Head of Engineering at Gusto | San Francisco, CA & New York, NY

We are seeking a visionary Head of Engineering to lead our dynamic team at Gusto. As the Head of Engineering, you will play a critical role in shaping our technology strategy and driving innovative engineering solutions. This is an exciting opportunity to influence the direction of our engineering practices and to mentor and grow our talented engineering tea…

About GustoAt Gusto, we are dedicated to empowering the small business economy. Our services simplify complex tasks like payroll, health insurance, 401(k)s, and HR, allowing business owners to concentrate on their passion and customers. With teams in Denver, San Francisco, and New York, we proudly support over 400,000 small businesses nationwide, committed to creating a workplace that reflects and honors the customers we serve. Discover more about our Total Rewards philosophy.About the Role:We are seeking passionate Mobile iOS Engineers who are eager to craft exceptional user experiences. In this role, you will develop features that are not only functional but also intuitive and delightful for our users. You will take charge of scaling our shared services while staying current with the latest iOS advancements. Collaborating with teams from Product Management, Identity, Security, System Design, and Infrastructure, you will build solutions that make a significant impact. If you are enthusiastic about creating elegant, scalable applications and want to be part of a supportive, innovative mobile team, we would love to connect with you!About the Team:At Gusto, we are at a transformative stage with over 1M+ monthly active users and the recent launch of our employer experiences on mobile. Our mission is to address the real challenges faced by small business owners and their employees, with mobile technology being crucial for delivering effective solutions. As a member of our mobile team, you will be at the forefront of this change, collaborating with talented engineers and designers passionate about providing a seamless mobile experience. Together, we aim to empower small business owners and their teams to succeed. If you are ready to make a difference in the mobile landscape at Gusto, we want you on our team!Here’s what you’ll do day-to-day:Architect, build, test, and enhance Gusto’s native iOS app, along with supporting mobile web views that elevate user experience.Develop, iterate, and refine product features that integrate core business functions, work tools, value-added services, and financial products.Collaborate closely with our product management, design, and partner teams...

Who We AreAt Pave, we are revolutionizing the compensation landscape with our cutting-edge platform that merges the largest real-time compensation dataset with advanced AI and machine learning capabilities. Our state-of-the-art solution empowers over 8,500 businesses to make informed compensation decisions with unparalleled confidence.Renowned companies such as OpenAI, McDonald's, Instacart, Atlassian, Synopsys, Stripe, Databricks, and Waymo leverage Pave to transform their pay strategies, managing over $190 billion in total compensation spend through our innovative workflows. Notably, 70% of the Forbes AI 50 utilize Pave to benchmark their compensation.As we pioneer the transition to real-time and predictive pay solutions, we are proud to have secured $160 million in funding from top-tier investors including Andreessen Horowitz, Index Ventures, Y Combinator, Bessemer Venture Partners, and Craft Ventures.The Paige Team @ PavePaige, Pave's AI compensation analyst, represents an innovative autonomous system built atop the world's largest proprietary compensation dataset and our existing workflow engine. This role involves crafting the technical vision and execution for Paige, collaborating with a team of talented engineers and data scientists to develop and market this groundbreaking product. We are seeking individuals with profound AI expertise, strong product intuition, and a founder's mentality to help us drive this initiative forward.

Senior Software Engineer - ConnectivityThe Connectivity team at Scale owns the foundational platform that empowers us to consistently generate, assess, and deliver high-quality training data to our clients. Our systems are integral to Scale’s data and AI infrastructure, facilitating large-scale workflows while enabling cutting-edge AI functionalities such as multi-modality, long-horizon reasoning, and agentic behavior.We are seeking a seasoned engineer with extensive experience in developing robust platforms. The ideal candidate will possess strong architectural judgment, a commitment to correctness and reliability, and the capability to design systems that can scale and adapt effectively over time. This role is primarily backend-focused but includes full-stack responsibilities and substantial ownership from design to long-term operations.

