Upwork Inc. · NASDAQ:UPWK
Upwork — Investor Day (November 2025)
132 slides from Upwork's investor day presentation, Nov 18, 2025
Slide 1: Investor Day
Investor Day November 18, 2025
Slide 2: Safe Harbor Statement
Safe Harbor Statement This presentation and accompanying webcast of Upwork Inc. (together with its wholly owned subsidiaries, the “Company,” “we,” “us,” or “our”) contain "forward-looking" statements within the meaning of the federal securities laws. Forward-looking statements include all statements
Slide 3: Today's Agenda
Today’s Agenda THE NEW UPWORK Hayden Brown, President & Chief Executive Officer ACCELERATING SMB GROWTH ON AN AI-POWERED MARKETPLACE Dave Bottoms, General Manager, Marketplace CUSTOMER PANEL Moderated by Peter Sanborn, VP, Strategy, Corporate Development & Partnerships BREAK UPWORK’S AI ADVANTAGE Andr
Slide 4: The new Upwork
The new Upwork Hayden Brown President & Chief Executive Officer 4 | Investor Day 2025 4
Slide 5: We are at a turning point for work
We are at a turning point for work. We’ve reinvented Upwork to lead the AI era of work. 5 | Investor Day 2025
Slide 6: A new growth era for Upwork
A new growth era for Upwork Q3 2025 GSV Revenue Adjusted EBITDA $1,018M $202M $60M +2% YoY +4% YoY 30% adjusted EBITDA margin Note: Adjusted EBITDA and adjusted EBITDA margin are non-GAAP financial measures. An explanation of non-GAAP financial measures and reconciliations to their most directly compa
Slide 7: The new Upwork
The new Upwork Fundamentally reinvented business for the next chapter Clear traction with three massive growth opportunities Accelerating growth and exceptional profitability 7 | Investor Day 2025
Slide 8: Headlines diverge
Headlines diverge “ AI is already taking “ Will AI improve or “ AI is not yet replacing white-collar jobs. eliminate jobs? It workers in the US, Economists warn depends on who researchers find. there’s ‘much more in you ask. the tank.’ 8 | Investor Day 2025
Slide 9: AI is a strong tailwind
AI is a strong Net-new AI work tailwind Fractionalization of full-time jobs 9 | Investor Day 2025 INVESTOR DAY 2025
Slide 10: New needs for writers and editors
relies on New needs for writers and editors Upwork talent works alongside AI tools 10 | Investor Day 2025
Slide 11: AI driving business results
AI driving business results +12% +5% YoY project size YoY GSV/active client +50% YoY AI clients Note: As of or for the three months ended September 30, 2025. 11 | Investor Day 2025 INVESTOR DAY 2025
Slide 12: Adoption of AI tools will likely increase demand
Indicate adoption 77% of AI tools will likely increase demand for fractional or flexible labor 12 | Investor Day 2025 Source: Upwork B2B Workforce Marketplace Survey, based on responses from U.S.-based hiring decision-makers (October 2025).
Slide 13: The human and AI-powered work marketplace
The human and AI-powered work marketplace Work delivery platform: Business demand: AI-powered & end-to-end SMB through enterprise clients Proprietary work data Category breadth: Talent supply: High spend & retention Global & highly skilled talent pool 13 | Investor Day 2025
Slide 14: Work delivery platform
Work delivery platform Built for long-term relationships and complex work AI-native platform 70% of new job posts touched by Uma 14 | Investor Day 2025
Slide 15: SMB and enterprise business demand
SMB and enterprise business demand ~800K high-quality active clients +7% YoY new client spend +11% YoY growth in new clients with >$1K spend in first quarter Note: As of or for the three months ended September 30, 2025. 15 | Investor Day 2025
Slide 16: Global, skilled talent supply
Global, skilled talent supply 18M active talent ~2M with advanced degrees 10K skills 16 | Investor Day 2025
Slide 17: The human and AI-powered work marketplace
The human and AI-powered work marketplace Work delivery platform: Business demand: AI-powered & end-to-end SMB through enterprise clients and agents Proprietary work data Category breadth: Talent supply: High spend & retention Global & highly skilled talent pool and agents 17 | Investor Day 2025
Slide 18: Category breadth
Category breadth >130 categories ~40% of clients are multi-category Drives superior economics Note: Multi-category clients for trailing four quarters ended September 30, 2025. 18 | Investor Day 2025
Slide 19: Proprietary work data
Proprietary work data 10+ petabytes of data Growing daily Powering AI-enhanced work delivery 19 | Investor Day 2025
Slide 20: Pg. Pg.
