Simplify Logo
Highlight AI

Highlight AI

On-screen AI assistant with private data

Member of Design Staff

Full-Time
$100k - $300k/yr

+ Equity package + Relocation package

Mid
San Francisco, CA, USA
In Person

Five days per week in the San Francisco office; relocation to San Francisco or New York City is required.

About the job

Requirements
  • World-class visual and interaction design ability.
  • Deep experience designing desktop interfaces and a proven track record of shipping outstanding user interfaces at scale.
  • Ability to work through ambiguity and turn half-formed ideas into confident, opinionated interfaces.
  • Ability to move quickly without lowering the quality bar.
  • Ability to provide work samples demonstrating exceptional craft.
  • Ownership mentality and willingness to handle tasks of all sizes.
  • Strong communication skills and a collaborative mindset.
  • Detail-oriented approach and commitment to shipping high-quality products.
  • Must be based in or willing to relocate to San Francisco or New York City.
  • Must work in a 100% in-office culture during the week.
  • Scrappy, motivated, and self-starting approach.
Responsibilities
  • Own visual and interaction quality across the product.
  • Regularly talk to users, identify creative solutions to their problems, and incorporate those solutions into designs.
  • Partner closely with the Head of Design to translate interaction concepts, product direction, and rough wireframes into confident, opinionated, high-fidelity user interfaces.
  • Collaborate daily with engineers to bring polished interfaces, motion, and micro-interactions into production.
  • Rapidly prototype AI-native interaction models through click dummies and code, often moving from an idea to a testable prototype within hours.
  • Design and refine micro-interactions, animations, transitions, and layout systems that make complex AI behavior intuitive and delightful.
  • Push beyond existing user-interface conventions and help define new patterns for interacting with AI systems.
  • Set and uphold a high bar for visual craft, consistency, and accessibility across the product.
Desired Qualifications
  • Experience shipping products that users strongly value.
  • Exceptional ability to turn rough interaction concepts and wireframes into polished, production-ready interfaces.
  • Strong interest and experience in micro-interactions, animation, and interaction details that elevate products.
  • Active experimentation with state-of-the-art user interfaces beyond existing design conventions.
  • Independent design and shipping experience at the level of Dia for Mac onboarding, Lapse for iOS, or Corner Maps for iOS.
  • Ability to prototype advanced interactions quickly, either through technical skills or fluency with tools such as Cursor or Claude Code.
  • Experience designing AI-native interaction patterns.

About the company

Highlight AI provides an on-screen AI assistant that sits on the user’s desktop and offers instant, smart, and shareable answers based on what the user sees and does. It works by staying constantly accessible on the screen and using the user’s on-device data to generate responses, with privacy kept by storing data locally until the user chooses to share it. The system can understand and respond to anything the user sees, hears, or says, and is customizable for different business software environments. Revenue likely comes from subscriptions or licenses for access to the AI platform. Compared with competitors, its main differences are a privacy-first approach (data stays on the device unless shared), on-screen accessibility, and easy-to-use customization across industries such as education, healthcare, legal, and engineering. The goal is to deliver a private, easily accessible AI experience that improves efficiency for professionals while protecting user data.

Company Size

11-50

Company Stage

Series A

Total Funding

$40M

Headquarters

New York City, New York

Founded

2024

Get referred to Highlight AI

See people who can refer or advise you

Simplify Jobs

Simplify's Take

What believers are saying

  • Highlight raised $40 million from Khosla Ventures on March 24, 2026.
  • The company claims over 500,000 users, including employees at Google and DoorDash.
  • New funding supports more integrations and headcount, accelerating product depth before 2027 renewals.

What critics are saying

  • Glean, Notion AI, Dust, and Carly attack the same shared-workspace knowledge layer.
  • Desktop-only Mac distribution blocks Windows and mobile workers, limiting enterprise rollout speed.
  • If the unified team memory engine fails, Highlight becomes a $20 note-taking utility.

What makes Highlight AI unique

  • Highlight AI’s Mac desktop app captures context across Slack, Zoom, Linear, and Claude Code.
  • Sergei Sorokin, ex-Discord VP, joined as CEO on March 24, 2026.
  • Highlight’s shared intelligence layer targets coordination, not another standalone chatbot or note-taker.

Help us improve and share your feedback! Did you find this helpful?

