Regional Sales Director, Midwest

OneDigital

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About The Position

The Regional Sales Director leads and executes OneDigital’s sales strategy across the Midwest to drive revenue growth, expand market share, and strengthen client relationships. The role combines strategic direction with hands-on leadership of the regional sales organization and partners with executive leadership, Marketing, Operations, Finance, and Client Services.

The director owns regional revenue targets, forecasting, pipeline health, and performance metrics; develops market-specific opportunities and expansion strategies; and ensures regional sales goals are achieved through talent development, performance management, and data-driven decisions. The role also represents the organization with key prospects, strategic accounts, and partners, and helps grow the Midwest market in support of the company’s overall sales objectives.

Requirements

• Bachelor’s degree required; preference for Business, Marketing, or a related field.
• 8–10 years of progressive sales experience, including 5+ years in a sales leadership role.
• Proven track record of meeting or exceeding revenue targets in a B2B environment.
• Experience leading sales teams in a services-based or consultative selling environment.
• Proficiency with CRM systems and sales performance tools.
• Strong strategic and analytical mindset, with ability to translate vision into execution.
• Excellent leadership, coaching, and talent development capabilities.
• Exceptional communication, presentation, and negotiation skills.
• Strong business acumen and financial literacy.
• Must be eligible to work in the United States without the need for work visa or residency sponsorship.

Nice To Haves

• Experience managing multi-state or regional sales teams.
• Ability to influence and partner with senior executives and cross-functional leaders.
• Adaptability and resilience in a fast-paced, growth-oriented environment.
• High level of integrity, accountability, and customer focus.

Responsibilities

• Develop and execute short- and long-term regional sales strategies aligned with enterprise revenue and growth objectives.
• Own regional revenue targets, forecasting, pipeline health, and performance metrics.
• Identify market-specific opportunities, verticals, and expansion strategies within the Midwest.
• Partner with executive leadership to align regional sales initiatives with overall business strategy.
• Lead, coach, and develop a regional sales team that includes sales managers and individual contributors.
• Establish sales goals, performance expectations, and accountability standards across the region.
• Oversee hiring, onboarding, training, and ongoing development of Midwest sales talent.
• Foster a collaborative, results-driven sales culture focused on integrity, accountability, and client value.
• Oversee pipeline development, opportunity management, and deal progression across the region.
• Ensure consistent use of CRM and sales tools to maintain data accuracy, visibility, and forecasting discipline.
• Monitor regional win/loss trends, conversion metrics, and sales cycle performance.
• Implement best practices and process improvements to increase efficiency and close rates.
• Represent OneDigital with key prospects, strategic accounts, and partners in the Midwest.
• Support complex or high-value deal negotiations and executive-level sales presentations.
• Maintain understanding of regional client needs, market conditions, and the competitive landscape.
• Ensure the regional sales approach aligns with the organization’s value proposition and brand.
• Partner with Marketing on regional lead generation, messaging, and go-to-market strategies.
• Collaborate with Operations, Finance, and Client Services to support smooth onboarding and delivery and client satisfaction.
• Provide regional market insights to inform product development, service offerings, and pricing strategies.
• Deliver accurate regional sales forecasts and executive-level reporting.
• Analyze sales performance data to identify Midwest-specific trends, risks, and opportunities.
• Use data and metrics to drive accountability, optimize performance, and support strategic decision-making.
• Establish scalable, repeatable sales processes and controls across the Midwest region.
• Ensure compliance with company standards, ethical sales practices, and regulatory requirements.
• Champion continuous improvement through innovation, training, and market intelligence.

Benefits

• Eligible employees are offered health, wellbeing, retirement, and other financial benefits.
• Paid time off.
• Overtime pay for non-exempt employees.
• Learning and development programs.
• Reimbursement of job-related expenses according to company policy.
• Employee perks and discounts.
• Some roles are eligible for variable compensation, commission, and/or an annual bonus based on individual and/or company performance.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior