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Seasoned marketing executive with a successful career in designing strategies, systems…
Articles by Michael
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5 Pillars for Marketing Growth in a Down Economy
5 Pillars for Marketing Growth in a Down Economy
Must I fear what others fear? Should I fear desolation when there is abundance?” – Laozi I don’t have to go into the…
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Has Marketing Lost the Art of Conversation?
Has Marketing Lost the Art of Conversation?
There’s a new generation of digital marketers, and they’re nothing like Don Draper. These marketers are highly…
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Michael M. reposted thisMichael M. reposted thisMarketing leaders from across the Mainsail portfolio came to Austin last week for a full day of testing, sharing and building what AI-native marketing looks like in practice. A few highlights from our Marketing AI Workshop: → Before automating anything, get the fundamentals right first. Clean data, defined ICPs, aligned lifecycle stages. → Ben Virdee-Chapman and Kyle Whatnall from CourtReserve showed the room what that looks like in practice with live demos of the skills, agents and co-pilots their teams use every day. → Travis Wingate (Skimmer), Anati Zubia (SmartMoving Software), and Carl Koussan-Price (Syncro) discussed what it takes to stay human as your systems get faster and why authenticity is something you must choose every day. → Justin Dunham and Amber Bogie on why your content strategy and marketing infrastructure need to be rebuilt around how buyers find answers today. → A hands-on build session to design and launch AI-powered workflows that solve real-time marketing problems. Thank you to every leader who made the trip, and to Teresa Zimmerman, Michael M., and Jeniffer Agudelo for hosting an energizing workshop.
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Michael M. posted thisKnow an exceptional Head of Demand Generation in Austin? MirrorWeb, a fast-growing disruptor in the compliance space, is hiring a Senior Director of Growth, reporting directly to seasoned, multi-exit CEO Romir Bosu. This is a true builder-operator role: owning demand and growth strategy end-to-end while partnering closely with sales to scale the business. Thankful for any intros or DMs.
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Michael M. reposted thisMichael M. reposted this🚀 Mainsail's AI Launch Labs just wrapped. Here's what 2+ months of focused AI training, building, and collaboration looks like. We brought together 70+ engineers and product managers from across the Mainsail portfolio for virtual instruction followed by an intensive, 2-week in-person AI build program—sunrise to sundown. 🔥 20+ agents were built from scratch in 10 days. The goal was not only to ship real products but shift our teams from building features by hand to fully agentic development. Learning side-by-side to use today's tooling to its fullest and leaving with a fundamentally different idea of what's possible and how to get there. The results spoke for themselves before anyone got on a plane home: - “In a short period of time, you managed to both elevate our understanding of AI and drive the teams to produce tangible, measurable results.” - “This was a career defining opportunity for me.” - “This was one of the most well-designed and effective sprint events we’ve participated in.” - "There were so many use cases shared across the portfolio. I can't wait to get back to my team and teach them what I learned." Across vertical markets, teams tackled the problems software founders and their customers know too well — repetitive manual work, reporting bottlenecks, compliance burdens, onboarding volume, reactive workflows. Building toward production-ready products with a clear path to launch. 🔓 It’s an example of what’s possible when ambitious founders don’t have to navigate the AI technology shift and opportunity on their own. 👈 Thank you to all our portfolio companies and teams for dedicating your time, pushing each other's limits, and celebrating the wins together. And thank you to the Mainsail team especially Nick Olsen, Bill Simpson, Prescott Nasser, Dan Blake, Bashir Abdallah and more for leading this charge! #agenticAI #AIdevelopment #verticalsoftware #MainsailAILabs
