Regional Sales Manager - Mid West

Travel-Based | Full-Time Required Location: Chicago, IL

The Family of Silver Oak—including Silver Oak, Twomey, OVID, Timeless, and Prince Hill—is seeking a Regional Sales Manager (RSM) to lead and grow our business within a designated territory. This role is ideal for a driven sales leader who thrives in the field, builds trust-based relationships, and takes pride in disciplined execution.

The RSM will be responsible for expanding distribution, strengthening key accounts, executing strategic sales initiatives, and elevating brand equity across Silver Oak, Twomey, OVID, Timeless, and Prince Hill. Success in this role requires curiosity, resilience, emotional intelligence, and a deep passion for wine and people.

WHAT YOU’LL DO

Field Leadership & Market Execution

• Own and execute the territory sales strategy in partnership with sales leadership and distributor management.
• Grow on- and off-premise business by identifying opportunities, opening new accounts, and deepening existing relationships.
• Work in the field an average of four days per week, independently and alongside distributor sales teams and managers.
• Collaborate closely with distributors to achieve volume, placement, and prestige goals.
• Lead compelling in-person and virtual tastings, trade events, and wine dinners (including evenings and weekends).
• Deliver impactful brand education, training, and coaching to distributor sales representatives and leadership.
• Manage pricing, programming, inventory, and allocations to protect brand integrity and maximize performance.

Team Leadership & Development

• Lead, coach, and develop Field Sales Managers, fostering accountability, ownership, and continuous improvement.
• Support FSMs with territory coverage, execution, and administrative responsibilities.
• Facilitate regular communication and alignment between the sales team and internal partners.
• Organize and lead sales meetings, business reviews, and planning sessions.

Strategy, Analysis & Administration

• Forecast sales and expenses, manage budgets, and deliver quarterly sales goals.
• Analyze sales data, market conditions, and performance metrics to inform strategy and execution.
• Coordinate new item launches, national account initiatives, and trade marketing activations.
• Build and maintain strong cross-functional relationships with wholesale, inside sales, marketing, and winery teams.
• Communicate consistently and promptly with leadership, distributors, and internal stakeholders.
• Ensure retail pricing consistency and optimal use of company resources.

WHO YOU ARE

You are someone who

• Is self-motivated, competitive, and relentlessly focused on growth and results.
• Is a team-first leader who listens, learns, and earns trust through actions.
• Is strategically minded, data-informed, emotionally intelligent, and adaptable.

You bring professionalism, integrity, and a genuine passion for building brands and relationships.

QUALIFICATIONS

• Bachelor’s degree in business or related field, or equivalent experience.
• Minimum 3 years of relevant sales experience; wine industry experience strongly preferred.
• Proven success driving business development and increasing case volume.
• Strong existing relationships with key on- and off-premise accounts.
• Experience managing supplier–wholesaler relationships at sales and management levels.
• Excellent selling, presentation, and public speaking skills.
• Proficiency in MS Office (Excel, PowerPoint) and CRM systems; VIP/iDIG experience a plus.
• Strong analytical, organizational, and communication skills.
• Entrepreneurial mindset with sound judgment and decision-making ability.
• Must reside in the territory and be willing to travel daily within it.
• Valid driver’s license with a clean driving record.

PHYSICAL & WORK ENVIRONMENT REQUIREMENTS

• Extensive weekly travel within the territory, primarily by car.
• Ability to manage multiple priorities, analyze complex data, and engage diverse audiences.
• Ability to lift and carry up to 35 pounds (sales materials, samples, briefcase).
• Work environment includes both office-based work and significant time in the marketplace.

WHY SILVER OAK

At Silver Oak, you’ll join a team that values craftsmanship, accountability, and long-term thinking. We invest in our people, empower leaders to own their business, and believe that great brands are built through consistency, curiosity, and care. If you are driven to grow, grounded in humility, and inspired by excellence—we’d love to meet you.

ABOUT SILVER OAK

Silver Oak is more than a winery—it’s a testament to resilience, bold vision, and the relentless pursuit of excellence. As one of Napa Valley’s most iconic Cabernet Sauvignon producers, we have set the standard for approachable luxury, crafting wines that are as refined as they are unforgettable. Silver Oak continues to be a symbol of achievement and prestige, embraced by those who appreciate true craftsmanship.

For over five decades, we’ve believed that “our best bottle is yet to come.” This unwavering commitment to quality has driven us to seek out the finest vineyard sites in Napa and Alexander Valley, build LEED Platinum Certified wineries, and invest in our own cooperage in Missouri—ensuring every barrel is 100% American oak and precisely toasted to complement our signature winemaking style.

At Silver Oak, we don’t just make wine; we create experiences that elevate life’s defining moments.