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Mid Market Retail Solutions Engineer in Chicago

27 active opportunities · Updated for October 2026

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Explore current mid market retail solutions engineer jobs in Chicago. Use filters to narrow by work mode, employment type, experience and date posted.

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Pinterest
📍 Chicago• Full-time• From $62.1K/yr
5mo ago

About Pinterest: Millions of people around the world come to our platform to find creative ideas, dream about new possibilities and plan for memories that will last a lifetime. At Pinterest, we’re on a mission to bring everyone the inspiration to create a life they love, and that starts with the people behind the product. Discover a career where you ignite innovation for millions, transform passion into growth opportunities, celebrate each other’s unique experiences and embrace the flexibility to do your best work. Creating a career you love? It’s Possible. At Pinterest, AI isn't just a feature, it's a powerful partner that augments our creativity and amplifies our impact, and we’re looking for candidates who are excited to be a part of that. To get a complete picture of your experience and abilities, we’ll explore your foundational skills and how you collaborate with AI. Through our interview process, what matters most is that you can always explain your approach, showing us not just what you know, but how you think. You can read more about our AI interview philosophy and how we use AI in our recruiting process here . As a Client Partner at Pinterest, you will manage and grow relationships with Mid-Market advertisers, helping them achieve business results through Pinterest’s advertising solutions. You will be responsible for driving revenue, identifying account growth opportunities, and delivering thoughtful, performance-focused recommendations across a velocity-based book of business. Success in this role requires strong sales execution, relationship management, and analytical problem-solving. You should be comfortable working in a fast-paced environment, using data to guide recommendations, and partnering with clients and internal stakeholders to improve outcomes. What you’ll do: Manage, retain, and grow a book of Mid-Market advertiser relationships to drive Pinterest revenue. Build strong relationships with clients, agencies, and internal partners. Underst

awsgitrest
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2mo ago

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 The Commercial Sales team is responsible for the acquisition, growth, retention, and expansion of mid-market customers. As a Grower Account Executive, you’ll set strategy for your territory, identify opportunities for existing customers to get the most out of Stripe, execute scaled sales strategies to grow revenue and drive end-to-end campaigns to nurture relationships and increase adoption of Stripe products. What you’ll do As an Account Executive, Commercial Grower you will play an instrumental role in fueling Stripe’s growth and expanding revenue from Stripe’s existing mid-market customers. In this role, you will also help build out a new team touching more of our install base and GTM motion at Stripe. Responsibilities Generate upsell opportunities to drive revenue growth in your territory Develop and implement sales strategies to grow revenue per user, adopt new products and ensure retention Identify and understand users’ pain points to propose Stripe solutions and own the full sales cycle, from business case development to close Own contract renewals and lead commercial negotiations to increase and retain existing customer revenue and increase Stripe share of wallet Work cross-functionally to solve user pain points and improve Stripe’s product You will be required to work from the Chicago office three (3) days per week Who you are We’re looking for someone who meets the minimum requirements to be considered for the role. If you me

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Pinterest
📍 Chicago• Full-time• From $79.2K/yr
5mo ago

About Pinterest: Millions of people around the world come to our platform to find creative ideas, dream about new possibilities and plan for memories that will last a lifetime. At Pinterest, we’re on a mission to bring everyone the inspiration to create a life they love, and that starts with the people behind the product. Discover a career where you ignite innovation for millions, transform passion into growth opportunities, celebrate each other’s unique experiences and embrace the flexibility to do your best work. Creating a career you love? It’s Possible. At Pinterest, AI isn't just a feature, it's a powerful partner that augments our creativity and amplifies our impact, and we’re looking for candidates who are excited to be a part of that. To get a complete picture of your experience and abilities, we’ll explore your foundational skills and how you collaborate with AI. Through our interview process, what matters most is that you can always explain your approach, showing us not just what you know, but how you think. You can read more about our AI interview philosophy and how we use AI in our recruiting process here . As a Sr. Client Partner at Pinterest, you will develop and grow relationships with some of our most strategic and performance based advertisers in the Mid Market channel. Your primary responsibilities include meeting performance targets, developing new business, maintaining and expanding customer relationships, and resolving specific customer issues. By guiding clients’ efforts, you'll drive value for millions of Pinners seeking inspiration and action, forming strategic alliances both internally and externally. Success in this role depends on your ability to drive substantial revenue growth and spearhead a vision for long-term client success. The Mid Market team is velocity based sales. What you'll do: Retain and grow partner relationships, ultimately driving Pinterest revenue. Build strong relationships with clients, agencies, C-suite, and key

awsgitrest
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Flexport
📍 Chicago• $110K – $137K/yr
1mo ago

