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Senior Strategic Solutions Architect in Chicago

47 active opportunities · Updated for October 2026

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Explore current senior strategic solutions architect jobs in Chicago. Use filters to narrow by work mode, employment type, experience and date posted.

Who we are About Stripe Stripe is a financial infrastructure platform for businesses. Millions of companies—from the world’s largest enterprises to the most ambitious startups—use Stripe to accept payments, grow their revenue, and accelerate new business opportunities. Our mission is to increase the GDP of the internet, and we have a staggering amount of work ahead. That means you have an unprecedented opportunity to put the global economy within everyone’s reach while doing the most important work of your career. About the team Stripe’s Commercial team sits within Stripe’s Americas Sales organization and is responsible for acquisition, expansion, and growth of mid market accounts in North America. This team sells the entire suite of Stripe products and owns the full customer lifecycle. What you’ll do As a Sales Manager, Commercial (Hunter), you will play an instrumental role in fueling Stripe’s growth through defining the sales motion and GTM processes needed to acquire, grow and expand mid market accounts. In this role, you will build the foundation of a new team and GTM motion at Stripe. You will hire and lead a team of high-performing Account Executives, helping them to develop their skills and deliver on their ambitious targets, as well as roll your sleeves up to work directly with customers. We are looking for a proactive leader who has demonstrated success dealing with ambiguity, operating in a high-growth environment, managing high-performing teams and solving complicated problems with limited oversight. Ideal candidates will have management and leadership experience scaling a technology sales team and possess first-class analytical, communication and relationship-building skills. Responsibilities Recruit, develop and lead a team of Account Executives who focus on mid market businesses Work with senior leadership to develop the long-term vision and strategy for the team, and manage day-to-day operations with a focus on performance against key sales and growt

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Fin
📍 Chicago• $139.3K – $166.4K/yr
21 days ago

Fin , now part of Salesforce, is on a mission to help businesses provide perfect customer experiences. Our AI Agent Fin is the highest-performing AI Customer Agent on the market today, enabling businesses to deliver impeccable, always-on customer support across the customer journey, from service, to sales, to ecommerce. Powered by our own AI models, Fin resolves complex customer issues end-to-end across every channel, with minimal set-up and integration. Fin can also be combined with our natively integrated Intercom help desk, giving modern support teams one single system. Together with Salesforce, the #1 AI CRM, where humans with agents drive customer success, we're building the future of customer experience. Here, ambition meets action. Tech meets trust. And innovation isn't a buzzword, it's a way of life. The world of work as we know it is changing, and we're looking for Trailblazers who are passionate about bettering business and the world through AI. Ready to level up your career at the company leading workforce transformation in the agentic era? You're in the right place. Agentforce is the future of AI, and you are the future of Salesforce. What's the opportunity? Implementation is an activity every Fin customer experiences, whether purchasing Fin for the first time, expanding Fin use to a new team, or adopting new features! As a Partner Services Manager at Fin, you’ll share ownership of this crucial process alongside our Service Delivery Partners. Your primary responsibility is ensuring customers implement Fin’s suite of AI tools to solve their most complex problems and ultimately drive incredible value for their business. Partner Services Managers have an outsized impact on the company. If you want to help make business personal for our customers and you want to work with an ever growing and changing team, you’re in the right place! What will I be doing? You will act as the Fin owner of partner-delivered services projects and the liaison who ensu

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Box
📍 Chicago• Full-time• From $135K/yr
28 days ago