20 | Investor Day 2025 Pg. 20 Pg. 20
Slide 21: Enables critical workforce agility
relies on Enables critical workforce agility Powers product and services growth 21 | Investor Day 2025
Slide 22: SMB client in marketplace
relies on SMB client in marketplace Built extensive CX and fraud operations team on Upwork 22 | Investor Day 2025
Slide 23: Upwork reinvented
Upwork reinvented Product Customers Operations Marketplace Tailored Smaller, more built on solutions for nimble and AI-native SMB and AI-powered platform enterprise: team Business Plus + Lifted 23 | Investor Day 2025
Slide 24: A $1.3T market opportunity in 2028
A $1.3T market opportunity in 2028 SMBs Enterprise Agentic AI $530B $650B $120B 2028 global spend on 2028 global spend on Agentic AI work aligned with contingent digital knowledge contingent digital knowledge or enhancing digital work in companies with work in companies with knowledge work by 2028 <
Slide 25: Three growth building blocks
Three 1 Transforming human + AI work growth 2 Accelerating SMB growth building blocks 3 Unlocking Enterprise expansion 25 | Investor Day 2025
Slide 26: Transforming human + AI work
Transforming 1 human + AI work Expanding AI-powered workflows Accelerating AI category growth Integrating AI agents 26 | Investor Day 2025
Slide 27: Expanding AI-powered workflows
Expanding 1 AI-powered workflows Driving $100M increase in GSV in 2025 Uma™, Upwork’s Mindful AI 27 | Investor Day 2025 27
Slide 28: Accelerating AI category growth
Accelerating AI 1 category growth $300M Annualized GSV from AI-related work +50% Q3 rise in GSV from AI-related work 28 | Investor Day 2025
Slide 29: Integrating AI agents
Integrating Clients 1 AI agents AI Human Agents Experts 29 | Investor Day 2025 INVESTOR DAY 2025
Slide 30: Accelerating SMB growth
2 Accelerating SMB growth 30 | Investor Day 2025
Slide 31: Unlocking Enterprise expansion
3 Unlocking Enterprise expansion Infrastructure + solutions that power enterprise contingent work programs 31 | Investor Day 2025 INVESTOR DAY 2025
Slide 32: Our 3-year outlook
Our 3-year outlook Targeting accelerating growth CAGR across GSV, revenue and adjusted EBITDA GSV Revenue Adjusted EBITDA 7- 9% 13 -15% ~20% CAGR CAGR CAGR 32 | Investor Day 2025 32
Slide 33: The new Upwork
The new Upwork Amplifying AI tailwinds Driving SMB and enterprise growth Growing top and bottom line results 33 | Investor Day 2025
Slide 34: Accelerating SMB growth on an AI-powered marketplace
Accelerating SMB growth on an AI-powered marketplace Dave Bottoms General Manager, Marketplace 34 | Investor Day 2025 INVESTOR DAY 2025
Slide 35: World's largest and highest-quality platform for flexible knowledge workers
World’s largest and highest-quality platform for flexible knowledge workers 18M active 10K professionals skills 250K 130+ AI experts categories Note: Largest as measured by GSV. 35 | Investor Day 2025
Slide 36: Uma powers our AI-native Marketplace
Uma powers our AI-native Marketplace 36
Slide 37: Uma helps clients post jobs and talent write proposals
Uma helps clients post jobs and talent write proposals 37 | Investor Day 2025 37
Slide 38: Uma assists with messaging and work summaries
Uma assists with messaging and relevant work summaries 38 | Investor Day 2025
Slide 39: Uma conducts candidate interviews and summarizes work delivery
Uma conducts candidate interviews and summarizes work delivery
Slide 40: AI is a strong tailwind
AI is a strong Net-new AI work tailwind Fractionalization of full-time jobs 40 | Investor Day 2025 INVESTOR DAY 2025
Slide 41: Demand for net-new AI work is accelerating
Demand for net-new AI work is accelerating AI & Machine Digital Marketing Learning Virtual Assistance Mobile Development Annual GSV AI Apps & Integration E-commerce Data Extraction Data Mining & Management ERP / CRM Software Community Management Blockchain & Crypto 0 10 20 30 40 Quarters since categ
Slide 42: AI is fractionalizing work and expanding demand for flexible expertise