About Flexport: At Flexport, we believe global trade can move the human race forward. That’s why it’s our mission to make global commerce so easy there will be more of it. We’re shaping the future of a $10T industry with solutions powered by innovative technology and exceptional people. Today, companies of all sizes—from emerging brands to Fortune 500s—use Flexport technology to move more than $19B of merchandise across 112 countries a year. The recent global supply chain crisis has put Flexport center stage as we continue to play a pivotal role in how goods move around the world. We are proud to have the support of the best investors in the game who believe in our mission, solutions and people. Ready to tackle global challenges that impact business, society, and the environment? Come join us. The opportunity: We’re looking for a pragmatic, growth-minded Sales Leader with a proven history of driving success to guide our Mid-Market Sales Team in Chicago, IL . In this role, you’ll coach and develop Account Executive, building high-performing, inclusive teams to achieve company goals for volume growth and net revenue. You’ll play a critical part in developing talent for progression and promotion within our fast-growing organization. Reporting directly to our General Manager, you’ll collaborate closely with the Mid-Market Leadership Team to deliver key outcomes. This role features a 50/50 compensation model (Base + Uncapped bonus), designed for strong leaders to effectively maximize their earnings through a heavily incentivized sales program. You will: Build, inspire, and lead strong sales teams that consistently meet and exceed targets. Provide inclusive leadership and clear direction to a high-performance team, including hiring, training, and development. Establish and drive specific, targeted goals and quotas to expand and accelerate revenue opportunities. Create, monitor, and manage key performance metrics to drive performance and results. Identify

supply chain
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Gong harnesses the power of AI to transform how revenue teams win. The Gong Revenue AI Operating System unifies data, insights, and workflows into a single, trusted system that observes, guides, and acts alongside the world’s most successful revenue teams. Powered by the Gong Revenue Graph, AI-powered intelligence, specialized agents, and trusted applications, Gong helps more than 5,000 companies around the world deeply understand their teams and customers, automate critical sales workflows, and close more deals with less effort. For more information, visit www.gong.io. At Gong, you will join a company built on innovative products, ambitious goals, and passionate people. We are shaping the future of revenue intelligence and we want people who are excited to build what comes next. You will work with a team that dreams big, moves fast, and cares deeply about the craft and about each other. Here, transparency and trust are core to how we operate, and every person has the opportunity to make a visible impact. If you want to grow, stretch, and do work that truly matters, Gong is the place to do the best work of your career. As a Mid-Market Account Executive specific for the Emerging Markets vertical , you’ll play a key role in expanding our business accounts and acquiring new customers within the financial services, healthcare, consulting, manufacturing, and energy industries. Being a champion of the entire sales process from start to finish, you will use your creative prospecting skills to strategically pursue net new business. Working through complex deals, your insatiable curiosity makes you a thought leader, and your drive to succeed keeps you at the top of the leaderboard. Those who challenge conventional wisdom & never settle for the status quo are strongly encouraged to apply! As a part of Gong's sales team, you will become a master of discovery & a strategic business partner for prospective customers. You will play a huge role in our company growth journe

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Harvey
📍 Chicago• Full-time• Remote• $125K – $145K/yr
4mo ago

Why Harvey At Harvey, we’re transforming how legal and professional services operate. By combining frontier agentic AI, an enterprise-grade platform, and deep domain expertise, we’re reshaping how critical knowledge work gets done for decades to come. This is a rare chance to help build a generational company at a true inflection point. We have strong product-market fit and world-class investor support. We’re scaling fast and defining a new category in real time. The work is ambitious, the bar is high, and the opportunity for growth — personal, professional, and financial — is unmatched. Our team moves fast, takes ownership, and is deeply committed to the mission — operating with intensity, staying close to our customers, and pushing each other for excellence. We live by three values: Decisiveness, Simplicity, and Job's Not Finished. We act quickly on clear judgment over perfect information, we believe simplicity is what scales, and we're never satisfied with where we are. If you want to do the best work of your career alongside people who share that drive, we'd love to build with you. At Harvey, the future of professional services is being written today — and we’re just getting started. Role Overview As a Customer Success Manager you’ll play a critical role in guiding our clients through their journey with Harvey, and help define the future of work at both law firms and in-house teams. This position is pivotal in ensuring our clients not only adopt but also derive maximum value from our technology. You'll act as a trusted advisor, deeply integrating Harvey into their business processes and workflows. This individual will also have a chance to design and deploy scalable 1:many solutions that will impact how we serve our broad mid-market customer base in a highly efficient manner at scale. What You'll Do Strategic Implementation: Lead the integration of Harvey into client workflows, ensuring seamless adoption and optimal use of our AI solutions. Training & Enable

