Matt Willis

Enterprise software sales isn’t about speed. It’s about alignment. When frontline users, IT, finance, and the C‑suite are aligned, deals move, commits are made. When they aren’t, no amount of pressure fixes it.

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In most B2B companies, the gong rings in sales and a fire drill starts in finance. Sales is signing custom deals while finance scrambles to figure out how to bill, invoice, and recognize the revenue. Quote to cash is one of the most fragmented processes in the CFO org. Legacy billing tools were built for v1 of the subscription economy. They handle simple subscriptions, then break the moment you add custom enterprise terms and usage-based pricing. In an AI world where everything is metered and usage-driven, that setup is unsustainable. That’s the gap Sequence is going after. Their end to end AI revenue platform is built for this reality, handling real-world Q2C complexity while automating the tedious work and keeping finance in control. An intake copilot turns messy custom contracts into billable schedules. A Rev Rec agent flags ASC 606 risk before entries hit the ERP. A Dunning agent tailors follow ups instead of spamming generic “please pay” emails. Huge thanks to Riya Grover, Enda Cahill, and the Sequence team for an incredible session. We’re grateful to everyone who joined and shared their questions. That wraps our final Scale CFO Demo Day of 2025, what a year! We’ll be back in the new year with more sessions and initiatives across the CFO community. If you’re interested in joining, link in the comments.

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The latest episode is live, and this one is fantastic. I sat down with Eric Gilpin, President, GTM of G2, a leader who’s spent over two decades scaling teams, navigating change, and driving growth in some of the most competitive technology markets in the world. What makes Eric stand out is how he thinks about people, performance, and presence. In this conversation we went beyond tactics and hit on: Being strong at work without losing your presence at home Work demands a lot. But the cost of absence, in relationships, in moments, in memory, isn’t on any spreadsheet. Why alignment with your spouse matters more than “balance” It’s not a 50/50 scorecard, it’s shared intention and honesty about what really matters. What “being present” requires, not just physically there, but mentally and emotionally engaged, even when everything else claws for your attention. The real talk on AI Will AI replace us? Maybe parts of what we do. But the parts of leadership no model can replicate are exactly what matter most going forward. Listening to understand, not to respond That might be the most underrated leadership skill in the age of speed. This episode is about the humanity beneath the headlines and what leaders need to actually thrive in the chaos of work, tech, and life. If you’re thinking about the future of work, AI, or how to show up better in the places that matter most, give this one a listen. 🎧 Youtube: https://lnkd.in/e4nrDEAu

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Interesting stat from the Gartner CSO on compensation as a driver of B2B sales people. I don’t know what this means just yet, but I have a feeling that it’s got big implications for commercial leaders.

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🌟 The SaaS world moves fast, and scaling efficiently requires strategic alignment, operational rigor, and cross-functional coordination. Fractional COOs are helping early- and mid-stage SaaS companies grow seamlessly while maintaining agility. At 𝗗𝗶𝗴𝗶𝘁𝗮𝗹 𝗥𝗲𝗳𝗲𝗿𝗲𝗻𝗰𝗲, we’re committed to 𝘁𝗿𝗮𝗻𝘀𝗽𝗮𝗿𝗲𝗻𝗰𝘆 𝗮𝗻𝗱 𝗮𝘂𝘁𝗵𝗲𝗻𝘁𝗶𝗰𝗶𝘁𝘆—spotlighting leaders who combine operational expertise with strategic insight to drive measurable results. 👋 𝗠𝗲𝗲𝘁 Dawn Strobel, 𝗙𝗿𝗮𝗰𝘁𝗶𝗼𝗻𝗮𝗹 𝗖𝗢𝗢 Dawn helps SaaS companies align strategic objectives with day-to-day execution, ensuring scalable growth without sacrificing agility. She specializes in operational strategy, cross-functional alignment, process optimization, and efficiency audits. Here’s what she’s known for: ✅ Operational strategy for scaling 🏷️ Cross-functional alignment 🌟 SaaS process optimization 🔎 Operational efficiency audits Dawn empowers SaaS teams to scale smarter, improve performance, and operate with clarity—turning strategy into action at every level. 🔗 Learn more about Dawn Strobel and other Fractional COO professionals for SaaS companies here: https://lnkd.in/dSzCuv-R

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How is it that every single GTM or RevOps solution provider has the ONLY expert solution to get your pipeline humming and close rates up to 90%? 😂 A great reckoning is coming.

