Column: How Should I Structure My Annual Review Process?

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.

How Should I Structure My Annual Review Process?

I've always hated annual reviews. That's not an encouraging start to giving advice, I know, but it's my reality, and unfortunately it's all too common. So why do so many of us loathe annual reviews?

For starters, they take too long. At all of my previous companies, we would spend at least three months on the process, from individual reviews to manager feedback to compensation and promotion approvals. The annual review conversation has also never been very useful outside of inducing anxiety at the end of the year; Due to its infrequency, the ups and downs of the year aren't accounted for, and we learn very little as managers and employees as a result. Topping it off, annual reviews have historically just been about performance, leaving a critical piece — employee engagement — unaddressed in the most influential evaluations throughout an employee's career.


Leaders and technology providers are grappling with how to solve these challenges now that company culture and employee engagement are widely accepted as performance drivers. We now know through data that business success is no longer just about "human engineering," or how we deploy our workforce effectively; it's now also about whether people are motivated and driven by the mission and culture. And, critically, success comes down to how these two pieces intersect to drive success forward.

To make annual reviews worthwhile and valuable to both managers and employees, we need to re-engineer the process. Your approach will be company and culture-specific, and in fact, mine has changed with each company I've founded, but focusing on these three areas will help guide a modern approach:

Check in Frequently with Two-Way Feedback

Having a review once a year sets both the employee and manager up for failure. So much happens within that time span, particularly at high-growth companies, and if you only talk about performance and engagement once a year you are leaving so many success-driving opportunities on the table. In fact, abandon the term "annual review" entirely.

Instead, focus on frequency. Conduct weekly 1:1 meetings to cover tactical work and ways in which managers can remove roadblocks, use quarterly check-ins to assess the overall state of employee engagement and have slightly longer check-ins every six months that focus on bigger picture performance as well as engagement topics like quality of work, delivery, collaboration, connecting to the mission and career development. Frequency ensures the end of year conversation — often the hardest one because it dictates promotions and compensation — will not come as a surprise.

Equally important, make sure these conversations or check-ins incorporate 360° feedback, anonymously and through technology so the employee feels empowered and safe to share honestly. It's just as critical for the employee to share what the manager can do to help drive performance and engagement as it is for the manager to provide feedback to the employee. This was something we did well at Zillow, and our implementation of 360° feedback ended up producing great insights that led to successful leadership training programs and artifacts like the "leadership playbook," a guide of principles that became words to live by similar to our core values.

Be intentional with Time and Topics

Help your teams keep the process manageable by providing specific guidance through time-boxing, ie. self evaluations should take no longer than 30 minutes, 360° feedback should take no more than 5 minutes per leader and manager feedback should take no more than 30 minutes per direct report. It's easy to get carried away, especially on the employee's side, when they know their evaluation is tied to their compensation. Time-boxing helps avoid this.

Focusing your topics is equally important, particularly when it comes to compensation. Limit conversations about compensation to once a year (because that's typically the only time you can do anything about it), and separate compensation discussions from those about performance, if only by a few days. This ensures employees hear both critical pieces; if you combine the two, they'll only pay attention to the numbers.

Invest in an HR Platform

Everything I've recommended thus far can be made better, less biased and more efficient with HR technology. But understanding engagement is where this space is getting really exciting and game-changing for companies, because as we lose cultural artifacts we've relied on, such as office environments, other aspects of our culture like how we communicate and how we make decisions shine brighter and have a greater influence on engagement.

At my latest startup, Pacaso, we use Officevibe to conduct weekly pulse checks of our virtual workforce, and these help us assess in real-time whether our employees are inspired by and mapping to the mission, understanding their role and feeling represented and supported by their manager and the company. It gives us actionable information to keep us on the right path.

Pulse checks are just one piece of the puzzle. CultureAmp, for example, provides insights on peer feedback and company-wide performance reviews that help combat bias and support representation. Qualtrics links regular engagement and pulse survey results with milestones like promotions, role changes and returning from parental leave — all at the company level to protect the individual employees but help the manager navigate performance and engagement needs. AllVoices (in which I'm an investor) provides an anonymous, direct line from employees to leadership to report bullying, harassment, bias or other cultural concerns with the goal of creating safer, more inclusive companies. There is so much we can do with technology to connect performance and engagement and just create better workplaces in general. HR platforms are quickly becoming a critical investment for companies.

