Senior Living Enterprise Sales Lead (Remote) – 2M+ Quota

Blacksmith Agency LLC; Milwaukee (WI); Remote; USD 180,000 - 280,000; Full time

Job summary

Blacksmith Agency is seeking a Head of Sales for Senior Living to own large multi-location deals from first meeting to signed contract. This role focuses on closing high-stakes accounts with ownership, regional operators and marketing leaders, with inbound and SDR support.

You will close complex, long-cycle sales across many communities, expanding services as groups sign on. This is a remote, full-time position with a substantial annual quota and growth opportunities across a growing AI-first

Qualifications

• Proven track record closing $1M+ annually on multi-location or enterprise accounts.
• Experience selling to senior living operators or similarly multi-location buyers.
• Long, consultative sales cycles with multiple decision makers.
• Prefer closing business over people management.
• Ability to work independently with limited supervision.

Responsibilities

• Manage full sales cycle for large deals spanning discovery to close over 3–12 months.
• Engage owners, regional operators and marketing leaders in negotiations.
• Expand deals to add locations and services after initial win.
• Collaborate with strategists and leadership to craft winning proposals.

Skills

Large account sales

Enterprise sales

Consultative selling

Multi-location deals

Strategic partnerships

Job description

Blacksmith Agency is seeking a Head of Sales for Senior Living to own large multi-location deals from first meeting to signed contract. This role focuses on closing high-stakes accounts with ownership, regional operators and marketing leaders, with inbound and SDR support.

You will close complex, long-cycle sales across many communities, expanding services as groups sign on. This is a remote, full-time position with a substantial annual quota and growth opportunities across a growing AI-first