Regional Director of Sales

Top Tier Transitions • Skokie, IL

1d • Remote

About The Position

Top Tier Transitions is seeking a relationship-first Regional Director of Sales to drive revenue growth across an assigned territory in the Chicagoland area. The role builds and manages strategic referral relationships with senior living communities, realtors, attorneys, financial advisors, healthcare professionals, and other referral partners. It also serves as the first point of contact for prospective clients, leads in-home consultations, prepares tailored service estimates, and guides families through the sales process with empathy and professionalism. The position is fully remote when not meeting with referral partners and clients, and requires local travel throughout the assigned territory.

The Regional Director of Sales manages the full sales cycle, collaborates with operations and service delivery teams to ensure a seamless handoff, and follows up after closing to support client satisfaction and referrals. The role maintains CRM records, tracks referral sources and conversion trends, and provides weekly pipeline reporting to the Senior Director of Growth. Success is measured by new partnerships, leads and conversion, revenue and estimate-to-close ratios, client and partner feedback, and CRM and reporting accuracy.

Requirements

• At least 4 years of experience in senior living sales or business development.
• Proven ability to build and maintain long-term strategic relationships and partnerships.
• Experience managing a CRM and tracking a full sales pipeline.
• Strong organizational skills and ability to manage multiple concurrent priorities.
• Bachelor's degree or equivalent professional experience.
• Valid driver's license and willingness to travel throughout the assigned territory.
• Located in or near the Chicagoland area, with reliable transportation and willingness to travel locally.
• Ability to lead client conversations, develop tailored proposals, and close complex, personal-need sales.
• Strong communication skills, including deep listening and persuasive presentation.
• Passion for serving seniors and making a meaningful difference in clients' lives.

Nice To Haves

• Experience in senior living, healthcare, real estate, or estate planning industries.
• An existing network of referral relationships in the Chicagoland senior services ecosystem.
• Strong background in B2B sales and complex consultative selling.
• Creative follow-up strategies for nurturing and converting leads over longer sales cycles.
• Demonstrated ability to collaborate across internal teams and external partners.

Responsibilities

• Identify, engage, and build lasting relationships with referral partners, including senior living communities, realtors, estate attorneys, financial advisors, and healthcare professionals.
• Represent Top Tier Transitions at industry events, professional associations, community forums, and senior-focused organizations.
• Create and execute targeted email, phone, and in-person outreach campaigns to grow brand visibility and the referral pipeline.
• Tailor outreach and follow-up by industry vertical, including senior living, real estate, and legal services.
• Set and track territory goals for quarterly leads, referral meetings, and closed business.
• Conduct in-home consultations to assess project scope and prepare tailored service estimates.
• Educate families about the company's full-service offering using a consultative sales approach.
• Manage the full sales cycle from lead qualification through consultation, estimate delivery, and closing.
• Coordinate with operations and service delivery teams to transition clients into project execution.
• Follow up with clients after closing to support satisfaction, continuity of service, and referral generation.
• Maintain accurate CRM records of sales activity, pipeline, partner relationships, and client engagements.
• Provide weekly pipeline updates, challenges, and opportunities to the Senior Director of Growth.
• Track referral sources and conversion trends to refine territory strategy.

Benefits

• Commission that can exceed 100% of salary based on performance, with $60,000+ indicated.
• Opportunity for market leadership and full P&L ownership of an entire territory as the company expands.
• Collaborative, high-energy culture within a fast-growing, mission-driven company.

What This Job Offers

• Job Type: Full-time
• Career Level: Director