Upwork

Role Description AI Frontiers operates like a funded startup inside Upwork: a small, senior team with a real product in market and a clear mandate to build the AI-native future of work. We're hiring a Principal Technical Product Manager to own one of our most strategically important 0-to-1 bets end-to-end, from product and go-to-market motion to the operational program behind it. You'll set the strategy for moving a human-assisted experience toward an increasingly automated one, deciding which human steps AI absorbs first and how to steer that transition without sacrificing quality or customer trust. Success in this role means customers moving through the experience end-to-end at a high rate, achieving meaningfully faster time-to-value than today's alternatives, and human effort per engagement trending down as automation lands. This is a builder's role: no committee approvals, no waterfall specs, and broad ownership backed by the infrastructure and runway of a public company. Responsibilities - Own the product end-to-end, setting the vision and roadmap, writing and maintaining the spec, and making hard scope calls across a multi-stage, AI-assisted workflow to drive validated customer outcomes at scale. - Drive the human-to-AI progression by deciding which human steps to automate first, instrumenting the system so each step is cleanly swappable for AI, and advancing automation on schedule without a drop in quality or unit economics. - Coordinate a broad cross-functional surface across engineering (frontend, backend, ML, architecture), design, data, and platform partners (payments, security, legal and privacy, search, reliability), keeping a small, high-velocity core team unblocked. - Run the operational program in partnership with Operations, scaling the human expert function, supply, and playbooks that power the experience today while steadily reducing human effort per engagement. - Own go-to-market for early cohorts alongside sales and customer engagement, routing the right customers into the funnel, sharpening the value proposition, and protecting the business model as it scales. - Present progress, learnings, and decisions to leadership, translating messy early-stage reality into crisp strategic recommendations. - Run the learning agenda by turning every workflow step into structured data, partnering with user research on moderated studies, and using both quantitative and qualitative signals to decide what to build, automate, or kill next. Qualifications - A track record of 0-to-1 product leadership, taking ambiguous, early-stage products from concept to real users and revenue, ideally more than once, with comfort operating when the spec is half-written. - AI-native product judgment grounded in agentic and LLM-driven systems, including human-in-the-loop design: knowing where AI embedded in a workflow wins, where bolt-on AI fails, and how to start with humans as the safety net and replace them as confidence grows. - Hands-on technical ability to prototype your own ideas and vibe-code working demos with AI coding tools, using build-alongside AI workflows to pressure-test concepts, align engineering, and move faster. You don't need to be a production engineer, but you're fluent enough with the technology to build with it, not just talk about it. - Strong technical partnership with engineering leaders on API boundaries, data modeling, and build-vs-buy trade-offs, alongside a service design and operations sensibility that treats the human-ops program as part of the product. - Executive-grade communication and a bias to ship, paired with the character to be direct in feedback, to be curious when plans change, and to be genuinely invested in the team's success. Benefits - Comprehensive medical coverage for you and your family. - Unlimited PTO. - 401(k) plan with matching. - 12 weeks of paid parental leave. - Employee Stock Purchase Plan.

Role Description The Chief of Staff to the COO exists to make that model work: not as a coordinator, but as a true operating partner who extends the COO's capacity, sharpens decision-making, and holds together a complex, fast-moving organization. - Strategic Partnership: - Serve as a trusted thought partner - making every interaction with the COO more valuable. - Prepare the COO for high-stakes conversations - drafting and driving board presentations, executive reviews, and cross-functional negotiations. - Operational Integration: - Own the operating rhythm of the COO organization, ensuring substantive and efficient monthly and quarterly business reviews. - Identify where alignment is breaking down and fix those issues proactively. - Execution and Clarity: - Maintain a clear line of sight across key initiatives and ensure the COO has the necessary information and context. - Unblock cross-functional friction when it stalls important initiatives. - Culture and Continuity: - Model the leadership values Upwork expects of its people. - Be the source of stability and continuity during transitions or periods of organizational change. Qualifications - 10+ years of relevant experience; MBA or equivalent strongly preferred. - Prior Chief of Staff experience or a similar senior operating role is a plus. - Experience in consulting, investment banking, or a high-growth tech company. Requirements - Ability to operate at the intersection of strategy and execution in a high-velocity environment. - Organized in a way that instills confidence and prevents things from falling through the cracks. - Discretion and judgment to be a confidant with sensitive information. - Ability to think clearly under ambiguity and communicate with precision. Benefits - Comprehensive medical coverage for you and your family. - Unlimited PTO. - 401(k) plan with matching. - 12 weeks of paid parental leave. - Employee Stock Purchase Plan.

