OneDigital

Mid-Market Sales Director

OneDigital$125K — $150K *
US-AnywhereRemote in Illinois, US
Business Services
8 - 10 years of experience
Job Overview by Ladders

Qualifications

  • Bachelor's degree in Business, Marketing, or related field required.
  • 8-10 years of progressive sales experience, with 5+ years in a leadership role.
  • Proven success in achieving revenue targets within a B2B setting.
  • Experience managing multi-state or regional sales teams is preferred.
  • Expertise in leading services-based or consultative sales teams.

Responsibilities

  • Develop and implement regional sales strategies to meet revenue goals.
  • Manage pipeline health, forecasting, and performance metrics for the Midwest region.
  • Lead and mentor a regional sales team, setting clear goals and expectations.
  • Oversee hiring, onboarding, and development of sales talent in the area.
  • Engage with key clients and prospects as an executive presence during negotiations.
  • Collaborate with cross-functional teams to optimize client onboarding and satisfaction.
  • Utilize data analytics to drive performance improvements and strategic decisions.

Benefits

  • Health, wellbeing, and retirement benefits offered.
  • Paid time off and overtime pay for non-exempt employees.
  • Eligible for variable compensation, commission, and/or annual bonuses.
  • Access to robust learning and development programs.
  • Reimbursement of job-related expenses per company policy.
Full Job Description
Our Newest Opportunity:
Role Objectives:

The Midwest Sales Director is responsible for leading and executing the sales strategy across the Midwest region to drive revenue growth, expand market share, and strengthen client relationships. This role provides strategic and hands-on leadership to a regional sales organization while serving as a key partner to executive leadership, Marketing, Operations, and Client Services.

The Midwest Sales Director balances regional strategy with disciplined execution, ensuring sales goals are achieved through strong leadership, talent development, performance management, and data-driven decision-making. This role plays a critical part in growing the Midwest market and supporting the organization's overall sales objectives.

Key Responsibilities

Regional Sales Strategy & Revenue Growth
  • 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.


Sales Leadership & Team Development
  • Lead, coach, and develop a high-performing regional sales team, including sales managers and individual contributors.
  • Establish clear 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.


Pipeline & Performance Management
  • Oversee pipeline development, opportunity management, and deal progression across the Midwest 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.


Client & Market Engagement
  • Serve as an executive-level presence with key prospects, strategic accounts, and partners in the Midwest.
  • Support complex or high-value deal negotiations and executive-level sales presentations.
  • Maintain a strong understanding of regional client needs, market conditions, and competitive landscape.
  • Ensure the regional sales approach aligns with the organization's value proposition and brand.


Cross-Functional Collaboration
  • Partner closely with Marketing to align regional lead generation, messaging, and go-to-market strategies.
  • Collaborate with Operations, Finance, and Client Services to ensure smooth onboarding, delivery, and client satisfaction.
  • Provide regional market insights to inform product development, service offerings, and pricing strategies.


Reporting, Forecasting & Analytics
  • Deliver accurate regional sales forecasts and executive-level reporting.
  • Analyze sales performance data to identify trends, risks, and opportunities specific to the Midwest.
  • Use data and metrics to drive accountability, optimize performance, and support strategic decision-making.


Governance & Continuous Improvement
  • 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.


Required Experience & Education
  • Bachelor's degree required; preference for Business, Marketing, or 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 managing multi-state or regional sales teams preferred.


Knowledge/Skills/Abilities
  • 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.
  • Excellent leadership, coaching, and talent development capabilities.
  • Exceptional communication, presentation, and negotiation skills.
  • Strong business acumen and financial literacy.


Preferred Skills
  • 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.


Your base pay is dependent upon your skills, education, qualifications, professional experience, and location. In addition to base pay, some roles are eligible for variable compensation, commission, and/or annual bonus based on your individual performance and/or the company's performance. We also offer eligible employees health, wellbeing, retirement, and other financial benefits, paid time off, overtime pay for non-exempt employees, and robust learning and development programs. You will receive reimbursement of job-related expenses per the company policy and may receive employee perks and discounts.

To learn more, visit: www.onedigital.com/careers

About OneDigital

OneDigital is a leading insurance brokerage and benefits administration company in the United States. The company was founded in 2000 and is headquartered in Atlanta, Georgia. OneDigital offers a wide range of insurance products and services, including health, dental, vision, life, disability, and voluntary benefits. The company serves clients in a variety of industries, including technology, healthcare, manufacturing, and retail. OneDigital has been recognized as one of the fastest-growing companies in the United States by Inc. Magazine and has received numerous awards for its innovative approach to employee benefits.
Learn more about OneDigital
Size
2,000 employees
Industry
Founded
2000

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