Vertical AI Deep Dive with OMERS Ventures

Pat McGovern - Bowery Capital - Where Vertical AI Wins

Our Guest: Pat McGovern [https://www.linkedin.com/in/pwmcgovern] is a Principal at Bowery Capital [https://www.linkedin.com/company/bowery-capital], an early-stage B2B fund investing primarily at pre-seed. He focuses on vertical AI and writes the newsletter Capital Efficient. [http://capitalefficient.substack.com] Episode Topics: * How Bowery approaches pre-seed in 2026 and what “first institutional capital” looks like today. * The shift from “SaaS contracts” to outcome-driven and services-driven models. * Pat’s vertical AI playbook. * Case study on Enata and how voice-first AI gives field sellers time back while improving CRM quality and sales insights. * Why more startups may compete directly for industry spend rather than selling tools to incumbents. * What Pat wants in founders. * The new definition of technical in the AI era. * How to run customer pilots well, including shorter timelines, mid-point check-ins, proof-of-value gates, and prioritizing referenceable logos. Resources: https://x.com/pw_mcgovern?lang=en [https://x.com/pw_mcgovern?lang=en] https://www.linkedin.com/in/pwmcgovern [https://www.linkedin.com/in/pwmcgovern]https://bowerycap.com/ [https://bowerycap.com/] https://capitalefficient.substack.com/ [https://capitalefficient.substack.com/] About Cloud Returns by Cloud Ratings: Cloud Returns covers ALL types of software investing, whether seed, venture capital, growth equity, private equity, debt, and the public markets. Our host - Matt Harney - is active on Twitter @saasletter [https://twitter.com/SaaSletter] and writes "SaaSletter [https://www.saasletter.com/]", an investing-oriented SaaS newsletter [https://www.saasletter.com/] on Substack. https://cloudradio.cloudratings.com/ [https://cloudradio.cloudratings.com/] https://twitter.com/SaaSletter [https://twitter.com/SaaSletter] https://www.saasletter.com/ [https://www.saasletter.com/] About Cloud Ratings: Cloud Ratings [https://cloudratings.com/] is a customer outcomes-focused, data-driven software research analyst firm. We exist to allow organizations to make more confident, lower-risk software purchasing decisions. Our Cloud Ratings Category Reports [https://cloudratings.com/category-reports/] combine user reviews with verified vendor data to impartially identify leading software products. Recent report examples include: Subscription Management Software [https://cloudratings.com/subscription-management-software/], Session Replay Software [https://cloudratings.com/session-replay-software/], Sales Compensation Software [https://cloudratings.com/sales-compensation-software/], and Digital Sales Room Software [https://cloudratings.com/digital-sales-room-software/] Built upon investigative customer interviews, our True ROI Reports quantify and provide 3rd party validation of a software product’s business value. https://cloudratings.com/ [https://cloudratings.com/]

Joey Brookhart - AlphaRepo - Software Buyside Realities

In this episode, host Matt Harney [https://www.linkedin.com/in/mattharneylinkedin/] speaks with Joey Brookhart [https://www.linkedin.com/in/josephbrookhart/], Co-Founder of AlphaRepo [https://alpharepo.com/] and a longtime long-short software investor, as Managing Partner and Portfolio Manager of Sandbrook Capital.  Joey explains the SaaS metrics that matter most, the overrated ones investors should avoid, and why earnings day volatility often comes down to “bogeys” and positioning rather than guidance. He also introduces AlphaRepo, the Excel-integrated platform he built to track model revisions and portfolio-wide trends, and offers advice for aspiring buy-side analysts. Episode Topics: * Joey’s background in long-short investing and the founding of AlphaRepo * The SaaS metrics that matter most: Net New ARR/ACV, sales efficiency, and free cash flow per share * Overrated metrics: NDR and net customer adds when they don’t tie to real drivers * Why earnings day reactions are driven by “bogeys” and positioning games * Forecasting rigor: buy-side models vs. public company guidance * Career advice: “Get at bats” with pitches and always start with primary documents * The role of AI in buy-side workflows — an opportunity, not a threat Memorable Quote: On overrated metrics: “Anything that’s really backward-looking, or doesn’t tie to the drivers of the business, is noise.” Resources: AlphaRepo [https://alpharepo.com] Joey Brookhart on LinkedIn [https://www.linkedin.com/in/josephbrookhart/] Joey on Twitter / X: https://twitter.com/@SaasquatchC [https://x.com/SaasquatchC]