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Michael M. reposted thisMichael M. reposted thisToday, we introduced Pilotbase. Flight Schedule Pro and LogTen Pilot Logbook now operate within the Pilot Experience Platform — a new category designed to connect flight operations with measurable student progression, instructor performance visibility, financing access, and long-term career outcomes. Flight Schedule Pro is not going anywhere. Contracts, workflows, and support remain unchanged. What expands is our scope. At Flight School Association of North America this week, we are sharing a preview of what comes next — including AI-driven scheduling, deeper integrations and partnerships, enhanced safety and flight insights, and a reimagined pilot experience. Read the full announcement or visit Booth 30 to learn more. https://hubs.li/Q044B-bz0 #Pilotbase #FlightTraining #Aviation #AI
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Michael M. reposted thisMichael M. reposted thisPricing is one of the most strategic levers for turning AI product investment into sustainable growth. But the same AI feature can justify very different pricing approaches depending on broader business objectives, customer value, and how the feature is actually used. Mainsail’s VP of Pricing, Brian Russell, and Growth Manager, James Moore, developed a simple decision framework to help B2B software companies determine the right AI monetization strategy for their specific use case. They ask (in this order): 1. Is this AI feature table stakes or primarily a driver of adoption and retention? 2. Is the value mostly about access, with similar value per customer? 3. Does usage vary widely and correlate with ROI, with meaningful COGS? 4. Do buyers clearly recognize standalone value from this capability? In their full guide, Brian and James share: - A step-by-step process for applying this pricing decision framework - Four common AI pricing models and when to use each of them based on your answers - Commons mistakes to avoid when monetizing AI - How to launch, measure and iterate AI pricing faster than traditional cycles For B2B software founders bringing AI features to market, it offers a structured way to make deliberate pricing decisions rather than reactive ones. 👉 Link in comments #B2BSoftware #SaaS #PricingStrategy #AIinSoftware #MainsailAILabs
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Michael M. reposted thisMichael M. reposted thisWe launched Mainsail AI Labs in 2025 to help our portfolio companies not just adopt AI – but lead with it. One year in, progress has been measured in momentum: clearer AI roadmaps, deeper internal engagement, and practical use cases moving from experimentation into production. We’re proud of the groundwork laid and excited to keep partnering with teams building durable, AI-enabled businesses. In partnership with our Investment and Growth Teams, 2025 saw Mainsail AI Labs deliver: ✔️ Hands-on support from a team of 10+ AI leaders, CTOs, and engineers* ✔️ Outcomes-based AI strategy, training, and roadmap execution ✔️ A shared space for portfolio leaders to test, learn, and share what works Most importantly, we're seeing real impact in the field. Throughout the year, we highlighted exciting, customer-first AI innovation across our portfolio—including: - Embedded AI agent for fire safety reporting from Inspect Point - AI answering service to qualify leads and book jobs from JobNimbus - Voice Assisted property management workflows within Rentvine - AI-human hybrid for on-demand language interpretation by Boostlingo - 24/7 Sales Assistant for lead capture & quoting via SmartMoving Software - Work Order AI agent for smarter facilities management from Fexa - Agentic AI workflows for complex treasury operations by GTreasury - LLM-powered compliance review acceleration in Red Oak - Intelligent compliance supervision engine from MirrorWeb Each of these represents not just a useful tool, but a leap in how vertical software businesses operate and optimize value for their customers. 🔥 We’re just getting started and excited for what Mainsail AI Labs will deliver in 2026! Get Mainsail’s full Year in Review here: https://lnkd.in/e-2-K7fE *Certain Mainsail AI and Tech Advisors are contractors and are not employees of Mainsail or its affiliates. They are engaged by Mainsail or its affiliates to provide operational and other services with respect to Mainsail’s investments.
