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Gtm Strategy And Operations Director in Chicago

27 active opportunities · Updated for October 2026

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Explore current gtm strategy and operations director jobs in Chicago. Use filters to narrow by work mode, employment type, experience and date posted.

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26 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 The Business Value Consulting and Proposals team supports long-term growth and value creation for Stripe’s largest and most strategic users. We translate Stripe's technical capabilities into measurable business outcomes and create value-led proposals that help secure and expand relationships with leading organizations. What you’ll do As a Proposal Lead, you’ll manage requests for proposals and requests for information (RFPs and RFIs) for Stripe’s largest pursuits. You’ll develop proposal strategy and narratives, coordinate contributors across Stripe, and deliver high-quality submissions that address customer requirements. You’ll also improve the processes, templates, and tools that help Stripe manage proposals consistently and at scale. You’ll bring structure to complex pursuits, build trusted relationships, and communicate clearly with contributors and leaders. This role is a good fit for someone who can balance strategic thinking with detailed execution while managing multiple deadlines and priorities. Responsibilities Lead the end-to-end bid management process, including reviewing bid invitations, supporting bid or no-bid analysis, defining the response strategy, and establishing timelines Translate customers’ business and technical requirements into clear, persuasive proposals that communicate Stripe’s value and competitive advantages Develop proposal content, including executive summaries, value propositions, and recommendations r

project managementPMPprocurement
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R
Reddit
📍 Chicago• $154.7K – $216.6K/yr
1mo 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 . Reddit's growth is driving a rapid expansion of its world-wide team and the need for an experienced Senior Technical Program Manager to support the global sales organization through the next several stages of growth. This role will report into the Go-to-Market Strategy organization, and support our major Go-to-Market Systems initiatives. The Go-to-Market Systems team drives high impact projects that aim to build best-in-class tooling for our global sales organization, and enable seamless advertiser experiences. As a Sr. Product Manager on the Go-to-Market Systems team, your focus will be to build the foundations, tools and workflows that will accelerate the growth and efficiency of our GTM organization. You will own the vision, strategy and roadmap of sales technology projects that will drive organizational transformation for Reddit. You’ll collaborate with other GTM leaders, product leaders, data teams, and engineering to run ambiguous business problems into scalable solutions. Location : Must be based within a commutable distance of one of our hub offices in Los Angeles, San Francisco, Chicago, or New York Key Responsibilities Define and drive the product vision, roadmap and architecture for our sales teams focused on growing our advertiser base. Deeply understand problems faced by sellers and advertisers, and proactively identify opportunities to automate and improve the experience. Build best-in-class tools that improve seller productivity in areas such as account planning, custom

artificial intelligenceaisalesforce
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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 Platform Sales team is a highly consultative, enterprise sales team that is responsible for some of Stripe’s largest and fastest growing partners. Stripe helps software platforms offer more value to their customers by embedding Stripe’s powerful payments technology into their solution. As a Platform Sales Manager, you will play a critical role on our go-to-market leadership bench-- leading a team of AEs to make payments-as-a-service a competitive advantage for high-growth organizations. What you’ll do Drive sales growth through successful leadership, organizational planning, customer service and outstanding execution Oversee the expansion of Stripe’s footprint with global saas platforms Make hiring decisions, honing our ideal candidate profile and onboarding strategy Create structure and focus for GTM ideas and product sales campaigns that the product team is exploring. Drive execution and measurement. Analyze results and make recommendations for action in a timely manner. Define key sales support mechanisms, processes, and programs to meet the rapid growth of the business and achieve revenue attainment and market development objectives Build a world-class organization and write the playbook for the era of monetizing payments on platform Responsibilities Lead a team of sophisticated Existing Business, Platform AEs focused on expanding our global footprint with enterprise SaaS platforms Drive deal strategy and partner across the

customer service
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A
Asana
📍 Chicago• $158K – $180K/yr
5mo ago

