Top Remote Sales Jobs in Chicago, IL

Originate and close corporate travel management opportunities for middle-market and large corporate clients. Lead complex sales cycles, develop executive relationships, build pipeline, negotiate solutions, and coordinate implementation handoffs. Partner with banking, product, operations, and servicing teams to deliver integrated solutions and strong client outcomes. Manage forecasting, analyze market trends, represent the business at industry events, and identify growth opportunities.

Own technical sales cycles for strategic enterprise accounts, including discovery, solution design, demonstrations, proofs of value, architecture reviews, and technical close. Help customers deploy and observe AI agents across platforms such as Databricks and Snowflake. Build technical champions, navigate procurement and infosec reviews, and partner with Account Executives to drive revenue growth and expansion.

Manage and develop an outbound SMB sales team selling SaaS-based HR solutions. Responsibilities include recruiting, coaching, prospecting, pipeline and forecast management in Salesforce, quota attainment, full-cycle sales execution, customer relationship management, and collaboration with internal teams. The role also engages HR technology prospects, builds industry partnerships, and provides market and competitive insights to support growth.

Lead and grow an inside sales team promoting a SaaS financial reporting platform. Responsibilities include recruiting and coaching representatives, developing sales and pipeline strategies, driving new business and account expansion, forecasting performance, supporting complex customer conversations, and presenting market insights to leadership. The role requires strong B2B enterprise software sales experience, sales methodology expertise, analytical forecasting skills, and the ability to build scalable revenue processes.

Lead and scale Strategic and Enterprise sales for large accounts: own GTM, pipeline, bookings, and deal execution; coach and recruit AEs/managers; enforce MEDDPICC and Mutual Action Plan rigor; partner with RevOps, CS, Marketing, and Product; represent segment to CRO and execs.

Owns net-new revenue as a quota-carrying individual contributor. The Sales Director develops pipeline through prospecting, referrals, partnerships, events, and inbound leads; leads consultative sales cycles; manages complex proposals, RFPs, negotiations, and contracts; builds senior buyer relationships; sells integrated data, research, media, technology, and measurement solutions; maintains CRM forecasts; and coordinates internal teams through successful client handoffs.

Own sales growth across a Midwest territory by prospecting, developing business, managing pipelines, closing new opportunities, and partnering with Customer Success on onboarding. The role requires consultative selling experience, knowledge of NGS or genomics products sold to hospitals and laboratories or enterprise software sales, strong new-business development skills, and willingness to travel at least 50%.

Owns strategic enterprise sales for consumer-directed healthcare benefits, managing named accounts and complex 9+ month sales cycles. Responsibilities include stakeholder mapping, discovery, business-case development, technical demos, procurement and legal coordination, forecasting, and closing high-value B2B partnerships. The role requires executive communication, multi-threaded relationship building, technical integration fluency, and experience with HSA, HRA, FSA, benefits platforms, or related markets.

Sell and scope Zscaler Professional Services for enterprise and commercial customers. Partner with sales, solution engineering, architecture, delivery, customer success, and channel teams to develop proposals, Statements of Work, resource plans, training recommendations, and technical solutions. Own services bookings quotas and attach-rate targets while translating complex security and technology concepts into customer value and deployment outcomes.

Partners with go-to-market leaders to analyze sales performance, pipeline, forecasts, seller productivity, and operational metrics. Leads cross-functional initiatives, improves sales processes, CRM hygiene, CPQ practices, reporting, workflows, and account coverage. Builds executive dashboards and practical recommendations, using Salesforce, spreadsheets, AI, automation, and analytics to improve sales execution and measurable business outcomes.

Leads the East enterprise sales team, driving quota attainment, account-based execution, forecasting discipline, win-rate improvement, and complex deal strategy. Manages, coaches, and performance-manages Account Executives while developing scalable sales processes and enterprise go-to-market motions. Partners cross-functionally with Marketing, Product, RevOps, Enablement, Solutions Engineering, Legal, and Customer Success to improve deal velocity, customer engagement, and segment performance.

Lead four Account Executives selling platform partnerships to ISVs and SaaS providers. Define the ISV go-to-market strategy, manage complex negotiations, oversee opportunities from creation through launch and activation, improve prospecting and forecasting, and represent partner insights in commercial and product decisions. Responsibilities include coaching, hiring, talent planning, performance management, executive relationship building, and driving revenue growth across the platform ecosystem.

