Column: How and When Do You Hire Your First Salesperson?

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: How and When Do You Hire Your First Salesperson?

The other day I had a call with a founder in my portfolio of angel investments who is preparing for a Series A round. His question was: At what point should he step back from personally leading sales and hire a real sales team?

Every seed or Series A company will go through this important step. There's no question that a founder's passion and knowledge of the product usually makes for a great salesperson. But at some point, it's time to let go and bring in the experts: true salespeople.

The challenge is, unless you cut your teeth in sales or have direct experience with the inner workings of a sales organization, many founders don't know much about recruiting or structuring a sales team. So where do you start?


First, with people:

There are many different types of sales professionals out there, all with different strengths, and in an unlimited capital situation you'd want to hire a bunch of different types and see which one performs best for your startup. But most companies at this stage can't afford to run that experiment. Here are the four types of salespeople you can start with as your first hire:

  1. Cheap and scrappy. This is your straight-out-of-college, hungry-to-prove-and-perform individual with no industry or sales experience but great coachability and drive. This person will need investment up front, but the right pick will pay off.
  2. Seasoned sales pro. This person has lots of sales experience and can be a vital asset in structuring and leading the sales team as it grows, but they have no industry experience or connections and will need to develop those.
  3. Seasoned industry pro. This person has both experience and connections within the industry you're operating but no sales experience. While this person can still be successful, arguably skill gaps are harder to fill than knowledge gaps.
  4. Sales and industry pro. This is a turnkey hire because of their sales experience within the industry, giving them the knowledge and connections to hit the ground running with the least amount of upfront investment.

I advised the founder that #4, a sales and industry pro, is probably the easiest place to start. That said, any one of these types of sales hires can be successful; ultimately it comes down to how much you can invest in them (less experience requires more time, training and coaching), and also who you come across in your search. You may find the perfect fit for your company's purpose and values in any of these buckets, and any additional investment or ramp up is worth it for the right hire.

Second, compensation:

The right compensation model helps you not only attract great professionals but help them do their jobs more effectively with the right incentives. But make peace with the fact that you will make a lot of mistakes in this area, and you will need to adjust and pivot throughout the growth, maturation and life cycle of your business. It's just part of building companies. With that disclaimer, here are two crucial pieces to sales compensation:

1. Compensation model. Your structure consists of a base salary plus commission, and understanding the right base salary depends on the type of salespeople you're hiring. A good guideline is a $40-60K base salary (remember, I'm talking about startups here), but it could be as high as $100K depending on experience and field.

Once you've established that base, the next step is to determine what percentage of total compensation is variable based on a commission, which is paid out if the salesperson meets or exceeds quota. A good rule of thumb here is setting the variable comp at 25% of the base salary and up to another 25% for exceeding quota. That means a sales person on a $50K salary will make an additional $25K for meeting quota and up to another $25K (double the salary) for crushing it.

2. Quota and revenue churn. This second piece is vital not just for the earning potential of the employee but also for the long-term health of the business, and you'll find much of your adjustments over time happen in this area. Quota and churn are inextricably linked; if you don't consider revenue churn when setting quota, your salespeople will "sell hot" into accounts that won't last — which will over time bury them in a hole that makes it difficult for them and the business to recover. An example: Say you set quota at $10K of new revenue per month, and in the first month your sales person meets it. But in month two, you see 10% ($1K) of that new business churn. To make quota, your salesperson will need to sell $11K, or quota plus 10%. Should this pattern continue, the hole gets deeper and more difficult to scramble out of. Churn guardrails are crucial.

Incorporating churn into quota is overall healthier for the business. Not only does it disincentivize "commission hole-digging," it also forces your salespeople to form more consultative relationships and take greater care in onboarding and account management since churn and quota are both front of mind in their efforts.

While there's no prescribed path to success with your first sales organization, you need to have a plan to scale from founder evangelism to mechanized sales that scale revenue. Founders should always be selling their own product, but even more important is their ability to create a scalable sales org beyond themselves.

