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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    ⚖️FTC’s "Click to Cancel" Rule and Its Ripple Effect on Tech

    🔦 Spotlight

    Happy Friday Los Angeles,

    The FTC’s new “Click to Cancel” rule is shaking up subscription-based tech. Now, instead of navigating a maze of cancellation hurdles, users can cancel subscriptions as easily as they signed up—with a single click. This shift is a wake-up call for SaaS, streaming, and app-based companies, where once-hidden exit options often kept users around simply because canceling was a hassle.

    The rule also requires businesses to send regular renewal reminders, ensuring customers stay informed about upcoming charges. It's more than a cancellation button—it’s about transparency and giving users control over their decisions.

    For startups, the impact goes deeper than UX adjustments. Many have relied on "dark patterns," which subtly discourage cancellations by hiding the exit. Now, companies must shift toward building genuine loyalty by delivering real value, not by complicating exits.

    While this might affect retention rates initially, it could lead to more sustainable business models that rely on satisfaction-driven loyalty. Investors may start prioritizing companies that emphasize transparent, long-term engagement over those that depend on dark patterns to maintain retention metrics.

    The rule opens the door to more ethical UX design and a truly user-centered approach across the tech industry. It may even set a precedent against manipulative design in other areas, such as privacy settings or payment methods.

    Ultimately, the “Click to Cancel” rule presents an opportunity for the tech industry to foster trust and build stronger customer relationships. Startups and established companies that embrace transparency will likely stand out as leaders in a new era of customer-centric tech, where trust—not tricky design—is what retains users.

    As the tech landscape continues to evolve, LA Tech Week 2024 offers a chance to explore these shifts in real-time. Check out the upcoming event lineups to stay informed and make the most of your time:

    For updates or more event information, visit the official Tech Week calendar.


    🤝 Venture Deals

    LA Companies

    • Ghost, a company supporting top brands and retailers with streamlined logistics and fulfillment solutions, raised a $40M Series C funding round led by L Catterton to fuel its continued growth and innovation. - learn more

    LA Venture Funds
    • Assembly Ventures participated in a $27M Series A round for Monogoto, a provider of software-defined connectivity solutions that enable secure, cloud-based IoT and cellular network management on a global scale. - learn more
    • Angeleno Group participated in a $32M Series C round for REsurety, a company that recently launched an innovative clean energy marketplace aimed at providing better financial and operational insights to support renewable energy transactions. - learn more

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      🌴🧑‍💻 Your Guide to LA Tech Week 2024

      🔦 Spotlight

      Happy Friday Los Angeles,

      As many of you know, LA Tech Week is right around the corner, kicking off next Monday October 14th bringing together founders, creatives, investors, and engineers for a week of immersive events, panels, and socials across the city. From blockchain and AI to biotech and design, LA Tech Week is a chance to dive into the ideas shaping today’s technology landscape.


      What to Look Forward To

      Insights from Visionary Leaders: Hear firsthand from industry trailblazers as they share stories, challenges, and key lessons from their experiences. Expect fresh perspectives on AI, venture capital, biotech, and the ethical questions around emerging technologies.

      Interactive Panels: This week isn’t about watching from the sidelines; it’s about engaging directly with the tech community. Participate in hands-on panels discussing everything from startup scaling to ethical AI, with honest insights from those actively shaping these fields.

      Networking Mixers & Social Events: Meet and connect with founders, VCs, developers, designers, and fellow techies across LA. Rooftop mixers, lunch meetups, and creative gatherings offer the perfect chance to spark ideas and collaborate.

      Plan your week with the daily lineup, organized by location for easy navigation:

      For updates or more event information, visit the official Tech Week calendar.

      Enjoy LA Tech Week 2024!!


