Mike Genstil

To build a strong, growing B2B software company, you need performance insights, not just a finance function.  In the latest chapter of our Founders’ Guide, Upliift CFO Jidde Douma and Upliift Advisory Board Member Onno Krap break down the metrics, tools, and mindset that will give you clearer numbers and drive stronger growth. Get the guide here: https://lnkd.in/evWt9VB6   #B2BSoftware #FoundersGuide #EuropeanTech #PermanentEquity #ScaleUp  

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When you don’t raise VC funding, the diversity of founder personalities, locations, styles, values, ages, speeds, and visions is almost limitless. But there are three critical traits that all successful SaaS founders share who are building valuable software companies without big VC funding. In this week’s Practical Founders Podcast episode, I share the hidden patterns from over 140 podcast interviews with successful founders. The first important trait that seems normal, but is actually very rare: 1. Practical founders love the steady compounding game. This is not normal in a world that loves the fast start, the short term, the quick fix, and the easy hack. It’s just not common to deliberately build a business (or anything) that you know will grow at the same steady (but not crazy) rate next year. Recurring revenue businesses require this approach, even when you are starting and surviving. Practical founders do the work to build a flywheel that will continue to grow and thrive--next year and the years after. They invest in the right things now that will pay off years from now. This is much harder to do than it sounds. A 30% growth rate is not interesting to investors when you are starting up. That’s why practical founders would rather be frugal and disciplined than raise silly investment. Ironically, a larger software company efficiently growing at 30% per year is EXACTLY what most acquirers are looking for. A lower growth rate doesn’t mean you’re creating a small company. “The simple math is that a $1 million ARR recurring revenue business that grows at 30% a year will become very valuable if it keeps growing. Not crazy growth, but a reasonable pace. This is the fundamental principle of recurring revenue businesses: it’s a compounding machine. “If you grow at 30% for nine years, you'll have a $10 million revenue business. And if you do that for another nine years, you will have a $100 million revenue business. That's probably worth a billion dollars by that time. That sounds simple and not everybody gets there, of course, but practical founders think in this way—steady, healthy compounding." There are many ways to create a valuable software company. Fast, slow, funded, bootstrapped. Practical Founders love to keep improving and do it efficiently with steady, healthy, compounding. Key takeaways from the podcast: - Frugal Yet Bold – Practical founders are unusually frugal in life but make well-timed bold bets inside their companies. - Managed Risk – They avoid betting the whole company, instead making small bets that can compound into larger wins. - Do-It-My-Way Premium – Protecting their ability to do it their way is treated as a strategic advantage. - Optionality Matters – Practical founders value flexibility to sell, go long, or change direction without outside control. Are you wired like a Practical Founder? Check out this episode on the Practical Founders Podcast: https://lnkd.in/gErbvkir

