Column: When Should a Startup Hire Its First HR Person?

Spencer Rascoff

Spencer Rascoff serves as executive chairman of dot.LA. He is an entrepreneur and company leader who co-founded Zillow, Hotwire, dot.LA, Pacaso and Supernova, and who served as Zillow's CEO for a decade. During Spencer's time as CEO, Zillow won dozens of "best places to work" awards as it grew to over 4,500 employees, $3 billion in revenue, and $10 billion in market capitalization. Prior to Zillow, Spencer co-founded and was VP Corporate Development of Hotwire, which was sold to Expedia for $685 million in 2003. Through his startup studio and venture capital firm, 75 & Sunny, Spencer is an active angel investor in over 100 companies and is incubating several more.

Column: When Should a Startup Hire Its First HR Person?

The tech industry has come a long way over the last few years in terms of recognizing the importance of HR. Most CEOs now share my long-held belief that HR can and should play a strategic role at a company, and that having "good HR" can be as important as having "good tech," "good marketing" or any other function.


What is "good HR"? It means thinking of human resources (HR) as a way to recruit, retain and motivate great people. "Bad HR" means thinking of HR purely from a risk-mitigation standpoint (e.g., "how can the HR department help make sure we don't get sued for discriminatory hiring practices?"). Even worse than "bad HR" is having no HR at all.

Which begs the question that all startups face: when should you hire your first HR person?

TL/DR: typically at about 15-20 employees, I believe it's time to hire a dedicated HR person.

Most startups are capital constrained, so it's easy to postpone that first HR hire and focus scarce resources on product, engineering or sales. And if your startup is unsure if you'll get to the next round, then you should delay the HR hire and hold your breath on adding HR resources. If the CEO cares deeply about HR, he/she can fill some of this gap in the short term. But you really are just "holding your breath," and as soon as you feel that it's likely you'll be able to raise the next round (or get to break-even on your current funding), it's time to add an HR person.

Ideally, that first HR person should be a generalist — part recruiter, part HR business partner (HRBP), part employee comms, part learning & development (L&D), part diversity equity & inclusion (DEI), part HR ops and benefits. At larger companies (more than 500 employees), those various disciplines are separate and there are people who dedicate their entire careers to being the best in the world at each of them. But startups don't have the luxury of specialization.

That first HR hire is extremely important. He/she sets the tone for the role HR will play at the company. He/she needs a strategic seat at the table with the senior team to help create policies and culture which the company will live with for years. Here are just a few examples of decisions that startup companies with 10-50 employees need to make which would benefit enormously from a HR person involved:

  • The first version of the product is almost ready to launch and we're starting to think about monetization. What type of sales function should we have (e.g., inside sales or field sales)? What should the compensation structure be for salespeople? How much of a role should product people (e.g., program managers) play in sales?
  • We need to design employee levels and titles, an employee review system, roll out an employee experience software package and create guidelines on appropriate workplace behavior
  • We need to create an employer brand (which overlaps with our consumer brand), so we need to decide what it means to work at our company. Why should candidates choose to join us, and why should our employees choose to stay?
  • We have an under-performer and we need to manage him/her out of the company. It's particularly complicated because of the work-from-home situation where it's hard to evaluate employee productivity.

For these examples and many more, it's important not to wait to add your first HR person. In tech, we talk a lot about "tech debt," the concept that products build up technical debt if you don't consistently invest in their maintenance. Likewise, companies can create HR debt, which is very hard to dig out of if you wait too long.

Startup CEOs: Hire an HR generalist as employee number 20 — you'll be glad you did.

Additional Resources:

    https://twitter.com/spencerrascoff
    https://www.linkedin.com/in/spencerrascoff/
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    🏈Snapchat’s Super Bowl Push & Apple’s New App 📲—Here’s What’s New

    🔦 Spotlight

    Hello, Los Angeles!

    With Super Bowl LIX coming up this Sunday, the buzz isn’t just about the Chiefs vs. Eagles matchup—it’s also about how tech is shaping the experience. From Snapchat’s interactive game-day features to Apple’s latest product launch, there’s plenty happening beyond the field.