Merge stands at the forefront of technology, providing innovative agentic tools and seamless customer-facing integrations for leading frontier LLMs, Fortune 500 companies, and B2B SaaS enterprises. Our platform features two flagship products: Merge Unified, which enables businesses to effortlessly integrate hundreds of applications through a single API, and Merge Agent Handler, which equips AI agents with secure access to a multitude of third-party tools. Renowned for its enterprise-grade capabilities, Merge oversees the entire integration lifecycle—from authentication and security to monitoring and maintenance. Countless organizations rely on Merge to enhance product development, streamline sales efforts, reduce customer attrition, and conserve engineering resources, allowing them to concentrate on their core offerings. Who are we looking for?We are seeking a proactive Solutions Engineer who will take charge of all technical interactions with prospects during their evaluation and deployment of Merge’s solutions. This role involves creating proofs of concept, providing technical demonstrations, and collaborating with engineering and platform teams to prioritize feature enhancements and resolve issues. As a Solutions Engineer, you will engage in high-value projects that command significant visibility both internally and externally.What you will do:Serve as the primary technical point of contact for prospects as they evaluate and implement Merge through proofs of concept and technical workshops.Develop and nurture relationships to ensure an exceptional developer experience.Collaborate with engineering and platform teams to identify product improvement opportunities based on insights gathered from prospects.Lay the groundwork for the rapid expansion of a successful solutions engineering team!

Become a Key Player in the Sleep RevolutionAt Eight Sleep, our mission is to unlock human potential through the power of optimal sleep. As pioneers in the sleep fitness industry, we are redefining wellness and developing cutting-edge hardware, software, and AI technology to enhance sleep quality. Our innovative products provide a personalized, data-driven recovery experience, empowering peak mental, physical, and emotional performance. Trusted by high achievers, professional athletes, and health enthusiasts in over 30 countries, we have been recognized as one of Fast Company's Most Innovative Companies in 2019, 2022, and 2023, and have earned a place in TIME's “Best Inventions of the Year” twice. Our high-performance team operates with agility, focus, and an unwavering commitment to delivering impactful solutions that help our members sleep better and wake up stronger.Every position at Eight Sleep offers the opportunity to create groundbreaking technology, collaborate with elite talent, and contribute to a future where sleep is an active instrument of personal well-being. If you seek to break free from the ordinary and are passionate about pushing the boundaries of innovation, this is your chance. Join us in leading the transformation of how the world sleeps and the potentials we unlock with every awakening.Excellence Without CompromiseOur mission demands intensity at Eight Sleep. We embody the mindset of the world's top performers: focused, relentless, and striving to be among the elite in our field. This is more than just a job; it requires a commitment akin to a 60+ hour work week—not because it’s expected, but because we are invested in our craft. We are here to innovate rapidly, push boundaries, and deliver exceptional outcomes. If you thrive in high-pressure environments and are eager to engage in the most meaningful work of your career, you will find your place here. If you are looking for an easier option—this is not it.Your RoleEight Sleep is at the forefront of sleep optimization technology, and we are seeking a talented Data Engineer to propel our next phase of growth. You will design and build the data infrastructure that informs decisions for millions of users while collaborating with some of the brightest minds in health tech.This role transcends standard data responsibilities; you will be the technical architect behind impactful systems that enhance human wellness at scale and drive our rapid growth trajectory. From real-time sleep analytics to machine learning-driven personalization to the data framework supporting our global expansion, your contributions will be pivotal.