REMOTEaisalesforce
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Gong harnesses the power of AI to transform how revenue teams win. The Gong Revenue AI Operating System unifies data, insights, and workflows into a single, trusted system that observes, guides, and acts alongside the world’s most successful revenue teams. Powered by the Gong Revenue Graph, AI-powered intelligence, specialized agents, and trusted applications, Gong helps more than 5,000 companies around the world deeply understand their teams and customers, automate critical sales workflows, and close more deals with less effort. For more information, visit www.gong.io. At Gong, you will join a company built on innovative products, ambitious goals, and passionate people. We are shaping the future of revenue intelligence and we want people who are excited to build what comes next. You will work with a team that dreams big, moves fast, and cares deeply about the craft and about each other. Here, transparency and trust are core to how we operate, and every person has the opportunity to make a visible impact. If you want to grow, stretch, and do work that truly matters, Gong is the place to do the best work of your career. As a Mid-Market Account Executive , you’ll fill a key role in acquiring new customers and creating raving fans. Being a champion of the entire sales process from start to finish, you will use your creative prospecting skills to strategically pursue net new business. Working through complex deals, your insatiable curiosity makes you a thought leader, and your drive to succeed keeps you at the top of the leaderboard. Those who challenge conventional wisdom & never settle for the status quo are strongly encouraged to apply! As a part of Gong's sales team, you will become a master of discovery & a strategic business partner for prospective customers. You will play a huge role in our company growth journey, while navigating your own individual growth journey as well. Are you looking for the opportunity to make big waves & to perfec

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Harvey
📍 Chicago• Full-time• Remote• $425K – $425K/yr
3 days ago

Why Harvey At Harvey, we’re transforming how legal and professional services operate. By combining frontier agentic AI, an enterprise-grade platform, and deep domain expertise, we’re reshaping how critical knowledge work gets done for decades to come. This is a rare chance to help build a generational company at a true inflection point. We have strong product-market fit and world-class investor support. We’re scaling fast and defining a new category in real time. The work is ambitious, the bar is high, and the opportunity for growth — personal, professional, and financial — is unmatched. Our team moves fast, takes ownership, and is deeply committed to the mission — operating with intensity, staying close to our customers, and pushing each other for excellence. We live by three values: Decisiveness, Simplicity, and Job's Not Finished. We act quickly on clear judgment over perfect information, we believe simplicity is what scales, and we're never satisfied with where we are. If you want to do the best work of your career alongside people who share that drive, we'd love to build with you. At Harvey, the future of professional services is being written today — and we’re just getting started. Role Overview This is a second line leadership role where you will lead frontline managers, build a world class team, and own the regional Mid Market number for North America. You will be responsible for turning strong early traction into a repeatable, high performing got to market engine across legal and professional services. We are still early. That means you will operate across altitudes, setting strategy, building structure, and staying close to the field on critical deals. You will help define how Harvey shows up in the North American market, shape our sales motion, and ensure we are delivering real value to customers adopting AI in high stakes competitive environments. We are looking for someone who has led multi team segments, hired and developed high potential sales manager

REMOTEai
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Pinterest
📍 Chicago• Full-time• From $101.7K/yr
2mo ago

About Pinterest: Millions of people around the world come to our platform to find creative ideas, dream about new possibilities and plan for memories that will last a lifetime. At Pinterest, we’re on a mission to bring everyone the inspiration to create a life they love, and that starts with the people behind the product. Discover a career where you ignite innovation for millions, transform passion into growth opportunities, celebrate each other’s unique experiences and embrace the flexibility to do your best work. Creating a career you love? It’s Possible. At Pinterest, AI isn't just a feature, it's a powerful partner that augments our creativity and amplifies our impact, and we’re looking for candidates who are excited to be a part of that. To get a complete picture of your experience and abilities, we’ll explore your foundational skills and how you collaborate with AI. Through our interview process, what matters most is that you can always explain your approach, showing us not just what you know, but how you think. You can read more about our AI interview philosophy and how we use AI in our recruiting process here . Pinterest is where inspiration leads to action. As an Industry Manager II, you will lead a team of sellers responsible for helping advertisers grow through Pinterest’s advertising solutions. This role is focused on strong frontline leadership: coaching sellers, driving day-to-day execution, and helping the team deliver against established revenue goals. This role is well suited for a newer people leader or a high-performing seller with leadership potential who is ready to step into people management. The ideal candidate brings strong sales fundamentals, credibility with clients, and the ability to coach others on core sales skills. They may be early in their people-management journey, but they are excited to develop talent, build team culture, and lead from the front. What you’ll do: Lead and support a team of Mid-Market sellers focused on achie