    Snapchat’s Super Bowl Features

    If you're watching the game, chances are you’ll be on your phone just as much as your TV. This year, Snapchat is rolling out AR Lenses, live score updates, and Spotlight challenges to make game day more interactive. Want to try on your team’s jersey? There’s a Lens for that. Need real-time updates? Snap has them covered. Attending the game in New Orleans? Live Location can help you track down friends in the crowd. As the second-screen experience becomes more ingrained in live sports, Snap is making sure it’s front and center.

    Snap’s New Initiative: The Department of Angels

    Super Bowl Sunday is about competition, but what happens when the challenge isn’t on the field? Yesterday, Snap announced The Department of Angels, a new initiative aimed at supporting communities recovering from disasters, offering independent funding and resources to help them rebuild on their own terms. Backed by $10 million from Snap Inc., Evan Spiegel, Bobby Murphy, and the California Community Foundation, the program shifts away from traditional corporate donations and toward grassroots, community-led recovery efforts. Could this be a model for how tech companies engage with real-world crises in the future?

    Apple Wants to Change How You Send Invites

    Apple is stepping into the event invite space with Apple Invites, a new app designed to make organizing gatherings simpler. Competing with platforms like Partiful and Evite, Apple’s version integrates directly into iMessage and Apple Calendar, making it an easy, built-in option for Apple users. With so many invite platforms out there, will Apple’s streamlined approach become the go-to for iPhone users, or will it simply be another tool in the mix?

    Where to Watch Super Bowl LIX

    The Chiefs and Eagles face off this Sunday at 3:30 PM PT on FOX. Here’s a helpful link to directly access ways to watch. You can stream the game for free on Tubi, or catch it on YouTube TV, Hulu + Live TV, NFL+, and fuboTV. And of course, we’ll be watching to see which brands—including tech giants—deliver the most memorable ads of the night.

    Between Snap’s game-day integrations, its push to support community-led recovery, and Apple’s move into digital invites, this week is full of shifts in how we connect. Which of these will redefine the way we interact? We’ll be watching.

    🤝 Venture Deals

    LA Companies

    • Musical AI, a company specializing in rights management for generative AI music, has raised a $1.5M seed funding round led by Build Ventures. The investment will support the development of Musical AI's attribution model, which analyzes tracks to determine the contribution of various data sources in AI-generated music. This enables rightsholders to monitor and manage the use of their works, while providing generative AI companies with access to quality licensed data and detailed usage reports. - learn more

    LA Venture Funds
    • Fika Ventures participated in a $16M Series A funding round for Ivo, a San Francisco-based AI-powered contract review platform, bringing its total funding to $22.2M. The company plans to use the funds to scale its AI-driven contract review solutions and has launched the Ivo Search Agent to enhance contract search and analysis capabilities. - learn more
    • Freeflow Ventures participated in a $7M seed funding round for Miist Therapeutics, a Bay Area-based company specializing in physics-based inhaled medicines. Miist plans to use the funds to advance its two lead programs: MST-01 for smoking addiction and MST-02 for migraine treatment. Their proprietary inhaler delivers sterile aqueous drug particles to the peripheral lung, achieving rapid absorption and symptom relief. - learn more
    • Fiore Ventures participated in a $9.5M strategic funding round for Little Otter, a digital mental health care provider specializing in whole-family services. The company plans to use the funds to expand its services to reach millions of families covered by Medicaid and commercial insurance plans, leveraging an AI-powered platform to enhance patient triage and personalized care. - learn more
    • Arca participated in a $13.5M Series A funding round for Beamable, a company specializing in providing live game services for game developers. The funds will be used to expand Beamable's decentralized gaming infrastructure and enhance its platform offerings. - learn more
    • Village Global participated in an $8M seed funding round for Desteia, a company leveraging AI and graph theory to address supply chain disruptions. The funds will be used to enhance Desteia's technology and expand its market reach. - learn more
    • TI Capital and QBIT Capital co-led a $7.5M Series A funding round for Largo.ai, a company specializing in AI-driven solutions for the film industry. The funds will be used to enhance Largo.ai's AI-powered platform and expand its market presence. - learn more
    • Strong Ventures participated in a ₩3.5 billion (approximately $2.9M) funding round for Class101, a South Korea-based all-in-one creator content platform. The company plans to use the funds to enhance its 'Creator Home' service, recruit top creators in fields such as economics, side jobs, art, crafts, and careers, and expand corporate subscription services for employee education and welfare. - learn more
    • Village Global participated in a $4M Seed funding round for Perspective AI, a Palo Alto, California-based company specializing in AI-mediated customer conversations. The funds will be used to expand operations and development efforts. - learn more