AI is fractionalizing work and expanding demand for flexible expertise Existing full-time roles augmented by fractional talent Traditional organizational Organizations seek fractional structures expertise to drive AI value 42 | Investor Day 2025
Slide 43: Accelerating SMB growth
Accelerating SMB growth 43 | Investor Day 2025
Slide 44: SMBs are the backbone of the global economy
SMBs are the backbone of $530B the global 2028 global market size economy Source: Upwork Market Study, a commissioned third-party study that estimates the flexible digital knowledge work market based on data from, among other sources, the Bureau of Labor 44 | Investor Day 2025 Statistics, World Bank,
Slide 45: SMB is our most valuable segment
SMB is our most valuable segment Greater share of wallet Hire more for complex jobs More satisfied with Upwork 45 | Investor Day 2025
Slide 46: Growing SMBs need tailored experiences
Growing SMBs need tailored experiences “ We need to find quality talent quickly for complex projects. Access to top 1% talent “ We need to hire a team and across multiple roles. Uma Recruiter “ We need different people involved in hiring decisions. Team-based hiring “ We need flexibility on payment opt
Slide 47: Instant access to top 1% talent on Upwork
Instant access to top 1% talent on Upwork Business Plus 47 | Investor Day 2025
Slide 48: Uma-powered recruiter helps SMBs hire teams rapidly
Uma-powered recruiter helps SMBs hire teams rapidly Business Plus 48 | Investor Day 2025
Slide 49: Team-based features help SMBs collaborate on hiring
Team-based features help SMBs collaborate on hiring Business Plus 49 | Investor Day 2025
Slide 50: Net-30 terms give SMBs financial flexibility
Net-30 terms give SMBs financial flexibility, boosting spend and retention Business Plus 50 | Investor Day 2025
Slide 51: Business Plus sees strong organic growth
Business Plus sees strong organic growth 36% QoQ active client 2.5x GSV per active client 33% QoQ GSV growth vs. Marketplace avg growth Note: As of or for the three months ended September 30, 2025. 51 | Investor Day 2025 INVESTOR DAY 2025
Slide 52: Activating demand for Business Plus
Activating demand for Business Plus INVESTOR DAY 2025 INVESTOR DAY 2025
Slide 53: Clear path to scale SMB growth
Clear path to scale SMB growth Future: 2027+ Develop new Next: 2026 value-added services for SMBs Complete AI-native Now: 2025 - Q126 end-to-end journey Orchestrate full work delivery across Uma, Introduce AI-native Strengthen Business agents, and talent marketplace Plus for growing AI categories 53
Slide 54: Accelerating SMB growth on an AI-powered marketplace
Accelerating SMB growth on an AI-powered marketplace AI-native marketplace transformation drives GSV growth Capturing net-new AI demand and fractionalized work adoption Business Plus powering SMBs’ growth and AI transformation 54 | Investor Day 2025
Slide 55: Customer panel
Customer panel 55 | Investor Day 2025 INVESTOR DAY 2025
Slide 56: Hearing directly from our customers
Hearing directly from our customers Peter Sanborn Gabe Richman Phil Rasori Cory Hymel VP, Strategy, Corporate Founder & CEO COO VP, Product and Development & Partnerships Research Moderator 56 | Investor Day 2025
Slide 57: Upwork's AI advantage
Upwork’s AI advantage Andrew Rabinovich CTO, Head of AI & Machine Learning 57 | Investor Day 2025 INVESTOR DAY 2025
Slide 58: A foundational layer behind the new Upwork
A foundational layer behind the new Upwork 58 | Investor Day 2025
Slide 59: State-of-the-art search and recommendation platform
State-of-the-art search and recommendation platform FROM TO RESULT Query Literal keyword In-house, multi-task deep Higher conversion understanding matching learning models with conversational intent driving: Retrieval Keyword lookups ● ● Higher recall Personalization ~5%for clients ● Faster surfacin
Slide 60: New tech layer for next-generation experiences