Vertical AI Deep Dive with OMERS Ventures

Our Guests: Marissa Moore [https://www.linkedin.com/in/marissa-schlueter-moore?trk=article-ssr-frontend-pulse_little-mention], and Taku Murahwi [https://ca.linkedin.com/in/taku-murahwi?trk=article-ssr-frontend-pulse_little-mention] of OMERS Ventures [https://ca.linkedin.com/company/omers-ventures?trk=article-ssr-frontend-pulse_little-mention], an early-stage venture capital firm investing in Series A-C companies with a first cheque size between $5-25M.  Episode Topics: * OMERS Venture’s investment criteria. * Type of founders Marissa and Taku prefer. * How does OMERS Ventures conduct due diligence on a company founder? * Overview of Marissa’s “The Green Room [https://sites.google.com/view/thefoundergreenroom/home]”, a “safe space for founders to practice their pitch, risk-free, in front of current investors and subject matter experts.” * Marissa’s advice for how founders can improve their pitches. * Deep dive into the Eight Core Factors in OMERS Ventures' AI Deep Dive Report. * How does unstructured and industry-specific data affect AI’s effectiveness? * Marissa’s insights and strategies from successful companies to gain the trust of their customers. * The rationale behind the degree of high-stakes decision-making factor. * How long it will take for a AI-native company to move from seed funding to Series A, factoring in the development timelines needed to refine an AI product and scale? * Is the Net Promoter Score bar higher for an AI company than a traditional software company? * Which industries are more or less suitable for vertical AI solutions based on the Vertical AI Deep Dive Report? * Great habits Marissa and Taku learned from someone in OMERS Ventures portfolio. Resources: OMERS Ventures Vertical AI Report: https://airtable.com/appcfwQFbRedHquqo/paghteBojIXj9d72g/form [https://airtable.com/appcfwQFbRedHquqo/paghteBojIXj9d72g/form] About Cloud Returns by Cloud Ratings: Cloud Returns covers ALL types of software investing, whether seed, venture capital, growth equity, private equity, debt, and the public markets. Our host - Matt Harney - is active on Twitter @saasletter [https://twitter.com/SaaSletter] and writes "SaaSletter [https://www.saasletter.com/]", an investing-oriented SaaS newsletter [https://www.saasletter.com/] on Substack. https://cloudradio.cloudratings.com/ [https://cloudradio.cloudratings.com/] https://twitter.com/SaaSletter [https://twitter.com/SaaSletter] https://www.saasletter.com/ [https://www.saasletter.com/] About Cloud Ratings: Cloud Ratings [https://cloudratings.com/] is a customer outcomes-focused, data-driven software research analyst firm. We exist to allow organizations to make more confident, lower-risk software purchasing decisions. Our Cloud Ratings Category Reports [https://cloudratings.com/category-reports/] combine user reviews with verified vendor data to impartially identify leading software products. Recent report examples include: Board Management Software [https://cloudratings.com/board-management-software/], Account-Based Marketing Software [https://cloudratings.com/account-based-marketing-abm-software/], Cap Table + Equity Management Software [https://cloudratings.com/cap-table-equity-management-software/], Lead Routing Software [https://cloudratings.com/lead-routing-software/], and Sales Training + Onboarding Software [https://cloudratings.com/sales-training-software/]. Built upon investigative customer interviews, our True ROI Reports quantify and provide 3rd party validation of a software product’s business value. https://cloudratings.com/ [https://cloudratings.com/]