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Michael M. reposted thisMichael M. reposted thisWe’re proud to share that Mainsail Partners has been named to Inc. Magazine’s 2025 Founder-Friendly Investors list, making this our 💠sixth💠consecutive year on the list! We believe this recognition reflects the trust and partnerships we’ve built with bootstrapped founders who chose Mainsail to help grow their businesses. “Receiving this recognition for the sixth consecutive year is a testament to the founders in our portfolio,” said Vinay Kashyap, Partner at Mainsail Partners. "We’re excited to help them adapt and innovate as AI reshapes the software landscape, but their deep vertical market experience and customer-first culture remain their greatest advantage. Our team is committed to helping founders navigate these changes and scale efficiently while preserving that unique, founder-led mindset.” #FounderFriendly #vSaaS #verticalsoftware #AIMainsail Partners Named to Inc.’s 2025 List of Founder-Friendly InvestorsMainsail Partners Named to Inc.’s 2025 List of Founder-Friendly Investors
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Michael M. posted thisNetwork: There are some fantastic open roles/opportunities to work with exceptional leaders within our portfolio companies. *all remote-friendly ◘Marketing Ops Manager @ Extensiv | HubSpot MA system admin Partner with Carey Ballard on process, tracking, and reporting. ◘Demand Gen Manager @ SmartMoving Software | Someone strong in Paid Media & SDR Alignment Work as Anati Zubia's right hand to drive inbound and ABM pipeline. ◘Senior Marketing Manager @ Teamfront | Act as a mini-marketing GM supporting two companies (for those who thrive in early-stage, high-velocity environments) Learn scalable marketing from one of the best, Autumn (Bitticks) Fleck. ◘Growth & Lifecyle Manager & Customer/Partner Marketing Manager @ Flight Schedule Pro Come build a united brand with the visionary Bryan Landaburu as a category leader. Know of someone exceptional, or are you open to new opportunities yourself? DM me or reach out to the hiring managers directly!
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Michael M. reposted thisMichael M. reposted thisMainsail first invested in GTreasury and founder Orazio Pater in 2017 to help grow its team of ~80 and scale its infrastructure to build a global leader in treasury management software. Following years of organic and inorganic growth, including three strategic acquisitions, GTreasury secured a majority investment from Hg in March 2023 and Mainsail remained a minority investor. Today, GTreasury serves 1,000+ customers in 30+ industries across 160 countries. And we’re excited to announce a signed agreement for GTreasury to be acquired by Ripple, a provider of digital asset infrastructure for the enterprise, for $1 Billion. It has been a true pleasure to work with CEO Renaat Ver Eecke and the entire GTreasury team over the last 8 years. We’re excited to see what GTreasury does next, as it continues to innovate and support the Office of the CFO at every stage of treasury complexity. #OfficeoftheCEO #treasurymanagement #vSaaS
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Michael M. liked thisMichael M. liked thisLast week, we wrapped Red Oak's inaugural Accelerate conference in Austin, and it was exactly what we hoped it would be. Hundreds of compliance and marketing professionals from across financial services spent three days in the same room, having conversations that don't happen anywhere else in this industry. Programming spanned the marketing and compliance partnership, the governance and architecture questions firms are facing around AI, and how generational dynamics and emerging technology are reshaping competition for AUM — alongside hands-on product sessions, roundtables, and peer-driven discussion. Attendees also got a first look at new platform integrations, a revamped Seismic connector, our new UI, and the 2026 product roadmap. Post-event webinars are coming soon, including a virtual encore of the Compliance-Grade AI™ panel. ➡️ Read the full recap: https://lnkd.in/gX3SYUwM #Accelerate2026
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Michael M. reacted on thisThank you marketing leaders for an incredible day!! As we navigate the AI Wild West, a special thanks to Michael M. Ben Virdee-Chapman Karen Roberto Justin Dunham Amber Bogie Travis Wingate Anati Zubia Carl Koussan-Price Jeniffer Agudelo Sarita Ray Kyle Young Bill Simpson for bringing these concept to life by sharing your learnings and leadership!! 🚀⚓️🤠Michael M. reacted on thisMarketing leaders from across the Mainsail portfolio came to Austin last week for a full day of testing, sharing and building what AI-native marketing looks like in practice. A few highlights from our Marketing AI Workshop: → Before automating anything, get the fundamentals right first. Clean data, defined ICPs, aligned lifecycle stages. → Ben Virdee-Chapman and Kyle Whatnall from CourtReserve showed the room what that looks like in practice with live demos of the skills, agents and co-pilots their teams use every day. → Travis Wingate (Skimmer), Anati Zubia (SmartMoving Software), and Carl Koussan-Price (Syncro) discussed what it takes to stay human as your systems get faster and why authenticity is something you must choose every day. → Justin Dunham and Amber Bogie on why your content strategy and marketing infrastructure need to be rebuilt around how buyers find answers today. → A hands-on build session to design and launch AI-powered workflows that solve real-time marketing problems. Thank you to every leader who made the trip, and to Teresa Zimmerman, Michael M., and Jeniffer Agudelo for hosting an energizing workshop.