New tech layer for next-generation experiences High-Quality Custom Model Mixture of Experts & Platform Data Training & Evaluation Knowledge Graph Active Learning Loop HIGHER QUALITY LOWER COST BETTER EXPERIENCES FASTER THROUGHPUT >50% ~70% ~20% <1 week Better content accuracy Less cost to compute Mo
Slide 61: The power of a closed loop ecosystem
The power of a closed loop ecosystem Work delivery platform: Business demand: AI-powered & end-to-end SMB through enterprise clients and agents Proprietary work data Category breadth: Talent supply: High spend & retention Global & highly skilled talent pool and agents 61 | Investor Day 2025
Slide 62: We have 10+ petabytes of real-world work data
We have 10+ petabytes of real- world work data Recognized by: 62 | Investor Day 2025
Slide 63: The first human + AI agent marketplace
The first Clients human + AI agent marketplace AI Human Agents Experts 63 | Investor Day 2025 INVESTOR DAY 2025
Slide 64: Flexible talent lead AI agent adoption
Flexible talent lead AI agent adoption ~1.5x more likely to use AI tools 78% 53% Independent Full-time Source: Upwork Future Workforce Index (April 2025). Denotes percentage using AI tools multiple times a week. professionals on employees Upwork 64 | Investor Day 2025
Slide 65: Clients want AI-enabled human talent
Clients want AI-enabled human talent >90% prefer human involvement 54% 38% Source: Upwork B2B Workforce 5% Marketplace Survey, based on responses from U.S.-based hiring decision-makers (October 2025). Shows percentage of decision makers’ 3% preference for human involvement with AI models. Human-in-t
Slide 66: A fast-growing, natural market extension for Upwork
A fast-growing, $120B natural market 2028 AI agent global market size extension for Upwork >50% CAGR Source: Upwork Market Study, a commissioned third-party study that estimates the flexible digital knowledge work market based on data from, among other sources, the Bureau of Labor Statistics, 66 | I
Slide 67: Clear path to integrating agents
Clear path to integrating agents Future: 2027+ Orchestrate full work delivery across Uma, Next: 2026 agents, and talent Roll out agents to the Now: 2025 - Q126 marketplace, tested and validated through Continue to evolve Uma – HAPI benchmark greater personalization, deeper insight Innovate agent col
Slide 68: Upwork's agent collaboration space
Upwork’s agent collaboration space Playground Testing Human experts environment Human experts where freelancers, and third-party Quality + agents agents collaborate to deliver work outcomes Agents Speed 68 | Investor Day 2025
Slide 69: Rapid integration into full marketplace next year
Rapid Upwork’s agent collaboration space integration into full marketplace next year 69 | Investor Day 2025
Slide 70: The Human + Agent Productivity Index: HAPI
Our new The Human + Agent Productivity Index: HAPI evaluation system to verify agents Recognized by… 70 | Investor Day 2025
Slide 71: Early results validate the future of work is human + AI
Early results validate the future of work is human + AI HAPI: Upwork’s Human + Agent Productivity Index human only up to Completion rate on selected ~70% low-complexity tasks improvement 55.9% 51.2% 41.0% 42.3% 39.8% 32.3% 33.5% 19.9% 19.6% AI only 1st human turn 2nd human turn Number of attempts Re
Slide 72: Uma becoming an orchestrator of work delivery
Uma becoming an orchestrator of work delivery between agents and talent Orchestrate Short term (prompt) Qualify Long term (RAG) Evaluate Reason & act LLM-as-a-judge Functions Talent Chain of thought Mixture-of-judges Client Project plan Outcome Delivery Match / discovery / recommendation Agent Propo
Slide 73: Slide 73
Slide 74: The new Upwork unlocks value for all
The new Upwork unlocks Clients Faster, higher-quality value for all outcomes grounded in trust More throughput, more demand, higher-value work, and new revenue streams AI Agents Human Experts New channels, unmatched Amplified productivity and feedback and trusted human input earnings potential 74 | I
Slide 75: Upwork's AI advantage
