Ryan Debenham

As CEO of a Customer Experience company, I’m always on the look-out for amazing customer experiences. Airtable is, hands-down, one of my favorites. Airtable is an $11B low‒code platform to build next‒gen apps. I first learned about Airtable 7+ years ago, when I met Howie Liu and Andrew Ofstad over coffee. I was blown away by the idea that the spreadsheet, a staple of productivity, could be re-invented to operate just like a database, the staple for app-building. They’ve since grown to an $11B unicorn, and the product is as amazing as ever. The idea that anyone can build an app without having to know how to code, is a beautiful concept. My wife sits on the Board and runs admissions for a pre-school in our area. When she was looking for ways to automate and speed up admissions processes, I suggested she build out an admissions base in Airtable. It now works like a charm, and she processes dozens of applications every year, from school tours to tuition fees to class registration. All without writing a single line of code 🤯! I was super delighted to see Airtable leveling up their customer experience yet again with their launch of the most advanced generative AI agent for customer support ( 👀)... I’ve asked it really complex questions like how to calculate a specific formula, and it worked like a charm 🤯. But I’m not surprised! Airtable has been at the forefront of technology and customer experience, and now they’re at the forefront of AI, both in their own product, and through their best-in-class generative AI agent. Love. To. See. It 👏. PS: Kudos to my friend Mikayla LaRosa who runs AI programs at Airtable, who is an absolute visionary when it comes to AI 👏🏾! #ai #genai #technology #transformation #databases #customerexperience #cx #openai #gpt #chatgpt

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🔴 You can't outrun churn by forcing CS teams to drive revenue through upsells, cross-sells, and referrals. Startups are missing are missing the forest for the trees. Chasing a 120% NRR? Good luck if you're bleeding customers left and right. If you were as obsessed with stopping the bleeding as you are with hitting sales quotas, you'd be far better off. 🤯 Here’s the brutal truth: even the best CS team can't save you if have a high churn rate. Reaching a 1-2% monthly churn rate takes discipline, effort, and consistency. Many startups struggle with this because they: ❌ Don't invest in better discovery. BANT and MEDDIC is not the answer. ❌ Think Customer = Company. Companies dont buy, people do. ❌ Confuse Initial Company Profile for Ideal Company profile. ❌ Deliver customer onboarding are like a 42km hurdle race. ❌ Rely too heavily on Buyer Personas and not JTBD. ❌ They lack the courage to stick 6 months to a plan. ❌ Build ICP from a acquisition pov, not retention. ❌ Fail at refining the Initial Company Profile. ❌ Don't delivery recurring outcome/values. ❌ Have short visioned sales incentives. ❌ Can't say no to bad-fit customers. 💡 Why should you focus on reducing churn? ✅ Lost referral opportunities. ✅  It shrinks your target market. ✅ Drives up your CAC as you fill up the sales funnel. ✅ A 5% increase in customer retention = 25% to 95% increase in profits. ✅ High churn rates can tank your startup’s valuation. ✅ Compounding revenue loss. The bottom line? 💡 You can’t outrun churn. Prove me wrong. PS: 👇 Do you think high churn rates are more a product issue or a sales issue? What strategies have you found effective in reducing churn? #customersuccess #saas #startups #careercoaching  #CS #CSM #SuccessHacks #customersuccessmanager #saas  

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This week, I interviewed a strong candidate for a senior GTM leadership role. In a short yet impactful 25-minute conversation, they nailed the art of "sharp-shooting" their message -- landing perfectly at the intersection of what they wanted to share and what I cared about (see pic).  We would've easily taken an hour with a less focused approach. That sweet spot—the center of the Venn diagram—is where true connection happens, creating impact without wasting a moment. Communication that is effective, productive, and ultimately, more human. What does "operating at the center of the Venn" look like in practice? Here are three reminders I try and live by as a GTM executive: - When speaking to a CFO: Focus less on the emotive aspects like brand and more on the empirical—think linking GTM strategy to contribution to revenue and ROMI. - When speaking to a Board: Highlight alignment wins across all areas of GTM - sales, alliances, marketing etc., not just the 'engine room' operational successes. - When speaking to your team: Connect the Big Company Big Rocks directly to their work, making it relevant and meaningful to what they’re driving today. No matter the audience, the center of the Venn is where clarity meets connection. Wishing everyone a meaningful and thoughtful Thanksgiving!