Benefits

Health Insurance

Dental Insurance

Vision Insurance

Parental Leave

Meal Benefits

Relocation Assistance

Company Equity

Growth & Insights and Company News

Headcount

6 month growth

-6%

1 year growth

-6%

2 year growth

0%
VentureBurn
Mar 25th, 2026
Highlight AI raises $40M to build shared intelligence for teams.

Highlight AI raises $40M to build shared intelligence for teams. 25 March 2026 Key Takeaways * Highlight AI raised $40 million in Series A funding led by Khosla Ventures. * The company is building a shared intelligence layer that connects workplace tools and captures organizational knowledge. * The funding highlights growing investor interest in AI productivity and collaboration platforms. Highlight AI has secured $40 million in Series A Funding to scale its platform that improves the collaboration of teams and artificial intelligence agents among digital tools. Khosla Ventures led the round, with leading investors including 359 Capital, General Catalyst, Valor Equity, Common Metal, Makers Fund, Collaborative Fund, Arcadia and SV Angel. The new cash injection will enable the company to ramp up development of its technology and grow its team to meet surging demand for AI-driven productivity tools. Building a shared intelligence layer. Highlight AI is building a "shared intelligence layer" for this digital work era. Employees are working across many apps like Slack, Figma, Linear, or whatever other project management or collaboration tool teams use. While these tools help teams communicate and build products, there is a side effect to it. Highlight AI addresses this problem by automatically extracting knowledge and context from several tools and converting it into a common memory. Rather than having employees search through chats, emails, and documents for information, Highlight AI creates a shared memory of work actions which can be accessed by either humans or AI. This concept is more and more relevant as companies go towards hiring AI agents to help perform their workflows, coding, design, project management, etc. Through the creation of this central layer of knowledge, Highlight AI aims to guarantee the same context & data access for human workers and the concerned agents. Why the problem matters. Today's teams are increasingly overloaded with information. Projects are spread across dozens of apps, conversations are held across dozens of channels, and decisions are buried in threaded messages or long documents. The bigger the company, the harder it is to stay coordinated. Highlight AI thinks the answer is to create an intelligent layer to link these existing tools together. The platform does not replace the existing tools. It is integrated with every system or tool. The result is a very structured knowledge base that is used as much by the AI models as by the employees. This approach could significantly reduce the time workers spend searching for information, following up on tasks, or trying to understand the context behind decisions. Growing demand for AI productivity tools. The funding round follows suit with this larger trend of AI-powered workplace applications and mediums. Companies everywhere are now turning towards AI to help automate admin tasks, provide faster insights into data, and enhance other key business aspects. But many companies have learned that the hardest part isn't the AI but the disconnected systems where data is stored. Highlight AI's strategy is about clearing up that coordination problem rather than making another standalone AI product. And by functioning as a layer of intelligence on all applications, the company aims to become an infrastructure provider for the "agentic age" of work, filled with nonstop human/AI, team and assisted agents. Having secured new funding, Highlight AI will use the money to further develop its product and build more integrations with common work tools. The company is also anticipated to expand its engineering and research teams to improve the custom AI models and data architecture, respectively. If everything goes well, Highlight AI would have been a major place for companies to organize their knowledge and take advantage of the power of AI-assisted work. I'm a crypto writer with 4+ years of experience passionate about turning big, technical ideas into content anyone can understand. From blockchain to stablecoins to everything in between, I enjoy helping readers stay informed in a space that never stops moving. Disclaimer VentureBurn is a media platform covering the latest in cryptocurrency, artificial intelligence, venture capital, and the startup ecosystem. Opinions expressed on VentureBurn are for informational purposes only and do not constitute investment advice. Before making any high-risk investments in digital assets or emerging technologies, readers should conduct their own due diligence. All transactions and financial decisions are made at your own risk, and any losses incurred are solely your responsibility. VentureBurn does not endorse or recommend the buying or selling of any digital assets and is not a licensed investment advisor. Please note that VentureBurn may participate in affiliate marketing programs.

SiliconANGLE Media
Mar 24th, 2026
AI productivity startup Highlight AI raises $40M, appoints new CEO.