Spencer Rascoff is the co-founder of dot.LA, Zillow and Hotwire, as well as the recent proptech startup Pacaso. He was CEO of Zillow for 10 years. He is a sponsor of Supernova Partners Acquisition Company, a special purpose acquisition company. Do you have a founder question? Let him know here!

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The LA Startup Taking on One of Parenting’s Most Frustrating Problems

🔦 Spotlight

Hello Los Angeles,

Every parent knows the feeling of becoming an overnight expert in something they never wanted to learn.

For families navigating developmental delays, behavioral health needs, autism, speech therapy, occupational therapy or pediatric mental health support, that learning curve can become a full-time job. Finding the right specialist is hard enough. Getting those specialists, pediatricians, insurers and families to actually coordinate with each other? That’s often where the system breaks.

That’s the problem Los Angeles-based Village is trying to solve.

The specialty pediatrics startup raised $9.5 million in seed funding this week, led by Upfront Ventures, with participation from Bling Capital, GTMFund and Perceptive Ventures.

Its AI-powered platform is designed to bring families, providers, pediatricians and payers into one coordinated care system for children with developmental, behavioral and mental health needs.

The company was born out of co-founder Brandon Terry’s personal experience navigating care for his daughter after she was diagnosed with a rare genetic condition. Like many parents, his family faced long waitlists, high out-of-pocket costs and a fragmented web of specialists who were not necessarily working from the same playbook.

The pitch is not simply “find a provider faster.” Village wants to coordinate the entire team around a child, including occupational therapists, speech-language pathologists, behavioral therapists and pediatricians. Its AI agent, Vera, is designed to help with the administrative drag that often slows pediatric practices down: scheduling, documentation, billing and care coordination.

The company’s raise also points to a less flashy, but deeply consequential corner of health tech: making complex care easier to navigate. In specialty pediatrics, the pain point is not always the quality of care itself. It is the space between appointments, referrals, insurance approvals and provider communication where families are often left to connect the dots themselves.

So far, Village says it has built a network of more than 400 independent pediatric specialty providers in Southern California and has contracts with major commercial insurers including Blue Cross & Blue Shield, Cigna and UnitedHealthcare. The new funding will help the company expand across Southern California, into other parts of California and eventually into new states.

In other words, the next wave of healthcare infrastructure may not look like one giant hospital system. It may look more like a connected network built around the people who have been holding the system together all along: families.

And yes, in this case, it really does take a Village.

Venture deals follow below.👇


🤝 Venture Deals

    LA Companies

    • MOSH, the brain health nutrition brand co-founded by Maria Shriver and Patrick Schwarzenegger, raised a $13M Series A led by Main Street Advisors to expand nationally across grocery retailers and accelerate product innovation. The Los Angeles-based company plans to use the funding to grow its retail footprint, including an upcoming Target launch, while expanding its lineup of brain-focused nutrition products with new high-protein bars designed to support both cognitive and physical performance. - learn more
    • Spring Labs raised $5M to expand its AI-native compliance platform for banks and fintechs, with the funding led by BankTech Ventures and Haymaker Ventures. The Marina del Rey-based company is building AI agents that automate complaint handling, dispute resolution, and other compliance workflows, helping regulated financial institutions scale operations more efficiently while maintaining oversight and auditability. - learn more
    • FlowPrompt.ai secured a strategic seed investment from ART Fund SP, part of ChainBLX SPC, as the company expands its AI orchestration platform designed to help developers build and manage complex AI workflows through a visual interface. Alongside the investment, the companies also launched a global AI hackathon and builder program that will give selected founders access to funding opportunities, platform tools, and a live investor pitch event in Los Angeles later this summer. - learn more
    • Chance Studios raised $3.2M to build a unified platform for trading card game collectors, aiming to bring inventory management, marketplace activity, and community features into a single ecosystem. The round was co-led by Makers Fund and Hashed, with participation from Arbitrum Gaming Ventures, GAM3GIRL VC, and others, as the company looks to modernize how collectors buy, track, and interact around physical and digital TCG assets. - learn more