• Own end-to-end product design from identifying funnel opportunities and forming hypotheses through rapid concepting, launch, and iteration, delivering high-quality designs that balance speed, craft, and measurable impact. • Collaborate deeply with cross-functional partners (PMs, engineers, researchers, data scientists, and other designers) to define problems, prioritize opportunities, and ship experiments that move key metrics. • Use quantitative data, qualitative insight, and emerging technologies to identify friction and unlock opportunities across acquisition, activation, retention, and monetization flows, including prototyping and testing AI-powered or automated experiences where they accelerate outcomes. • Drive experimentation and continuous improvement by running A/B tests, conducting qualitative user research, and using rapid prototyping to validate hypotheses and evolve the product based on real-world feedback. • Design, test, and refine targeted experiences, from onboarding and upsell flows to pricing, incentives, and lifecycle touchpoints, ensuring clarity, trust, and strong value exchange for users. • Create and socialize clear, lightweight design artifacts that support rapid decision-making, align stakeholders, and enable fast execution, prioritizing learning and outcomes over documentation for its own sake. • Mentor others and contribute to design culture, sharing best practices, giving constructive feedback, and championing design quality across the team.

Role Description Search & Recommendations sits at the center of how work happens on Upwork. In this role, you will lead the engineering organization responsible for building the systems that connect millions of clients and freelancers across the globe. You will shape the future of Upwork’s matching platform by setting technical direction, scaling core systems, and delivering experiences that power everything from search and browse to conversational matching, agentic workflows, and emerging AI-native surfaces. This is a high-impact leadership opportunity to guide a strong engineering team while partnering closely with product, machine learning, and executive leadership on a platform central to Upwork’s long-term growth. Responsibilities - Define and drive the technical strategy for Upwork’s Search & Recommendations platform, aligning engineering investments with long-term business goals, marketplace performance, and platform scalability. - Lead, grow, and develop a high-performing organization of software and machine learning engineers, fostering a culture of ownership, inclusion, high standards, and continuous learning. - Deliver a unified Search & Recommendations platform that powers matching experiences across client and talent journeys, including search, recommendations, conversational experiences, and agentic workflows. - Modernize search infrastructure by guiding the migration from legacy systems to scalable, maintainable, and high-performance architectures with clear APIs, observable pipelines, and strong experimentation support. - Partner closely with product, ML, data science, design, and senior leadership to prioritize roadmaps, navigate tradeoffs, and translate complex platform decisions into measurable business outcomes. - Champion engineering excellence through strong practices in system reliability, latency, data integrity, responsible AI development, and operational health across critical marketplace systems. - Establish clear operating mechanisms, metrics, and team rhythms that improve execution, support long-range planning, and track platform health, engineering effectiveness, and business impact. Qualifications - Significant experience leading engineering teams in high-scale environments, with a strong track record of delivering search, recommendations, ranking, or retrieval systems that drive meaningful business results. - Deep technical fluency in distributed systems, data pipelines, search architecture, and modern machine learning infrastructure, with the ability to guide architecture decisions and mentor senior engineers and managers. - Proven success leading integrated teams of software engineers and machine learning engineers while building strong partnerships across product, data science, and executive stakeholders. - Ability to operate effectively at multiple altitudes, translating technical depth into strategic clarity and making sound decisions in ambiguous, fast-moving environments. - Strong applied understanding of AI-native engineering workflows, including using AI to accelerate design, experimentation, and delivery while ensuring technical accuracy, responsible use, and scalable team adoption. Benefits - Comprehensive medical coverage for you and your family. - Unlimited PTO. - 401(k) plan with matching. - 12 weeks of paid parental leave. - Employee Stock Purchase Plan. Company Description Upwork Inc.’s (Nasdaq: UPWK) family of companies connects businesses with global, AI-enabled talent across every contingent work type including freelance, fractional, and payrolled. This portfolio includes the Upwork Marketplace, which connects businesses with on-demand access to highly skilled talent across the globe, and Lifted, which provides a purpose-built solution for enterprise organizations to source, contract, manage, and pay talent across the full spectrum of contingent work. Since its founding, Upwork Inc. has facilitated more than $30 billion in total transactions and services as it fulfills its purpose to create opportunity in every era of work.