        LA Exits

        • SpringboardVR, a provider of virtual reality (VR) venue management software and a leading content marketplace for location-based entertainment, has been acquired by SynthesisVR. Previously owned by Vertigo Games, SpringboardVR is known for its platform that enables VR arcade operators to manage content licensing and operations efficiently. With this acquisition, SynthesisVR aims to enhance its offerings for VR arcades and developers, supporting the growth and innovation of the VR industry. - learn more
        • Generation Genius, an educational streaming platform that provides K-8 science and math videos, activities, and lessons, has been acquired by Newsela to enhance its instructional content and strengthen real-world connections in science and math education. - learn more

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          AI Dominates the Headlines, but Defense Tech Is Gaining Speed

          🔦 Spotlight

          Hello, Los Angeles!

          This week, DeepSeekAI has been dominating the tech conversation. The Chinese AI startup’s chatbot app surged to the No. 1 spot on the App Store, drawing both excitement and scrutiny. Supporters see its open-weight model as a potential game-changer, offering developers more flexibility compared to closed AI systems like OpenAI’s. But the rapid rise has also raised questions about security, data governance, and global AI competition. Whether DeepSeek will be a long-term disruptor or just a momentary sensation remains to be seen, but one thing is clear—AI remains the tech industry’s driving force.

          But while AI continues to dominate headlines, another sector is quietly making waves—defense technology. And one LA-based startup just secured a major endorsement from investors and the U.S. government.

          Castelion’s Hypersonic Bet—Can It Outrun the Defense Industry’s Red Tape?

          Image Source: Castelion

          El Segundo-based Castelionjust raised$100 million to accelerate its mission to build hypersonic weapons faster, cheaper, and at scale. The financing—$70 million in equity (led by Lightspeed Venture Partners with participation from a16z, Lavrock Ventures, Cantos, First In, BlueYard Capital, and Interlagos) and $30 million in venture debt (from Silicon Valley Bank)—is the latest sign that venture capital sees national security startups as a high-growth opportunity.

          Unlike traditional defense contractors, Castelion is operating like a fast-moving startup, not a slow-moving government supplier. Founded by former SpaceX engineers, the company is applying an iterative, test-heavy approach to building long-range hypersonic strike weapons—which travel at speeds exceeding Mach 5 (3,800+ mph) and are designed to evade modern missile defenses.

          Not Just VC-Backed—The U.S. Military is Betting on Castelion Too

          While the $100 million raise is a major milestone, Castelion already has funded contracts with the U.S. Navy, U.S. Air Force, and U.S. Army. These contracts are focused on hypersonic technology development and scaled manufacturing, areas where the military has struggled to move quickly due to bureaucratic delays and reliance on traditional defense giants.

          To prove it can execute, Castelion recently successfully launched a low-cost ballistic missile from a self-built launcher in Mojave. Now, with both government contracts and venture capital behind it, the company is pushing forward on more flight tests and building out its scaled production capabilities.

          Image Source: Castelion - Castelion launches a missile prototype in Mojave, CA

          With rising geopolitical tensions and an increasing focus on faster, cost-effective deterrence, Castelion is positioning itself as a new kind of defense player—one that moves at startup speed. Whether it can sustain that pace while navigating the complexities of government procurement remains to be seen, but one thing is clear: the future of defense tech isn’t just about who can build the best weapons—it’s about who can build them fast enough.