    LA Venture Funds
    • Rebel Fund participated in Moritz’s $9M seed round, backing the AI-native law firm as it looks to automate large portions of routine corporate legal work. The company combines software with experienced attorneys to speed up contract drafting and review, and says it has already handled more than $2 billion worth of contracts across over 100 companies since launching earlier this year. - learn more
    • Rebel Fund participated in Corvera’s $4.2M seed round, backing the AI-native supply chain platform as it automates back-office operations for consumer packaged goods brands. The Y Combinator-backed startup is building AI agents that can handle workflows like order processing, invoicing, and demand planning across fragmented enterprise systems, helping brands scale operations without significantly increasing headcount. - learn more
    • Chaac Ventures participated in Astrocade’s $5.6M funding round, backing the gaming startup as it builds a social gaming platform centered around community-created interactive experiences. The company is focused on blending gaming, streaming, and creator tools into a more collaborative entertainment platform, and plans to use the funding to expand development and grow its creator ecosystem. - learn more
    • Fusion VC participated in MSICS Pharma’s $3.6M funding round, backing the biotech company as it advances psilocybin-based treatments for PTSD, depression, and OCD. The company is developing medical-grade psychedelic compounds and plans to use the funding to expand production, accelerate clinical trials, and prepare for broader commercialization as interest in psychedelic therapies continues to grow. - learn more
    • JAM Fund participated in Fun’s $72M Series A, backing the payments infrastructure startup as it scales its platform for moving money across fintech and digital asset applications. The round was co-led by Multicoin Capital and SignalFire, and the company plans to use the funding to expand internationally, pursue acquisitions, and deepen its infrastructure stack as demand grows for faster global payment systems. - learn more

    LA Exits

    • Tapin2 was acquired by Greater Sum Ventures, joining MyVenue as part of GSV’s expanded point-of-sale technology platform for stadiums, arenas and live entertainment venues. Tapin2 provides self-service, suite catering and mobile ordering technology for high-volume sports and entertainment venues, while MyVenue offers cloud-native POS software across concessions, premium seating, retail, in-seat ordering and other venue operations. Together, the companies say their technology is used in more than 70% of MLB and NFL stadiums. Terms of the transaction were not disclosed. - learn more
    • Motiv Space Systems signed a definitive agreement to be acquired by Rocket Lab, bringing its space robotics, motion control systems and precision spacecraft mechanisms into Rocket Lab’s growing space systems business. Motiv’s technology has supported major missions including NASA’s Mars Perseverance rover and lunar rover programs, and the company will be rebranded as Rocket Lab Robotics after the deal closes, which is expected in the second quarter of 2026. - learn more
    • Robyn was acquired by Los Angeles-based Tot Squad, bringing its AI-powered doula tool into Tot Squad’s broader support platform for expecting and new moms. Robyn’s AI was trained on more than 70,000 de-identified messages between parents and doulas, and the acquisition will help Tot Squad offer free, around-the-clock pregnancy and early motherhood guidance alongside access to human experts like doulas, lactation consultants and sleep coaches. Terms of the deal were not disclosed. - learn more

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      Match Goes Niche With $100M Move

      🔦 Spotlight

      Hello Los Angeles,

      It’s May, and LA is about to have one of its more important weeks.

      The Milken Institute Global Conference 2026 returns to Beverly Hills next week, bringing together thousands of investors, operators, policymakers, and executives. It’s one of the few places where public markets, private capital, and tech actually overlap in the same rooms, and where you can usually get an early read on what capital is leaning into before it fully shows up in the data.

      This year, one theme is already starting to surface. Platforms are getting more specific, not more broad.

      This week’s news is a good example.

      Match Group is investing $100 million into Sniffies, a fast-growing, location-based platform built for gay, bi, trans, and queer men. It’s a notable move for a company best known for mainstream dating apps like Tinder and Hinge, and it signals a deeper push into more niche, community-driven platforms.

      Sniffies operates very differently from traditional dating apps. It’s more real-time, more map-based, and more focused on immediacy than long-term matching. In other words, it’s built around behavior, not profiles.

      And that’s what makes the investment interesting.

      For years, the dominant strategy in consumer platforms was scale, build one product that works for everyone. But what we’re seeing now is the opposite. The platforms that are gaining traction tend to be the ones that understand a specific audience deeply and build for how that group actually behaves.

      Match leaning into that shift isn’t just about expanding its portfolio. It’s a recognition that growth is coming from focus.

      And in a city like Los Angeles, that’s usually where things start.