The People Team at Asana works to enable all Asanas to achieve our goals as a company in a way that is consistent with our values. We focus on recruiting, developing, and retaining exceptional talent from diverse backgrounds, ensuring that everyone can thrive, grow, and make a meaningful impact. Our work supports Asana’s broader mission: to help humanity thrive by enabling all teams to collaborate seamlessly and effectively. As a People Partner, you will operate as a true business leader, bringing organizational strategy, change leadership, and deep consulting acumen to shape talent transformation agendas at the functional leadership level. In this role you will support AMER Sales team and CMO. This role is based in our Chicago office with an office-centric hybrid schedule. The standard in-office days are Monday, Tuesday, and Thursday. Most Asanas have the option to work from home on Wednesdays. Working from home on Fridays depends on the type of work you do and the teams with which you partner. If you're interviewing for this role, your recruiter will share more about the in-office requirements. What you’ll achieve Drive strategic thought partnership by building and implementing department-level talent strategy initiatives that align directly with business outcomes. Navigate ambiguity to identify root issues in complex situations, presenting findings and socializing change with clarity to senior stakeholders. Lead change management by partnering with senior leaders to develop scalable change strategies, proactively planning for contingencies and championing the vision through effective storytelling. Consult and advise functional leads as a trusted advisor, leading complex people situations and supporting leaders in building their own capability. Leverage data literacy to interpret complex people data to identify trends, translate findings into actionable decisions, and champion a data-driven culture. Influence at scale by actively participating in business headcoun

S
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

I
Instawork
📍 Chicago• Full-time
2mo 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. Role Type: Contract (3–6 months, with potential to extend) Location: San Francisco or Chicago We are looking for a GTM Recruiting Consultant (3- 6 months contract with potential for full time), you are at the absolute center of our growth engine. The Sales and Account Management teams you build are the ones bringing new businesses onto our platform and ensuring their success. By finding and hiring top-tier commercial talent, you directly accelerate our market expansion and fuel our revenue growth. it is a direct lever on Instawork’s top-line business success. Key Responsibilities Full-Cycle Recruiting: Manage the end-to-end recruitment process for a variety of GTM roles (e.g., Account Executives, Enterprise Account Managers, and Business Development Representatives). Strategic Alignment: Partner closely with GTM hiring managers to deeply understand their business objectives, team dynamics, and specific hiring needs. Creative Sourcing: Actively source passive talent (LI recruiter, Juicebox etc.), specialized networks, and creative outbound strategies to build robust, diverse pipelines. Candidate Experience Champion: Deliver a high-touch, transparent, and inclusive candidate experience from initial outreach through to the offer stage. ATS Hygiene: Maintain impeccable data hygiene in our Applicant Tracking System (Greenhouse) to ensure accurate reporting and seamless collaboration. What We’re Looking For Growth mindset with hands on AI powered recruiting expertises. Experience: 5+ years of full-cycle

restaigo
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B
Box
📍 Chicago• Full-time• From $109.5K/yr
2mo 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 part of the broader Go-To-Market (GTM) Enablement team, the Commercial Sales Enablement Manager will drive revenue growth by architecting and delivering strategic enablement programs that equip our Small and Medium Business (SMB) and Mid-Market sales teams with the strategies, skills, content, and modern tools necessary to accelerate productivity and win rates. In this role, you will operate as an autonomous subject matter expert and trusted advisor to Commercial Sales leadership. You will develop comprehensive enablement roadmaps, translate global strategic vision into clear "why" context for the field, advocate for segment priorities, and independently determine the methods and procedures to design, execute, and govern high-impact ena

aigorust
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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 Velocity Grower team covers existing businesses within Stripe’s Americas Sales organization and is responsible for expansion and growth of mid-market (Commercial) 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, Grower Healthcare you will play an instrumental role in fueling Stripe’s growth through defining the vertical sales motion and GTM processes needed to grow and expand Stripe product adoption with existing customers. The book will be majority Healthcare but also include other top accounts. In this role, you will build the foundation and define the Healthcare growth motion. You will hire and lead a team of high-performing Account Executives, help 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 with tech sales experience calling on Healthcare companies, 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, working with Healthcare businesses and regulatory requirements and possess first-class analytical, communication and relationship-building skills. Responsibilities Recruit, develop and l

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 - Grower you will play an instrumental role in fueling Stripe’s growth through defining the sales motion and GTM processes needed to grow and expand Stripe product adoption with existing mid market customers. In this role, you will build the foundation and define the GTM motion for a new team. 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 Be accountable for driving product attach, increase share of wallet to deliver revenue at high rates of growth Work wi