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2-weeks into a successful POC, this client ramped from 40 to 440 instances. THE POC SUCCESS CRITERIA: 1️⃣ Cost Savings 2️⃣ No Service Disruption 3️⃣ Easy to use. THE POC TEST RESULTS: ✅ Reporting 68% Savings ✅ Zero Issues (Even went on PTO) ✅ Easy Management via Terraform 🤔Think they’ll buy❓ 😀 Wouldn’t you❓ LET US HELP YOU SAVE, TOO: https://lnkd.in/dsibkiKE #ec2 #aws #kubernetes #k8s #costoptimization #finops #gcp #googlecloud #SpotVM #GoogleCloudConsulting Xosphere FinOps Foundation

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My first job was at a company with 7 layers of management. It felt like washing dishes by hand - slow and inefficient. This kills output on small (<50 FTE) teams, even those within larger orgs. Let me explain: I run my company as a flat org. A single layer. Information flows freely, decisions happen at light speed. People have the obligation (not the option) to make important decisions within their domain. And, most importantly, we automate entire workflows with AI whenever possible. This is our 'Hobart moment' - a concept I borrowed from Tom Tunguz's brilliant analogy. Just as the Hobart dishwasher revolutionized kitchens, AI and a flat org structure revolutionized our business. Here's what a high-performance team looks like in 2024: - Flat and fast: We stripped away bureaucracy. Now, great ideas can come from anywhere, and they do. - Remote-first: Our team spans three continents. We fish for talent in the global ocean, not just the local pond. - Outcome-driven: We pay for results, not hours. It's amazing how productive people become when you trust them. - AI-first: We automate entire workflows with AI. Even if the output isn't perfect today, soon a new model will come out and with a single line of code the output will be better and 100x faster than any human. We have been able to go from product idea to revenue in weeks, not years (e.g. our Showback(TM) product, our FinOps consulting BU, etc). This isn't just about our success. It's about survival in the AI age. Companies clinging to old structures are like cafes still scrubbing plates by hand. Meanwhile, we're moving faster than ever, with a team that's lean, mean, and keen. TAKEAWAY: Even if you're at a large enterprise, you can transform your own team into a flat, fast moving, AI-first org. Are you in the "layers of management" or "flat as a pancake" bucket?

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When companies *openly* engage their employees in cutting costs and increasing revenue (w/o layoffs), there typically is a deluge of good ideas, hidden gems, low hanging fruit, invisible wastes, and hard to acknowledge, but ultimately important to face challenges. Which begs the question...why don't companies do this more often? Some ideas: - Leadership may not trust employees to contribute valuable ideas - Misalignment of goals between leadership and employees (principal-agent problem) - Employees may not feel safe sharing ideas if there isn’t psychological safety - Groupthink and confirmation bias - Short-term financial pressures. Incentive structures may reward short-term gains, making layoffs more appealing. - Sorting through numerous employee suggestions can feel overwhelming. But in many cases, there's an assumption that if these ideas haven’t already bubbled to the surface, or if people haven’t taken action, they simply don’t exist (or were not feasible, or something/someone was standing in the way). Paradoxically, if those ideas do emerge and lead to change, it could cast doubt on previous efforts, creating a reluctance to explore them in the first place.

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Top H1 takeaway from QBR's about our Rev Org: "We're an ecosystem, not a hierarchy." (h/t Alexandra B.) We collaborate, everyone's voice matters, and we strive to put people in roles they love so they can be madly successful. Hearing this statement was validation that what we are building in the Revenue Org at LibraryPass is unique, and scalable, and contagious. And we have roles coming soon! So if you're interested in being part of an ecosystem, let's chat. Here's to an even better H2!

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I'm a big proponent of AI and what it can do for software. But I've gotten so many AI written sales emails lately that all look the same. This is the latest: > Your commitment to seamless incident management and continuous improvement resonates deeply with my passion for driving efficiency and scaling operations. FireHydrant's mission to empower teams through automation and actionable insights aligns with my interest in enhancing business resilience and growth. This "AI-SDR" practice feels like a race to the bottom.

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I’m seeing a lot of products emerge to support outbound plays. Plays are “if-this-then-that” logic to automate an action (e.g. a sequence) when a trigger occurs (e.g. customer job change, website visit, etc.). As we work with larger outbound teams, I'm increasingly convinced that this is 𝐧𝐨𝐭 the best approach. Plays are are brittle, conflict with one another, and lack nuance. If real outbound could be modeled by a series of Plays, then we should be able to set up dozens of “if-this-then-that” rules and no longer need BDRs. AI is not needed for this -- it could've been done 8 years ago. Outreach even has an automation system called triggers for this use-case. At Bluebirds, our mantra is that AI should replicate how humans work. That is the exciting upside of LLMs -- to work like we do, but better. It takes an average BDR 6 months to ramp up on the nuance of prioritizing accounts, finding the best people to prospect into, and personalizing sequences well. Managers teach them with enablement material and real-time coaching as they’re doing actual outbound. There’s no substitute on-the-ground feedback. Reps need to build their outbound mental model, which Plays lack entirely. We think the future of Plays is Agentic. To us, that means the following: 1) Agents start with clear inputs on personas, target accounts, signals, and sequences. It should also be able to learn from all of your enablement material. 2) Agents then prioritize accounts, find the best people, and tee up personalized sequences for reps directly in your sales engagement platform. 3) Managers and reps coach the Agent in natural language, just like a BDR. 4) Agents improve on its approach to targeting and messaging in that moment, and also generalize your feedback to all future situations, codifying learnings as a memories. 5) Agents rack up a repository of memories and learn your unique outbound nuances over time, getting dramatically better just like your best BDRs. Unlike your best BDRs, Agents will always be there to serve your entire team. It doesn't care about getting promoted to AE or leaving the org. The future of BDR training is going to change dramatically. With well-executed Agents helping BDRs, I wouldn't be surprised if ramp time drops by 10x.