About GustoAt Gusto, we are dedicated to empowering the small business economy. We take care of the complex tasks like payroll, health insurance, 401(k)s, and HR, allowing business owners to concentrate on their passions and their customers. With teams located in Denver, San Francisco, and New York, we proudly support over 400,000 small businesses nationwide, while fostering a workplace that represents and celebrates the diverse communities we serve. Discover more about our Total Rewards philosophy.Symmetry Software, a division of Gusto, serves as the payroll backbone for software and payroll platforms, facilitating the paychecks of more than 64 million workers annually. Our fully integrated suite of payroll tax APIs and software tools empowers companies to address tax compliance challenges and develop applications throughout the payroll process.What Product Management Looks Like at Symmetry:Our Product team is streamlined, giving you significant impact and ownership. We value small, empowered teams that operate quickly with minimal overhead. You will combine strong product insights with proficiency in AI tools to automate inefficiencies and enhance creativity and performance.We are builders at heart. Roles are intentionally fluid, and our Product Managers do whatever it takes to drive results. You will prototype, automate, design, and deploy solutions, leveraging AI as your co-creator to transform challenges into robust solutions that deliver rapid customer value.We are committed to enhancing the payroll industry. Our technology influences over 64 million paychecks in the U.S. each year. We are motivated by profound customer empathy and an unwavering drive for innovation.We embrace change. Our fast-paced environment allows Product Managers to flourish in ambiguity, merging curiosity, experimentation, and AI-driven craftsmanship to redefine how products (and work itself) are developed at Symmetry.About the Role:We are seeking a visionary product leader to spearhead the creation of new business lines focused on payroll tax products. This role, centered on developing new initiatives from scratch, will grant you considerable autonomy to lead discovery, strategy, and execution for innovative payroll tax products. You will be tasked with delivering impactful business results, including new revenue streams and enhancing existing revenue.

Become a Catalyst in the Sleep Fitness RevolutionAt Eight Sleep, we are dedicated to unlocking human potential through exceptional sleep. As pioneers in the sleep fitness industry, we are reshaping the concept of restful sleep by developing state-of-the-art hardware, software, and AI technologies that facilitate this transformation. Our innovative products enhance mental, physical, and emotional performance, converting each night’s rest into a personalized, data-driven recovery journey.We have earned the trust of high achievers, professional athletes, and health-focused individuals across over 30 countries. Celebrated as one of Fast Company's Most Innovative Companies in 2019, 2022, and 2023, and recognized by TIME's “Best Inventions of the Year” on two occasions, we pride ourselves on operating as a high-performance team: swift, focused, and driven by impactful outcomes. We don’t merely deliver; we continuously enhance and obsess over the details that empower our members to sleep better and awaken stronger.Every position at Eight Sleep presents an opportunity to engineer groundbreaking technology, collaborate with elite talent, and contribute to a future where sleep is not just a passive experience, but a formidable tool for improved living. If you are seeking to break free from the mundane and are passionate about pushing the boundaries of what's possible, seize this moment. Join us as we lead the transformation of how the world sleeps and the potential we can unlock upon waking.Uncompromising Standards. Relentless PursuitWe operate with unmatched intensity, driven by the demands of our mission. At Eight Sleep, we embody the focus and relentless spirit of the world’s top performers: always striving to be in the top 1% of our craft. Inspired by Kobe Bryant’s mamba mentality, we apply this mindset to bold concepts, next-gen technologies, and impeccable execution. This isn’t a standard 9-to-5; our team commits to extra effort, not out of obligation, but from a genuine concern for the impact of our work. We are here to innovate rapidly, challenge limits, and deliver without compromise. If you excel under pressure and desire to engage in the most significant work of your career, you’ll find your place with us. If you seek something easier, this may not be the right fit.The RoleWe are in search of a Full Stack Engineer to serve as the technical cornerstone of our Customer Experience (CX) transformation. In this role, you will develop tools, integrations, and monitoring systems that enable our AI agents and human support teams to resolve customer issues with increased speed and efficiency. This is a unique opportunity to work at the convergence of AI, customer experience, and software engineering, creating solutions that tangibly impact hundreds of thousands of customers.

About AnthropicAt Anthropic, we are dedicated to developing AI systems that are reliable, interpretable, and steerable. Our goal is to ensure that AI serves as a safe and beneficial tool for users and society alike. Our rapidly expanding team comprises passionate researchers, engineers, policy experts, and business leaders who collaborate to create beneficial AI technologies.About the TeamThe Security Engineering team at Anthropic is committed to safeguarding our AI systems and upholding user trust. We establish the authentication architecture for our training infrastructure, design cryptographic systems to protect model weights and training data, and oversee a developer security program that influences how our engineers create and deploy software.This team operates across various interconnected domains: identity and secrets management, developer security and supply chain, infrastructure security, and secure frameworks. You will take ownership of one or two of these domains while also contributing to others, with your area of focus influenced by your expertise and the team's objectives. This role primarily involves greenfield projects, allowing you to help shape the architectural landscape.About the Role:Design, scope, and implement complex security systems from start to finish, ensuring their maintenance in production while navigating ambiguous technical challenges with minimal supervision.Identify systematic risks through comprehensive threat modeling and risk assessment, subsequently developing the necessary controls and infrastructure to mitigate these risks.Mentor engineers within the security team and the wider engineering organization, participate in the hiring process, and foster a robust security culture at Anthropic.Empower other teams to develop their own security solutions by offering design pattern guidance and expanding security ownership beyond the security team.Developer Security and Supply ChainEnhance our developer security program by integrating security practices into the software development lifecycle and developer workflows.Fortify CI/CD pipelines against supply chain threats through isolated build environments, signed attestations, dependency verification, and automated policy enforcement.Identity and Secrets ManagementDesign systems that safeguard sensitive assets, including model weights, customer data, and training datasets.Establish and maintain credential issuance, rotation, and workload authentication across our multi-cloud environments.