Diamond Innabi - SaaS M&A 101: Selling Your Software Company

Our Guest: Diamond Innabi [https://www.linkedin.com/in/diamondinnabi/] is a Principal at Software Equity Group [https://www.linkedin.com/company/software-equity-group/] (SEG), a boutique M&A advisory firm headquartered in San Diego that focuses on B2B vertically focused software and SaaS companies. Episode Topics: * Understanding the full cycle - from prep to closing - of selling your company. * When should CEOs engage with an investment banker or consider an M&A path? * Common mistakes that founders, CEOs, and boards make during the M&A process. * Diamond's advice to founders who are interfacing with potential acquirers. * Overview of SEG’s 20 Factor Valuation Scorecard. * Difference between strategic buyers and private equity firms in terms of acquisition criteria.  * Diamond elaborates on the 2023 M&A Report: “The higher-than-usual volume of low multiple deals is a result of from negative transaction catalysts like evaporating cash runway, challenging debt dynamics, competitive concerns, or investors opting to exit their lower-performing assets to focus on high performers.” * Factors influencing premium valuations for select companies. Resources: https://softwareequity.com/research/ [https://softwareequity.com/research/]  https://softwareequity.com/company-valuation-formula/ [https://softwareequity.com/company-valuation-formula/] https://softwareequity.com/research/saas-ma-buyers-perspectives [https://softwareequity.com/research/saas-ma-buyers-perspectives] About Cloud Returns by Cloud Ratings: Cloud Returns covers ALL types of software investing, whether seed, venture capital, growth equity, private equity, debt, and the public markets. Our host - Matt Harney - is active on Twitter @saasletter [https://twitter.com/SaaSletter] and writes "SaaSletter [https://www.saasletter.com/]", an investing-oriented SaaS newsletter [https://www.saasletter.com/] on Substack. https://cloudradio.cloudratings.com/ [https://cloudradio.cloudratings.com/] https://twitter.com/SaaSletter [https://twitter.com/SaaSletter] https://www.saasletter.com/ [https://www.saasletter.com/] About Cloud Ratings: Cloud Ratings [https://cloudratings.com/] is a customer outcomes-focused, data-driven software research analyst firm. We exist to allow organizations to make more confident, lower-risk software purchasing decisions. Our Cloud Ratings Category Reports [https://cloudratings.com/category-reports/] combine user reviews with verified vendor data to impartially identify leading software products. Recent report examples include: Board Management Software [https://cloudratings.com/board-management-software/], Account-Based Marketing Software [https://cloudratings.com/account-based-marketing-abm-software/], Cap Table + Equity Management Software [https://cloudratings.com/cap-table-equity-management-software/], Lead Routing Software [https://cloudratings.com/lead-routing-software/], and Sales Training + Onboarding Software [https://cloudratings.com/sales-training-software/]. Built upon investigative customer interviews, our True ROI Reports quantify and provide 3rd party validation of a software product’s business value. https://cloudratings.com/ [https://cloudratings.com/]

Paul Stansik of ParkerGale Capital - An Operating Partner’s POV on Value Creation

Our Guest: Paul Stansik [https://www.linkedin.com/in/paulstansik/] is the Private Equity Operating Partner at ParkerGale Capital [https://www.linkedin.com/company/parkergale-capital/], a B2B focused private equity firm, buying profitable technology companies from founders. Episode Topics: * Paul and PartnerGale Capital's investment criteria. * What does an operating partner do? * A brief overview of Paul's weekly sales playbook at PartnerGale Capital. * Approach to gaining a deeper understanding of a business's dynamics. * Paul elaborates: "Always scrubbing the pipeline means never scrubbing the pipeline." * Assessing the “sales machine” of a target investment during due diligence.. * Paul’s view on the impact of AI on sales and marketing. * An overview of ParkerGale's hiring playbook. * Realities and challenges of building teams in the middle market. Resources: Paul Stansik’s Substack: https://hellooperator.substack.com/ [https://hellooperator.substack.com/] The Weekly Sales Metrics Playbook [https://www.parkergale.com/salesmetricsplaybook]  Hiring Playbook Slides: How We Hire At ParkerGale  [https://www.parkergale.com/how-we-hire-parkergale] "What CEOs Should Expect From Their Sales Leader" [https://www.linkedin.com/posts/paulstansik_what-ceos-should-expect-from-their-sales-activity-7167181690241576961-qrtG?utm_source=share&utm_medium=member_desktop]  "AI’s Impact on Sales + Marketing" [https://hellooperator.substack.com/p/ais-impact-on-sales-marketing-2a5820ba4bf3?r=7m40j&utm_campaign=post&utm_medium=web]  About Cloud Returns by Cloud Ratings: Cloud Returns covers ALL types of software investing, whether seed, venture capital, growth equity, private equity, debt, and the public markets. Our host - Matt Harney - is active on Twitter @saasletter [https://twitter.com/SaaSletter] and writes "SaaSletter [https://www.saasletter.com/]", an investing-oriented SaaS newsletter [https://www.saasletter.com/] on Substack. https://cloudradio.cloudratings.com/ [https://cloudradio.cloudratings.com/] https://twitter.com/SaaSletter [https://twitter.com/SaaSletter] https://www.saasletter.com/ [https://www.saasletter.com/] About Cloud Ratings: Cloud Ratings [https://cloudratings.com/] is a customer outcomes-focused, data-driven software research analyst firm. We exist to allow organizations to make more confident, lower-risk software purchasing decisions. Our Cloud Ratings Category Reports [https://cloudratings.com/category-reports/] combine user reviews with verified vendor data to impartially identify leading software products. Recent report examples include: Board Management Software [https://cloudratings.com/board-management-software/], Account-Based Marketing Software [https://cloudratings.com/account-based-marketing-abm-software/], Cap Table + Equity Management Software [https://cloudratings.com/cap-table-equity-management-software/], Lead Routing Software [https://cloudratings.com/lead-routing-software/], and Sales Training + Onboarding Software [https://cloudratings.com/sales-training-software/]. Built upon investigative customer interviews, our True ROI Reports quantify and provide 3rd party validation of a software product’s business value. https://cloudratings.com/ [https://cloudratings.com/]