Ready To Make An Impact?

    Head of Sales
    Chicago / Remote

    Casechek is on a mission to innovate the implant supply chaiand bring greater transparency to the cost of patient care. From procurement to payment, Casechek automates workflows for vendor supported surgical procedures. Our emergent Bill Only solution provides a comprehensive system of record for Hospitals and Health Systems to manage the complexity of surgical cases with implantable medical devices, expose hidden expenses and surface revenue opportunities.

    ​​We are seeking a Head of Sales to lead our high-impact sales team. This individual will drive Casechek’s top-line revenue, predominantly focused on our new Payment Solution. You must be a self-starter, professional and creative problem-solver with strong organizational and interpersonal skills who can operate effectively in a start-up environment.

    The Head of Sales will be responsible for leading our regional business development team as well as generating business at new accounts and expanding business at existing accounts. You will be expected to develop, manage, and execute a territory sales plan, close deals independently, and lead the existing sales team. 

    • Casechek is based out of Chicago’s Fulton Market, but we’re a hybrid remote and in-person team.
    • We are highly motivated and passionate about solving healthcare’s messiest problems with new technologies.
    • We value diversity, curiosity, and a passion for learning. The team has a lot of advanced degrees and even a few professional musicians.
    • Innovating the implant supply chain is a marathon and not a sprint – we support each other in long-term growth and value developing transferrable skills.
    • Competitive salary and annual bonus
    • Opportunity for LTI
    • 401k match
    • Work from home flexibility
    • Full medical and dental benefits
    • Brand new pro level laptop
    • Annual educational budget
    • Proven track record for managing complex enterprise sales of a technical nature.
    • Passion for introducing and driving disruptive solutions to help customers evolve and transform healthcare.
    • Ability to balance team management/development and deal pursuits. 
    • Exceptional interpersonal skills to build strong relationships with executives and other customer stakeholders.
    • Experience managing, growing, and scaling teams.
    • Highly motivated and thrives in a fast-paced, start-up environment.
    • Proven ability to lead and collaborate with leadership, marketing, clients, and product management to launch high-performing solutions.
    • Healthcare industry experience, ideally in Supply Chain and enterprise SaaS solutions.

    Team Management

    • Manage and coach all phases of the sales cycle, including business development, lead identification, qualification, scope construction, proposal development, client presentations, and contract negotiation.
    • Manage the day-to-day activities of the RVPs of Business Development while balancing your individual pipeline.
    • Ensure the sales team understands the customer's business model, pain points, growth objectives while positioning offerings to support accomplishing those goals.


    • Lead by example by participating in sales activities.
    • Actively pursue and hunt for new business opportunities within existing accounts and identify and win new logos.
    • Establish and maintain relationships at all client levels, including C-suite.
    • Accurately forecast and deliver on sales across the US.
    • Meet and exceed company booking quotas.
    • Network within the industry, market, and accounts to identify new opportunities.

    Pipeline Management

    • Define sales strategy and approach and ensure effective and consistent management of the pipeline through Salesforce and similar tools.

    Strategic Leadership

    • Identify and develop critical strategies for specific customers and market segments.
    • Develop and maintain strong and trusted relationships cross-functionally with the broader Casechek team, especially marketing, customer success, and product development.
    • Collaborate with the SVP of Marketing on go-to-market strategies and channel partners to drive opportunities and maintain alignment during and post-sales cycles.
    • 10+ years of experience in complex services sales, solution selling, and strategic accounts selling in the relevant healthcare segment (Supply Chain, OR, C-Level).
    • Direct sales management experience or equivalent leadership experience that demonstrates strong leadership qualities and a team-oriented approach to selling is essential.
    • Healthcare industry experience within the OR, Clinical Assets/Medical Devices, or other relevant healthcare verticals is preferred. 
    • Strategic account planning and execution skills.
    • Proven track record of meeting and exceeding quotas.
    • Strong project management skills, including stakeholder management, effective communication, and driving for results.
    • Self-motivated, detail-oriented, self-starter, and a cross-functional collaborator.
    • Experience with CRM software (e.g., Salesforce) and Marketing Automation (e.g., Pardot).
    • Comfortable with Microsoft Excel (analyzing spreadsheets and charts) as well as Microsoft PowerPoint.
    • Ability to travel to support sales objectives.
    • Bachelor's degree. 

    Interested? Send your resume to [email protected]