          🤝 Venture Deals

          LA Companies

          • Omnitron Sensors, a Los Angeles-based pioneer in microelectromechanical systems (MEMS) fabrication technology, has secured over $13M in a Series A funding round led by Corriente Advisors, LLC, with participation from L'ATTITUDE Ventures. The company plans to use the funds to expand its engineering and operations teams and accelerate the mass production of its first product, a reliable and affordable MEMS step-scanning mirror designed for various applications, including AI data centers, advanced driver assistance systems (ADAS), drones, extended reality (XR) headsets, and toxic gas-detection systems. - learn more
          • Camouflet, a Los Angeles-based technology company specializing in AI-driven dynamic pricing solutions, has secured a $12M Series A funding round led by QVM. The company plans to utilize the proceeds to scale its platform across various industries, expand into international markets, and enhance its technology and team to better serve its clients. - learn more
          LA Venture Funds
          • Clocktower Ventures participated in a $6.2M Seed funding round for Foyer, a New York-based fintech startup that assists individuals in saving for home purchases. The funds will be used to enhance Foyer's platform and expand its user base. - learn more
          • Smash Capital participated in ElevenLabs' $180M Series C funding round, bringing the company's valuation to $3.3 billion. Based in New York, ElevenLabs specializes in AI-powered text-to-speech and voice cloning technology. The newly secured funds will be used to enhance its AI audio platform and expand its global presence. - learn more
          • March Capital participated in a $25M Series C funding round for SuperOps to support the company's efforts in advancing AI research and development, expanding offerings for mid-market and enterprise managed service providers (MSPs), and scaling its global presence. Additionally, SuperOps is launching an AI-powered Endpoint Management tool to enhance IT team productivity. - learn more
          • Cedars-Sinai participated in a $2M funding round for Neu Health to support its AI-driven neurology care platform for conditions like Parkinson’s disease and dementia. Originating from the University of Oxford, Neu Health will use the funds to enter the U.S. market, beginning with a six-month pilot program at Cedars-Sinai focused on improving neurology patient care. - learn more
          • Chapter One Ventures participated in a $2.8M seed funding round for Mevvy, a blockchain startup aiming to democratize Maximal Extractable Value (MEV) trading by simplifying access and reducing technical complexities. The funds will be used to further develop Mevvy's platform, expand its user base, and enhance its offerings. - learn more

            LA Exits

            • Kona, an AI-powered assistant and coach for remote managers, has been acquired by 15Five, a performance management platform. Founded in 2019, Kona integrates with virtual meeting platforms like Zoom and Google Meet to provide tailored coaching and enablement for remote managers. The acquisition aims to enhance 15Five's offerings by incorporating Kona's capabilities to improve manager effectiveness within existing workflows. - learn more

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              Can Technology Outpace Wildfires?

              🔦 Spotlight

              Hello, LA!

              This week, tech headlines are buzzing with OpenAI's launch of Operator, a tool that promises to transform task automation, and TikTok’s major outage, which left millions disconnected. But closer to home, as wildfires blaze across Southern California, survival has become the focus—and technology is making it possible.

              When the plume of smoke reappeared on the horizon, residents across Southern California turned to tools like Watch Duty. Over the past week, as flames surged, the app gained 600,000 new users in just one night, delivering critical, real-time information to help residents stay ahead of danger. Watch Duty, designed to provide wildfire updates, has proven to be much more than an alert system. It’s a lifeline.

              The app integrates live data, satellite imagery, and community reports to send updates directly to users. Information includes fire locations, evacuation orders, and air quality indices, empowering quick, informed decisions. Its community-driven ethos—with contributions from locals, firefighters, and volunteers—ensures hyper-local and timely updates, filling gaps where traditional news outlets often fall short.

              Image Source: Watch Duty

              A New Era of Fire Alerts

              Watch Duty redefines wildfire preparedness through technology and collaboration:

              • Fire Detection: Monitors data from satellites, agencies, and ground sources to identify wildfires.
              • Data Verification: A team of experts ensures reported activity is accurate.
              • Real-Time Alerts: Notifications are sent within 60 seconds of detection.
              • Community Contributions: Local residents provide photos and updates.
              • User Notifications: Alerts include fire size, location, and evacuation details.

              These features make Watch Duty an indispensable tool during wildfire season. In 2024, the app processed over 2 million alerts and supported 50,000 evacuations, with plans to expand predictive modeling by 2025 to anticipate threats before they escalate.

              Innovations Reshaping Wildfire Management

              Early Detection Leaders:

              • AlertCalifornia: Operates over 1,000 cameras with machine learning to monitor high-risk areas.
              • Pano AI: Uses cameras and sensors to detect smoke and alert responders.
              • Torch Sensors: Deploys heat-detection sensors to identify anomalies early.

