Mid-Market Sales Director

Are you looking to accelerate your career without having to hide your authentic self - a place where you can be you? A career that’s making a bigger impact on the world? At OneDigital, we are on a mission to help people do their best work and live their best lives. From the services we offer to the way we show up for each other each day, we are fueling dreams, achieving big goals, and embracing each other’s truest selves. We understand that pursuing a new job is a big deal. Maybe you’re afraid you won’t fit in. Well, here’s the good news. For us, the days of “fit in to get in” are over and being different is not a barrier to getting ahead. Greatness comes in all shapes, sizes, colors, and experience levels. If you are looking for a people-first culture that is wired for growth, driven to serve, and totally committed to having your back, give us a shot. Your best life awaits. Must be eligible to work in the United States without the need for work visa or residency sponsorship. We kindly ask that external recruiters, agencies, and search firms do not contact our hiring managers or employees directly regarding open positions. All candidate submissions must go through our official application process and must be made aware to our internal Talent Acquisition team to verify candidate ownership. Unsolicited resumes or candidate profiles sent to OneDigital without a prior signed agreement will be considered the property of OneDigital. In such cases, OneDigital reserves the right to pursue and hire those candidates without any financial obligation to the agency or recruiter. 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 OneDigital is an equal opportunity employer. Not only as a matter of standard, but to honor and celebrate our differences. We believe that the power of ONE starts with you. We are committed to cultivating and preserving a culture that celebrates diversity, insists on equity and inclusion, and connects us. Ensuring our people feel seen, valued, respected, and supported is fundamental to our core values and business goals. OneDigital provides equal employment opportunities to all employees and applicants for employment regardless of their: veteran status, uniformed servicemember status, race, color, religion, sex, sexual orientation, gender identity, age (40 and over), pregnancy (including childbirth, lactation and related medical conditions), national origin or ancestry, citizenship or immigration status, physical or mental disability, genetic information (including testing and characteristics) or any other category protected by federal, state or local law (collectively, “protected characteristics”). A copy of the Federal EEO poster is linked here . Pursuant to local Fair Chance Ordinances, we will consider qualified applications with arrest or conviction records for employment. For applicable candidates, the following ordinances are linked here to inform you of your rights as an applicant: City and County of San Francisco City of Los Angeles County of Los Angeles Employment decisions shall comply with all other applicable federal, state and city/county laws prohibiting discrimination in employment. OneDigital complies with all criminal history inquiry [or ‘ban the box’] laws in California, Connecticut, Colorado, Hawaii, Illinois, Maine, Maryland, Massachusetts, Minnesota, New Jersey, New Mexico, Oregon, Rhode Island, Vermont and Washington. In short, we believe in hiring the most qualified applicant for the position, regardless of background. This posting will remain live while OneDigital is actively accepting applications. Once candidates have been selected, the posting will be removed. OneDigital understands the immense responsibility and opportunities provided by Artificial Intelligence. We utilize advanced Artificial Intelligence [AI] technologies to enhance our recruitment process. This includes using AI to filter candidates based on their qualifications and to rediscover potential candidates from our existing applicant pool. Our AI systems help us efficiently identify the best fit for our open positions, ensuring a streamlined and effective hiring experience. However, AI does not replace the humans in our process. If you have concerns about our use of AI, you may opt out where laws allow. If you have questions about our hiring policies and practices, we would be happy to discuss upon receiving your application. We hope to welcome you to OneDigital and look forward to hearing from you. Thank you for your interest in joining the OneDigital team!