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SaasRise CEO Mastermind Recaps for the Week of November 2-6, 2025 This week on SaasRise Masterminds, SaaS founders and CEOs tackled real-world strategies for growth, marketing efficiency, AI adoption and competitive positioning. Key challenges and recommendations: 1️⃣ Competing with Well-Funded Rivals Challenge: Competing against data-rich competitors with broader integrations and flexible pricing. Recommendation: ↳ Build prospect relationships, review competitor decks, identify differentiators. Match core capabilities in 3–4 months, compete strategically on price, and consider low-margin deals to open new markets. 2️⃣ Lean Marketing & Sales Teams Challenge: Defining clear roles after failed outsourcing. Recommendation: ↳Start lean: 1–2 marketers + 1 salesperson. Combine roles where possible. Agencies can help early, then transition to internal hires. 3️⃣ Authentic Content Creation Challenge: Generic/off-brand content from contractors. Recommendation: ↳Founders/internal teams draft content; outsource editing/distribution. Use AI for research/drafting, disclose AI use. 4️⃣ Paid Ads & Brand Growth Challenge: Balancing SaaS ad spend with cash flow and partner resistance. Recommendation: ↳Start with high-ROI campaigns ($100–$1,000/mo). Separate SaaS P&L from services. Diversify channels: Google, Meta, LinkedIn, YouTube. 5️⃣ Lead Generation & Funnel Optimization Challenge: Low conversion despite high ad spend. Recommendation: ↳Use LinkedIn Message Ads, Meta lookalikes, enriched email lists, plus direct outreach to convert problem-aware leads. 6️⃣ B2B Partnerships & Affiliates Challenge: Attracting real partners vs. just tracking users. Recommendation: ↳Use Rewardful, PartnerStack, Impact.com. Cold outreach + strong referral incentives = real partners. 7️⃣ AI Adoption & Integration Challenge: Low employee engagement. Recommendation: ↳Assign AI by department, create task forces, make adoption measurable, appoint AI champions. 8️⃣ AI in Support & Legal Ops Challenge: Inconsistent support; legal uncertainty. Recommendation: ↳AI handles up to 85% of low-complexity tickets. Use AI for NDAs/LOIs; high-value contracts require lawyer review. 9️⃣ Revenue & Department Alignment Challenge: Balancing budgets, aligning teams with revenue. Recommendation: ↳Tie sales/marketing to revenue; others focus on efficiency. Avoid allocating revenue % by department. 🔟 Financial Focus Challenge: Founders distracted by tax optimization. Recommendation: ↳Keep growth primary. Use profits for scaling/acquisitions; tax strategies supplement, don’t distract. 💡 Recommended Tools: Google Ads, Meta Ads, LinkedIn Ads, HubSpot, LinkedIn Sales Navigator, Rewardful, PartnerStack, ChatGPT, Intercom, Stripe. Scaling SaaS isn’t just about ideas—it’s about execution, structure and focus. Join next week’s SaasRise Masterminds to see these strategies in action and accelerate growth. (Links to apply and to read the full article in comments below 👇)

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Operating agreements pile up — but bottlenecks in your review process don't have to. Operating agreements are the backbone of fund governance, and yes, they pile up — especially during active fundraising or deal flow. But the bottleneck shouldn't be your review process. When every operating agreement sits in queue waiting for attorney review of standard provisions, distribution waterfalls, and governance terms you've seen a hundred times, you're creating unnecessary delays. The solution isn't rushing through reviews or compromising quality — it's using investment legal AI to automate the routine so your team can focus on the exceptions, the negotiated terms, and the provisions that actually require legal judgment. #InvestmentLegalAI #CyrapidLawAI #LegalTech #FundFormation #PrivateEquity #AI

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Kristian Andersen and Paul Hedrick shared some great lessons at the High Alpha CEO Summit. What can a room of B2B SaaS founders learn from the founder of Tecovas? A surprisingly large amount. 1) be careful with who you give a board role but liberal with who you let be an advisor. I firmly agree with this. We should let as many people help Nostra as possible without creating a 30 person board. 2) Paul got rejected a lot (including from business school). Turns out the amount of time you fails doesn’t matter as much as if you eventually succeed. I started Nostra in college. I focus less on the times we failed but more on the success we have had. 3) test and learn is what most people do. It is what we do at Nostra. It isn’t what Paul believes in. In software we can update our programs. In DTC boots - the customer gets the boots and that’s it. In case other don’t kno Kristian Andersen was one of the first checks into Tecovas !

