Product launches • Market expansion At any given time your company is focused on at least one or more of these. And the smart teams are using ABM is the uniting factor to help GTM teams achieve these. Don't get distracted by the old narrative still pushed by legacy ABM platforms.

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There’s a moment every GTM leader remembers. The one where a customer churns... and you realize you saw it coming. The champion stopped showing up to calls. Product feedback slowed. Decision-makers went quiet. And instead of confronting it, You focused on expansion plays. Optimized email sequences. Refreshed the QBR deck. Hoping to signal value without having to ask the hard question. I’ve been there. And I’ve seen high-performing teams fall into the same trap. The catch is, most churn isn’t about features. It’s not about pricing. It’s not about competition. It’s about 𝗺𝗶𝘀𝗮𝗹𝗶𝗴𝗻𝗺𝗲𝗻𝘁. Misalignment between what the customer needed vs. what the business prioritized. Misalignment between what was promised vs. what was delivered. And misalignment between how success is defined internally vs. externally. And that misalignment builds quietly, until the only path left is the exit. Here’s where most GTM teams go wrong: They don’t lack data. They lack confrontation. They see the signs. But they hesitate to act because raising uncomfortable truths internally can feel political. And bringing them to the customer can feel risky. So they wait. Until churn makes the conversation unavoidable. But at that point, the trust is already gone. Here’s the shift I push for in every team I work with- Retention isn’t a lagging metric. It’s a real-time indicator of how honest you’re willing to be, early, and often. The best GTM operators know this: → Comfortable conversations preserve the moment. → Uncomfortable conversations preserve the relationship. And the difference between those two is millions in lost revenue over time. ... “𝘽𝙚 𝙠𝙞𝙣𝙙 𝙩𝙤 𝙤𝙣𝙚 𝙖𝙣𝙤𝙩𝙝𝙚𝙧 𝙖𝙣𝙙 𝙡𝙞𝙛𝙩 𝙨𝙤𝙢𝙚𝙤𝙣𝙚 𝙪𝙥”

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