About HebbiaHebbia is an innovative AI platform designed for investors and bankers, delivering exceptional insights that generate alpha and maximize potential returns.Founded in 2020 by George Sivulka and supported by notable investors such as Peter Thiel and Andreessen Horowitz, Hebbia empowers investment decisions for major firms including BlackRock, KKR, Carlyle, and Centerview, along with 40% of the world's largest asset managers. Our flagship product, Matrix, offers unparalleled accuracy, speed, and transparency in AI-driven analysis, entrusted to manage over $30 trillion in global assets.We empower finance professionals with intelligence that provides a definitive competitive edge. Our AI uncovers unseen signals, reveals hidden opportunities, and accelerates decision-making with unmatched speed and confidence. We don't just enhance workflows; we revolutionize how capital is allocated, risk is managed, and value is created in the markets.Hebbia is not merely a tool; it is the competitive advantage that drives performance, alpha, and market leadership.The TeamThe Integrations team serves as the crucial link between Hebbia’s AI platform and the diverse data sources our customers depend on. We design and maintain the pipelines that integrate content from enterprise systems—such as Snowflake, S3, SharePoint, Dropbox, and more—enabling Hebbia to effectively analyze it.This role involves critical infrastructure work that directly impacts our customers. When integrations are swift, reliable, and seamless, our clients trust Hebbia with their most vital workflows. Conversely, any disruption is immediately felt. Our team is responsible for the entire process: creating new connectors, reinforcing existing ones, and ensuring a continuous data flow.The RoleThis is not a standard backend engineering position with just a few integrations. You will primarily focus on developing, troubleshooting, and managing data integrations across numerous third-party platforms. This hands-on role directly influences customer experiences and requires a passion for delivering exceptional solutions.

About UsAt Pave, we are revolutionizing the compensation landscape with our cutting-edge platform that combines the world’s largest real-time compensation dataset with advanced AI and machine learning expertise. We empower over 8,500 companies with unparalleled confidence in their compensation strategies.Renowned organizations such as OpenAI, McDonald’s, Instacart, Atlassian, Synopsys, Stripe, Databricks, and Waymo trust Pave to transform their pay decisions into strategic advantages. Our workflows manage a staggering $190 billion in total compensation, with 70% of the Forbes AI 50 leveraging Pave for compensation benchmarking.The future of pay is real-time and predictive, and we are leading the charge. With $160M raised from top-tier investors like Andreessen Horowitz, Index Ventures, Y Combinator, Bessemer Venture Partners, and Craft Ventures, we are poised for significant growth.The Design Team @ PaveOur design team is a close-knit, dynamic group that thrives on collaboration and creativity. We are deeply committed to understanding our customers and ensuring their needs are met with innovative design solutions. We foster an environment where creativity flourishes, discussions are meaningful, and complex problems are tackled head-on. If you are excited about a role that blends passion, commitment, and challenge, we invite you to connect with us!

Join Anthropic as a Product Designer and help shape the future of AI technology. We are looking for a creative and detail-oriented individual who thrives in a collaborative environment. In this role, you will work closely with engineers, product managers, and other designers to create innovative solutions that enhance user experience.