• Define and maintain product success metrics and KPI frameworks for key product areas (e.g., quality signals, transparency, outcomes), ensuring clarity, alignment, and consistency across teams. • Build and evolve measurement approaches that connect product changes to business outcomes (funnel metrics, engagement, and revenue impact). • Design and analyze experiments (A/B tests, quasi-experiments) and apply causal inference techniques where randomization isn't feasible. • Develop durable reporting and dashboards that provide ongoing visibility into product health, leading indicators, and strategic goals. • Partner with Product and Engineering to improve instrumentation and event logging, ensuring data is accurate, complete, and decision-ready. • Conduct deep-dive analyses to identify user behavior patterns, friction points, and opportunity areas; translate findings into clear, prioritized recommendations. • Create compelling narratives that synthesize complex analyses into actionable insights for product and business leaders. • Establish lightweight analytics "operating rhythms" (regular readouts, metric reviews, launch measurement plans) to accelerate learning and accountability. • Partner to support survey data governance by analyzing sampling strategies, monitoring and interpreting response trends, and ensuring survey execution aligns with agreed standards.

• Lead integration efforts for acquired entities across multiple regions, ensuring alignment with organizational goals. • Oversee end-to-end project execution for new legal entity creation in various global markets. • Coordinate cross-functional internal teams and external experts to drive successful project outcomes. • Track milestones, timelines, and deliverables, ensuring projects stay on schedule and within scope. • Identify potential risks and proactively develop mitigation strategies related to global entity setup. • Provide clear, consistent updates and reporting to stakeholders across different levels of the organization.

• Define and maintain product success metrics and KPI frameworks for reputation and trust-related product areas. • Build and evolve measurement strategies that connect product changes to user behavior, engagement, and business outcomes. • Design, execute, and analyze experiments (A/B tests and quasi-experiments), applying causal inference methods where appropriate. • Develop and maintain dashboards and reporting to monitor product health, leading indicators, and strategic goals. • Partner with cross-functional teams to improve data instrumentation, ensuring high-quality and reliable datasets. • Conduct deep-dive analyses to uncover user behavior insights, friction points, and growth opportunities. • Translate complex analyses into clear, actionable recommendations and narratives for stakeholders. • Establish analytics best practices and operating rhythms, including reporting cadences and measurement plans. • Support survey data governance, including sampling strategies and interpretation of response trends.

• Design and implement scalable agentic frameworks that coordinate multiple AI agents to deliver accurate and reliable outcomes. • Build and optimize natural language query solutions that provide compliant, intuitive, and self-service access to enterprise data. • Develop and maintain evaluation frameworks for LLMs and prompts, driving measurable improvements in accuracy, scalability, and resilience. • Partner with data engineering peers to integrate AI orchestration with Python, SQL, and Snowflake pipelines. • Contribute to AI-powered summarization and explanation tools that enhance reporting, insights, and executive reviews. • Collaborate cross-functionally with product, analytics, and business teams to ensure solutions meet measurable business goals.

• Define and lead the company’s internal communications strategy, ensuring employees are informed, aligned, and connected to company priorities and how their work connects to the broader mission • Build and evolve communication channels, cadences, and formats to improve reach, engagement, and clarity across a distributed organization • Support the broader Leadership Team on internal communications, helping leaders communicate clearly and consistently with their teams • Partner with HR/People to develop communications around talent programs, benefits, and organizational changes • Establish metrics and feedback loops to evaluate effectiveness and continuously improve internal communications strategy • Own the planning and execution of regular company meetings and all-hands, delivering informative and compelling connection moments both virtually and in person • Shape and reinforce company culture, values, and mission through consistent, meaningful storytelling • Partner with the VP of Communications and external communications team to develop content that supports the CEO's communications strategy across both internal and external channels, including company-wide messages, speeches, board materials, LinkedIn, and media bylines • Serve as a steward of the CEO's editorial voice and point of view, ensuring consistency and authenticity across all content • Anticipate communications needs tied to business milestones, industry moments, and cultural conversations • Support prep for the CEO for all-hands meetings, town halls, and key internal moments with messaging, talking points, and Q&A prep • Manage and develop an internal communications team, setting priorities and alignment to teams, building processes and standards, providing coaching, and ensuring high-quality execution across workstreams

• Support the execution of lifecycle marketing campaigns across email, mobile, in-product messaging, and related channels, ensuring timely delivery and alignment with engagement and conversion goals. • Assist in testing and optimization efforts by analyzing campaign performance and translating insights into actionable improvements. • Build and optimize nurture sequences to support demand generation, activation, and retention initiatives. • Implement and manage campaigns within Braze (or similar platforms), ensuring audience accuracy, personalization, and quality assurance prior to launch. • Maintain and update lifecycle documentation, campaign briefs, and process guidelines; contribute to audits to ensure accuracy and operational excellence. • Monitor campaign performance dashboards, identify trends or anomalies, and recommend optimizations to enhance efficiency and user experience.