Costanoa Ventures

Vertex Ventures is a venture capital firm who makes high-conviction Seed/Series A investments in SaaS and infrastructure software startups. We invest in only a few new companies each year, allowing us to concentrate our time and capital on a small portfolio. Our initial check sizes range from $500K to $10M, and we continue to support companies as they scale. Who we back: Having been founders and operators ourselves, we are inspired by practitioners - entrepreneurs with deep technical or market experience across software infrastructure, SaaS, data, developer tools, security, and fintech. How we help: We have the experience, resources, focus, and network for the early-stage journey. Even though one or two of us might be your closest confidantes, the benefit of our partnership is that we help you build your company and improve your odds of success -- be it in the form of potential hires, customers, or business partners. Why Vertex Ventures? Personalized Talent Programs The success of any company depends exclusively on having the right people. We help bring in great talent - from your first Account Executive to a Chief Revenue Officer - and we help implement strategies to retain great talent by building a healthy and inclusive culture. Our industry-wide best practices are tailored based on a founder's individual needs and a company's ethos, thus establishing a strong foundation as you grow. Support beyond capital through our platform Vertex Ventures is an upstart venture capital team in a world filled with staid, stalwart funds. Phone calls, dinners, webinars, you name it. We give you the support, network, and resources so you can focus on building your company, your idea, and your team. From hiring your first account executive to helping win customers, we’re partners along your entire journey. No BS transparency Our founders appreciate our no BS approach to coaching and counseling. Whether we’re two days into our partnership or two years, we’ll tell you what we think. We tell you why we’re excited, where there’s risk, where there’s potential, and where we need to pivot. Ultimately, we’re not telling you what to do. It’s up to you to take the driver's seat, make those decisions, and grow from a technologist to a visionary leader.

Citi Ventures (CV) is Citi’s corporate innovation arm. Citi is a global financial institution with over $70B in Revenue, $8B+ in technology spend, presence in 98 countries and daily processing flow of ~$4T. Citi Ventures has invested in over 100 companies in the last decade, has top quartile returns and the current portfolio includes a 25+ companies valued at > $1B including high growth companies such as Datarobot, Docker, Plaid, Grab, Snyk, Cribl, Tanium, Eightfold.ai, Harness and Trulioo. Portfolio exits include Braze, Grab, Square, Docusign, Jet.com, Honey, Cylance. The Venture Investing team focuses on identifying and investing in entrepreneurs whose unique approach to core challenges will help define the future of financial services. The team brings together Citi’s business needs with portfolio companies’ technologies, services and business models to accelerate Citi’s ability to evolve in a dynamic marketplace and help portfolio companies scale.

Our investments commonly range from $1M to $20M, with our ownership percentages usually below 20%. Why USAASTRATEGIC VALUE: We partner with companies that offer strategic value, driving benefit to our members and mission. FUND COMMITMENT: Our focus is on making members' lives easier rather than investment horizons and exit timelines. ACTIVE INVESTORS: Introductions are made to USAA lines of business that are often active in the growth of your portfolio. USAA strategically invests in four key focus areas:FinTech: Technologies relating to payments, lending, investing, etc. that enable USAA to provide simpler, more effective financial solutions for its members. Security, Data, and AI: Systems enabling secure authentication and identity management systems plus fraud prevention, personalization, underwriting and risk detection and avoidance. InsurTech: Technologies enabling connected cars, homes and wearables that are transforming the future of our insurance products: auto, property, life and health. Enterprise Infrastructure: Solutions enabling member and employees including communication technologies, operational capabilities (Cloud, Containerization, DevOps, etc.) and distribution/mobility platforms.

Our global sphere of knowledge drives our investment thesis across all industries. We serve on the boards on some of the most innovative technology companies in the world. We see global trends as they are emerging. We combine this knowledge with data, lots of data, to know where the world is heading during the next seven-to-ten-years. We partner with the extraordinary We’ve developed a world class reputation for identifying, investing, and serving extraordinary entrepreneurs. We don’t meddle in their business. When asked, we deliver critical thinking that leads to scale and hypergrowth. We go beyond the investment We drive strategic growth, shorten the time to reach global scale, facilitate introductions, but we don’t stop there. We stick with it until the ink is dried. We drive revenue, recruit, and introduce future investors. As we look out at the next 10 years, we couldn't be more excited as the global world becomes smaller and more tightly connected. Read more to see where we think the industry is heading! We drive real value to our portfolio Through our Revenue Bearing Relationships, we have driven $400M in revenue to more than 40% of our portfolio companies. Technology buyers around the world trust our cohesive vision of the future. They come to us to identify emerging solutions that can give their businesses a competitive advantage.