AI productivity startup Highlight AI raises $40M, appoints new CEO. Highlight AI Inc., a startup with an artificial intelligence app designed to make knowledge workers more productive, has raised $40 million in funding. Khosla Ventures led the Series A round. Highlight stated in its funding announcement today that more than a half-dozen other investors contributed as well. Additionally, the company disclosed that it has appointed former Discord Inc. Vice President of Product Sergei Sorokin chief executive. Highlight launched in 2024 as a spinoff from Medal Inc,. a startup with a program for recording video game footage. The company develops a desktop application that uses AI to help users analyze business data. Workers can upload complex files such as product diagrams and have Highlight generate a natural language explanation. The software also speeds up other day-to-day tasks. One feature can automatically generate meeting notes, while another turns information scattered across multiple files into to-do items. An MCP tool enables users to sync data from Highlight to external applications. Highlight is available in a free version and a paid edition, Highlight Premium, for $20 per month. The latter plan offers access to more advanced AI models from OpenAI Group PBC and other providers. Customers can use those advanced models to automate complex tasks and relegate simpler work to smaller, faster models that offer lower latency. The company says its application has been adopted by more than 500,000 users since launch. Its installed base includes employees at Google LLC, Doordash Inc. and other major tech firms. Highlight will use the proceeds from its funding round to significantly expand its feature set. According to the company, its engineers are working on a "unified team memory engine" that automates complex tasks involving multiple workers and applications. The software maker estimates that the tool can save up to several hours per task. One use case is that Highlight's memory engine promises to simplify project management. A design team working on a new website interface could use the tool to automatically assign tasks to each participating employee. Highlight determines which designer should do what by reviewing the interface being developed, relevant Slack discussions and other data assets. According to the company, its memory engine can also complete some tasks on its own. For example, designers could have Highlight generate the code necessary to turn an interface design into a functioning website. It performs such tasks by sending instructions to third-party automation tools such as the Cursor code editor. "Without a shared memory across tools, people are forced to copy and paste between systems and track work by hand, spending countless hours reassembling work instead of moving it forward," Sorokin said. Highlight is currently testing its new AI features with a limited number of customers. A future update will enable users to deploy AI agents capable of automating a broader range of use cases. According to Highlight, its memory engine will enable those agents to complete tasks with the help of world models, neural networks optimized to generate three-dimensional virtual environments. A message from John Furrier, co-founder of SiliconANGLE: Support its mission to keep content open and free by engaging with theCUBE community. Join theCUBE's Alumni Trust Network, where technology leaders connect, share intelligence and create opportunities. * 15M+ viewers of theCUBE videos, powering conversations across AI, cloud, cybersecurity and more * 11.4k+ theCUBE alumni - Connect with more than 11,400 tech and business leaders shaping the future through a unique trusted-based network. About SiliconANGLE Media SiliconANGLE Media is a recognized leader in digital media innovation, uniting breakthrough technology, strategic insights and real-time audience engagement. As the parent company of SiliconANGLE, theCUBE Network, theCUBE Research, CUBE365, theCUBE AI and theCUBE SuperStudios - with flagship locations in Silicon Valley and the New York Stock Exchange - SiliconANGLE Media operates at the intersection of media, technology and AI. Founded by tech visionaries John Furrier and Dave Vellante, SiliconANGLE Media has built a dynamic ecosystem of industry-leading digital media brands that reach 15+ million elite tech professionals. Its new proprietary theCUBE AI Video Cloud is breaking ground in audience interaction, leveraging theCUBEai.com neural network to help technology companies make data-driven decisions and stay at the forefront of industry conversations.

Benzinga
Mar 24th, 2026
Highlight AI raises $40M Series A to build shared intelligence layer for teams and AI agents

Highlight AI has raised $40 million in a Series A round led by Khosla Ventures, with participation from 359 Capital, General Catalyst, Valor Equity and others. Former Discord VP of Product Sergei Sorokin has joined as CEO to lead the company's development of an intelligent operating system for teams and AI agents. The startup aims to eliminate the "coordination tax" that consumes up to 24 hours per employee weekly. Highlight's platform captures, models and retrieves team context in real time across tools like Slack, Figma and Linear, automatically drafting follow-ups, syncing documentation and orchestrating tasks. Sorokin brings eight years of experience from Discord, where he helped grow the platform from 5 million to nearly 300 million monthly active users. Highlight plans to double its headcount, focusing on hiring engineers and operators in San Francisco.