Regional Vice President, Sales-Midwest

Hallmark - Healthcare Workforce Technology; United States; Remote; USD 150,000 - 165,000; Full time

Job summary

Join a fast-growing healthcare technology firm transforming workforce management. As Regional Vice President of Sales, you'll leverage your experience to lead sales efforts for their flagship SaaS platform, partnering with internal teams and driving significant growth while working remotely in the Midwest.

Benefits

Health insurance

Dental insurance

Vision insurance

Unlimited paid time off

HSA company contributions

401k

Qualifications

• 5+ years of enterprise sales experience in healthcare or SaaS.
• Ability to connect with C-suite and clinical executives.
• Comfortable working independently in a remote environment.

Responsibilities

• Own the full sales cycle with a focus on growth targets.
• Serve as a trusted advisor and product expert.
• Develop data-driven territory plans and account-based strategies.

Skills

Enterprise Sales

Consultative Selling

Relationship Building

Strategic Thinking

Technical Savvy

Education

Bachelor’s degree

Tools

Salesforce

Job description

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Regional Vice President, Sales – Midwest

Hallmark Health Care Solutions (HHCS)

Position Summary

Hallmark Health Care Solutions is seeking a bold, strategic, and driven sales leader to help us transform healthcare workforce management. As a Regional Vice President of Sales, you’ll drive growth for our flagship platform, Einstein II, a SaaS solution solving complex staffing challenges across health systems.

This is a remote role based in the Midwest, with Chicago or Minneapolis–St. Paul strongly preferred.

We’re looking for a self-starter with grit, imagination, and intellectual curiosity—someone who thrives in a fast-paced environment and loves building strong relationships. The ideal candidate brings enterprise healthcare sales experience, but we also welcome clinical leaders with deep operational insight who are ready to pivot into a commercial role.

You’ll collaborate closely with executive leadership, marketing, and customer success to unlock value for our clients and drive revenue. Success in this role requires both strategic thinking and a hands-on, roll-up-your-sleeves mentality.

At HHCS, no one wins alone. We’re a team that rallies around one another. Your ability to work cross-functionally and embrace the strengths of others is essential.

Key Responsibilities

• Own the full sales cycle — from prospecting and qualification through demos, negotiation, and close — with a sharp focus on growth targets
• Serve as a trusted advisor and product expert, translating complex workforce problems into clear solutions using Einstein II’s full capabilities
• Partner with internal teams (marketing, customer success, solution consultants) to align strategies and deliver exceptional value to prospects
• Develop territory plans and account-based strategies that are data-driven, creative, and designed to win
• Present confidently to C-suite and clinical executives, tailoring each conversation to their unique challenges and goals
• Maintain an active pulse on the healthcare labor landscape, evolving customer needs, and competitor activity
• Represent HHCS at key industry events and conferences
• Lead with a collaborative, team-first mindset — supporting peers, mentoring up-and-comers, and contributing to a strong sales culture
  
  

Who You Are (Qualifications)

• 5+ years of enterprise sales experience in healthcare, staffing, or SaaS — OR a clinical leader (RN, operations exec) looking to transition into a sales career. We value expertise and insight equally
• Track record of exceeding quotas and driving measurable growth in complex sales environments
• Strong executive presence and the ability to connect with stakeholders at all levels — from nurse managers to CEOs
• Deep curiosity and a hunger to learn — about our platform, our customers, and the market
• Skilled in consultative selling, storytelling, and translating business problems into software-driven solutions
• Technically savvy — comfortable learning and demonstrating software platforms; experience with Salesforce or similar CRM tools is a plus
• Comfortable working independently in a remote environment while staying closely connected to the team
• Willingness to travel within the Midwest and to key national meetings as needed
  
  

Preferred Locations

Chicago or Minneapolis–St. Paul are preferred, but other Midwest locations may be considered based on proximity to a major airport.

About Hallmark Health Care Solutions (HHCS)

Hallmark Health Care Solutions is a fast-growing healthcare technology company transforming how hospitals and health systems manage their workforce. Our flagship platform, Einstein II, offers an end-to-end solution for internal float pools, agency staffing, and workforce deployment — delivering cost savings, efficiency, and better patient coverage.

We’re more than just software. We bring deep healthcare expertise, pairing our technology with clinical and operational insight to solve the real-world challenges our clients face every day. Our team includes former nurse executives, staffing leaders, and health system operators who understand the stakes — and build accordingly.

We partner with health systems, hospitals, and staffing agencies nationwide to streamline labor management, reduce dependency on contract labor, and create a better experience for both staff and administrators. Bold thinking, smart tech, and a passion for improving care — that’s what drives us.

Job Type: Full-time

Salary range: Base $150k-165k , 10% bonus plus incentive/commission plan

Work Location

• Remote
  
  

Benefits

• Health insurance
• Dental insurance
• Vision insurance
• Unlimited paid time off
• HSA company contributions
• 401k
  
  

HHCS is an Equal Opportunity Employer. All employment decisions are based on business needs, job requirements and individual qualifications, without regard to race, color, religion or belief, national, social or ethnic origin, sex, age, physical, mental or sensory disability, sexual orientation, gender identity and/or expression, marital, civil union or domestic partnership status, past or present military service, family medical history or genetic information, family or parental status, or any other status protected by the laws or regulations in the locations where we operate. Hallmark Healthcare Workforce Technology reserves the right to amend the job description, duties or qualifications based on company needs.

Seniority level

• Seniority level

  Not Applicable

Employment type

• Employment type

  Contract

Job function

• Job function

  Sales and Business Development

• Industries

  IT Services and IT Consulting

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