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It takes a pretty special human to say "yes" without hesitation. When I first joined Cin7, one of my immediate tasks was to build out a strategic upsell motion. I figured I'd dive in and establish the infrastructure, processes, and team—nope. We needed it yesterday. Initially, I thought we could equip all CSMs to handle it, but the pace of change was overwhelming, making it a tough environment for everyone. As part of my onboarding, I met with each team member individually for my "New Manager Discovery 1:1s," asking questions like: What motivates you? What are your short- and long-term goals? How do you define success? From those conversations, someone stood out immediately: Zoey. Zoey was energetic, poised, and eager—looking for opportunities to make an impact. So, I approached her with a candid proposal: Would you be open to taking on a side project? I laid it all out: it was going to be messy and unstructured, fast-paced, and tough. But in exchange, she’d be in the room making key decisions with me, tapping into her creativity, getting exposure to company leadership, and pushing her skills to the next level. I knew this might not align perfectly with her career trajectory, but I also knew it was a chance for her to grow and shine. Without hesitation, Zoey said yes. From the moment she jumped in, she was unstoppable—helping build the framework, identifying problems, and bringing forward solutions and innovative ideas. Her energy, focus, and customer-first mindset were magnetic. She didn’t just rise to the challenge; she thrived in it. We officially transitioned her into an Account Manager role, and she hit the ground running—leading group demos, crafting compelling customer programs and automations, hosting external webinars and internal training sessions, creating videos, and providing invaluable feedback to improve our approach. This is just the beginning for Zoey, and I couldn’t be prouder of the impact she’s already made. I’m deeply grateful for the trust she placed in me, the opportunity to dream, build, and iterate alongside her, and the incredible impact we’ve created together. As our team expands and we refine our strategic approach to better support our customers, Zoey’s contributions have been pivotal. It’s no surprise that our story "Growth at Scale: Launching a Strategic Upsell Program for 8k Customers" has been nominated for the Top 25 CS Awards. Behind every success story is a team of remarkable people, and in this case, it’s Zoey Zawacki :) Please consider voting for our story—it’s one worth celebrating!

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Leaders use business jargon and metrics as short-hand and they want to work with others who can speak the same language, people they don’t have to translate for. At Section, NDR is one of our key metrics so I need my team to know what it means – REALLY know what it means. Not just what it stands for, but how it changes our priorities and drives behavior in our company. Get to know the key jargon and metrics in your business - your boss will be more likely to strategize with you because you speak the same language. If you work in SaaS or a recurring revenue business, NDR is a key metric to understand. We broke it down and why it’s so important to your CEO in today’s Personal Math. Link in comments.

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It all starts with getting your company values right.

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Curious what folks currently think about product marketing having its own tech stack in the future. In my experience we've always used what our marketing/sales counterparts have, never anything specialized for the work we do. Competitive platforms like Klue are one example of what could be included. I know Ignition is working on a GTM platform. Do we think this has legs to become an actual stack? Will we get more defined budget for these things, or does our interconnectedness within the company make it too difficult? I'm fully undecided on this. We pull from so many departments and areas it feels difficult unless we become the hub discipline for tech that others latch onto, and I'm not sure I see that happening anytime soon. #productmarketing

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I didn't realize how bad people's inboxes had gotten until we started getting a surprisingly high number of new users a week setting up automations to sort their emails. One often-repeated use case is invoice management. People buy a *ton* of stuff for their companies that they either need to get reimbursed for or save for accounting. We help users solve this with an AI agent that... 1. Watches for new receipts in their inbox 2. Puts the invoice attachment into drive for storage 3. Puts the details into a sheet where they can sort & see them

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My advice for navigating change as a leader: Connect personally with every team member. Don’t assume they understand the “why” behind a restructure or a change in direction. Be deliberate in asking the hard questions. How do you feel about it? What are you concerned about? What questions do you have? This shows you care personally about each and every team member. It shows you’re invested and transparent.