Sierra Ventures invests in the future of The Enterprise. We invest early – primarily Seed and Series A – and look for proven product market fit, disruption in the market, and strong IP. We tend to lead investment rounds and reserve capital for follow on rounds to support our entrepreneurs as they grow. We believe that partnership is paramount. We work closely with all of the entrepreneurs we invest in, guiding them with expertise and capital to help their companies grow and deliver on their promise. We understand that great companies don’t get built overnight, and we don’t mind rolling up our sleeves and getting our hands dirty. In fact, we enjoy it. Sierra’s Investment FocusDATA/AI The volume of data has exploded, and with the emergence of the cloud, new tools are being developed with many data infrastructure software platforms focusing specifically on artificial intelligence (AI) & machine learning (ML). We’re excited about companies that make it easier to ingest, access, and analyze data. Sub-sectors within Data/AI include AI/ML and Big Data. VERTICAL SAAS Many industries that rely on excel or pen and paper have been forced to dramatically increase the pace of technology adoption. Vertical SaaS represents the shift to specialization where software is business-specific and is designed for a specific domain. Sub-sectors within Vertical SaaS include FinTech, EnterpriseApps, and Security. INFRASTRUCTURE Next-Gen Infrastructure will be the core connecting fabric for all future technology capabilities. Wide-scale improvement is needed in order to enable applications to run consistently in almost any location across the globe. Organizations have expedited infrastructure modernization strategies which continues to drive growth in the sector. Sub-sectors within Infrastructure include Cloud and IoT. Next-Gen TechnologiesDIGITAL HEALTH Adoption of Health software has been faster than ever before due to the pandemic tailwind and technology trends that put the consumer in charge. New tools are being developed to reach patients creating opportunities with Pharma, Providers, and Payers. We anticipate a dramatic shift towards more value based care (payer / provider) and digitization and decentralization (pharma). WEB3 Web3 promises to make the internet as accessible, open sourced, secure, and decentralized as possible with the goal of benefiting the people engaging, not central organizations. We are looking at the full Web3 ecosystem including Decentralized Applications (DApps), Decentralized Finance (DeFi), Non-Fungible Tokens (NFTs), Decentralized Autonomous Organizations (DAOs), Cryptocurrencies, and more. A sub-sector we focus on within Web3 includes Blockchain. INDUSTRIAL AUTOMATION Digitally non-native industries like Manufacturing, Supply Chain, and Logistics are seeking ways to find cost parity and production reliability while adhering to increasing demand across the globe. Humans alone will not be able to keep pace with these market trends and automation will be a key driver in movements like Industry 4.0. Sub-sectors within Industrial Automation include Robotics and Devices. CONSUMER The ubiquity of smartphones has enabled consumers to access goods and services with relative ease and companies are tuning into customer needs and engaging with their increasingly loyal customer base, leading to viral adoption patterns. Additionally, Consumer social platforms have allowed individuals to express themselves and make money doing it, giving more power to the “Creator Economy”. We are interested in Creator Economy and mission driven D2C Applications & Marketplaces. ECOMMERCE A fast growing eCommerce market has been bolstered by the pandemic and every part of the value chain is seeing disruption. The eCommerce software market is driven by market trends like headless eCommerce and ReCommerce. B2B eCommerce has exploded globally and we think the US market will catch up in the coming years. A sub-sector we focus on within eCommerce is Marketplaces. EDTECH Digital and tech-enabled learning has been accelerated in the classroom and the boardroom by the pandemic and social trends such as “the great resignation”. Trends like VR/AR and the Metaverse becoming mainstream combined with the price of enablement devices like smartphones, tablets, and computers decreasing to make technology more accessible than ever have created a market that is ripe for EdTech to flourish.