WHAT IS BOX? Box (NYSE:BOX) is the leader in Intelligent Content Management. Our platform enables organizations to fuel collaboration, manage the entire content lifecycle, secure critical content, and transform business workflows with enterprise AI. We help companies thrive in the new AI-first era of business. Founded in 2005, Box simplifies work for leading global organizations, including JLL, Morgan Stanley, and Nationwide. Box is headquartered in Redwood City, CA, with offices across the United States, Europe, and Asia. By joining Box, you will have the unique opportunity to continue driving our platform forward. Content powers how we work. It’s the billions of files and information flowing across teams, departments, and key business processes every single day: contracts, invoices, employee records, financials, product specs, marketing assets, and more. Our mission is to bring intelligence to the world of content management and empower our customers to completely transform workflows across their organizations. With the combination of AI and enterprise content, the opportunity has never been greater to transform how the world works together and at Box you will be on the front lines of this massive shift. WHY BOX NEEDS YOU As an AI-first company, we are on a mission to reimagine the way work gets done. We are operating in a time of dramatic disruption and change and must anticipate the ways in which organizational structures, teams and individual jobs will need to evolve. Success will ensure our business is set up to thrive and we will be able to attract and retain the very best talent in the market. We're looking for someone who can build the structural backbone — job families, leveling criteria, career frameworks — and also assess what's happening across a large organization's data and formulate a point of view on what to change and improve. This is a consultative architect and builder's role: you'll be designing frameworks and programs that don't exist ye

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project44
📍 Chicago• $130K – $190K/yr
1mo ago

Why project44? At project44, we believe in better. We challenge the status quo because we know a better supply chain isn’t just possible—it’s essential. Better for our customers. Better for their business. Better for the world. With our Decision Intelligence Platform, Movement , we’re redefining how global supply chains operate. By transforming fragmented logistics data into real-time, AI-powered insights, we empower companies to connect instantly, see clearly, act decisively, and automate intelligently. Our Supply Chain AI enhances visibility, drives smarter execution, and unlocks next-gen applications that keep businesses moving forward. Headquartered in Chicago, IL with a 2nd HQ in Bengaluru, India we are powered by a diverse global team that is tackling the toughest logistics challenges with innovation, urgency, and purpose. AI at project44 We expect every project44 team member, regardless of role or function, to actively leverage AI in their day-to-day work. Whether you're building product, serving customers, managing people, or running operations, AI is a tool you're expected to use with intent, curiosity, and judgment. We don't expect everyone to be a data scientist. We do expect everyone to be an intelligent user of AI: able to identify where it adds value, direct it effectively, evaluate outputs critically, and govern it responsibly. We invest in our team's AI fluency because we believe it's a competitive advantage for every person at project44, not just our engineers If you’re driven to solve meaningful problems, leverage AI to scale rapidly, drive impact daily, and be part of a high-performance team – we should talk. The Role project44 is looking for a Senior DevOps/SRE/Platform Engineer to join our Foundations Engineering team. You will work in a fast-paced Agile environment designing, building, and operating the

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Box
📍 Chicago• $85.5K – $107K/yr
1mo ago

WHAT IS BOX? Box (NYSE:BOX) is the leader in Intelligent Content Management. Our platform enables organizations to fuel collaboration, manage the entire content lifecycle, secure critical content, and transform business workflows with enterprise AI. We help companies thrive in the new AI-first era of business. Founded in 2005, Box simplifies work for leading global organizations, including JLL, Morgan Stanley, and Nationwide. Box is headquartered in Redwood City, CA, with offices across the United States, Europe, and Asia. By joining Box, you will have the unique opportunity to continue driving our platform forward. Content powers how we work. It’s the billions of files and information flowing across teams, departments, and key business processes every single day: contracts, invoices, employee records, financials, product specs, marketing assets, and more. Our mission is to bring intelligence to the world of content management and empower our customers to completely transform workflows across their organizations. With the combination of AI and enterprise content, the opportunity has never been greater to transform how the world works together and at Box you will be on the front lines of this massive shift. WHY BOX NEEDS YOU We are seeking a Senior Compensation Analyst to join our People Operations, Intelligence, and Total Rewards (POINTR) team . In this key role reporting to the Global Compensation & People Analytics Director, you will serve as the primary analytical engine for the compensation team while driving core projects across annual compensation cycles and POINTR initiatives. You will lead complex financial modeling, manage program execution, leverage modern AI tools to optimize workflows and deliver data-backed insights to support Box’s continued growth. WHAT YOU'LL DO Conduct annual and ad-hoc market pricing to evaluate and maintain global salary bands, equity ranges, geographic pay differentials, and total cash target compensa