awsgitrest
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3mo ago

For over 20 years, Smartsheet has empowered teams to manage work seamlessly and scale solutions smarter. Now, in our most ambitious chapter yet, we are uniting human teams with AI agents. By orchestrating the work agents do best, automating manual tasks and uncovering insights at scale, we create the space for people to focus on what truly matters: judgment, creativity, and big thinking. That is magic at work, and it’s what we show up for every day. Smartsheet is seeking change agents to join our Central/East Commercial Sales Team as an Account Executive . You will be responsible for increasing software sales and driving expansion across a territory of accounts. You will be motivated, passionate, and opportunistic. You will be a proactive and curious member of the commercial sales team, identifying growth opportunities for clients before they identify a need or gap for themselves. This remote role is part of the Commercial Sales team based in the US and reports a Manager, Commercial Sales. You Will: Build and manage a sales pipeline to meet or exceed software and services sales quotas within your book of business Execute a solution-based sales process encompassing multiple groups within our commercial mature accounts equivalent to (500-4,999 employee size) Develop new business opportunities within existing customers by analyzing and proactively targeting high-value needs across multiple departments and lines of business Leverage existing relationships to expand Smartsheet's footprint and drive revenue or growth during renewals Expand Smartsheet brand awareness at the c-suite, operational and team level Facilitate and manage partnerships with Sales Engineers, Solutions Consultants and Customer Success teams to support full sales cycle and close business Create and maintain Joint Engagement Plans for strategic solution deals Maintain accurate and up-to-date records in Salesforce leveraging MEDDICC qualification guidelines to accurately forecast Utilize existing

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DoorDash USA
📍 Chicago• $81.6K – $120K/yr
10 days ago

About the Team The DoorDash Mid-Market Grocery team manages the strategic vision, acquisition, and growth of the largest regional grocery partnerships across North America. About the Role The Grocery Partnerships Associate will support DoorDash’s efforts to acquire, grow, and deepen partnerships with grocers and CPG brands across the industry. As digital grocery continues to expand, DoorDash is investing to become a leading partner to the sector. Reporting to a Grocery Partnerships Manager, you will help drive strategic partner initiatives and support the growth of key merchant relationships. This role requires flexibility across remote work, in-office collaboration, and travel to meet with merchant partners. You’re excited about this opportunity because you will… Steer the development, adoption and scaling of new business opportunities Develop long-term business plans alongside our partners for their multi-channel customer strategies Maintain pitch decks and sales content to help create new business opportunities Build product testing and roll-outs on the ground with grocery and cross-functional team members Work with partners across DoorDash to align companywide resources to help build-out our partners' digital businesses We’re excited about you because… You’re Impact Motivated -- You have a natural desire to improve the overall business You’re Curious -- You love digging into low levels of detail to extract insights You’re Strategic -- You love to find the win-win in developing novel agreement structures to grow business with partners You’re Resourceful -- You are happy juggling many priorities concurrently and being creative with solutions to move fast You’re Collaborative - You enjoy working with lots of different people, both external and internal Qualifications: 3-5 years of account management, consulting, banking, or strategic partnerships in technology or high growth / early stage startups 3+ years of cross-functional operational experience Bach