S
1mo ago

At Snowflake, we are powering the era of the agentic enterprise. To usher in this new era, we seek AI-native thinkers across every function who are energized by the opportunity to reinvent how they work. You don’t just use tools; you possess an innate curiosity, treating AI as a high-trust collaborator that is core to how you solve problems and accelerate your impact. We look for low-ego individuals who thrive in dynamic and fast-moving environments and move with an experimental mindset — who rapidly test emerging capabilities to discover simpler, more powerful ways to deliver results. At Snowflake, your role isn't just to execute a function, but to help redefine the future of how work gets done. Our GSI partners play a key role in bringing our customers' data-backed ambitions to life by implementing and harnessing the power of the Snowflake AI Data Cloud for cutting edge workloads and use cases. Through our partnerships, we enable companies to empower their employees with the data they need when and how they need it to better engage their customers, optimize their operations, and transform their products. The Partner Development Manager, Deloitte role involves driving and building relationships with one of our top Global System Integrator (GSI) partners. Your primary objective is to strengthen and expand the collaboration between Snowflake and Deloitte to drive growth. Acting as the single point of accountability for the health and velocity of this leading partnership. The success of our partnership is demonstrated by driving growth with our joint customers, delivering key Go-To-Market (GTM) programs, establishing critical executive relationships, enabling partners to grow their Snowflake competency, and delivering customer success. We are looking for a builder and a finisher—someone who doesn't just draft the plan, but drives it to completion, mobilizes the field, and uses data to "unstick" challenges before they become blockers. KEY RESPONSIBILITIES: Strategic Go

gitrestai
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EC
Energy CX
📍 Chicago• Full-time
1mo ago

About Energy CX: Energy CX is redefining the energy brokerage industry as the fastest-growing player in the US. By bringing cutting-edge technology, advanced analytics, and innovative solutions, we are disrupting a space that has operated in the dark for too long. Why Energy CX? Recession proof industry Entrepreneurial and ambitious culture with a great team oriented environment Fastest growing energy broker in the country One of the fastest growing companies in Chicago Recognized by Fortune and Great Places to work US Named on Inc 5000’s list of America’s fastest growing companies Compensation Year 1 Expected Earnings → $130,000 - $170,000 Title: Revenue Operations Manager About this Job Energy CX is hiring a Revenue Operations Manager to build and own the revenue operating system that powers how the company makes decisions, turning fragmented data into a trusted, self-sustaining system for pipeline, forecasting, and capacity planning. This person will own HubSpot and the broader revenue tech stack, build the metrics and forecasting infrastructure the business runs on, and connect marketing, sales, customer success, and finance around a single source of truth, ensuring the right answers surface before anyone has to ask. Objectives of this Role Own and evolve ECX's revenue operating system, including pipeline intelligence, forecasting, and capacity planning, as the foundation for how the company makes revenue decisions. Own HubSpot and the broader revenue tech stack as the system of record, enforcing data quality standards across the full lead-to-cash lifecycle Diagnose and anticipate structural gaps in data, process, and cross-team handoffs Build a metrics layer that runs on its own: pipeline, forecast, and revenue reporting that requires no manual reconciliation Support GTM enablement infrastructure: comp plans, quota tracking, territory design, and capacity/headcount planning Daily and Monthly Responsibilities Maintain revenue data in

sqlfinanceCRM
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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 net 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 team is a high-velocity sales team focused on acquiring new, under-penetrated mid-market customers. As an Account Executive on the Commercial Hunter sales team, you’ll be responsible for sourcing and closing net new business, executing outbound sales strategies, and running end-to-end sales cycles to bring new customers onto Stripe. You’ll play a critical role in expanding Stripe’s reach by identifying high-potential prospects and converting them into long-term users of our platform. What you’ll do As a Account Executive, Commercial Hunter you will play an instrumental role in fueling Stripe’s growth by acquiring net new mid-market customers. In this role, you will also help build out a new team and go-to-market (GTM) motion at Stripe. Responsibilities Identify high-potential prospective users and use effective prospecting strategies to generate leads that drive net-new revenue growth in your territory Develop and implement scaled sales strategies for acquiring new customers and driving adoption of Stripe’s products across new accounts Identify and understand users’ pain points to propose Stripe solutions and own the full sales cycle, from business case development to close Work cross-functionally to solve user pain points and improve our product to better serve new customer needs Who you are We’re looking for a high performing, well-rounded seller who can manage high velocity deal cycles, enjoys building and has demonstra

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