      🤝 Venture Deals

      LA Companies

      • Clout Kitchen, a Los Angeles and Manila based startup, has raised $4.45M in seed funding, co-led by a16z SPEEDRUN and Peak XV’s Surge, to develop AI-powered digital twins, which enables gaming creators to produce realistic virtual avatars for content and fan engagement. - learn more
      • MeWe, a privacy-focused social media platform, has raised an initial $6M in Series B funding led by McCourt Global to support Web3 integration and expand its decentralized network for 20 millions users. - learn more

        LA Venture Funds
        • EGB Capital participated in a $10M Series A funding round for MiLaboratories, which develops software that enables biologists to independently analyze complex genomic data, accelerating research and discovery in fields like drug development. - learn more
        • Crosscut Ventures participated in the $13.75M seed round for Airloom Energy, a company focused on developing airborne wind energy technology to harness high-altitude winds, with plans to accelerate a pilot project in Wyoming. - learn more
        • Overture VC participated in a $5.5M Seed funding round for Molg Inc., a company developing robotics and software for circular manufacturing, designed to disassemble electronics efficiently and recover valuable materials to reduce e-waste and support sustainable production. - learn more


          LA Exits

          • Options MD, a Los Angeles based telemedicine platform that provides care for people suffering from severe and treatment-resistant mental illness, is set to be acquired by Resilience Lab, an AI-driven provider focused on enhancing mental health care access. - learn more

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          LA Tech Week 2024: Saturday-Sunday Event Lineup
          tech-week

          Here’s what’s happening during the closing weekend (Oct 19 - Oct 20) of LA Tech Week 2024! Events are organized by location so you can easily catch the sessions that interest you most.

          SATURDAY EVENTS

          BEVERLY HILLS

          12:00 PM

          • BIG Showcase (Invite Only):

          BIG Showcase (Invite Only)

          2:00 PM

          Light Dao

          Struck Capital, Seahorse Express

          EAGLE ROCK

          12:00 PM

          Sunrise Integration, Shopify

          EL SEGUNDO

          9:00 PM

          Administratum, Valar Atomics

          HOLLYWOOD

          10:00 AM

          Passes

          MALIBU

          6:00 PM

          • Malibu Beachfront Investors Networking & Wine Tasting:See Details

          Gaya Ventures

          MARINA DEL RAY

          6:00 PM

          • Awaken Your Spirit: A Journey of Transformation (Invite Only)

          Sagos Distro, Alma Wellness

          SANTA MONICA

          7:00 AM

          Founders Running Club

          8:30 AM

          Techstars

          9:00 AM

          Magic Mind

          StartupStarter, Inc., City of Santa Monica

          10:00 AM

          Gen She

          AI LA

          Crea, Barry's, Unsubscribe

          10:30 AM

          Plantologist

          11:30 AM

          • Pickleball Palooza (Invite Only)

          YouTube

          1:00 PM

          • Realfren Games: From strangers to an inner Realfren within 52 weekends: See Details

          Office for Humanity and Circuit Works

          • Talking blockchain technology with special guests: See Details

          LadyDayDao

          5:00 PM

          KARD, What's Plots

          THE VALLEY

          7:00 AM

          Camino5

          VENICE

          9:00 AM

          Westside Yogis

          11:00 AM

          Open App

          1:00 PM

          Ripe and Teddy's Hot House

          4:00 PM

          • Fashion Forward: How AI is Redefining the Fashion Industry: See Details

          VIAVIA, BNTO.RENT, ALMA.AI

          VIRTUAL

          11:00 AM

          BLCK UNICRN

          WEST HOLLYWOOD

          7:00 PM

          Next Sequence

          SUNDAY EVENTS

          INGLEWOOD

          12:00 PM

          Entrepreneur Ventures, VCPE GROUPS

          PLAYA DEL RAY

          2:00 PM

          AI LA, DELL, NVIDIA

          SANTA MONICA

          10:00 AM

          • Women Founders, Cold Brew & Beach View, Rooftop: See Details

          Clutch Talent

          11:00 AM

          11DollarSunglasses.com, Less Litter Foundation

          12:00 PM

          Data in LA, Amplitude

          12:30 AM

          New Moon, Warner UK Innovations

          TOPANGA CANYON

          3:00 PM

          Dreamore

          VENICE

          8:00 AM

          • Surf session with founders, investors, creators: See Details

          Surfed Club, Bow Shock

          12:00 PM

          • Podcast Panel and Brunch: LA Tech Community Builders: See Details

          WeAreLATech.com, Blankspaces.com

          VIRTUAL

          2:00 PM

          BLCK UNICRN


          For updates or more event information, visit the official Tech Week calendar.

          Enjoy LA Tech Week 2024!


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