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I cannot stress this enough to marketing operations folks: make sure you check out the leadership you’ll be working for at a new job, not just the team. If the leadership at the top is lost, confused, dysfunctional, or toxic…run. You can’t out-work dysfunction at the top, and it won’t be gratifying. It’ll be exhausting and you’ll wonder what you’re even doing anymore, since your day will be filled up with meetings about managing feelings about the dysfunction at the top instead of meetings about progress on your initiatives. 😬 #marketing #marketingoperations #revenueoperations P.S. You can screen for this by asking about department and company-wide goals, backchanneling via prior employees who recently left, and of course asking to interview with leaders if possible.

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For any PMM having a hard time nailing messaging… Facts - There’s no ‘Don Draper’ moment where inspiration will strike in the middle of a meeting. The good news is you have everything you need. 1. Look at your wins. Find the last 6 months of closed/won deals in your CRM. Find the patterns, and talk to the AEs if you need to. Better yet go talk to the customers themselves. Why did they buy? What made them pick you? 2. Once you have a good sample, use your judgement and distill out 3-5 ‘winning use cases’. These are the foundational proof points of why you’re differentiated. And they’re real 3. Then build the top and bottom. Top = what’s the one unifying value prop across the winning use cases. Bottom = what’s the product capabilities that support those use cases 4. Document this, turn it into your first call deck, and your website nav + core pages Refine this every 6 months. Sales will love it, and customers will actually believe you #productmarketing #messaging

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Running branded sponsor integrations isn't cheap -- how do you know it's resonating with your audience and driving meaningful KPIs like purchase intent? At Rival Technologies and Reach3 Insights, we've been helping both media / streaming brands as well as advertisers figure this out using a new approach called "Watch Party." It works well for several reasons: ✔️ It's in-the-moment, so you get real-time, gut-feel reactions rather than relying on recall ✔️ It's quant and qual (including photos and videos), providing deeper insights than traditional approaches ✔️ It's holistic, involving (in most cases) a pre- and post-test to quantify brand lift, share ability and more Really proud of how our product and approach helps address an important use case for many of our customers. Curious how it works? Our next masterclass webinar with Jenna Shuster and Matt Kleinschmit will walk you through the details. Register here: https://lnkd.in/gFa7rzbW #insights #marketingeffectiveness #advertising

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New week, new hustle. Got my iced coffee on deck, and these startups didn’t wait for anyone to catch up. If your Monday’s just getting started, these companies are already miles ahead, setting the stage for a week of serious moves. Let’s see who’s kicking off the week strong: Zephyr just locked down $60M, backed by Elda River and The Pritzker Organization, to bring fresh respect and real growth to home services. CEO Shawn Weidmann's making sure techs get the career paths they deserve in a $125B industry that’s ready for real change. Level AI landed a cool $39.4M Series C, with Adams Street Partners and a stacked lineup of Cross Creek, BrightLoop, Battery Ventures, and Eniac Ventures. CEO Ashish Nagar’s crafted a contact center that does more than talk—it connects, with real-time sentiment analysis and NLP that’s making big brands take notice. Nirvana scored a $24.2M Series A, thanks to Northzone, Inspired Capital, Eniac Ventures, and Surface Ventures, to take healthcare insurance verification out of the dark ages. With a 94% accuracy rate and names like Headspace Health onboard, CEO Akshay Venkitasubramanian is delivering a level of efficiency healthcare’s been missing. Kindo raised $20.6M to secure enterprise AI, with Drive Capital, RRE Ventures, and Marlinspike backing the play. Ron W. and Bryan Vann are building a platform that keeps AI adoption as secure as it is scalable. This isn’t just a system—it’s the foundation enterprise AI’s been waiting for. SchooLinks just pocketed $80M from Susquehanna Growth Equity (SGE) to rewire career counseling for high school students. Katie Fang and team have taken over 40 states, gamifying career prep and building a real bridge from high school to the workforce. Career planning is about to get a serious upgrade. Carbon Robotics locked in a solid $70M Series D, led by BOND with nVentures (NVIDIA’s VC arm), Anthos Capital, and IGNITION PARTNERS. Paul Mikesell’s LaserWeeder is taking on weeds with laser precision, cutting costs, and changing the game for farmers globally. That’s your Monday iced coffee rundown—cool, sharp, and ready for the week. Want the full breakdown? Head over to my Substack👇 for all the details and a little extra heat. https://lnkd.in/egxETsUc #HomeServices #HVAC #AI #HealthCare #HealthTech #Education #EdTech #AGTech #Agriculture #Farming #FarmTech #Technology #Technology #TechEcosystem #StartupEcosystem #VentureCapital #StartupFunding

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