Top Senior Sales Jobs in Milwaukee, WI

Lead and grow a Central-region mid-market sales organization targeting employers (50–9,999 lives). Manage Regional Directors and AEs, set and execute sales strategy, develop broker/partner relationships, hit revenue targets, collaborate cross-functionally, and ensure compliance. Coach and scale a high-performing team focused on measurable impact and adoption of AI-enabled tools.

Lead and scale West-region employer sales for mid-market accounts by managing Regional Directors and Account Executives, building broker partnerships, executing sales strategies, tracking performance, and ensuring compliance. Drive revenue growth, coach a high-performing team, and collaborate cross-functionally to meet company objectives.

Lead and manage Regional Directors and Account Executives across the East region to drive sales to mid-market employers (50–9,999 lives). Develop and execute sales strategies, build broker and partner relationships, identify new business, monitor performance, and collaborate cross-functionally to meet revenue targets while ensuring compliance and team accountability.

Leads Microsoft's Global Business Operations team, overseeing executive operating rhythms, portfolio governance, cross-functional alignment, performance insights, and strategic execution. Establishes scalable operating models, drives AI-enabled process automation, communicates business impact to senior stakeholders, and ensures decisions translate into measurable outcomes. Manages, coaches, and develops a high-performing strategic operations team while improving cadence efficiency, accountability, and organizational adoption.

Drive adoption of Guidewire PricingCenter among North American P&C insurance carriers. Engage actuarial, underwriting, and pricing leaders to understand models, workflows, and modernization goals; translate needs into solution proposals; guide enterprise evaluations through commercial agreement; build pricing-focused pipeline; support go-to-market strategy; represent Guidewire at industry events; and provide customer insight to product and engineering teams.

Generate qualified enterprise opportunities through inbound follow-up, outbound prospecting, and multichannel outreach. Research decision-makers, tailor messaging, conduct discovery conversations, explain Fiddler’s AI trust platform, achieve pipeline and conversion targets, and maintain accurate Salesforce records. Collaborate with Account Executives, Marketing, and Product to improve targeting, messaging, campaigns, and lead quality.

Lead district-level sales for K-12 EdTech: build pipeline from prospecting to close, cultivate relationships with superintendents and curriculum/IT leaders, run pilots and procurement, create repeatable district sales playbook, inform product roadmap, and represent the company at conferences and educator communities.

Lead RevenueCat’s Sales and Sales Engineering functions, setting strategy, goals, forecasting practices, hiring plans, budgets, and performance standards. Build a multi-motion sales system spanning enterprise, mid-market, product-led, outbound, partner, and regional opportunities. Develop qualified pipeline, coach leaders, improve cross-functional collaboration, remain involved in complex customer opportunities, and turn deal insights into repeatable playbooks and training.

Leads sales planning, territory and account design, quota allocation, capacity modeling, and sales compensation strategy. Owns governance for quota exceptions and disputes, builds scenario models for executive decision-making, and continuously optimizes coverage, productivity, attainment, and cost of sale. Partners with Finance, HR, sales leadership, and GTM Engineering to improve planning systems, automate processes, and apply AI to quota and incentive management.

Own the Greater San Diego region by building enterprise and mid-market pipeline, acquiring new logos, managing consultative sales cycles, delivering cybersecurity value demonstrations with Solutions Engineers, partnering with VARs, forecasting revenue, and maintaining predictable pipeline performance. The role requires quota achievement, cybersecurity enterprise sales experience, value-based selling, MEDDICCC and Command of the Message training, Salesforce proficiency, and strong relationships with local cyber partners.

Drive new-logo enterprise sales for Keeper’s cybersecurity platform within an assigned geography. Responsibilities include developing strategic sales plans, prospecting, building executive relationships, managing the full sales cycle, conducting presentations and negotiations, forecasting pipeline, exceeding quotas, and collaborating with legal, sales operations, marketing, product, and customer success teams. The role requires enterprise SaaS sales experience, cybersecurity and PAM expertise, C-level relationships, CRM proficiency, and up to 50% travel.

Owns global sales operations for Education and Nonprofit segments, including revenue integrity, segmentation, account parenting, quota shifts, territory design, employee assignments, and sales performance management configuration. Governs business rules, audits, reporting, and operational controls across the Americas, EMEA, and Asia. Oversees vendor execution, resolves escalations, drives cross-functional alignment, and delivers analytics and process improvements using tools such as Power BI, Excel, SharePoint, Copilot, and SPM.

The role involves leading sales efforts for power stability solutions targeting data centers within Hyperscalers, developing strategies, maintaining customer relationships, and achieving sales goals.