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Michael M. reacted on thisMichael M. reacted on thisMarketing leaders from across the Mainsail portfolio came to Austin last week for a full day of testing, sharing and building what AI-native marketing looks like in practice. A few highlights from our Marketing AI Workshop: → Before automating anything, get the fundamentals right first. Clean data, defined ICPs, aligned lifecycle stages. → Ben Virdee-Chapman and Kyle Whatnall from CourtReserve showed the room what that looks like in practice with live demos of the skills, agents and co-pilots their teams use every day. → Travis Wingate (Skimmer), Anati Zubia (SmartMoving Software), and Carl Koussan-Price (Syncro) discussed what it takes to stay human as your systems get faster and why authenticity is something you must choose every day. → Justin Dunham and Amber Bogie on why your content strategy and marketing infrastructure need to be rebuilt around how buyers find answers today. → A hands-on build session to design and launch AI-powered workflows that solve real-time marketing problems. Thank you to every leader who made the trip, and to Teresa Zimmerman, Michael M., and Jeniffer Agudelo for hosting an energizing workshop.
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Michael M. liked thisMichael M. liked thisWe're excited to announce that Inn-Flow has acquired Lilo, an AI-powered procurement platform designed for hospitality, and with it, the launch of Inn-Flow Procurement. This brings hotel accounting, labor, and procurement together in a single platform, helping close the gaps that limit spending visibility and operational efficiency across hotel operations. It also adds specialized AI and engineering capabilities to continue product innovation across the broader Inn-Flow platform. Lilo co-founders Nadine ElAshkar and Javier Araya Kopaitic will join Inn-Flow in leadership roles to support continued product innovation and AI-driven development. Congratulations to the Inn-Flow and Lilo teams! Read more: https://lnkd.in/egP8XuCg #hoteltech #hospitalityTech
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Google AdWords™ Premier SMB Partner
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Aligned the Paid Media Team to exceed Google's qualification guidelines. Established consistent communication with our Google executive support teams, ensuring milestones were being met.
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PPC AdWise
How Smart CMOs/ VPs Buy Back Sanity at $2M+/Month Ad Scale It’s not just CPC or ROAS. Once you’re spending $2M+ per month, the real challenges show up in: • Cross-functional misalignment • Automation misfires • Signal decay • Scaling bottlenecks This is where dashboards look “fine” but performance quietly slips. If you’re a VP of Marketing or CMO and want clarity across infrastructure, optimization, and automation, let’s connect. Find Guide, video strategy, and complimentary audit details. Full article here: https://lnkd.in/e5nSy6qM
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Conversional.io
The most expensive part of your marketing team isn’t headcount. It’s false confidence. The deck looks clean. The calendar is full. The team is “aligned.” But you don’t feel it. No signal. No shift in pipeline velocity. No shift in conviction. It’s not a content problem. It’s not even a strategy problem. It’s an infrastructure gap. Your system doesn’t learn. Your system doesn’t close the loop. Your system doesn’t adapt. And the worst part? You can’t afford to burn another quarter on "looking busy." / conversional.io /
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PackedData AI - B2B Data Intelligence
Your SDRs spend 70% of their time researching leads. Meanwhile, your best opportunities stay buried. The difference between rule-based scoring and AI prioritization? 25% more conversions + 30% better ROI. Rules rank activity. AI predicts conversion. That’s the shift from chasing every lead to focusing on the ones that actually matter. Lead volume doesn’t win deals. Lead intelligence does. The real question isn’t: “How many leads did we generate?” It is: “Did we prioritize the right ones?” 👉 Read the full analysis here- https://lnkd.in/dt3THd92 Hot Take: Rule-based lead scoring is quietly costing B2B teams revenue. Agree or disagree? #B2BMarketing #LeadScoring #DemandGeneration #RevenueMarketing #SalesAnalytics #PackedData
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nRev