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Most businesses have the same cash tension: You need cash available to run the company (payroll, vendors, surprises). You also don’t want excess cash sitting around earning nothing. This Treasury Management Playbook is a really solid, straightforward guide to doing both - without overcomplicating it. Venture-backed teams: there’s a QSBS note in here that was new to me, and it’s a big one. A treasury decision you might make as a diligent finance pro - like putting some cash into public index funds - can create QSBS risk. That can turn into a multi-million-dollar surprise at exit for early employees and investors, and a tough board conversation. Thanks, Alex Wu, for saving me from that fate. If you’re a founder, finance lead, or board member - worth saving. #CFO #Startups #SmallBusiness #CashManagement #Finance #QSBS

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One of the best indicators of liquidity and financial health in the broad economy is the IPO market. This is because the IPO market plays a key function in the capital markets lifecycle. Without profitable exits that transform narrow private sector equity into broad public sector capital, LP's in venture funds aren't able to recycle & re-deploy that capital into new early-stage bets. This breakdown has many bad knock-on effects: reducing the availability of institutional risk capital across the entire economy, depressing entrepreneurial activity generally & substantially lowering monetary velocity/consumption...all of which you (or your retirement portfolio!) have probably felt over the last few years. But did you know the biggest IPO of the year just happened last week and the issuer was able to raise +$2.5B dollars in a 5x oversubscribed offering?? You'd think this would be front-page news, yet almost nothing about this IPO has been covered by mainstream news despite being almost the size of both the Circle + CoreWeave IPOs combined. There's a simple reason they don't want to publicize this one. Can you guess why?

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The CTO role in PE is being completely redefined. I’ve been watching the CTO role in private equity get redefined in real time. Five years ago, my role didn’t exist at our company. Today, AI capability is part of the value creation plan. I’m the CTO at BRE Hotels & Resorts, a Blackstone portfolio company. We’re a hospitality real estate ownership platform — we don’t operate hotels. We own assets, invest in them, and allocate capital across a portfolio. The old model for tech leadership in PE portfolio companies: keep systems running. Manage vendors. Don’t break anything. The new model: CTO as value creation partner. Build capabilities that improve EBITDA, accelerate underwriting and asset strategy, and create decision advantages competitors can’t easily replicate. Here’s what changed: The board conversation used to be about IT spend. Now it’s about intelligence—decision velocity, performance drivers, and board-ready narrative that informs capital allocation with conviction. We’re building multi-agent AI systems where specialized agents generate KPIs, forecasts, variance explanations, and risk signals across the portfolio. Work that used to take days now happens continuously. This isn’t property-level AI. No chatbots. No smart thermostats. It’s enterprise intelligence at the ownership level—where strategy gets set and capital gets deployed. For PE firms thinking about technology leadership in their portfolios: 1. Hire CTOs who understand the business model — and can speak the language of returns. 2. Put technology at the value creation table from day one (not as a support function). 3. Measure technology like every other lever: by impact on outcomes. PE outperformance is becoming an intelligence game. Not dashboards—decision systems. The next decade of advantage won’t be won in spreadsheets. It will be won in systems that turn data into decisions—continuously, at scale. The question isn’t whether AI belongs in the value creation plan. It’s who owns it—and how fast it compounds across a hold period. The modern CTO in PE isn’t a technology leader. They’re a value creation leader, building a portfolio-wide repeatable playbook for intelligence. #PrivateEquity #AI #CTO #ValueCreation #HospitalityRealEstate #Leadership

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Founders, CMOs, and GTM leaders: whether or not you're engaging with industry analysts, they're already shaping how your market is defined and how your buyers make decisions. After 11 years as a Gartner analyst, 10 years in startups building go-to-market teams, and 4 years advising founders here at a16z, one truth stands out: Analysts don’t wait for you to show up — they shape the narrative with or without you. So, the question becomes: Are they talking about you — or your competitors? In this new piece, Stacy D'Amico and I share what we’ve learned about when and how to engage analysts, turning analyst relations into a strategic advantage, and what it takes to build an enterprise analyst relations program that actually drives revenue. Full piece in the comments 👇

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https://lnkd.in/geSxUcPk Interesting read..AI-native SaaS startups under $25M ARR are scaling with ~38% leaner GTM teams by leaning heavily on AI for onboarding, support, and RevOps—delivering growth without the usual headcount. But as these companies cross $50M ARR, the efficiency gains start to flatten, and in M&A scenarios, the traditional playbook of achieving operating leverage post-acquisition may not apply—AI-native orgs don’t scale in the same formulaic way as their non-AI peers, and integrating them into legacy structures can actually erode the very efficiency buyers are hoping to acquire.