aiExcellogistics
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D
1mo ago

At Dscout, we’re building the most flexible and powerful UX research platform on the market—trusted by the world’s top brands in finance (JP Morgan Chase, Intuit, Charles Schwab, PayPal), healthcare (Aya, Headspace), consumer goods (Keen, Verizon, Target, Northface), and tech (Google, Amazon, Facebook, Meta, Spotify, AirBnB). Our tools help teams deeply understand the humans behind their products, so they can build better ones. We are expanding our smart and driven team and would love for you to join us. Lead Research Advisor, Mid-Market (Austin or Chicago) Job Description We are looking for a Lead Research Advisor to join our growing Customer Success department. You will drive and grow important relationships by helping our customers find new ways to use our platform, ensuring they achieve maximum value from their investment. This role is a critical function that merges research expertise with a customer success motion, focusing on driving platform adoption and mitigating churn risk. You will also collaborate closely with a team of Research Advisors to design, recruit, and field research projects for our customers You will have a chance to make a real difference for Dscout’s customers and build your career at the intersection of customer success and research. You are an incredible communicator and a genuine, creative problem-solver. You are our customer’s dedicated partner in success, helping them learn a new digital tool, execute powerful research, and maximize the return on their Dscout subscription. You collaborate closely with Account Directors to help to identify Dscout methodologies that best meet customer needs, build new use cases, identify growth opportunities, and ensure strong platform adoption across their organization. Internally, you are our customers’ champion, driving larger improvements to the platform and overall user experience. The Lead Research Advisor position is among the most central to Dscout’s operations, so you’ll work with people fr

salesforcefinanceCRM
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Fin
📍 Chicago• $226K – $251K/yr
4 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? As a Mid-Market Relationship Manager, you’ll be at the forefront of growth; turning momentum into mastery. You’ll own a portfolio of fast-growing customers and help them unlock the full power of Fin. We’re building a world-class sales organization; fast, ambitious, and unapologetically driven. At Fin, we do sales differently. We don’t just pitch; we partner. We’re asking our customers to make Fin the heartbeat of their business, and that starts with salespeople who can think bigger, move faster, and win with integrity. We invest deeply in every Relationship Manager’s growth. Development isn’t a slogan here, it’s baked into how we promote, learn, and lead. In a high-velocity environment where ownership, creativity, and ambition are rewarded, you’ll find room to stretch, influence, and make

aisalesforceprocurement
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S
12 days ago

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 SMB Solutions Architecture (SA) team works with technical and business leaders (CTO/ CIO/ CEO/ Founders etc.), payments leaders and product engineering teams in the mid-market segment to evangelize Stripe’s solutions in the market. A solutions architect’s role is to build relationships with decision makers and think strategically about the business needs of Stripe’s customers. Solution Architects identify and propose Stripe solutions to solve complex business challenges and drive growth for our customers. SAs establish and prescribe best practices around a customer’s strategy, provide business and technical thought leadership and are viewed as a trusted advisor. They work on scaling business processes aligned to maximizing account coverage while working closely with customer and partner resources to deliver a solution that can be adopted quickly. What you’ll do As a member of the team, the Solutions Architect will build highly consultative trusted relationships with c-level executives and technical decision makers in the customer’s organization to provide business and technical thought leadership, and become a trusted advisor in solving mission-critical business challenges. She/he will architect business models with them so they can drive new monetization opportunities and growth for both the user and Stripe. Responsibilities Drive thought leadership and build executive relationships with key business and technical stake

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E
27 days ago

Everpure (NYSE: P) has evolved from storage pioneer to data platform, closing fiscal 2026 with $3.7 billion in revenue, its first billion-dollar quarter, and accelerating growth into FY27. Our strategic agenda spans the companies defining the next era of technology - hyperscalers, AI labs, the AI hardware supply chain, data platform providers, and the broader AI ecosystem. This type of work—work that changes the world—is what the tech industry was founded on. So, if you're ready to seize the endless opportunities and leave your mark, come join us. THE ROLE Everpure is looking for a Territory Account Executive. In this role, you will be selling into a territory in Everpure's Central region with a focus on mid-market accounts in Indiana and Kentucky. WHAT YOU'LL DO Directly sell through an inside, direct marketing environment to deliver sales targets and consistently achieve quota Drive account strategies and coordinate team selling efforts with partners to close business on a quarterly and annual basis Develop channel relationships that will bring the sales and technical resources to each opportunity and lead to closed deals Prospect into and penetrate new accounts, reaching decision-makers and closing business Develop and present proposals to prospective customers with information that demonstrates the ability of the Everpure solution to meet customers’ business objectives and justify the sale Manage pipeline with a keen focus on conversion success and delivering an accurate forecast We are primarily an in-office environment and therefore, you will be expected to work from the office in compliance with Everpure’s policies, unless you are on PTO, or work travel, or other approved leave. WHAT YOU BRING Consistent track record of exceeding quota and driving referenceable business in a B2B technology sales environment Experience working in or understanding sales channel selling models A desire to work the bookends of the sale, from prospecting to clos

REMOTEaisupply chain
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