Top Tech Jobs & Startup Jobs in Chicago, IL

Lead strategy and execution to attract, engage, and retain a global community of Pluralsight authors. Build author communications, engagement programs, communities, recognition, and events. Elevate author visibility (Author Fellows), integrate author expertise across Sales, Marketing, Customer Success, Product, and Learning Experiences, and lead a multidisciplinary team to drive measurable business impact.

Lead global paid media, demand generation, and email lifecycle programs. Own strategy, execution, agency relationships, budget forecasting, and measurement across B2B, B2C, ABM, and brand. Build and coach a high-performing team, establish operational and financial rigor, and drive measurable pipeline, revenue, retention, and customer expansion through integrated digital campaigns and lifecycle marketing.

Lead design, launch, and lifecycle management of Pluralsight solutions (AI, Cloud, Security). Define expert POV, build curricula, labs, assessments, and blended learning programs. Own roadmap, metrics, GTM partnership with Sales and Marketing, and continuous iteration using data and SME collaboration to drive enterprise customer outcomes.

Own and evolve Pluralsight's Cloud and Security learning solutions by defining strategy, roadmaps, curricula, and KPIs. Partner cross-functionally to design blended programs (courses, labs, assessments, instructor-led training), support sales, monitor market trends, and iterate product offerings using data and customer feedback to drive adoption, pipeline, and measurable business outcomes.

Drive net-new logo acquisition and revenue expansion by owning the full sales cycle, building and managing a robust pipeline, engaging C-level decision-makers, executing territory plans, using solution-oriented sales methodologies, collaborating with internal teams, maintaining forecast accuracy, and consistently meeting or exceeding revenue targets.

Drive new business and expand existing enterprise accounts by managing full sales cycles, developing territory and account plans, researching customer priorities, applying Pluralsight's sales framework, partnering cross-functionally, and closing complex, multi-stakeholder SaaS deals. Travel to customer sites as needed to advance partnerships and revenue.

Lead analytics engineering for Revenue, Marketing, and Finance by building scalable data solutions, data models, and dashboards; provide training and consultation, support ad hoc data needs, and translate technical findings into executive-level insights to improve operational performance.

Lead a North American midmarket Commercial Account Executive team to define and execute sales strategy, hit bookings, coach using MEDDPICC, manage forecasts and funnel metrics, support senior stakeholders, cultivate key accounts, and represent the company at events. Role requires operational rigor and occasional travel (~30%).

The Machine Learning Engineer develops production ML algorithms and recommendation systems, collaborates with teams, and optimizes user experiences.

Own revenue expansion for assigned State, Local, and Education (SLED) accounts. Manage full sales cycle from lead to close, build executive relationships, develop account strategies, drive adoption of Pluralsight, coordinate extended account team, manage pipeline and forecasting, and meet quota while supporting customer success.