Upwork’s AI advantage State-of-the-art search and rec and next-generation AI infrastructure Strong moat from our closed loop, data-rich ecosystem Clear path to unlock value for agents, talent and clients 75 | Investor Day 2025
Slide 76: Unlocking Enterprise expansion
Unlocking Enterprise expansion Ernesto Lamaina General Manager, Lifted 76 | Investor Day 2025 INVESTOR DAY 2025
Slide 77: One solution built for enterprise companies
One solution built for enterprise companies to source, contract, manage and pay contingent talent. , 77 | Investor Day 2025
Slide 78: Enterprise contingent labor is massive
Enterprise $650B contingent 2028 global market size labor is massive Access to talent Flexibility Efficiency Source: Upwork Market Study, a commissioned third-party study that estimates the flexible digital knowledge work market based on data from, among other sources, the Bureau of Labor 78 | Investor
Slide 79: AI is a major tailwind
AI is a major tailwind “ AI is pushing functional leaders to leverage 77% contingent more than FTEs; all our expected headcount growth is Companies that expect increased demand for fractional labor to happening in contingent. support adoption of AI tools CWP Program Leader, Global Financial Institut
Slide 80: How enterprises access contingent labor
How enterprises access contingent labor Independent contractor Established workflows, policies Agent of and compliance Outcomes record requirements Engagement types Engage through 5 contract types Staff Employer of augmentation record 80 | Investor Day 2025
Slide 81: Trusted by 300+ enterprise companies
Trusted by 300+ enterprise companies 81 | Investor Day 2025
Slide 82: Why clients have been working with us
Why clients have been working with us High-quality talent network Fast delivery Enterprise grade 82 | Investor Day 2025
Slide 83: High-quality talent network
High-quality talent network “ Active professionals 18M Our partnership has been transformative, providing us Skills access to a global talent pool that boosts our productivity 10K and creativity while ensuring cost-efficiency and flexibility Average rating for our team. 4.92/5 Director of Strategy & Bu
Slide 84: Fast delivery
Fast delivery “ To receive shortlist As fast as same day Made hiring this talent seamless and To fill incredibly fast – they 3 days were up and running in less than 48 hours. To redeploy As fast as 30 Director of Creative, Multinational Conglomerate of minutes Prestigious Beauty Brands 84 | Investor
Slide 85: Enterprise grade
Enterprise grade Global “ To reach our goals, we need to move faster, better, and cheaper, with ironclad Compliant security and trust. I sleep well at night because I know it is all taken care of. Platform & VP of IT, Leading AI-Powered Identity Verification Platform service 85 | Investor Day 2025
Slide 86: Prior barriers to unlocking additional growth
Prior barriers to unlocking additional growth Enterprise ecosystem and workflows Engagement types Limitations in ability to deliver talent via existing Directly provided 2 types, workflows and distribution channels dependent on partners Functional Centralized Leaders & Contingent Hiring Workforce IC A
Slide 87: Recent acquisitions filled gaps
Recent acquisitions filled gaps Enterprise ecosystem and workflows Engagement types Able to deliver talent via existing Directly provide all workflows and distribution channels contract types Functional Centralized Leaders & Contingent Hiring Workforce IC AOR managers Programs (CWP) Contingent Staff EOR
Slide 88: Comprehensive solution for enterprise contingent needs
Fast access to Comprehensive Ability to meet clients solution for enterprise high-quality Upwork where they are Marketplace talent contingent needs 88 | Investor Day 2025
Slide 89: Access to fraction of annual spend
Access to fraction of annual spend Spend available before launching Lifted $50M $1B+ IC / AOR spend Actual share of wallet: ~20% Annual spend for contingent Large pharma company $950M+ EOR / Staff Aug / Outsourcing spend 89 | Investor Day 2025 89
Slide 90: Full contingent spend access with Lifted