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My biggest takeaways from Jeanne DeWitt Grosser (ex-Chief Business Officer at Stripe, currently Vercel COO): 1. What failed seven years ago now works with AI. In 2017, Jeanne tried to build a system at Stripe that would automatically personalize outbound emails based on company data. Despite working with world-class data scientists, it failed due to too many errors. Today, that exact same approach works. This shows how AI has made previously impossible ideas suddenly viable. 2. A single GTM engineer at Vercel reduced a 10-person sales team to 1 (in just 6 weeks). Jeanne’s team at Vercel had an engineer build an AI agent that handles inbound lead qualification, outbound prospecting, and deal loss evaluation. The agent costs $1,000 per year to run versus over $1 million in salaries for the sales team. The nine displaced team members moved to higher-value work rather than being laid off, and the remaining salesperson is 10 times more efficient. 3. Their AI deal-loss agent has become better at understanding what went wrong than humans. When Jeanne analyzed her biggest loss of the quarter, the salesperson blamed pricing. But an AI agent reviewed every email, call transcript, and Slack message and discovered the real reason: they never spoke to the person who controls the budget, and when ROI came up, the customer clearly didn’t believe the value claims. They are now using AI to analyze sales calls in real time and send alerts like “You’re halfway through the sales process and haven’t talked to a budget decision-maker yet.” 4. Wait until $1 million in revenue before hiring your first salesperson. Founders should continue selling themselves until they reach around $1 million in annual revenue with a repeatable process. The key is having a defined ideal customer profile—customers who look alike. 5. Segment customers on what drives their buying decisions, not just company size. OpenAI has roughly 3,000 employees, which would typically put them in the “mid-market” category. But they’re a top-25 website globally by traffic, so Vercel treats them as enterprise customers requiring complex sales. Effective segmentation combines company size with growth rate, web traffic, workload type, and industry—because selling to e-commerce companies requires completely different language than selling to crypto companies. 6. Most customers buy to avoid risk, not to gain opportunity. About 80% of customers purchase to reduce pain or avoid problems, while only 20% buy to increase upside. This means you should focus your sales messaging on what could go wrong without your product—like falling behind competitors or damaging their reputation—rather than just talking about exciting features. This is especially true when selling to larger companies, where individual careers are on the line. Full conversation: https://lnkd.in/gj47Efek

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Transformational leadership is within reach for CMOs—if they earn it. In my latest article, I outline six actionable strategies that empower CMOs to evolve from being sidelined to leading change. It's about understanding the business, creating impactful strategies, gaining credibility, and proving results. Let's reshape the marketing narrative and drive real growth together!

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Layer is tackling one of the most overlooked pain points for SMBs: accounting. They’re gaining real traction doing so. Emergence is leading their seed round to bring embedded, AI-powered accounting to the SMB software stack. Kevin Spain highlights what makes this team and product so compelling. 

