Director of Engineering, Search, Recommendations, Discovery and Distribution

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. From Fortune 100 enterprises to entrepreneurs, businesses rely on Upwork Inc. to find and hire expert talent, leverage AI-powered work solutions, and drive business transformation. With access to professionals spanning more than 10,000 skills across AI & machine learning, software development, sales & marketing, customer support, finance & accounting, and more, the Upwork family of companies enables businesses of all sizes to scale, innovate, and transform their workforces for the age of AI and beyond.

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. Learn more about the Upwork Marketplace at Upwork.com and follow us on LinkedIn, Facebook, Instagram, TikTok, and X; and learn more about Lifted at Go-Lifted and follow on LinkedIn.

We’re seeking a Director of Engineering to lead our Search, Recommendations, Discovery and Distribution teams—mission-critical functions that connect talent to opportunity across the Upwork ecosystem. You will lead engineering strategy and execution for our relevance systems, discovery pipelines, and AI-powered personalization efforts along with third party integrations. This is a unique opportunity to shape core components of our user experience and create impact at global scale through advanced retrieval models and ranking systems. Join us to build the next generation of search, recommendation and distribution infrastructure powering the future of work.

Responsibilities

• Lead and scale engineering teams responsible for Upwork’s search, recommendations, and job/talent distribution systems
• Technical SEO Mastery: Expertise in crawlability, indexing, and site architecture is essential to ensure search engines can navigate the website efficiently.
• Drive architectural decisions and system design for high-performance, low-latency retrieval and ranking pipelines
• Partner cross-functionally with product, data science, and infrastructure teams to define strategy and measurable outcomes (Focals) across discovery surfaces
• Lead and support multiple engineering teams building ML-enabled Collaboration and project / task management systems.
• Champion and refine AI-driven personalization, ensuring reliable performance and responsible use of generative and retrieval-based models
• Implement engineering best practices that support high velocity, quality, and team autonomy
• Hire, mentor, and develop engineering managers and technical leads across multiple teams
• Set a high bar for execution, system quality, and customer impact across platforms serving millions of users

What it takes to catch our eye

• Proven 10+ years of experience leading engineering teams focused on search, discovery, seo/sem , recommendations, ranking, and/or similar large-scale distributed systems.
• Deep understanding of relevance modeling, vector retrieval, or recommender systems with measurable production impact
• Strong alignment to leadership principles—especially around ownership, excellence, and customer-centricity
• Demonstrated ability to drive organizational clarity and scalable team processes across multiple workstreams
• Adaptive-level AI fluency: experience integrating AI into engineering workflows, iterating on prompt strategies, 3rd party integrations and evaluating AI outputs for technical soundness

Come change how the world works.

Upwork is establishing an operational hub in Toronto, Canada. This role will require 3 days in the office once the office is open.

This position will initially be employed through a partner to ensure a seamless hiring process while we establish the hub. Once the hub is established, there may be opportunities to transition to employment with Upwork, depending on business needs and other requirements. While employed by the partner, you’ll work as part of Upwork’s team, with access to our resources, culture, and growth opportunities.

Our partner will offer competitive benefits. When Upwork’s hub is established, we will be excited to offer employment and benefits directly as business needs require. 

Upwork is committed to building a diverse, inclusive, and equitable workforce. Employment decisions are made without regard to race, color, religion, gender, sexual orientation, gender identity, national origin, disability, or any other status protected by applicable law.

Upwork is an Equal Opportunity Employer committed to recruiting and retaining a diverse and inclusive workforce. We do not discriminate based on race, religion, color, national origin, gender (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, genetic information, or other legally protected characteristics under federal, state, or local law.

Please note that a criminal background check may be required once a conditional job offer is made. Qualified applicants with arrest or conviction records will be considered in accordance with applicable law, including the California Fair Chance Act and local Fair Chance ordinances. The Company is committed to conducting an individualized assessment and giving all individuals a fair opportunity to provide relevant information or context before making any final employment decision.

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