In the past 15 years, Canada’s innovation ecosystem has taken off. Startups, accelerators, incubators, investors, and forward-thinking policies have created a true hotbed of entrepreneurship. Bold ideas are flourishing, transformative ventures are thriving, and Canadian technology is reshaping industries, driving growth at home and societal impact worldwide. We could look back and self-applause our progress, but let’s be radically transparent: major challenges remain and there is still a lot left to be done. A majority of our technology companies are not achieving the global scale they legitimately could attain. They do not achieve their full potential; frequently selling prematurely instead of being the market consolidator and building for the long term. ​ A central cause of this problem is the lack of early-stage venture leadership and risk-taking at the true “inflection point” - when startups have early revenue, signs of product-market fit, and are ready to scale. Canada has no shortage of funds willing to follow on, but far too few are prepared to lead Seed and Series A rounds: to structure financings, set valuations, negotiate terms, and define the conditions for success. The “Death Valley” is real. Canadian venture capital lacks leadership, and needs to contribute more expertise. The “Death Valley” is the critical scaling stage that most companies fail to overcome. It happens as a company attempts to bridge the gap between early commercial success and achieving significant revenue scale. In 2024, roughly six in ten Canadian seed rounds included foreign investors, a dynamic that intensifies by Series A and beyond. Half of that was led by US Too often, the most promising Canadian startups saw their early rounds led by U.S. VCs. While we welcome foreign investors, global connections strengthen our ecosystem, Canada simply lacks enough lead investors to keep ownership at home. For early-stage and scale-up companies, the shortage of funding alternatives is a major barrier. Many of our best founders head south in search of stronger capital partners. The gap is readily filled by international investors, and who can blame them? Canadian founders are known to outperform and to be more capital efficient than their U.S. peers. The best founders will always attract global capital and seek out the strongest partners. But this comes at a cost. Every time leadership is ceded abroad, Canada loses ownership of its most successful businesses. An ecosystem of “follower investors” produces an economy of subsidiaries, when what we need are global leaders. The problem is twofold: not enough Canadian capital to lead at the inflection point, and not enough seasoned expertise to scale our champions. If you believe, as we do, that local technology champions will be the cornerstone of our future economic prosperity, then our ecosystem must level up. We need more early-stage capital that doesn’t just follow, but leads. Equity financing must evolve to deliver not only dollars, but expertise, resources, and technology to nurture local champions. Understandably so, when they lead funding rounds, most Canadian VC firms will either focus on the pre-seed stage, where the power-law is magnified and placing many small bets is more important than bringing expertise, or the growth stages (Series B+) where significant risk is already behind and larger checks drive the outcomes. A paradigm shift is required. New organizations must emerge that add real value and aren’t afraid to take the lead at the Seed stage. This is why we are launching Amiral Ventures. Amiral Ventures is a new venture capital firm on a mission to empower Canada’s most ambitious founders with dynamic capital and scaling expertise, building the next generation of technology flagships with lasting societal impact. Vaisseau Amiral (French for Flagship): A ship or building that is recognized for its size and strength, making it the pride of a fleet or an organization As entrepreneurs ourselves, we have utmost respect for the founder journey. We don’t just invest, we aim to deserve the right to partner with them along the way. Amiral creates the ecosystem where visionary founders thrive, with capital, expertise, global networks, and technology to fuel their growth. We’ve built scale-ups, felt the entrepreneurial highs and lows, and now channel that experience into backing the founders solving the world’s toughest problems. Prosperity Decoded Backing Canadian founders at seed to series-a to drive enterprise productivity, sustainability & resilience The challenges we face, low productivity, climate urgency, and fragile infrastructure, are systemic. But they also represent one of the greatest investment junctures of our time. New enterprise technologies, powered by AI and software, can equip leaders with transformative, mission-critical solutions. Productivity. Canada’s productivity gap is real—our workers produce only ~70% of what their U.S. peers achieve. The answer isn’t more talk, it’s action: applied AI, automation, robotics, and digital platforms. We back Canadian founders building these solutions at home and scaling them worldwide. Sustainability. Profitability and environmental impact can no longer be at odds. The transition to renewables and the optimization of energy use are urgent. Software and AI will be the linchpins of this shift, from clean energy production to efficient consumption. Resilience. Supply chains, industries, and critical infrastructure are under strain. Building resilience means more autonomy, security, and sovereignty, enabled by smart industry, robotics, digital twins, cybersecurity and intelligent manufacturing. More than just capital. Founders-led and founders-backed. Amiral Ventures will focus on leading early-stage rounds between theSeed and Series A and will actively support companies to achieve a strong global position. Capital is a commodity, expertise is not. An integral part of our investment thesis is having a dedicated impact team that will create value post-investment. Our initial focus is helping portfolio companies expand globally and seize international opportunities to scale. Over time, Amiral’s impact team will operate like a service organization, combining internal expertise, external networks, and proprietary technology to empower founders. Our goal is clear: every dollar invested by Amiral should deliver a measurable impact on a founder’s trajectory. Beyond the Amiral team’s expertise, we are surrounding ourselves by an unprecedented group of investors who are themselves founders, CEOs, CTOs, CROs, and not only share our vision but are eager to roll up their sleeves to help our flagship companies. ​Building an enduring franchise We are proudly Québécois but our market is much wider. We believe that for Québec & Canada to succeed, we must expand beyond our borders just like the Admiral butterfly. Papillon Amiral (French for Admiral Butterfly): Emblem of Québec, it is known for its rapid flight, its impressive migration, resilience and its noble appearance. Building a dynamic, resilient, and cleaner economy means securing local ownership while scaling globally. Amiral is an investment firm with an entrepreneurial mindset, built to create value for the next generation of innovators. We stand on the shoulders of the Canadian venture pioneers who came before us. History will mark the early 2020s as an inflection point. Technologies once magical are now everyday tools. The means to create prosperity are in our hands. But good is no longer good enough. High-paying jobs, economic development, and new technologies are necessary but we must also increase Canadian ownership in our champion companies, deploy smarter capital, and elevate our ecosystem. The “Death Valley” for Canadian startups must be crossed. Ambitious founders are ready to take flight on the global stage. Let’s build the next generation of Canadian flagships.