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Fin
📍 Chicago• $208.2K – $248.7K/yr
1mo ago

Fin , now part of Salesforce, is on a mission to help businesses provide perfect customer experiences. Our AI Agent Fin is the highest-performing AI Customer Agent on the market today, enabling businesses to deliver impeccable, always-on customer support across the customer journey, from service, to sales, to ecommerce. Powered by our own AI models, Fin resolves complex customer issues end-to-end across every channel, with minimal set-up and integration. Fin can also be combined with our natively integrated Intercom help desk, giving modern support teams one single system. Together with Salesforce, the #1 AI CRM, where humans with agents drive customer success, we're building the future of customer experience. Here, ambition meets action. Tech meets trust. And innovation isn't a buzzword, it's a way of life. The world of work as we know it is changing, and we're looking for Trailblazers who are passionate about bettering business and the world through AI. Ready to level up your career at the company leading workforce transformation in the agentic era? You're in the right place. Agentforce is the future of AI, and you are the future of Salesforce. What's the opportunity? Fin is looking for an exceptional Senior Solutions Engineer to join our vibrant Customer Solutions Team. In this role, you’ll engage directly with our customers as their trusted advisor, playing a pivotal part in defining and demonstrating value across the entire sales cycle. With a natural curiosity, independent thinking, and strong problem-solving skills, you’ll partner closely with Product, R&D, and Engineering to ensure our customers’ needs and insights are at the core of our AI powered solutions. What will I be doing? Lead technical discovery to identify and address our customers’ needs Deliver an exceptional pre-sales experience by articulating Fin's value and technical expertise Conduct impactful, value-based solution reviews and in-depth technical sessions Design and lead tail

aisalesforceCRM
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Reddit
📍 Chicago• $190.8K – $267.1K/yr
3mo ago

Reddit is a community of communities. It’s built on shared interests, passion, and trust, and is home to the most open and authentic conversations on the internet. Every day, Reddit users submit, vote, and comment on the topics they care most about. With 100,000+ active communities and approximately 130 million daily active unique visitors, Reddit is one of the internet’s largest sources of information. For more information, visit www.redditinc.com . We are looking for a Senior Engineer to deepen our team's knowledge in ingestion, processing, storage, and distribution of media at global scale. You’ll help us build, operate, and scale the media platform that powers Reddit for hundreds of millions of users around the world. As a Senior Engineer on this team, you’ll be a technical coach and mentor. You’ll draw on your technical expertise to build Reddit’s next generation media platform and to ensure all of our systems have high uptime and strong performance while working with your team to build a roadmap to match the needs of an ever growing engineering organization and to fuel the next wave of Reddit’s growth. Additionally, as part of The Core Systems & Libraries team you’ll design, build, and run many critical foundational services, platforms, and libraries (media and non-media) that all engineering teams at Reddit rely on to serve our users and partners. Join us and help build the future of Reddit! You will: Develop and design new and innovative solutions to scaling Reddit Build platform API projects that scale to the rest of the organization Mentor and coach more junior engineers on your direct team to achieve our mission Build, deliver, and operate services that scale to millions of transactions per second at 5+ 9’s of availability Help us to optimize Reddit’s media experience for hundreds of millions of users across the world. You have: Strong software development experience in one or more general purpose programming languages; Python, Go or

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Instawork
📍 Chicago• $160K – $200K/yr
7mo ago