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Standing Together Through the Flames

🔦 Spotlight

To our Los Angeles family,

This week’s wildfires have brought immense pain and hardship to our beloved city. Many of our friends, neighbors, and colleagues have faced evacuations, power outages, and the devastating loss of homes and livelihoods. Our hearts go out to everyone affected by this tragedy.

At dot.LA, we want to express our deepest sympathy to those suffering in this moment. We see your resilience and stand with you during this challenging time. This community has always been defined by its strength and compassion, and now is the time to come together in support.

If You or Someone You Know Has Been Impacted, Resources Are Available:

Evacuation Shelters:

  • Calvary Community Church: 5495 Via Rocas, Westlake Village, CA 91362
  • Ritchie Valens Recreation Center: 10736 Laurel Canyon Blvd., Pacoima, CA 91331
  • Pan Pacific Recreational Center: 7600 Beverly Blvd., Los Angeles, CA 90036
  • Westwood Recreation Center: 1350 Sepulveda Blvd., Los Angeles, CA 90025
  • Pasadena Civic Auditorium: 300 East Green Street, Pasadena, CA 91101
  • Pomona Fairplex: 1101 W McKinley Ave, Pomona, CA 91768
  • Stoner Recreation Center: 1835 Stoner Ave, Los Angeles, CA 90025

Animal Shelters:

Small Animals:

  • Agoura Animal Care Center: 29525 Agoura Rd, Agoura Hills, CA 91301
  • Baldwin Park Animal Care Center: 4275 Elton St, Baldwin Park, CA 91706
  • Carson Animal Care Center: 216 W Victoria St, Gardena, CA 90248
  • Downey Animal Care Center: 11258 Garfield Ave, Downey, CA 90242
  • Lancaster Animal Care Center: 5210 W Ave I, Lancaster, CA 93536
  • Palmdale Animal Care Center: 38550 Sierra Hwy, Palmdale, CA 93550

Large Animals:

  • Pomona Fairplex: 1101 W McKinley Ave, Pomona
  • Industry Hills Expo: 16200 Temple Ave, City of Industry, CA 91744
  • Antelope Valley Fair: 2551 W Avenue H, Lancaster, CA 93536
  • Los Angeles Equestrian Center: 480 W Riverside Dr, Burbank, CA 91506
  • Pierce College Equestrian Center: 7100 El Rancho Dr, Woodland Hills, CA 91371

Disaster Relief Information:

  • LA County Assessor: Information for property owners and FAQs about disaster relief.

Mental Health Support:

  • Los Angeles County Department of Mental Health: Crisis counseling and support for those affected. Access services through their website or call their hotline at (800) 854-7771.

Temporary Housing Support:

  • Airbnb: In partnership with 211 LA, offering free temporary housing for displaced residents. Spaces are limited; complete the form to be notified of availability.

Transportation Support:

  • Uber: Use promo code WILDFIRE25 for 2 free rides up to $40 each to/from active shelters.
  • Lyft: Code CAFIRERELIEF25 offers 2 rides up to $25 each for up to 500 riders, valid until 1/15.
  • Metro: Fare collection is suspended systemwide.

Staying Informed:

  • Watch Duty App: Provides real-time wildfire tracking, evacuation warnings, and updates.
  • Los Angeles Fire Department Alerts: Visit their website for the latest information on fire status and safety guidelines.

Safety Precautions:

  • Ready, Set, Go!: Personal Wildfire Action Plan by the Los Angeles County Fire Department.

To those in our community who are volunteering, donating, or offering aid in any form—thank you. Your efforts embody the spirit of LA: strong, compassionate, and unstoppable.

At dot.LA, we’re committed to amplifying stories of resilience and support. If you’ve seen inspiring acts of kindness or have resources to share, please let us know. Together, we can shine a light on the incredible ways this community is stepping up during these trying times.

In the days ahead, let’s hold tight to the bonds that unite us and remember that we are stronger together. The fires may scar the land, but they cannot dim the collective spirit of Los Angeles.

We’re here for you, and we’re with you.