Join Our Team at AirOpsAt AirOps, we are pioneering the first comprehensive content engineering platform tailored for the AI-driven landscape. As traditional search methods transition towards AI-enhanced platforms, we empower brands to enhance their visibility and maintain a strong presence. Our recent growth surge, achieving a fivefold increase in revenue over the past year, is a testament to our success in enabling marketing teams at industry leaders like Ramp, Chime, Carta, and Rippling to transform content quality into a sustainable competitive edge.Our innovative platform enables marketers to adeptly navigate the ever-evolving discovery landscape, prioritize impactful opportunities, and generate accurate, brand-consistent content that garners recognition from AI systems and builds trust with audiences. Supported by prominent investors such as Greylock, Unusual Ventures, Wing VC, and Founder Collective, we are developing intelligent systems designed to empower the next wave of marketing leaders. Our headquarters are located in San Francisco, New York, and Montevideo.As we establish our platform engineering function from the ground up, you will be among the initial US-based hires, responsible for the infrastructure that every engineer in our organization relies on. Currently, our deployment processes involve manual steps that have led to production outages, and our development environments do not align with production. Your contributions will be pivotal in creating a robust foundation for productivity. This is not a role focused on maintaining established systems; you will have the opportunity to design and implement the deployment pipeline, health check protocols, alert systems, and developer tools that the entire engineering team will depend upon. With real challenges to tackle and a substantial backlog of tasks, your work will have a direct impact on our operational speed and efficiency.

About GustoAt Gusto, we are dedicated to empowering small businesses by managing essential services like payroll, health insurance, 401(k)s, and HR, allowing owners to focus on their passions and customers. With offices in Denver, San Francisco, and New York, we proudly support over 400,000 small businesses nationwide, fostering a workplace that reflects and celebrates the diverse customers we serve. Explore our Total Rewards philosophy. About the Role:We are seeking a seasoned engineer with extensive knowledge in distributed data systems to help shape the future of Gusto's storage architecture. In this impactful role, you will oversee intricate migrations, design high-scale systems, and establish benchmarks for automation, resilience, and security. Your work in implementing distributed database solutions will facilitate Gusto's ongoing growth and scalability.About the Team:The Datastores Infrastructure Engineering team is responsible for designing, building, and maintaining the data platforms that drive Gusto's products, including MySQL, Postgres, Redis, Kafka, and S3. We are committed to ensuring that our infrastructure is consistent, dependable, and equipped to support Gusto's expanding requirements. As we transition to self-hosted distributed databases, our focus lies in minimizing the blast radius, enhancing operational resilience, and enabling sustainable scalability.Here’s what you’ll do day-to-day:Architect, deploy, and manage the complete lifecycle of distributed database systems (TiDB) on Kubernetes at scale, ensuring high availability, data consistency, and operational excellence.Coordinate complex, zero-downtime migrations from monolithic to distributed architectures, including vertical sharding to isolate Product Services.Define and implement efficiency enhancements across the storage infrastructure through query optimization, caching strategies, and workload management.Establish standards and develop reliable automation to maintain data consistency, integrity, and security across distributed systems.Continuously enhance operational excellence by decreasing on-call burdens with sustainable, long-term solutions.Collaborate with product engineering teams and technical partners to enable rapid and reliable product development.

Join doss as the Head of Engineering, where you will lead a talented team of engineers dedicated to building innovative solutions. In this pivotal role, you will oversee the engineering department's strategic direction and ensure the successful execution of engineering projects. You will collaborate with cross-functional teams to drive technology initiatives and enhance operational efficiency.

Join Stripe as a Security Engineer and play a pivotal role in ensuring the security and integrity of our systems. You will collaborate with cross-functional teams to identify vulnerabilities and implement state-of-the-art security measures. Your expertise will help us safeguard sensitive data and maintain trust with our customers globally.

Taskrabbit connects people with skilled Taskers for a variety of home services, including furniture assembly, handyman projects, and moving assistance. The company partners with IKEA and supports flexible work for Taskers, aiming to improve lives one task at a time. Taskrabbit values innovation, inclusivity, and collaboration. Team members are encouraged to share ideas and help shape the future of the platform. Employees are located across the US and EU, and Taskrabbit has earned recognition from Built In as a Best Place to Work in 2022, 2023, and 2024. Work location and schedule The Senior Business Operations Analyst position is hybrid, with two days per week in the office. The role can be based in San Francisco or New York City. The New York office is scheduled to open in March 2026.