Instawork is on a mission to create meaningful economic opportunities for skilled hourly professionals in communities around the globe. Our AI-powered labor marketplace helps local businesses scale, and enables global technology companies to push the frontiers of robotics and AI. Backed by world-class investors like Benchmark, Spark Capital, Craft Ventures, Greylock, Y Combinator, and others, we’re looking for exceptional talent to reimagine the way the world works. We are seeking a Senior Manager of Product Operations to help us transition from an app-based marketplace to an agent-first world. We believe the future of work isn't about browsing feeds or tapping buttons - it’s about having intelligent agents that work on your behalf. We need a technical operator who can bridge the gap between high-level business goals and this new user interface. You won't just optimize processes; you will prototype the logic, agents, and automation layers that fundamentally change how our Pros and Partners experience the platform. Who You Are: An Architect of the "Agent-First" World: You understand that the next iteration of the internet is not point-and-click, but intent-and-action. You see a future where users interact with our marketplace through conversation and delegation, not just navigation. A UX Builder, Not Just a Process Fixer: You realize that in an AI world, "Operations" is the Product. You are obsessed with reducing user friction, believing that if a human has to manually search or sift through data, the agent has failed. An AI Pragmatist: You know how to deploy the right model for the job. You distinguish between where a reasoning model is needed to handle complex user intent versus where a deterministic script suffices. A "Hands-On" Visionary: You don't just write specs for Engineering; you prototype the solution yourself. You are comfortable building the first version of an agentic workflow to prove it works before we scale it globally. What You’ll Do: Build the Agen

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Instawork
📍 Chicago• From $80K/yr
Just now

Instawork is on a mission to create meaningful economic opportunities for skilled hourly professionals in communities around the globe. Our AI-powered labor marketplace helps local businesses scale, and enables global technology companies to push the frontiers of robotics and AI. Backed by world-class investors like Benchmark, Spark Capital, Craft Ventures, Greylock, Y Combinator, and others, we’re looking for exceptional talent to reimagine the way the world works. The future of hourly work has arrived, and we are looking for a top-performing Senior Account Executive to help lead the charge. Instawork is the #1 marketplace connecting businesses with skilled hourly workers, with 10M+ workers across 40+ markets in North America. Backed by Benchmark, Greylock, and other world-class investors, we are reinventing how businesses hire, and we are just getting started. This is your chance to sell a product that genuinely changes lives. Our AI-powered platform creates real economic opportunity for workers while solving one of the most pressing challenges businesses face: reliable, on-demand staffing. You will be selling into an expansive and exciting total addressable market, including Major Sports Stadiums, E-commerce brands, major universities, AI companies, and beyond. This is a high-impact role for a hunter who thrives on competition, loves to win, and wants to be part of something that matters. You will report to a Sales Manager and play a critical role in driving Instawork’s next phase of growth, on-site 5 days per week in our downtown Chicago office. Who You Are 3+ years of B2B sales experience with a proven, consistent track record of exceeding quota A relentless competitor who lives at the top of the leaderboard and will not settle for anything less Energized by coaching and obsessed with leveling up your craft A true hunter who thrives in fast-paced environments and knows how to build pipeline from scratch through outbound prospecting Fluent in a robust sales stac

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Fin
📍 Chicago• $208K – $248.7K/yr
Just now

Fin , now part of Salesforce, is on a mission to help businesses provide perfect customer experiences. Our AI Agent Fin is the highest-performing AI Customer Agent on the market today, enabling businesses to deliver impeccable, always-on customer support across the customer journey, from service, to sales, to ecommerce. Powered by our own AI models, Fin resolves complex customer issues end-to-end across every channel, with minimal set-up and integration. Fin can also be combined with our natively integrated Intercom help desk, giving modern support teams one single system. Together with Salesforce, the #1 AI CRM, where humans with agents drive customer success, we're building the future of customer experience. Here, ambition meets action. Tech meets trust. And innovation isn't a buzzword, it's a way of life. The world of work as we know it is changing, and we're looking for Trailblazers who are passionate about bettering business and the world through AI. Ready to level up your career at the company leading workforce transformation in the agentic era? You're in the right place. Agentforce is the future of AI, and you are the future of Salesforce. What's the opportunity? Fin is looking for an exceptional Portuguese and Spanish Speaking Senior Solutions Engineer to join our vibrant Customer Solutions Team. In this role, you’ll engage directly with our customers as their trusted advisor, playing a pivotal part in defining and demonstrating value across the entire sales cycle. With a natural curiosity, independent thinking, and strong problem-solving skills, you’ll partner closely with Product, R&D, and Engineering to ensure our customers’ needs and insights are at the core of our AI powered solutions. What will I be doing? Lead technical discovery to identify and address our customers’ needs Deliver an exceptional pre-sales experience by articulating Fin's value and technical expertise Conduct impactful, value-based solution reviews and in-depth technic