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    A Strong Finish to 2024 for LA Tech: Crosscut Ventures Leads the Way

    🔦 Spotlight

    Happy Friday LA!

    As we close the book on 2024, Los Angeles has had a remarkable year in tech and venture capital. From groundbreaking funding rounds to industry-defining innovations, the city’s tech ecosystem has showcased its ability to adapt and thrive. Among the year’s final highlights was the announcement that Crosscut Ventures, one of LA’s premier early-stage venture capital firms, has added Jon Ylvisaker as its newest Partner.

    Crosscut Ventures’ Bold New Direction

    Announced in late December, Jon Ylvisaker’s appointment reflects Crosscut Ventures’ commitment to advancing its focus on the energy transition. Ylvisaker brings decades of experience in driving investments in energy technologies and digital infrastructure. As the founding partner and managing director of Yield Capital Partners, he led investments in startups and established companies shaping the future of sustainability. At Wolfacre Global Management, a Tiger Management hedge fund, he further honed his expertise in supporting impactful climate-focused solutions.

    Brian Garrett, Managing Director and Co-Founder of Crosscut Ventures, said, “Jon's extensive experience in climate and digital infrastructure investments, coupled with his impressive track record of bringing groundbreaking technologies to market, makes him the ideal partner to help lead our focus.”

    Since its founding in 2008, Crosscut has played a key role in shaping LA’s tech landscape. Ylvisaker’s addition reinforces the firm’s commitment to addressing global challenges like energy transition and sustainability, further solidifying its leadership in venture capital innovation.

    What’s Next for LA Tech in 2025

    The momentum from 2024 has set the stage for an even bigger year ahead. Entrepreneurs, investors, and innovators in LA are poised to take on new challenges and create meaningful change across industries.

    As we step into 2025, we want to thank everyone who helped make 2024 such a standout year. Here’s to another year of progress, innovation, and success. From all of us at dot.LA, Happy New Year!

    🤝 Venture Deals

    LA Companies

    • First Resonance, a company specializing in digital manufacturing software through its ION Factory OS, has raised a $20M funding round led by Third Prime with participation from Blue Bear Capital and others. This brings its total funding to $36M and will be used to accelerate product development, grow its customer base, and enhance support for advanced manufacturing sectors like aerospace, robotics, and clean energy. - learn more
    LA Venture Funds
    • Finality Capital Partners led a $17M Seed funding round for ChainOpera AI, a California-based company developing blockchain networks for AI-powered agents and applications, to accelerate product development, expand its team and enhance its blockchain and AI integration capabilities. - learn more

    LA Exits

    • Thirteen Lune, an inclusive beauty e-commerce platform, has been acquired by SNR Capital, marking a significant milestone in the platform's mission to amplify underrepresented beauty brands while fueling its next stage of growth. - learn more
    • Ergobaby, a leading brand in juvenile products known for its high-quality baby carriers, has been acquired by Highlander Partners. The acquisition aims to bolster Ergobaby’s growth, expand its product offerings, and strengthen its position in the parenting solutions market. - learn more

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    Salt AI’s $3M Bet, Snapchat’s Creator Cash, Rivian’s EV Tech, and ŌURA’s $200M Win

    🔦 Spotlight

    Happy Friday, LA - let’s dive right in to this week’s highlights:

    Salt AI, a forward-thinking AI startup based in Los Angeles, has secured a $3 million seed funding round led by Morpheus Ventures with participation from Struck Capital, among others, to tackle the complexity of managing workflows.Salt AI's blog details how its platform centralizes tools like CRM systems, project management software, and data trackers into one interface, eliminating inefficiencies and freeing up teams to focus on meaningful work. With new funding in hand, Salt plans to scale its platform and expand its reach, a move that underscores how AI can solve everyday business challenges.

    Image Source: Salt AI - Aber Whitcomb

    While Salt AI focuses on the workplace, Snapchat is doubling down on creators, with its latest updates introducing revenue-sharing opportunities and direct monetization features. The company’snewsroom update outlines how enhanced analytics will help creators better understand their audiences and sustain their work. The platform's latest updates introduce revenue-sharing opportunities and direct monetization features, along with analytics that give creators deeper insights into their audience. By making it easier for creators to grow and sustain their work, Snapchat positions itself as a key player in the creator economy, offering features that rival platforms like YouTube and TikTok.