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Over the last several months, one theme keeps coming up in conversations with behavioral health leaders across California: Growth is NOT the problem Operational clarity IS. With SB 43 implementation, CARE Court workflows, county integration of SUD + specialty mental health, and increased scrutiny around documentation quality and outcomes, 2026 feels like the year where policy turns into operational pressure. That's why the following stat stood out to me: 76% of organizations report having NO DEFINED EXIT STRATEGY. That tells me that the industry isn't chasing quick flips as often. Leaders are building for longevity. But in California, that doesn't happen by accident. It means clean documentation that stands up to audits. It means financial visibility across sites and levels of care. It requires intake processes that can handle higher-acuity referrals and data you can confidently use when negotiating with counties or payers. Kipu Health is hosting a conversation with Joan Leroux and Christina Rosenberg on what sustainable growth actually looks like in 2026 and why operational excellence is the foundation that enables it. If you're leading a program in CA and feeling the weight of expansion + compliance + margin pressure all at once, this webinar is for you. Register here: https://lnkd.in/gPKA75Zf #kipu #behavioralhealth #sb43 #CARE

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The sales machine has changed. Buyers don’t enter our selling process anymore. We’re stepping into their buyer journey. The top of the funnel used to rely on human qualification. Today? Buyers qualify themselves — often before they ever talk to us. If your machine isn’t built to catch that early signal, you’re already behind. Interactive demos and self-serve product tours are no longer “nice to haves.” They’re frontline qualification engines. The companies tuning their sales machines for modern buyers are doing three things: Meeting buyers with product experiences before the first call. Capturing demo engagement signals to prioritize the right leads and features. Accelerating time-to-context so every rep conversation is sharper. I write about creating a better buyer experience — and a more predictable machine — in my latest @Reprise blog: https://lnkd.in/eQGatw2H 

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Over the past decade, we’ve run one of the leading talent marketplaces, helping the world’s top companies access independent talent to power their most critical work. Along the way, we’ve learned what modern staffing firms need to succeed: speed, automation, digital candidate experiences, and fewer manual, repetitive tasks.  We’ve been quietly building our own proprietary technology to solve these workflow challenges and improve our own productivity as a company. Today, we’re bringing that technology to the broader industry with the launch of GraphiteOS, an AI-powered recruiting operating system that we believe will fundamentally transform how staffing firms operate in the years to come. This isn’t just a product. It’s the technology infrastructure staffing firms need to operate faster and more effectively in an AI-driven, “agent-first” world.  We believe this technology will enable levels of recruiter productivity and client satisfaction that have never been seen before. Recruiters shouldn’t be stuck juggling disconnected tools and performing repetitive tasks. With GraphiteOS, we’ve built an all-in-one platform that connects the dots - sourcing, matching, screening, onboarding and billing - so teams can focus on what matters most: the high-value work that drives placements. I’m incredibly proud of what our team has built and, more importantly, what it will enable for our early customers where the platform is being deployed as we speak! Learn more at www.graphiteos.ai #GraphiteOS #StaffingTech #FutureOfWork #AIRecruiting #StaffingInnovation

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Big news! 🚀 Mission Andromeda has landed, kicking off Gong’s new product launch cadence. This launch brings powerful new capabilities to help revenue teams move faster and execute with confidence, including: ✨ Gong Enable AI role-plays to help reps practice real moments before they happen live ✨ Gong Assistant Always-on conversational guidance for everyday workflows ✨ Account Boards Unified view of all accounts to align AE + CS ✨ Account Console Deep dive view of a single account ✨ Gong MCP Support Integrated AI across your tech stack Proud to be part of a team building the #1 revenue AI OS,  and excited to see how customers put these updates to work. Learn more: https://lnkd.in/dHsPJtTN

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This AI moment is brimming with opportunity. It’s also delicate. The leaders who will thrive are those who adopt a "serendipity mindset," says Christian Busch, professor at USC Marshall School of Business. This approach requires fostering moments of happy accidents. It demands that leaders remain receptive to unexpected blessings. Your best-laid plans alone won't suffice. The pivotal moments that will define your organization will unfold in hallway conversations and spontaneous coffee chats. Are you creating space for serendipity? Check out Great Place To Work's full list of leadership skills that will make a difference in 2026: https://ukg.inc/4lipuXC