Full contingent spend access with Lifted Spend available after launching Lifted $50M $1B+ IC / AOR spend Remains fully available Annual spend for + possible to increase contingent share of wallet Large pharma company $950M+ EOR / Staff Aug / Outsourcing spend Becomes available 90 | Investor Day 2025
Slide 91: Focus on 5,000 companies in our Ideal Customer Profile
Focus on 5,000 companies in our Ideal Customer Profile SPEND $50M-1B+ Contingent labor budgets per year / per company ICP Thousands of employees & billions in revenue 91 | Investor Day 2025
Slide 92: Expand share of wallet with existing clients
Expand share of wallet with existing clients Expand share of wallet within Gain share of wallet in existing contract types new contract types Execution via existing account management and customer success management (CSM) structure 92 | Investor Day 2025
Slide 93: Win net-new customers with 3-step approach
Win net-new customers with 3-step approach Expand Adopt Pilot Execution via agile marketing and sales team 93 | Investor Day 2025
Slide 94: Positive leading indicators
Positive leading indicators Existing client Prospect Large services company Large financial network FROM TO FROM TO “Impossible to Leveraging us for Final stages of work together as Inviting us to one contract RFP for 3 you do not offer next RFP type contract types the contract types we need” 3x GSV $
Slide 95: Why Lifted?
Why We provide Lifted? high-quality talent, fast We unify and elevate the ecosystem We unlock an estimated 10-30% cost savings 95 | Investor Day 2025
Slide 96: Clear path to expand in Enterprise
Clear path to expand in Enterprise Future: 2027+ Scale Next: H2 2026 Expand with existing Now: 2025 - H126 customers Drive expansion Land pilots with new conversations and land customers discovery 96 | Investor Day 2025 96
Slide 97: Unlocking Enterprise expansion
Unlocking Enterprise expansion Significantly expanded available market with launch of Lifted Early positive indicators from both existing clients and prospects Target growth in H2’26 and scale in FY27 97 | Investor Day 2025 97
Slide 98: A foundation for accelerating growth
A foundation for accelerating growth Erica Gessert Chief Financial Officer 98 | Investor Day 2025 INVESTOR DAY 2025
Slide 99: Delivering profitable growth
Delivering profitable growth Confident growth outlook Foundation of durable profitability Strong balance sheet to accelerate growth 99 | Investor Day 2025
Slide 100: The human and AI-powered work marketplace
The human and AI-powered work marketplace Work delivery platform: Business demand: AI-powered & end-to-end SMB through enterprise clients and agents Proprietary work data Category breadth: Talent supply: High spend & retention Global & highly skilled talent pool and agents 100 | Investor Day 2025
Slide 101: The human and AI-powered work marketplace
The human and AI-powered work marketplace Work delivery platform: Business demand: 70% of new job posts ~800K active touched by Uma clients Proprietary work data Category breadth: Talent supply: 50 categories with 18M active over $10M GSV professionals Note: Category spend for trailing four quarters
Slide 102: A platform built to deliver high-value, recurring work
A platform built to deliver high-value, recurring work 85%+ $5K+ of GSV comes from GSV per active client 90% of GSV comes from retained clients high-value work Note: As of or for the three months ended September 30, 2025. High value work defined as greater than $1,000. 102 | Investor Day 2025 INVESTO
Slide 103: Attracting and retaining a higher quality customer base
Attracting and retaining a higher quality customer base +11% 170bps 6x new clients spend >$1K YoY improvement higher GSV from in their first quarter to churn retained clients Note: As of or for the three months ended September 30, 2025. 103 | Investor Day 2025 INVESTOR DAY 2025
Slide 104: Building the new Upwork