Talked to 100+ GTM leaders this year 📌 Here's the pattern: 🪜 Rung 1: Manual everything. "We'll automate later." 🪜 Rung 2: Basic Zaps. Breaks constantly. 🪜 Rung 3: Clay workflows. Needs an agency to maintain. 🪜 Rung 4: 12 specialized tools. $42K/year. Nothing integrated. 🪜 Rung 5: Describe what you want. It runs. Most teams think they're on Rung 4. They're actually on Rung 2 with better branding. The jump from 4 → 5 isn't adding another tool. It's removing the ladder entirely. Swipe through to find where you actually are 👉
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Databox
Marketers aren’t fixing the funnel - they’re funding it. 67% of GTM leaders increased paid budgets this year. Almost half did it to replace lost organic pipeline. That’s not strategy. That’s triage. And it raises a tough question: Are we solving attribution... or buying temporary visibility? When paid covers your blind spots: → You stop fixing broken handoffs → You skip over disappearing buyer signals → You build a funnel with no foundation This is the hidden cost of misattribution. Not just wasted budget, but missed insight. The best GTM teams aren’t just spending more, they’re getting smarter: ✔ Rebuilding trust in their data ✔ Aligning around what’s actually working ✔ Making performance visible across the org Because when the budget dries up, only the insights survive.
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Webapper Services, LLC
Your $10K monthly marketing stack isn't showing ROI? Over half of SaaS companies can't prove their marketing automation value to stakeholders. The problem isn't lack of data—it's measuring the wrong things. Companies scaling predictably focus on these revenue-driving KPIs... → Customer Acquisition Cost (CAC) → LTV:CAC ratio (aim for 3:1 minimum) → Marketing Sourced Revenue → Net Revenue Retention The difference between SaaS companies that scale and those that stagnate often comes down to measuring what matters. Even avoiding common SaaS bugs in your tracking setup can dramatically improve your ROI visibility. Check out our complete guide to the 10 KPIs that actually drive growth... #SaaS #SaaSGrowth #SaaSMarketing
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SmartReach.io
If your leads don’t respond, do your follow-ups know what to do next? SmartReach.io’s Conditional Multichannel Drips give you full control to build if-this-then-that workflows across Email, LinkedIn, SMS & more. No response after 2 emails? - Auto-trigger a LinkedIn message. Opened your email but didn’t click? - Send a contextual SMS. Clicked your link but ghosted the meeting? - Hit them with a re-engagement email. This is how high-performing sales teams personalize at scale—without wasting time on manual follow-ups. You stay in the driver’s seat, while your outreach adapts based on real-time actions (or inactions). Whether you're an SDR, a Growth Marketer, or a Founder, this is how you run smarter outbound campaigns that actually convert. Start using behavior-based outbound automation today 🚀 📌 Learn more and try this feature inside SmartReach.io → https://lnkd.in/dhXbRPQW #SalesAutomation #B2BSaaS #ColdOutreach #SalesEngagement #SmartOutreach #SmartReach #Dripcampaign #featurebreakdown
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Brainfish
One thing we see in every scaling GTM org: Reps keep asking the same questions, even when documentation exists. Not because people aren't trained... But because knowledge lives everywhere. - Slack threads - Outdated docs - PM tribal memory - One-off answers in someone’s head - The “only happens sometimes” answers The best enablement content is useless when it's buried.
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WhatConverts
Is lead volume leading you in the wrong direction? PPC marketers are taught to chase lead volume — more clicks, more conversions, more leads. But here’s the truth 👉 Experts are saying steer clear of lead volume as a core metric. Why? Because it doesn't prove or improve ROI (what clients really care about). This article breaks down: 📉 Why volume-based goals create blind spots 💰 How lead quality impacts your ad budget 🔁 The smarter shift toward value-focused optimization You’ll learn why chasing quantity often means ignoring what actually drives revenue — and how top agencies are flipping the script. 📈 Don’t get stuck measuring what doesn’t matter. 👉 Read the full article: https://lnkd.in/gnsfeAsj #PPCMarketing #LeadQuality #MarketingROI #DigitalAdvertising #Attribution #WhatConverts
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