Regional Director Jobs in Wisconsin
Regional Director jobs in Wisconsin concentrate in healthcare systems, financial services, retail operations, and manufacturing, with demand at both the mid-level management and senior executive tiers. Milwaukee, Madison, and Green Bay are the most active hiring metros, anchored by employers such as Advocate Aurora Health, Northwestern Mutual, and Kwik Trip. Operations management and multi-site retail oversight are the most consistently posted specialties across the state. See the openings below and apply to the ones that match your experience.
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About Gillis
At Gillis, we believe that sales is the lifeblood for all organizations. Our mission is to make sales accessible and achievable to all hotel owners. We also believe that our associates are our biggest asset and we put our people first over profit. If you are looking for a company that invests in its culture in a fast-paced, supportive, and dynamic environment, we would love to hear from you.
Our clients trust us to increase their revenue and build both short-term and long-term business. We embrace the dynamic nature of our industry and always ask ourselves, “How can this be done better?” and “How can we provide more value?”
Role Overview
- The Regional Director of Sales (RDOS) will provide strategic, outbound and proactive sales for 6 multi-branded, select-service hotels, located across Canada and/or the USA.
- This position is home-based and reports to an Executive Director of Sales Performance.
What’s in it for you?
- Position is home-based (remote) during client’s business hours and requires travel for in-market visits (2-4 visits per year).
- Working within a fun and fast-paced environment, Gillis’ culture offers dynamic training, ongoing coaching, and a deep commitment to taking care of our employees.
- Base salary of $70K USD, quarterly incentives and an annual profit-sharing bonus.
- 31 paid days off annually:
- 15 PTO Days
- 13 Holidays/Gillis Days
- 3 Wellness Days
- Comprehensive benefits package.
- Team offsites.
Responsibilities
- Provide strategic, outbound and proactive sales for a portfolio of 6 multi-branded hotels while also creating a sales-focused culture with the General Managers and Front Desk staff by sharing best practices and peer to peer coaching.
- Accountable for driving ROI for hotel partners while achieving revenue milestones on a shortened sales cycle of 6 months.
- Activate new accounts in the local market and increase market share from existing accounts through intentional and strategic prospecting. Deliver bi-weekly sales strategy presentations over MS Teams with each of your designated hotels to report progress.
- Develop and nurture a sales pipeline utilizing Salesforce CRM to manage accounts and shorten the sales cycle.
- Support the Dynamic Sales Solution model by working closely with your assigned POD (team) to drive revenue across our portfolio of hotels.
- Create remarkable client experiences, manage client expectations, and maintain a high level of client satisfaction by acting as a seamless extension of the hotel and representing your clients with professionalism and integrity.
- Ability to travel for in-market visits to elevate and strengthen client relationships.
What You'll Bring
- 3+ consecutive years of hotel guestroom sales experience across all market segments; multi-property sales experience preferred.
- Proven ability to generate new business, grow market share, and achieve revenue goals.
- Strong knowledge of hotel sales strategies, RFP processes, brand tools, account management, and hotel operations.
- Experience building trusted relationships with hotel owners, General Managers, and key local accounts.
- Proficiency with Salesforce (or similar CRM), Microsoft Office, AI tools, and sales technology.
- Excellent communication, organization, and presentation skills, with the ability to manage priorities and deliver results in a remote, fast-paced environment.
- Ability to work at a computer and participate in virtual meetings for extended periods.
- Reside in the United States and able to travel for client visits approximately 2-4 times annually.
Our Commitment to Fair Hiring
- At Gillis, we may use technology, including AI, to support aspects of our recruitment process; however, all interviews and hiring decisions are conducted by people.
- Gillis is committed to fostering an inclusive and accessible workplace. Accommodations are available through the recruitment process upon request.
See All 24 Regional Director Jobs in Wisconsin
Find roles in Wisconsin that match your experience and apply in just a few clicks.
Find Regional Director JobsRegional Director Jobs by City in Wisconsin
Where Wisconsin roles are concentrated, by current openings.
Regional Director Job Market in Wisconsin
A snapshot from current Wisconsin openings, updated as new roles post.
Who's Hiring


Top Industries Hiring
- Distribution & Wholesale
- Education
- Insurance
What Wisconsin Employers Look For
The qualifications that appear most often in regional director jobs across Wisconsin.
- Bachelor's degree in business administration, management, or a related field required
- Five or more years of progressive leadership experience managing multiple locations or teams
- Demonstrated ability to develop and execute regional business strategies and growth plans
- Proficiency with financial reporting, budget management, and P&L accountability
- Strong experience recruiting, coaching, and evaluating district or site-level managers
- Willingness to travel regularly within the assigned Wisconsin region
Regional Director Jobs in Wisconsin: Frequently Asked Questions
How do you become a regional director in Wisconsin?
Most regional director roles in Wisconsin require a bachelor's degree in business, operations, or a related field, followed by several years of progressively responsible management experience, often starting as a store manager, district manager, or department head. Wisconsin does not issue a state license specific to the regional director title, but candidates in regulated industries such as healthcare or financial services must hold the relevant professional credentials, such as a Wisconsin-issued nursing administrator license or FINRA registrations, before assuming oversight responsibilities.
How much do regional directors make in Wisconsin?
Regional directors in Wisconsin earn a median of about $107,050 a year, based on May 2025 Bureau of Labor Statistics wage data, ranging from around $59,990 for the lowest 10% to over $193,630 for the top 10%. Pay rises with experience, specialty, and employer.
Which companies hire regional directors in Wisconsin?
Employers hiring regional directors in Wisconsin right now include Wissota Chophouse - De Pere, Goldbelt, and Complete Care Management, based on current listings on Migrate Mate as of October 2026. Wisconsin's concentration of major healthcare networks, insurance carriers, and multi-site retail chains makes it a consistent market for regional leadership roles across multiple industries.
Which Wisconsin cities have the most regional director jobs?
Madison, Milwaukee, and Green Bay account for the largest share of regional director openings in Wisconsin. Milwaukee drives the most volume as home to major corporate headquarters in financial services, healthcare, and distribution, while Madison's state government presence and university-anchored economy add consistent demand, and Green Bay's manufacturing and regional retail base supports openings across northeast Wisconsin.
Are there remote regional director jobs in Wisconsin?
Yes, but they are rare. Regional director roles are by nature tied to in-person oversight of teams, facilities, or territories, which limits full remote work. About 75% of regional director openings tied to Wisconsin are remote or hybrid as of October 2026, and those arrangements typically apply to roles in software, financial services, or business development where direct site visits are less frequent.
How can I get hired as a regional director in Wisconsin with little or no experience?
The most realistic entry path is building a record in assistant management or department leadership roles at Wisconsin employers who promote internally, such as large healthcare systems like Advocate Aurora Health or retailers like Kwik Trip, which run structured leadership development programs. Moving from roles like district sales coordinator, operations supervisor, or area manager gives candidates direct exposure to the multi-site responsibilities regional directors own. Earning a Project Management Professional certification or completing a Wisconsin Technical College System business leadership program can strengthen a candidacy before the experience threshold is fully met.
Where can I find and apply to regional director jobs in Wisconsin?
You can find and apply to regional director jobs in Wisconsin on Migrate Mate, which lists current openings across the state. Search the roles that fit your industry and experience level and apply directly to the ones that match.
See All 24 Regional Director Jobs in Wisconsin
Find roles in Wisconsin that match your experience and apply in just a few clicks.
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