Building the new Upwork Strategic acquisitions Platform development AI-driven job post generator AI recruiter AI interviews AI proposal writer Conversational search AI work experience summaries Freelancer Plus Business Plus 104 | Investor Day 2025 INVESTOR DAY 2025
Slide 105: Outperforming the market
Outperforming the market +8% Online marketplaces 0% Staffing industry -4% Note: Average revenue CAGRs for fiscal years 2022 - 2025E for overall staffing industry and online marketplace peers. 105 | Investor Day 2025
Slide 106: Untethered from the macro environment
Untethered from the macro environment rolling 3-month GSV Job openings 2018 2019 2020 2021 2022 2023 2024 2025 Source: The Bureau of Labor Statistics - Job Opening and Labor Turnover Survey (JOLTS). Seasonally adjusted, total nonfarm job openings through August 1, 2025. 106 | Investor Day 2025
Slide 107: Poised for accelerating GSV growth
Poised for accelerating GSV growth +16% YoY Q3’25 +2% +1% 0% -3% 2022 2023 2024 2025 2026 2027 2028 107 | Investor Day 2025
Slide 108: Traction in three large markets
Traction in three large markets SMBs Enterprise Agentic AI $530B $650B $120B 2028 global spend on 2028 global spend on Agentic AI work aligned with contingent digital knowledge contingent digital knowledge or enhancing digital work in companies with work in companies with knowledge work by 2028 <500
Slide 109: Three growth building blocks
Three 1 Transforming human + AI work growth 2 Accelerating SMB growth building blocks 3 Unlocking Enterprise expansion 109 | Investor Day 2025
Slide 110: Transforming human + AI work
Transforming human + AI work 1 AI-powered AI category AI agents workflows $100M $300M ~12x incremental GSV in Estimated GSV run rate YoY growth in 2025 driven by AI year end 2025 searches for talent platform optimization with agentic Growing 50%+ YoY experience Note: Growth in searches for the three
Slide 111: Accelerating SMB growth
Accelerating SMB growth 2 2.5x Business Plus GSV per 5%+ active client vs. Marketplace in Q3 33% QoQ GSV growth rate Target Marketplace 20+bps in Q3 GSV from Business Plus in 2026 take rate contribution in Q3 111 | Investor Day 2025
Slide 112: Unlocking Enterprise expansion
Unlocking Enterprise expansion 3 300+ enterprise companies Target contract size 25% 10x FY26 Lifted GSV growth target 112 | Investor Day 2025
Slide 113: The building blocks for GSV growth are clear
The building blocks for GSV growth are clear Ads and FY 2028 Enterprise pricing Target expansion SMB growth Human + AI work FY 2025 AG R 7-9 %C 113 | Investor Day 2025
Slide 114: Monetization momentum built on proven growth engines
Monetization momentum built on proven growth engines Connects & Subscriptions Variable 2027 ads products freelancer fee 18% YoY 24% YoY Early Value-added revenue Freelancer experimentation services for growth in Q3 Plus revenue in 2025 SMBs growth in Q3 114 | Investor Day 2025
Slide 115: Substantial room to grow take rate
Substantial room to grow take rate Average Industry Take Rate 30%+ Ads and FY2028 Enterprise pricing Target expansion ~23% SMB Human + AI growth work FY2025 Take Rate Note: Average industry take rate based on 2025 reports by public online work marketplace companies. 115 | Investor Day 2025
Slide 116: Accelerated revenue growth from GSV growth and take rate expansion
Accelerated revenue growth from GSV growth and take rate expansion Take rate expansion contribution Ads and FY2028 pricing Target GSV contribution Enterprise expansion SMB growth Human + AI AG R work % C Total 13 -15 FY2025 116 | Investor Day 2025
Slide 117: We've built a foundation of profitable and scalable growth
We’ve built a foundation of profitable and scalable growth $223 $168 Adjusted EBITDA ($M) 28% Adjusted EBITDA Margin 22% $73 -$4 11% -1% 2022 2023 2024 2025E Note: 2025 represents midpoint of full year 2025 guidance. Adjusted EBITDA and adjusted EBITDA margin are non-GAAP financial measures. An explan
Slide 118: Sales: Lower cost to acquire and serve