      Below are this week’s venture deals and fund announcements across LA 👇


      🤝 Venture Deals

        LA Companies

        • Illuminant Surgical raised an $8.4M seed round to accelerate the rollout of its real-time anatomical projection platform, which aims to give surgeons enhanced visibility during procedures. The company’s “Skylight” system is designed to project internal imaging directly onto the patient, improving precision and reducing risk, and the funding will support product development and early commercialization efforts. - learn more
        • Jupid raised $840K in early funding to support its AI-native accounting platform, which is designed to automate bookkeeping, tax filing, and compliance for small businesses directly within banking platforms. The company is building what it describes as an embedded “AI accountant” that integrates with financial institutions to streamline operations for entrepreneurs, and plans to use the funding to expand partnerships and accelerate product development as demand grows for automated financial tools. - learn more
        • Lumicup raised a $4.38M Series A to expand its product line and scale manufacturing as it looks to meet growing demand for its consumer health and wellness products. The company plans to use the funding to increase production capacity, invest in new product development, and strengthen its distribution as it continues to grow its footprint in the market. - learn more
        • Counterpart raised a $50M Series C to expand its AI-driven “agentic insurance” platform, which helps small businesses manage growing legal and employment risks tied to AI adoption. The round was led by Valor Equity Partners with participation from existing investor Vy Capital, bringing the company’s total funding to $106M, and the capital will be used to launch new insurance products, expand risk management capabilities, and scale its underwriting platform. - learn more
        • Nervonik raised a $52.5M Series B to advance its next-generation peripheral nerve stimulation technology, which aims to deliver more precise, personalized treatment for chronic pain. The round was led by Amzak Health with participation from Elevage Medical Technologies, U.S. Venture Partners, Lumira Ventures, Foothill Ventures, and Shangbay Capital, and the company plans to use the funding to accelerate clinical programs and move toward commercialization. - learn more
        • LighthouseAI raised an $8M Series A to expand its AI-powered platform that helps pharmaceutical companies manage state licensing and regulatory compliance. The round was led by Boxcars Ventures with participation from TGVP and existing investors, and the company plans to use the funding to enhance product development, improve service delivery, and support continued growth as it scales across the pharma supply chain. - learn more

        LA Venture Funds
        • MANTIS Venture Capital participated in Rogo’s $75M Series C, backing the AI platform as it builds autonomous financial agents designed to streamline complex workflows for banks and investment firms. The round was led by Sequoia Capital and included a mix of major financial institutions and venture firms, signaling strong demand for AI tools that can augment decision-making across high-stakes finance. - learn more
        • M13 participated in Chord’s $7M funding round, backing the AI commerce platform as it builds a “context layer” designed to unify fragmented data, tools, and workflows for retail brands. The round was led by Equal Ventures with participation from Chingona Ventures and CEAS Investments, and the company aims to help operators move beyond dashboards toward systems that can make real-time decisions and automate actions across the business. - learn more
        • Fika Ventures participated in Lumian’s funding round, backing the startup as it launches an AI-native Amazon agency designed to automate and optimize how brands operate on the marketplace. The company is focused on replacing traditional agency workflows with AI-driven systems that can manage everything from advertising to operations in real time, reflecting a broader shift toward automation in e-commerce. - learn more
        • Riot Ventures co-led True Anomaly’s $650M Series D, backing the defense space startup as it scales spacecraft, software, and autonomous systems designed for national security missions in orbit. The round values the company at around $2.2 billion and brings total funding to over $1 billion since its 2022 founding, and the company plans to use the capital to accelerate mission deployments, expand manufacturing, and grow its workforce as demand increases for space-based defense capabilities. - learn more
        • Clocktower Technology Ventures participated in Clarasight’s $11.5M Series A, backing the AI-powered travel and expense platform as it works to unify fragmented enterprise data into a single system. The round was led by AlleyCorp with participation from several travel and fintech-focused investors, and the company plans to use the funding to expand product development and scale go-to-market efforts as demand grows for AI-driven efficiency in corporate travel. - learn more
        • Halogen Ventures and Mucker Capital participated in SkyfireAI’s $11M seed round, backing the startup as it builds an AI-native platform for coordinating autonomous, multi-drone operations. The company’s software is designed for public safety and defense use cases, helping teams deploy and manage fleets of drones with greater speed and efficiency without increasing staffing, and it plans to use the funding to accelerate product development, expand its team, and scale deployments with government and mission-critical customers as demand grows for autonomous drone systems. - learn more
        • Matter Venture Partners led OpenLight’s $50M Series A-1, with participation from Acclimate Ventures, Catapult Ventures, and existing investors, backing the photonics company as it scales its next-generation chip platform for AI infrastructure. The funding brings total capital raised to $84M and will be used to accelerate global deployment of its silicon photonics technology across data centers, telecom, and other high-bandwidth applications. - learn more
        • Alexandria Venture Investments participated in Fathom Therapeutics’ $47M Series A, backing the biotech startup as it applies quantum chemistry and AI to design next-generation small molecule drugs. The oversubscribed round was led by Sutter Hill Ventures with participation from Chemistry and other investors, and the company plans to advance its platform, which simulates protein behavior inside living cells to accelerate drug discovery. - learn more

