About The Position

The Regional Sales Director leads and executes sales strategy across OneDigital’s Midwest region to drive revenue growth, expand market share, and strengthen client relationships. The role provides both strategic and hands-on leadership to 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 sales performance. They lead and develop sales managers and individual contributors; oversee hiring, onboarding, training, and performance management; and foster a collaborative, accountable, results-driven sales culture. The role also engages with strategic prospects, accounts, and partners, supports complex negotiations and executive presentations, and uses market and performance insights to improve regional strategy and execution. The position requires a bachelor’s degree and 8–10 years of progressive sales experience, including at least five years in sales leadership. Experience managing multi-state or regional teams is preferred. The role is based on the Midwest regional remit; a specific work location or workplace arrangement is not stated.

Requirements

  • Bachelor’s degree required.
  • 8–10 years of progressive sales experience.
  • At least 5 years of experience 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 the ability to translate vision into execution.
  • Strong 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

  • A degree in Business, Marketing, or a related field is preferred.
  • 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 regional 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 results-driven, collaborative sales culture focused on integrity, accountability, and client value.
  • Oversee pipeline development, opportunity management, and deal progression across the Midwest.
  • 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 the organization at an executive level 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, 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 Midwest sales performance to identify 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 may receive 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 per company policy.
  • Employee perks and discounts.
  • Some roles are eligible for variable compensation, commission, and/or annual bonus based on individual and/or company performance.
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