aisalesforceCRM
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Why p44LSP.ai? At project44, we believe in better — and p44LSP.ai is what better looks like for the logistics service provider market. For years, project44 focused on global shippers as our core customer. That focus worked. Our Shipper business is a category leader growing 20% year-over-year. That strength is what makes the next chapter possible. Shippers and LSPs are fundamentally different businesses. Shippers buy logistics software to support their core operations. Logistics Service Providers — freight forwarders, brokers, and 3PLs — sell logistics as their product. Their software is their competitive edge. They buy fast, build on APIs and agents, and reward teams that ship in weeks, not quarters. This is why we created p44LSP.ai: a dedicated, AI-native division built to serve the LSP market with the focus, speed, and resources it deserves. It's the scope and ownership of an AI startup, backed by the infrastructure of a $124M business — 259K carriers, billions of shipment outcomes, agents in production, and direct access to project44's data graph, carrier network, and enterprise relationships. This is a small, hand-picked team operating across Chicago, San Francisco, Bangalore, and the EU. Flat org. Forward-deployed engineering. AI coding tools across the workflow. Agents as the product surface. Customers who pilot in weeks and tell you what they think directly. The LSP market is moving fast. AI agent startups are growing 300%+ year-over-year, and seven of eight sell to LSPs. We have the data position, the platform, the customers, and now the team. We're hiring the engineers who will build it with us. AI at LSP44 Every LSP44 team member is expected to be an intelligent, hands-on user of AI - and for Product, that bar is even higher: the products you’re defining are AI agents. We don’t expect

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SALT XC
📍 Chicago• Full-time• $57K – $65K/yr
Just now

Designer, Portfolio At Kraft Heinz Design, we believe creativity has the power to make ideas unforgettable. We're looking for a Senior Designer to join our Portfolio Team and help shape the visual expression of seasonal campaigns across some of the world's most iconic brands. Working alongside the Kitchen, Creative Directors, Senior Designers, Art Directors, Copywriters, and Strategists, you'll help create compelling retail experiences and campaign assets that connect with consumers at the point of purchase. This is an opportunity to grow your craft while contributing to integrated campaigns that span retail, shopper marketing, and beyond. This role reports directly to the Head of Design at Kraft Heinz. If you're passionate about branding, retail Design, and creating beautifully crafted work, we'd love to meet you. What You'll Do Support the development of seasonal campaigns across a portfolio of Kraft Heinz brands. Design retail and shopper marketing assets, including point-of-sale materials, displays, merchandising, signage, promotional materials, and campaign collateral. Assist in developing campaign visual identities, design systems, and brand guidelines under the direction of Senior Designers and Creative Directors. Apply existing brand standards consistently across a wide variety of retail and marketing touchpoints. Collaborate with cross-functional teams to ensure designs are strategically aligned, on brand, and production-ready. Contribute ideas during creative development and help evolve concepts through design exploration. Prepare artwork and files for production while maintaining a high level of accuracy and attention to detail. Stay curious about design trends, retail innovation, and emerging creative tools to continuously develop your craft. What You'll Bring Experience in graphic design, branding, retail design, shopper marketing, or integrated marketing through an agency, in-house team, or equivalent experience. A portfolio demonstrating strong design