    Image Source: Snap

    On the roads, Rivian is redefining what it means to drive an electric vehicle. The company’s latest software update includes advanced route planning, energy management tools, and customization options that make every trip more intuitive and efficient. Additionally, Rivian has introduced new entertainment features, including Google Cast, YouTube, and SiriusXM, as featured in Rivian’ssoftware spotlight, enhancing the in-cabin experience for drivers and passengers alike. This isn’t just about convenience; Rivian is showing how thoughtful software design can elevate the entire EV experience, blending practicality with sophistication.

    Image Source: Rivian

    ŌURA is making headlines with a fresh $200 million Series D funding round, with participation from Fidelity Management & Research Company and Dexcom, which now values the company at $2.55 billion. This investment, as reported byBusiness Wire, highlights the growing demand for wearable health technology and positions ŌURA as a leader in the space. With its sleek design and emphasis on actionable health insights, the funding will enable ŌURA to expand its reach and further integrate wearables into daily health management, strengthening its position in the competitive health tech market. With this funding, ŌURA aims to reach more users and expand its capabilities, further embedding wearables into daily health management.

    Image Source: ŌURA

    Stay tuned as Salt AI, Snapchat, Rivian, and ŌURA continue to evolve, offering us new ways to work, connect, and live better.

    🤝 Venture Deals

      LA Venture Funds
        • Undeterred Capital participated in a $7M Seed funding round for Portal, a Watertown, Mass.-based biotech company specializing in advanced intracellular delivery technology to drive innovations in biological research and cellular therapeutics. - learn more
        • Vamos Ventures participated in a $7.9M Series A funding round for Culina Health, a Hoboken, NJ-based company that provides personalized, science-based virtual nutrition care by connecting patients with registered dietitians, with plans to use the funds to expand its offerings for dietitians and patients, implement AI-driven tools to enhance care efficiency, and strengthen its leadership team through key hires. - learn more
        • Humans Ventures participated in a $3.8M Seed funding round for Hamming.ai, a San Francisco-based company specializing in automated tools for testing and optimizing voice agents, with plans to expand its platform, enhance reliability and perform, and accelerate product development. - learn more
        • Fifth Wall led, with participation from Starshot Capital and others, in a $9.5M Series A funding round for Mojave, a Sunnyvale, CA-based company developing energy-efficient commercial air conditioning technology. The funds will be used to accelerate the adoption of its innovative systems and reduce energy consumption in the cooling industry. - learn more
        • ReMY Investors participated in a $17M Series B funding round for Scripta Insights, a company that leverages data analytics to help employers and healthy plans reduce prescription drug costs, with the funds aimed at expanding its platform and scaling operations. - learn more
        • Mantis VC participated in a $16.5M funding round for Nuon, a company specializing in Bring Your Own Cloud (BYOC) solutions that streamline AI, data, and infrastructure software deployment. The funds will support product development, readiness for general availability in 2025, and efforts to expand customer acquisition. - learn more
        • B Capital participated in a $102M Series C funding round for Precision, a company developing minimally invasive brain-computer interfaces to treat neurological disorders, with plans to use the funds to expand its team, advance clinical research, and refine its AI-powered brain implant for helping users with severe paralysis operate digital devices using their thoughts. - learn more
        • The Games Fund led a $3M Seed funding round for Dark Passenger, a Poland-based game studio founded by veterans of The Witcher 3 and Cyberpunk 2077, to create an unannounced, innovative, first-person multiplayer PvPvE stealth-action game set in a distinctive universe inspired by feudal Japan and martial arts cinema. - learn more

            LA Exits

            • Calliope Networks, a generative AI company providing licensed media content like movies, TV shows, and news, has been acquired by Protege to strengthen its platform’s capabilities in advancing AI development. - learn more

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