Supports Federal enterprise sales teams by preparing quotes, processing orders, managing contract requirements, coordinating hardware and services, handling returns, and providing customer updates. Maintains knowledge of products and government requirements, manages rollout orders and contract vehicles, develops customer relationships, and mentors coworkers. The role requires strong communication, multitasking, technology and federal sales experience, and familiarity with SPS, AS400, and Office applications.

Leads sales operations analytics and strategic initiatives, including forecasting, pipeline and funnel analysis, KPI reporting, deal structuring, process improvement, and revenue predictability. Partners with sales leadership and cross-functional teams to improve sales execution, automation, dashboards, and operating cadences. Mentors junior analysts and drives alignment across marketing, sales, and customer success.

Leads and scales the global Sales Engineering team while serving as Field CTO and the company’s external technical voice. Owns technical sales methodology, demos, evaluations, proof-of-value cycles, solution design, deployment handoffs, executive engagements, competitive positioning, market content, and field-driven product feedback. The role is a player-coach position requiring deep cybersecurity expertise, executive presence, public speaking, and significant travel.

The Manager, Sales Architect leads the Sales Architect team, qualifying prospects, managing project handoffs, and designing solutions for technology sales.

Manages strategic financial services accounts, builds executive relationships, leads account planning and client business reviews, identifies retention and expansion opportunities, coordinates internal resources, and drives adoption of new products. The role requires prospecting, negotiation, deal closing, and trusted-advisor engagement with complex organizations. It is remote with occasional in-person work-related events.

Handle inbound and outbound calls to current policyholders to explain and add additional life, accident, and health coverage; use the eService web system to assess eligibility, complete paperwork, correct errors, and assist with correspondence while maintaining confidentiality and strong customer service.

Generate qualified sales pipeline through outbound prospecting, inbound lead follow-up, personalized email, phone, and LinkedIn outreach. Research healthcare provider accounts, identify stakeholders, conduct discovery and qualification calls, maintain CRM data, and partner with Account Executives. The role also helps develop outbound playbooks, improve AI-driven campaigns, follow up after events, and establish scalable SDR processes.

Generates qualified meetings and sales pipeline through inbound lead management, account research, discovery conversations, and multichannel outreach. Collaborates with marketing and sales teams to develop target lists, messaging, and call strategies. Tracks activities in Salesforce and Outreach.io, reports results, documents processes, and mentors new SDRs. The role is fully remote and includes onboarding and training in GitLab and DevOps.

Respond to and qualify inbound leads from marketing campaigns, website inquiries, and content engagement. Research prospects, nurture sales-ready opportunities through email and phone follow-up, schedule qualified meetings, meet pipeline and quota targets, track activity in Salesforce, and partner with marketing on lead quality and campaign performance.

Prospect hospitals, health systems, and medical groups through phone, email, and social channels. Research accounts, identify decision-makers, qualify inbound and outbound opportunities, schedule discovery calls and demos, and document activity in Salesforce. Partner with sales teams on territory and expansion strategies, communicate Hospital Solutions’ value, manage funnel metrics, and consistently meet or exceed meeting and pipeline quotas.

The Client Partner will drive enterprise sales and client growth for Aera’s decision intelligence platform. Responsibilities include acquiring large enterprise clients, expanding existing accounts, managing executive relationships, developing strategic transformation roadmaps, articulating platform value, building pipelines, closing strategic deals, and achieving revenue targets. The role requires consultative, outcome-based selling to senior business and technology stakeholders, close collaboration across teams, and frequent travel.

Lead technical sales engineering for major customers by presenting products, gathering requirements, configuring solutions, managing evaluations, and designing test plans. Partner with customers to demonstrate Zscaler’s cloud security platform and guide successful technical outcomes. The role requires cybersecurity and networking expertise, customer-facing communication, and experience applying AI tools to improve workflows.

The Regional Sales Manager will sell identity and access management solutions to medium and large commercial accounts across the Central United States. Responsibilities include exceeding booking quotas, developing territory and account strategies, engaging executive decision-makers, managing demonstrations and evaluations, partnering with resellers and internal sales teams, maintaining Salesforce and Clari forecasts, and supporting customer expansion and issue resolution.