Outbound Strategist in Chicago

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

CLEAR is building THE secure identity company of the future. Our mission is to make experiences safer and easier—physically and digitally. With more than 43 million Members and a growing network of partners across the world, CLEAR's secure identity platform is transforming the way people live, work, and travel. Whether it’s at the airport, stadium, or throughout your everyday life, CLEAR unlocks the magic of frictionless experiences. The Enterprise Account Executive will drive C1’s growth by identifying, structuring, and closing strategic deals with large enterprise organizations. This role will expand CLEAR’s networked identity platform across industries by building high-impact relationships and delivering scalable, revenue-generating deals. What you'll do: Drive enterprise growth by sourcing, developing, and closing strategic partnerships across key industries Own the full deal lifecycle from prospecting through negotiation, contracting, and launch Build and manage a robust enterprise pipeline, leveraging outbound efforts, industry relationships, and market insights Partner cross-functionally with Product, Legal, Security, and Partner Success to align solutions with partner needs and CLEAR capabilities Represent CLEAR externally through executive meetings, industry events, and thought leadership to strengthen market presence How you'll measure success: Total contract value (TCV), annual contract value (ACV), and revenue generated from enterprise partnerships Pipeline growth, conversion rates, and deal velocity across enterprise opportunities Number of new enterprise logos and expansion within existing partners Successful launch and activation of enterprise partnerships What you're great at: 8+ years of experience in enterprise business development, partnerships, or B2B sales within SaaS, identity, fintech, or enterprise technology Proven track record of sourcing, negotiating, and closing complex, high-value enterprise deals Strong executive presence

At ClickUp, we're building the future of work: the first truly converged AI workspace unifying tasks, docs, chat, calendar, and enterprise search, all supercharged by context-driven AI. We are an AI-native company. Every team member is expected to leverage AI daily, and we evaluate AI fluency as part of our hiring process. Join us and help redefine what's possible. 🚀 We’re looking for an ambitious, high-energy Enterprise Account Executive based in Chicago who’s passionate about helping organizations transform the way they work. In this role, you’ll be at the forefront of driving growth by connecting with leading enterprises, understanding their unique challenges, and delivering tailored solutions that empower teams to do their best work. If you thrive in a fast-paced, collaborative environment and are excited to champion a platform that’s redefining productivity, we’d love to meet you. The Role: Drive net new business by proactively identifying, engaging, and converting high-value Enterprise and Strategic prospects into customers. Develop and execute strategies to penetrate new accounts, build strong relationships with key decision makers, and create tailored solutions that address complex business needs. Consistently exceed pipeline and sales targets by generating new opportunities through outbound prospecting, networking, and leveraging marketing-qualified leads. Lead expansion efforts within existing Enterprise accounts by uncovering additional use cases, identifying upsell and cross-sell opportunities, and driving adoption across multiple business units. Deliver compelling presentations and product demonstrations to both new prospects and current customers, effectively communicating value and ROI. Collaborate closely with Growth, Marketing, and Customer Success teams to optimize lead generation, accelerate sales cycles, and maximize expansion revenue. Analyze customer segments and market trends to identify new business opportunities and continuously improve the