Renewals Specialist in Chicago

About OfficeSpace: OfficeSpace Software provides the leading AI operating system for the built world, that helps teams plan, connect, and perform in the workplace. As a performance-based, PE-backed company, we hire based on merit and a willingness to do what it takes to succeed long-term. You’re a great fit for the role if you’re entrepreneurial, passionate, motivated by building at light speed, and an Agentic AI early adopter. Our world-class teams operate in the US, Canada, and Costa Rica in a culture of trust, respect, growth, and impact. Role Summary: You own growth at the highest level. As a Client Executive – Enterprise, you build, expand, and protect strategic relationships across complex organizations with our highest value clients. You operate as a value architect, and executive partner to drive strategic and transformational client value - using data, AI, and sharp commercial discipline to grow enterprise accounts. What You Will Do Own and grow a portfolio of high-value strategic accounts by developing and executing multi-year expansion strategies aligned to each client’s business priorities. Develop and execute strategic account plans that translate client priorities into actionable expansion plays with clear value hypotheses, timelines, and deal strategies. Create and close pipeline proactively - not tied to renewal cycles - by identifying whitespace, shaping opportunities, and aligning to executive-level priorities within your accounts. Lead complex, multi-threaded sales motions by engaging economic buyers and key stakeholders across business, finance, and operations to build consensus and urgency. Sell platform-level solutions, not product features, positioning OfficeSpace as a mission-critical operating system that drives measurable business outcomes. Part

About Chicago Public Media Chicago Public Media is one of the nation’s largest local nonprofit news organizations. Home to WBEZ 91.5FM, the Chicago Sun-Times, and Vocalo. Chicago Public Media reaches more than 3.3 million people weekly across broadcast, print, and digital platforms. As a mission-driven organization, we aspire to be the most trusted news source Chicagoans turn to for understanding the people, events, and ideas shaping our community. Chicago Public Media is a 100% community-funded newsroom powered by nearly 97,000 members whose support makes our journalism possible. This sustained community investment helped drive nationally recognized work in 2025, including 29 awards from esteemed organizations, including the Public Media Journalists Association, the Edward R. Murrow Awards, and the National Association of Black Journalists. We believe independent journalism is essential to a healthy democracy and that access to objective, fact-based news is a right for every citizen. We serve the public interest by creating diverse content that informs and enriches our community, supported by a dedicated staff of approximately 250 professionals. For more information, please see the Chicago Public Media Annual Report . The Opportunity The Director of Lifecycle & Retention leads Chicago Public Media’s enterprise lifecycle strategy across brands, platforms, and audience touchpoints. This role is responsible for designing the systems, frameworks, and strategies that strengthen retention, loyalty, participation, and long-term supporter value following acquisition. The Director establishes the lifecycle architecture, audience segmentation, performance goals, and optimization priorities that guide onboarding, engagement, renewal, sustainer conversion, upgrades, reactivation, advocacy, and long-term relationship development. The role partners closely with Product, Marketing, Insights, Development, Editorial, and the Membership team to translate

Account Manager, Enterprise Location availability: Boston/Chicago: Hybrid working 2 days a week in the office Austin: Twice a month Remote US About the position We are seeking an Account Manager, Enterprise to bring hyper growth to a selected portfolio of our most important and strategic customer accounts. Key aspects of the role include Achieve annual and quarterly revenue targets Identify up-, cross-sell and expansion opportunities Ensure the delivery of a continuous pipeline of qualified opportunities through various prospecting means, including research, networking, cross-selling, cold calling, exhibitions, partnerships etc. Provide timely and accurate pipeline forecasts and reporting Organise meetings with right stakeholders to pitch Sales Enablement and the strength of the Showpad platform Help steer the creation of high quality sales collateral which can be included in customer specific ABM Steer and manage a lead generation plan that can be executed and effectively nurtured by your dedicated BDR Develop an account plan and chessboard for each of your key account Work with clients to promote Showpad’s product capabilities throughout their business, utilising joint events, marketing strategies, community calls etc. Negotiate contracts / SLA’s that achieve company objectives Effectively use the resources of the organisation to support the sales process Indirectly lead an account support team of technical and customer success resources to help achieve your objectives Work with internal teams to ensure complete organisational understanding of client needs Support the establishment of strong, lasting client relationships Identify and report on market trends, competitor activity, customer demand, buying process developments and other relevant market intelligence Key Performance Indicators Revenue forecasted and achieved on a quarterly and annual basis Value and quality of leads and opportunities Client satisfaction – feedback, contract renewal etc. Cont