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PE Growth TAILWIND: The January Fast Start Series (Conclusion) - How PE-Backed GTM Leaders Turn January Into Predictable Growth & Higher Exit Multiples Over the past week, I shared January “Fast Start” recommendations for seven critical GTM roles in PE-backed companies. The feedback was clear: lower middle-market teams don’t need generic advice. They need role-specific, actionable guidance that works with limited resources. The PE Lower Middle-Market Reality: • Moving from founder-led dependence to repeatable, scalable systems • Tight budgets where every GTM decision matters • Incomplete data, immature processes, limited training, thin infrastructure • 5-7 year hold periods where Year 1 sets the exit trajectory • Time-to-value matters - no tolerance for 18-month “transformations” The January Truth: yes, motivation matters, but without clear metrics, priorities, and sequencing, it's difficult to translate January goals into execution - and by March, little has changed. By June, teams are behind plan. By December, they’re explaining variances to the Board. Winning teams use January to validate data, align teams, protect revenue, clearly define targets & sequence GTM initiatives. Early in Q1, they build the system that makes Q2-Q4 execution predictable. This Series Covered 7 PE-Backed Roles Influencing GTM: 1. CEO: Lock alignment, protect revenue, and shape the board narrative that drives multiples 2. CRO / VP Sales: Turn strategy into math - pipeline quality, sales velocity & forecast credibility 3. Operating Partner: Portfolio-level orchestration that prevents sequencing mistakes & protects value 4. Marketing Leader: ICP clarity + GTM alignment driving higher win rates 5. Sales Manager: Pipeline rigor, process enforcement & team upskilling 6. Sales Rep: Segmentation discipline and math-driven execution 7. Customer Success Leader: Retention & expansion systems that grow NRR without increasing CAC   Access series posts and 250+ other PE growth posts here: https://lnkd.in/egaTG95M Why This Matters for LMM PE: fancy PowerPoint decks and promised growth don’t cut it anymore. In $20M-$200M businesses with limited hold periods, you need to drive measurable improvement in key growth levers within 90-180 days. And what you do in January matters. That’s the Fast Start advantage. Typical Outcomes: • 15-25% improvement in sales velocity • 10-15% reduction in customer churn • 20-30% faster ramp for GTM hires • ROI on prior GTM investments • Revenue engine earning premium exit multiples • Improved Board confidence   Ready to make 2026 count? If you’re a PE Sponsor, Operating Partner, CEO, CRO or Board Director needing faster GTM traction, let’s talk. The January window is closing. The portfolios that act now compound all year. 👍 React 📩 DM me or comment with your GTM challenge ♻️ Repost ➕ Follow Brian Gustason for PE growth strategies/tips 🔗 Access 250+ PE Growth posts: https://lnkd.in/egaTG95M #PrivateEquity #GTM #OperatingPartner

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As a young company, your forecast is how you think about what and how much to invest in your business. Without years worth of performance data, it can be very challenging to think about how to weight the different stages of your pipeline for an accurate forecast. Step 11 of our 12 step acceleration blog is guidance on forecasting accuracy! Check in out here! https://lnkd.in/dKDQqiBj

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I was recently featured in Insider Weekly sharing my evolution from high-stakes sales into what I now call Authority Architecture -the strategic positioning of leaders to increase influence, access, and revenue. One of the biggest lessons I’ve learned: Talent gets you qualified. Authority gets you chosen. In today’s market, visibility alone isn’t enough. It’s about where you’re visible. • The rooms you’re in • The media you’re aligned with • The stages you’re invited onto • The conversations you’re included in Influence compounds when it’s intentional. If you’re exceptional at what you do but know you’re under-leveraged, this piece will resonate. #insiderweekly #media #press #press

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**The Future of Enterprise SaaS with AI** Aaron Levie, CEO of Box, envisions a transformative future where AI seamlessly integrates with enterprise SaaS, enhancing core business workflows. As General Partners at ElevenX Capital, we recognize that the convergence of AI and SaaS opens new avenues for efficiency and innovation, presenting significant opportunities for investors. How is your organization preparing for this shift in the enterprise software landscape? #investing #innovation #venturecapital #entrepreneurship

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"My favorite CEO comes in, and the first ten minutes of the meeting is actually psychotherapy." We are excited to welcome Paul Martino, Managing Partner at Bullpen Capital, for Episode 2 of Charting the Course. A nine-time founder and veteran investor, Paul brings a unique perspective on the "post-seed" gap—backing founders who build in categories and geographies that others often ignore. To Paul, being misunderstood isn't an obstacle; it's often an early signal of opportunity. Full episode drops this Friday - follow to be notified. #ChartingTheCourse #VC #Startups

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