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6mo ago

Envoy Global is a proven innovator in the global immigration space. Our mission combines our industry-leading tech platform with holistic service to streamline, simplify and expedite the immigration process for employers and individuals. Immigration Operations Specialist (IOS) Onsite | Full‑Time | Chicago, IL Build a Career in Immigration Operations The Immigration Operations Specialist (IOS) plays a vital role in supporting employment‑based immigration cases by providing hands‑on administrative and case support to Envoy Global’s affiliate law firm. This is a great opportunity to build foundational skills, work with cutting‑edge legal technology, and grow within a collaborative operations team. Are you detail‑oriented, organized, and interested in immigration or global mobility? What You’ll Do Prepare correspondence, filings, and mailings for immigration petitions Scan, upload, and manage sensitive case documents with accuracy and care Support standard immigration case types under the guidance of senior specialists Maintain accurate case updates and notices in Envoy’s platform Perform quality checks to ensure work meets accuracy and compliance standards Assist with online applications and client document intake Use AI and automation tools to improve efficiency Support high‑volume projects such as H‑1B cap season and other peak periods What You Bring High School Diploma required 2+ years of administrative or clerical experience in a corporate environment Comfort handling confidential, time‑sensitive information Basic proficiency in MS Word, Excel, and Outlook Strong attention to detail and excellent organizational skills Clear written and verbal communication skills Genuine interest in immigration, global mobility, or legal operations Additional Details Must work onsite In Chicago, IL five (5) days per week Flexibility to work overtime during high‑volume periods Ability to lift up to 25 lbs and work at a computer for extended periods Why Envoy Global You’

Who we are About Stripe Stripe, LLC. is a financial infrastructure platform for businesses. Millions of companies - from the world’s largest enterprises to the most ambitious startups - use Stripe to accept payments, grow their revenue, and accelerate new business opportunities. Our mission is to increase the GDP of the internet, and we have a staggering amount of work ahead. That means you have an unprecedented opportunity to put the global economy within everyone's reach while doing the most important work of your career. What you’ll do Responsibilities Leading post-sale engagement, retention, and growth of customers in close collaboration with the Account Executive; Supporting account expansion by identifying opportunities, driving business outcomes, and ensuring customers achieve success, working closely with the account team; Cultivating relationships with senior executives in various departments, such as business, product, engineering, finance, and IT, in partnership with the Account Executive and team; Evangelizing Stripe's customer success stories, as well as its systems and processes; Articulating and driving customer use cases, value, and expansion while maintaining a trusted advisor status; Serving as a knowledgeable payments and commerce advisor, educating customers on the benefits of our products and industry. Who you are Minimum requirements Requires 8 years of experience in a client-facing role, managing relationships with large, global organizations. Position also requires the following: 8 years of experience executing customer facing activities to drive value and ROI from Billing and payments technical products; 8 years of experience collaborating with internal teams to create optimization plans that align with ROI opportunities, providing in depth analysis and suggestions for the user; 8 years of experience monitoring and managing client’s technical experience and engagement experience, proactively monitoring performance metrics a

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FourKites
📍 Chicago• Remote• $90K – $120K/yr
2mo ago

At FourKites we have the opportunity to tackle complex challenges with real-world impacts. Whether it’s medical supplies from Cardinal Health or groceries for Walmart, the FourKites platform helps customers operate global supply chains that are efficient, agile and sustainable. Industry Context: AI-driven supply chain innovations reduce logistics costs by 15%+, inventory by 35%+, and improve service efficiency by 65%+. Companies prioritize AI-enabled automation as the key enabler for customer experience, sustainability, and resilience. Join a team of curious problem solvers that celebrates differences, leads with empathy and values inclusivity . We're looking for a sharp, curious, and execution-oriented Associate Product Manager to join the OTR & Core Visibility team — the flagship product line at FourKites, used by some of the world's largest shippers to track billions of dollars of freight every day. This is not a traditional PM support role. You will own meaningful product outcomes from day one — working hands-on with data, engaging directly with enterprise customers, and partnering with engineering and design to ship features that move the needle on adoption, retention, and customer experience. You'll sit at the intersection of supply chain operations and modern software product development, and you'll need both: deep empathy for how freight actually moves, and the analytical rigor to translate that into product bets worth making. What you'll be doing Product Ownership & Adoption (40%) Track and analyze feature adoption, engagement, and retention KPIs for OTR and core visibility products Identify friction points and adoption gaps through usage data, customer interviews, and feedback loops with Customer Success and Sales Build and prioritize a backlog of targeted product enhancements that drive measurable improvement in customer stickiness Support roadmap planning alongside senior PMs, contributing well-reasoned prioritization recommendations Data &

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