Regional Director of Sales

Top Tier Transitions • Naperville, IL

6d • $60,000 - $60,000 • Remote

About The Position

Top Tier Transitions is Chicago's premier, full-service senior move management company. From sorting cherished belongings to creating a beautiful new home, our team delivers white-glove relocation, downsizing, decluttering, and luxury resale solutions with compassion, efficiency, and care. We don't just manage a move—we honor a lifetime of memories.
As a NASMM member and the only true end-to-end senior transition provider in the Chicagoland market, we handle every detail in-house. Our clients and their families deserve nothing less than excellence…and that starts with the team we build.
Make a Difference Every Day
We are seeking a driven, relationship-first Regional Director of Sales to lead growth across an assigned territory. This is a high-impact role for someone with a genuine passion for serving seniors, deep referral network instincts, and the business development skills to match. If you thrive at the intersection of strategy, community, and purpose—this is your seat at the table.
Our Core Values
🌿 Act with Empathy — Every client's story is different. We listen deeply and tailor our approach to honor each person's journey with sensitivity and respect.
🔒 Live with Integrity — Clients entrust us with their most personal spaces and possessions. We act with discretion, reliability, and transparency at every step.
🤝 Simplify the Process — From planning to execution, we manage every element of the transition—so families can focus on what truly matters.
💎 Rehome with Pride — We are passionate about giving new life to cherished items, ensuring every piece is respectfully rehomed or sold to maximize its worth.
🌟 Strive for Excellence — Our white-glove standard means going above and beyond—offering refined, reliable, and responsive support from start to finish.
Your Role: Regional Director of Sales
This high-impact, externally-facing role drives revenue growth across an assigned territory by building and managing strategic referral relationships. As Regional Director of Sales, you will serve as a key ambassador for the Top Tier Transitions brand - developing trusted partnerships with senior living communities, realtors, attorneys, financial advisors, and healthcare professionals.
You will also lead client consultations in your region, translating family needs into high-value service estimates and guiding prospects through our full-service offering. This role is ideal for a relationship-first professional with business development acumen, strong emotional intelligence, and a heart for helping seniors navigate life's most significant transitions. While not meeting with referral partners and clients, this is a fully remote role.

Requirements

• 3+ years of experience in sales, business development, or referral-based partnership roles
• Proven track record of building and maintaining long-term strategic relationships
• 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 assigned territory
• 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
• Existing network of referral relationships in the Chicagoland senior services ecosystem
• Strong background in B2B sales and complex consultative selling
• Creative follow-up strategies to nurture and convert leads over longer sales cycles
• Demonstrated ability to collaborate across internal teams and external partners

Responsibilities

• Identify, engage, and build lasting relationships with key referral partners including senior living communities (independent, assisted, memory care), realtors, estate attorneys, financial advisors, and healthcare professionals.
• Actively network and represent Top Tier Transitions at industry events, professional associations, community forums, and senior-focused organizations.
• Create and execute targeted outreach campaigns—email, phone, and in-person—to grow brand visibility and referral pipeline within your territory.
• Segment outreach by industry vertical (senior living, real estate, legal) to tailor messaging and follow-up cadence.
• Set and track territory goals including quarterly lead targets, referral meetings, and closed business metrics.
• Serve as the first point of contact for prospective clients—conducting in-home consultations to assess project scope and deliver tailored, high-value service estimates.
• Use a consultative sales approach to educate families on Top Tier Transitions' full-service offering, guiding them with empathy and professionalism.
• Manage the full sales cycle: lead qualification → in-home consultation → estimate delivery → close.
• Collaborate with internal operations and service delivery teams to ensure seamless handoff from consultation to project execution.
• Follow up with clients post-close to ensure satisfaction, continuity of service, and referral generation.
• Maintain accurate and up-to-date records of sales activities, lead pipeline, partner relationships, and client engagements in CRM.
• Provide weekly reporting to the Senior Director of Growth on pipeline progress, challenges, and opportunities.
• Track referral sources and conversion trends to continuously refine territory strategy.

Benefits

• Make an Impact — Be the trusted advisor for families navigating some of life's most emotional and logistical transitions.
• Earn a Growing Income — Help expand our reach into new markets with the support of an experienced, values-driven team—commission targeting 100% of base salary.
• Work with Purpose — Our clients entrust us with their most personal spaces and stories. We act with empathy, excellence, and integrity in everything we do.
• Grow with Us — As we expand, this role offers a clear path toward market leadership and full P&L ownership of an entire territory.
• Join a Winning Team — Fast-growing, mission-driven company with strong market demand, a unique service offering, and a collaborative, high-energy culture.

What This Job Offers

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