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#12 (Part 2)  Scaling vs Growth - 💡 Go-to-Market Blueprints - Can’t outsource a mess Part 2 Find out if you're truly ready to scale through partners, or if you need to get your own GTM house in order first. By popular request, we've created a tool to help you assess if your GTM is partner-ready or just a mess: Take the Partner Sales Assessment → https://lnkd.in/ew99_8sn The hard truth: If your direct sales GTM isn't a well-oiled machine, your partners don't stand a chance. Too many companies expect their channel partners to work miracles with a flawed playbook. But here's the reality – partners need a proven, scalable framework, not your experimental rough draft. The Scale & Refinement Deficit When your internal GTM strategy is poorly defined, inconsistently executed, or still being "figured out," you're asking partners to test your hypotheses on their valuable client relationships – a recipe for failure. Partners require validated playbooks, consistent messaging, proven value propositions, and scalable processes. A strong GTM strategy aligns teams and optimizes resources. Without it, partners are set to fail. Before expecting partner excellence, ensure your direct sales team is successful. Partners amplify your output: chaos creates chaos, while a proven system delivers predictable results.

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The gap between good and great CROs isn’t strategy. It’s consistency, adaptability, and trust. That’s one of the themes explored in Bullingstone Associates’ new paper, CROs Who Succeed, where I was fortunate to contribute alongside a group of world-class GTM leaders and Operating Partners from across PE and VC. This white paper is a sharp piece of work that unpacks why CRO tenure remains short, what investors now look for in revenue leadership, and how the role itself is evolving. If you care about how great GTM organisations are built, or want to understand what the best CROs do differently, this is well worth a read. Wayne, thank you once again for the opportunity to contribute. 👉 CROs Who Succeed: https://lnkd.in/erX_PP7S #CRO #RevenueLeadership #GTM #PrivateEquity #VentureCapital

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With NetSuite, franchises get the tools to grow faster, operate smarter, and support every location with confidence. See how the franchise program helps drive success at scale: https://lnkd.in/giy--hpZ

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In PE due diligence, sellers create beautiful reports and tell a good story. But here are THE TOP 3 ways we've seen them hide weaknesses as strength. You’ve seen them before: 1. Broken ops hidden behind a slick dashboard 2. Legacy tech pitched as “proprietary advantage” 3. Overworked heroes framed as a “resilient team” These are the big red flags. The ones that kill deals… right? Well no… there are no magic bullets here! Outside of fraud, most red flags are fixable. Tech can be rebuilt. Ops can be professionalized. Teams can be supported. We wouldn’t have a business if all these things were deal killers. The real killer? Surprise. It’s walking into a deal with blind spots, then discovering post-close that your growth story has a critical flaw. It takes “diligent” work and practiced human interaction to find everything. Great due diligence isn’t about killing deals. It’s about calling out reality early, clearly, and without spin. Because when you spot the problems up front: - You can quantify the fix - You can use it in the valuation - You give finance time to model the downside and the upside Good diligence doesn’t eliminate risk. It lets you walk in eyes open, with the leverage to negotiate and the clarity to decide. Fixing hard problems is part of the job. There's value to unlock in them. It’s the surprises that wreck your return.

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B2B Sales Tips: Quantify Fast, Quantify Better (vol. 3) Want to close more B2B deals? Learn why you should quantify the benefits of your solution, qualify opportunities, identify and use best practices, and learn storytelling keys that win more clients. Watch now and level up your sales game! Each video is under 1 minute, and we focus on an actionable strategy that helps you connect with decision-makers and prove the worth of your solution. Let’s tackle this together! www.ROI-Calc.com or glenn@ROI-Calc.com #B2BSales #SalesTips #GTMStrategy #B2BSaaS

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Your Cloud Infrastructure bill is the new headcount plan. For years, startup board meetings obsessed over hiring velocity to drive growth. Now we’re seeing a shift. CFOs are putting cloud spending in the spotlight. In the age of AI, the marginal cost of delivering value isn’t a new developer for a salesperson; it’s a token, a model call, or a GPU hour. That’s why we backed Matt Biringer and Yassine Açoine at North.cloud. Their AI-powered financial system helps high-growth startups and Fortune 500 companies alike manage cloud costs with the same visibility and rigor they bring to development, hiring, and GTM. • No FinOps headcount required • Massive savings in minutes, not quarters • 500%+ net retention, hundreds of millions of cloud spend under management • Customer DevOps teams can focus on... drum roll... development and deployment, not forensic cloud accounting exercises. Cloud COGS are becoming core to your business model. North makes them predictable & controllable. Here's why we led their Series A round and why you'll never go back after trying this solution in your cloud infrastructure: https://lnkd.in/eQFHp9ku #DevOps #CFO #venturecapital #FinOps #AIinfrastructure

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Chomps is snacking on success with NetSuite. Find out how faster financial processes and increased business visibility is helping fuel growth for the business. https://lnkd.in/gBAxaxqA

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