              Image Source: Torch Sensors

              Predictive and Analytical Pioneers:

              • Chooch AI: Employs drones and computer vision to monitor fire hazards.
              • Data Blanket: Uses analytics to forecast fire behavior and assist evacuations.
              • Rain: Leverages advanced atmospheric sensing and AI-driven technology to provide precise fire detection and tracking. Its real-time data on fire weather conditions and environmental factors helps agencies anticipate and respond to wildfires with greater efficiency.
              • SCEPTER: Tracks air quality and wildfire emissions using AI and satellite data.

              Image Source: Rain

              A Vision for the Future

              As Los Angeles continues to adapt to the realities of a changing climate, tools like Watch Duty, Pano AI, and AlertCalifornia are proving to be invaluable. These technologies are not just reactive measures; they represent a shift toward proactive disaster preparedness. The question now isn’t whether technology can help but how much more it can achieve in the years to come.

              With the integration of predictive modeling, AI, and real-time data, there’s hope for a future where wildfires are no longer unpredictable forces of destruction. Imagine every household equipped with predictive wildfire maps, heat-detecting drones, and AI-driven tools to guide safety decisions. The innovations are here—it's up to us to support and scale them to ensure they reach the communities that need them most. Which company, which app, or which breakthrough will emerge as the next lifeline? The possibilities for a safer, more prepared Los Angeles feel closer than ever.

              🤝 Venture Deals

              LA Companies

              • Favorited, a new livestream app positioning itself as an alternative to TikTok, has raised a $1.3M Pre-Seed from HF0, Soma Ventures, and several angel investors from the entertainment and social space. The platform, which participated in the a16z Speedrun accelerator program, offers features like streaks and leaderboards to boost user engagement. Favorited plans to use the funds to enhance its app's functionalities and expand its user base. - learn more
              LA Venture Funds
              • Overture VC participated in a $12M Series A funding round for Bedrock Energy, an Austin, Texas-based startup specializing in geothermal heating and cooling systems. Bedrock Energy plans to use the funds to advance its geothermal technologies and expand deployments in Colorado, Utah, and neighboring states. - learn more
              • Navigate Ventures LLC participated in a $7.2M Series A funding round for XILO, a San Diego-based insurance technology startup that provides a quoting and sales automation platform to help independent insurance agencies convert the next generation of insurance shoppers; the funds will be used to scale operations, manufacturing, and commercial efforts for its acne products. - learn more
              • Upfront Ventures participated in a $5.25M Seed funding round for 1up.ai, a New York-based company that automates knowledge for sales teams; the funds will be used to empower their growing customer base, including industry leaders like WalkMe, Gladly, and Deliveroo. - learn more
              • MTech Capital participated in a $2.2M Pre-Seed funding round for Qumis, a Chicago-based AI platform designed to transform insurance knowledge work; the funds will be used to scale its AI capabilities, accelerate product development, and expand its customer base. - learn more
              • Amboy Street Ventures participated in a SEK 304M Series B funding round for Gesynta Pharma, a Stockholm-based pharmaceutical company specializing in anti-inflammatory and pain-relief treatments, with the funds directed toward advancing a Phase II clinical trial of their lead candidate, vipoglanstat, for endometriosis. - learn more

              LA Exits

              • Bandy Manufacturing, a Los Angeles-based provider of aerospace fasteners and components, has been acquired by Novaria Group to enhance its portfolio and expand its capabilities in the aerospace and defense industries. - learn more
              • Pangea, a company specializing in eco-friendly and sustainable products with a focus on innovative technology solutions, is being acquired by Nature's Miracle Holding Inc. to accelerate growth and capitalize on synergies in sustainability and tech-driven product development. - learn more
              • Notisphere, a healthcare communication platform streamlining recall and alert management, has been acquired by Par Excellence Systems to enhance its capabilities in delivering efficient supply chain solutions for the healthcare industry. - learn more
              • Cryogenic Machinery Corp., a North Hollywood, California-based manufacturer specializing in cryogenic pumps for industrial gas and energy applications, has been acquired by PSG, a Dover company, to enhance PSG's portfolio of specialized fluid handling solutions. - learn more

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