About Herewith

Herewith is reimagining caregiving by connecting families, facilities, and providers to vetted Helpers through our tech-enabled platform. We empower senior living communities, Clinics, corporations, and individual families with flexible, on-demand caregiving solutions that reduce stress and enhance quality of life.

We're expanding nationally and we’re looking for driven sales leaders who want to help us reshape the future of non-medical staffing!

About the Role

As a Regional Sales Manager, you will drive B2B growth across assigned territories, focusing on senior living communities, healthcare facilities, dialysis clinics, corporate wellness partners, and more.

You will be responsible for opening doors, nurturing relationships, and closing strategic deals that place Herewith Helpers into organizations and communities that need them most.

Key Responsibilities

Own full-cycle B2B sales: prospecting, qualifying, presenting, negotiating, and closing
Manage a broad territory with a focus on strategic verticals (Senior Living, Post-Op Clinics, Healthcare, Corporate Wellness)
Represent Herewith at conferences, local networking events, and webinars
Build deep relationships with decision-makers: Executive Directors, HR Leaders, Wellness Managers, Clinical Managers, and Procurement Officers
Partner with the marketing team to support localized campaigns and event-driven sales activities
Accurately forecast and report pipeline in CRM
Collaborate cross-functionally with product and operations teams to ensure customer success

About You

3+ years B2B sales experience, preferably in healthcare, senior living, staffing, or tech-enabled services
Startup mindset: flexible, self-motivated, highly organized
Track record of hitting or exceeding sales quotas
Excellent communication and presentation skills (both virtual and in-person)
Ability to manage a large geographic region independently
Comfortable selling into both small businesses and enterprise-level organizations
Passion for improving caregiving access and supporting vulnerable communities

Perks & Benefits

Competitive base salary + uncapped commission
Healthcare benefits package
Remote-first work environment with travel as needed
Huge growth potential in a scaling organization
Opportunity to truly make a difference in people’s lives