Sales Lower cost to acquire and serve Since 2022, we’ve… Reduced sales Reduced enterprise customer Reduced enterprise costs by acquisition cost by cost to serve by 35% 40% 20% Note: Sales costs and cost to serve 2025E compared to fiscal year 2022. Customer acquisition cost fiscal year 2024 compared to
Slide 119: Marketing: Lower cost with higher yield
Marketing Lower cost with higher yield Since 2022, we’ve… Reduced marketing Increased GSV yield from Increased marketing-led spend by marketing by GSV/contract by 55% 24% 113% Note: Nine months ended September 30, 2025 compared to nine months ended September 30, 2022. 119 | Investor Day 2025 INVESTO
Slide 120: R&D: Higher productivity and throughput
R&D Higher productivity and throughput 25-35% 32% 16% AI-assisted code reduction in cost per faster code production line of code Note: AI-assisted code on a monthly basis. Reduction in cost ten months ended October 31, 2025 compared to fiscal year 2022. Code production speed year-over-year for traili
Slide 121: Efficient cash conversion fueling growth and flexibility
Efficient cash conversion fueling growth and flexibility $223 85% $168 Adjusted EBITDA to FCF 28% conversion 2023-2025E Adjusted EBITDA ($M) 22% $216 $73 Adjusted EBITDA Margin $139 Free Cash Flow ($M) -$4 11% $39 $3 -1% 2022 2023 2024 2025E Note: 2025 represents midpoint of full year 2025 guidance. Ad
Slide 122: Capital deployment focused on shareholder value
Capital deployment focused on shareholder value Focused organic investment Adjusted EBITDA margin target of 35% by 2029 Total value of share repurchase since 2024 Targeted M&A Continue record of high-ROI M&A Capital return Offset stock-based compensation and opportunistic additional share repurchases
Slide 123: Accelerating our growth in 2026
4-6% GSV growth rate target Accelerating our growth 6-8% Revenue growth rate target in 2026 ~29% Adjusted EBITDA margin target *Absorbing 2pp dilution from Lifted growth investment 123 | Investor Day 2025 123
Slide 124: Our 3-year outlook
Our 3-year outlook Targeting accelerating growth CAGR across GSV, revenue and adjusted EBITDA GSV Revenue Adjusted EBITDA 7- 9% 13 -15% ~20% CAGR CAGR CAGR 124 | Investor Day 2025 124
Slide 125: The new Upwork
The new Upwork Fundamentally reinvented business for the next chapter Rebuilt platform, customer focus and operations Growing traction in massive markets +50% YoY GSV growth in $300M+ AI work; projected GSV growth: 100% YoY in Business Plus and 25% YoY in Lifted Accelerating growth and exceptional p
Slide 126: Q&A
Q&A 126 | Investor Day 2025
Slide 127: The new Upwork
The new Upwork 127 | Investor Day 2025
Slide 128: Appendix and definitions
Appendix and definitions 128128| Pg. Investor Day 2025
Slide 129: Key definitions
Key definitions Active Clients Enterprise Revenue We define an active client as a client that has had spend activity on any Upwork We define Enterprise revenue as revenue from our Enterprise offerings, which platform or other workforce solution during the 12 months preceding the date of primarily consis
Slide 130: Key definitions
Key definitions Marketplace Revenue Marketplace revenue represents the revenue derived from the Upwork Marketplace and is the primary driver of our business. Marketplace Take Rate Marketplace take rate measures the correlation between Marketplace revenue and Marketplace GSV and is calculated by divid
Slide 131: GAAP to non-GAAP reconciliation
GAAP to non-GAAP reconciliation Reconciliation of GAAP Net Income (Loss) to adjusted EBITDA (In thousands) (Unaudited) Three Months Ended Twelve Months Ended December 31, 30-Sep-25 2024 2023 2022 Net income (loss) $ 29,335 $ 215,586 $ 46,887 $ (89,885) Add back (deduct): Stock-based compensation exp
Slide 132: GAAP to non-GAAP reconciliation
GAAP to non-GAAP reconciliation Reconciliation of Cash Provided by Operating Activities to Free Cash Flow (In thousands) (Unaudited) Twelve Months Ended December 31, 2024 2023 2022 Cash provided by operating activities $ 153,563 $ 52,708 $ 11,497 Less: purchases of property, plant & equipment and ca