Upwork

• 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.

• Own and drive product-led growth strategy, with accountability for improving acquisition, activation, conversion, and revenue performance • Bring a strong, informed point of view on product growth strategy, grounded in data, experimentation, and marketplace dynamics • Identify, prioritize, and execute high-impact growth opportunities within the product experience (e.g., onboarding, matching, pricing, user flows) • Analyze product funnel performance end-to-end and implement optimizations to improve conversion rates and efficiency • Design, run, and scale in-product experiments (A/B tests, feature changes, UX improvements) to drive measurable impact • Partner closely with Product, Engineering, Design, Marketing, and Analytics to rapidly test and ship growth initiatives • Develop and refine segmentation, targeting, and user journey strategies to improve demand quality and user engagement

• Lead product strategy and execution for talent monetization initiatives, with a focus on subscription growth • Own the end-to-end subscription lifecycle, including activation, engagement, and retention • Define and deliver subscription features (benefits, packaging, pricing) in partnership with Analytics, Design, Engineering, Marketing, and Product teams • Design, execute, and analyze experiments across pricing, promotions, and feature adoption • Monitor performance metrics, synthesize customer feedback, and iterate on features to maximize impact