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          Netflix Doubles Down on LA

          🔦 Spotlight

          Hey Los Angeles.

          Goodbye Coachella, hello Stagecoach. The desert doesn’t stay quiet for long, and neither does LA’s entertainment machine.

          This week, that momentum showed up in a more permanent way.

          Netflix is expanding its footprint in Los Angeles with a major move to take over and invest in Radford Studio Center, a historic production lot in Studio City. The company is planning a long-term transformation of the site, with upgrades to soundstages, production offices, and infrastructure designed to support the next generation of film and television production.

          It’s a notable shift in a moment when production has been under pressure in California, with studios increasingly looking outside the state for cost advantages. Netflix going deeper in LA, and specifically into a legacy studio lot, signals a different kind of commitment. Not just to content, but to where that content actually gets made.

          And it comes at a time when the streaming wars have matured. Growth is harder, budgets are tighter, and the focus has shifted from scale at all costs to efficiency and control. Owning or operating more of the production environment gives Netflix tighter control over timelines, costs, and output.

          For Los Angeles, it’s a reminder of what still anchors the city. Even as AI, defense tech, and infrastructure startups continue to rise, entertainment remains one of the few industries where LA isn’t just competitive, it’s foundational.

          Different headlines each week, but a consistent theme underneath them. Whether it’s power, autonomy, or content, the companies that matter are investing in the layers they don’t want to outsource.

          And in this case, that layer is Hollywood itself.

          Below are this week’s venture deals, fund announcements, and acquisitions across LA 👇


          🤝 Venture Deals

            LA Venture Funds

            • UP Partners and Calm Ventures participated in Reliable Robotics’ $160M funding round, backing the autonomous aviation company as it advances pilotless flight technology for cargo and passenger aircraft. The round included a mix of new and existing investors, and the company plans to use the capital to accelerate certification efforts and expand deployment of its autonomous systems across commercial aviation. - learn more
            • Blue Heron Ventures participated in Tava Health’s $40M Series C, backing the company as it expands its tech-enabled mental health platform into a more integrated, full-stack system for providers, employers, and health plans. The round was led by Centana Growth Partners with participation from existing investors, and the company plans to use the funding to roll out new AI-powered tools and broaden access to care while reducing administrative friction across the system. - learn more
            • Vamos Ventures participated in Zócalo Health’s $15M Series A, backing the company as it scales its tech-enabled, community-based primary care model focused on high-need and underserved populations. The round was led by .406 Ventures with participation from existing and new investors, and the company plans to use the funding to expand its clinics and deepen partnerships with Medicaid programs as demand for accessible care grows. - learn more

            LA Exits
            • Studio71 has been acquired by Fixated as part of a broader deal in which German media company ProSiebenSat.1 sold its North American creator business, giving Fixated a large-scale network of creators and podcast operations and significantly expanding its footprint as it continues an aggressive roll-up strategy in the creator economy. The move signals continued consolidation in the space, with Fixated building a more vertically integrated platform across talent management, content production, and distribution. - learn more
            • Bonsai Health has been acquired by ModMed, bringing its AI-powered patient engagement platform into a broader healthcare software ecosystem. The deal is aimed at integrating Bonsai’s “agentic AI” capabilities into ModMed’s platform to automate patient outreach, fill care gaps, and improve scheduling across a network of nearly 50,000 providers. - learn more

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