About AirOpsAirOps is pioneering the first comprehensive content engineering platform designed for the AI era. As the landscape of discovery transitions from traditional search to AI-driven platforms, we empower brands to enhance their visibility and maintain relevance. Our recent phase of rapid growth has seen a remarkable 5x increase in revenue over the past year, supporting marketing teams at renowned organizations like Ramp, Chime, Carta, and Rippling to transform content quality into a sustainable competitive edge.Our innovative platform enables marketers to adeptly navigate the evolving discovery landscape, identify high-impact opportunities, and generate precise, on-brand content that garners citations from AI and earns human trust. With backing from esteemed investors such as Greylock, Unusual Ventures, Wing VC, and Founder Collective, we are dedicated to building intelligent systems that will empower the next generation of marketing leaders. AirOps has its headquarters in San Francisco, New York, and Montevideo.About the RoleAt AirOps, we operate at the convergence of AI and brand intelligence, processing millions of AI-generated responses daily across all major AI providers. Our data platform is experiencing exponential growth: currently processing 2 million answers each day, with an increase of hundreds of thousands monthly, as new providers and product features come online regularly. The data engineering decisions you make today will directly influence our product tomorrow. You will take charge of the pipelines, ingestion infrastructure, and data quality systems that underpin everything our customers interact with. As we establish a dedicated data team for the first time, the frameworks you create will shape the operational patterns of this function for years to come. You will engage with technologies such as ClickHouse, distributed ingestion pipelines, and a multi-provider scraping stack, with significant responsibility for ensuring reliability and accuracy. If you are eager to work on data that is central to our product rather than merely internal tools, this is the opportunity for you.

About UsAt Pave, we are revolutionizing the compensation landscape through our cutting-edge platform that merges the largest real-time compensation dataset with advanced AI and machine learning capabilities. Our solution empowers over 8,500 companies to make confident and informed compensation decisions.Leading organizations such as OpenAI, McDonald’s, Instacart, Atlassian, Synopsys, Stripe, Databricks, and Waymo leverage Pave to transform their pay strategies into competitive advantages. We oversee a staggering $190+ billion in total compensation spend, with 70% of the Forbes AI 50 utilizing Pave to benchmark their compensation.The future of compensation is real-time and predictive, and we are at the forefront of this transformation, having secured $160 million in funding from prominent investors including Andreessen Horowitz, Index Ventures, Y Combinator, Bessemer Venture Partners, and Craft Ventures.The Paige Team @ PaveJoin us in developing Paige, Pave’s AI compensation analyst designed to harness the world’s largest proprietary compensation dataset and our advanced workflow engine. As an autonomous agent, Paige will reason over structured compensation data and execute complex workflows including market pricing, cycle planning, and attrition analysis. In this role, you will define the technical vision and execution for Paige, collaborating closely with engineers and data scientists to build and launch the product. This position demands extensive AI expertise, strong product instincts, and a founder’s mindset.

About Chalk Chalk is revolutionizing the data platform landscape, enabling the future of machine learning applications. Our innovative solutions eliminate the complexities, latency, and scaling limitations that have historically hindered ML capabilities. With Rust-speed performance and a suite of elegant tools, we cater to developers' needs. Our platform is trusted by leading organizations to combat fraudulent credit card transactions, verify identities, and optimize clean energy capture. Recently, we secured a $50 million Series A round led by Felicis. About the Role As a Forward Deployed Engineer, you will leverage your exceptional software engineering skills to create tailored technical solutions in collaboration with our machine learning teams. You will engage directly with Chalk's customers to construct efficient feature pipelines addressing challenges in healthcare, finance, and recommendation systems. This position offers a unique chance to work closely with clients, gathering requirements and engineering pipelines for critical use cases such as cancer detection, fraud prevention, and product recommendations. Join us in-person as an early employee and significantly impact our high-growth startup. Note: We operate in-office five days a week, with flexibility for unavoidable conflicts. This is not a hybrid role.