Develop and execute consultative sales strategies for College Board financial aid software, managing opportunities from prospecting through close. Build relationships with higher education leaders, conduct tailored demonstrations, expand existing accounts, maintain Salesforce pipelines and forecasts, support renewals, identify cancellation risks, and use customer and market intelligence to inform sales and retention strategies.

Own US institutional sales for Prividium, targeting banks, asset managers, market-infrastructure providers, and payment firms. Responsibilities include account strategy, outbound pipeline creation, executive discovery, navigating complex regulated buying processes, negotiating strategic agreements, and delivering revenue outcomes. The role also feeds customer, competitor, and regulatory insights into product and go-to-market decisions. Candidates need enterprise B2B sales experience, institutional financial-services expertise, large-deal success, technical credibility, and experience selling emerging products.

Own the full enterprise sales cycle for Fortune 2000 accounts across targeted verticals, from prospecting through negotiation and close. Carry and exceed quota, build qualified pipeline, manage forecasts and Salesforce CRM hygiene, and execute account-based strategies. Navigate complex stakeholder groups, engage executive buyers, represent Trackforce at industry events, and collaborate with Sales Engineering, Customer Success, Product, and Marketing. The role requires disciplined MEDDPICC selling and supports vertical go-to-market initiatives.

Manage sales and business development across Eastern Canada, driving profitable growth, market share, customer retention, and territory performance. Responsibilities include developing territory plans, managing distributor, dealer, retailer, and OEM accounts, forecasting sales, identifying opportunities, providing product solutions, monitoring competitors, maintaining CRM data, and collaborating on product launches and customer events. The role is fully remote in Quebec and requires bilingual English/French communication and travel throughout the territory.

Drive international and domestic polymer and resin sales across LATAM by developing customer relationships, expanding market share, meeting sales and margin targets, negotiating contracts, monitoring market trends, coordinating order execution, forecasting sales, maintaining CRM records, and ensuring cross-border trade compliance. The role requires extensive regional travel and fluency in Spanish or Portuguese alongside English.

Leads global sales operations rhythms and strategic projects across field sales, specialists, and partners. Responsibilities include managing performance reviews, delivering executive business updates, providing performance insights, supporting localized planning, implementing sales initiatives, and aligning cross-functional teams. The role partners with senior sales leaders and operations groups to standardize planning, improve adoption of transformational programs, and drive operational excellence across a large technology sales organization.

Build and optimize automated SDR campaigns, workflows, sequences, lead handoffs, reporting, dashboards, and multichannel experiments. Manage sales and marketing automation systems, improve pipeline conversion, document processes, and train SDRs and marketers on new tools and workflows while coordinating across marketing, sales, and operations teams.

Grow revenue in data center power generation and microgrid markets across North America. Responsibilities include developing new accounts, selling Emerson’s Monarch Platform, creating strategic account plans, building executive and technical relationships, delivering technical presentations, analyzing territories, negotiating commercial and technical issues, maintaining CRM records, and representing Emerson at industry events. The role requires strong operational technology sales experience and travel throughout the United States and Canada.

Manage sales compensation, commission administration, territory planning, quota setting, and sales-planning governance. Design and model incentive plans, allocate quotas, balance territories, resolve commission issues, maintain accurate Salesforce and Workday data, and oversee related systems, controls, reconciliations, and documentation. Partner cross-functionally with Sales, Finance, HR, Legal, Accounting, and leadership to ensure financially sustainable plans, accurate payouts, effective coverage, and timely annual planning execution.

The Director of Sales owns outbound prospecting, lead generation, qualification, pipeline development, and new client acquisition for a radiology revenue cycle management organization. Responsibilities include managing HubSpot CRM records and reporting, attending healthcare and radiology conferences, coordinating follow-up, supporting proposals, and collaborating with marketing, operations, and executive leadership. Regular overnight travel is required. The role requires healthcare and radiology sales experience, strong communication skills, and a proven record of business development success.

Leads new business development for PBS Radiology, owning prospecting, lead generation, qualification, pipeline advancement, CRM management, and transition of new healthcare clients. Builds relationships with radiology practices, imaging centers, and healthcare organizations, engages in conferences and industry events, and collaborates with internal teams. Success is measured through leads, opportunities, and new client wins. Regular overnight travel is required for client meetings, conferences, and industry events.

Drive new enterprise business across the North American technology sector by prospecting, managing complex $100K–$1M+ sales cycles, conducting value-based demonstrations, building predictable pipelines, and closing high-value SaaS and AI deals. Engage executives, procurement, legal, and security stakeholders while partnering with regional leadership, solutions engineering, and product teams.