Strategic Sales Director

Meet Ascertain

Ascertain is building AI agents to automate the administrative work that burdens care teams. We are in major health systems and large specialty groups, saving hundreds of staff hours every week.

Our backers include Northwell Health, New York’s largest health system, and Deerfield Management, a leading healthcare investment firm.

Together, we’re on a mission to restore time, trust, and focus to the people who keep healthcare running. Our work is urgent — not because of startup timelines, but because our customers rely on us to drive financial resilience and operational clarity in a system under strain.

About the role

Ascertain is looking for a Director, Strategic Sales – Cardiology to help build and grow our cardiology business. You’ll be responsible for winning new business with cardiology practices, MSOs, regional groups, and affiliated health system practices—and helping establish Ascertain as a meaningful commercial partner in the cardiovascular market.

This is a true hunter role. You’ll own the sales cycle from prospecting through close, building your own pipeline, opening doors, and carrying a multimillion-dollar revenue target. You’ll work directly with senior healthcare leaders to understand how their organizations operate, identify where administrative complexity is creating financial and operational challenges, and build a compelling case for Ascertain.

You won’t do it alone, but you will own the outcome. You’ll have access to leaders and experts across Ascertain—from Product and Partner Solutions to Implementation and clinical and operational SMEs—and you’ll be responsible for bringing the right people into the sales process at the right time to move complex opportunities forward.

This is an opportunity for someone who wants to do more than sell an established product into an established market. You’ll help define how Ascertain wins in cardiology—turning relationships into revenue, bringing what you learn from the market back into the business, and helping build the commercial playbook and team as we grow.

What you'll do

• Own the full enterprise sales cycle for Ascertain’s cardiology business, from prospecting and pipeline development through negotiation and close, working with MSOs, regional groups, and affiliated hospital cardiology practices to deliver against a multimillion-dollar revenue target.

• Lead sophisticated, consultative sales conversations with executives, operators, clinicians, and financial stakeholders, building consensus across complex buying groups.

• Orchestrate the right Ascertain resources to advance opportunities, bringing in Partner Solutions, Implementation, Product, and clinical or operational SMEs at the right points in the sales process.

• Maintain strong commercial and forecasting discipline, keeping CRM and pipeline data current and partnering with Product, Finance, and other internal teams to provide reliable visibility into the business.

• Help build Ascertain’s cardiology commercial function, using customer insights, market feedback, and competitive intelligence to shape go-to-market strategy and developing additional commercial teammates as the business grows.

What we're looking for

• 8–12+ years of B2B enterprise healthcare sales experience, ideally selling software, digital health, medical devices, revenue cycle solutions, or other complex solutions into healthcare organizations.

• Demonstrated success building pipeline and winning new business in the cardiovascular market, rather than primarily managing or expanding an existing book of accounts.

• Strong consultative enterprise selling skills and commercial judgment, with the ability to understand a customer’s business model, build a compelling economic case for change, and navigate complex sales cycles; experience with Challenger, MEDDICC, or similar methodologies is a plus.

• Entrepreneurial, relationship-driven approach to sales, with the ability to earn credibility with senior healthcare leaders and effectively orchestrate technical, operational, implementation, and subject matter experts throughout the sales process.

• Bachelor’s degree and a track record of performing against ambitious commercial goals, with motivation to succeed in a performance-driven environment where exceptional results are meaningfully rewarded.

Bonus points

• Experience selling into vascular, ambulatory surgery, or ambulatory imaging organizations.

• Experience with healthcare revenue cycle management, prior authorization, practice management, or other administrative workflows.

• Experience at a healthcare technology, medical device/imaging, or enterprise technology organization known for rigorous sales training, with existing relationships with leaders across cardiology practices, cardiology groups, or adjacent ambulatory healthcare organizations.

• Experience helping establish a new market, service line, or commercial motion rather than inheriting a mature territory.

Compensation

The anticipated base salary range for this role is $130,000-$150,000 plus equity. On-target earnings (OTE) are approximately $250,000-$300,000 with significant (uncapped) upside for exceeding sales goals.

Why Ascertain? Make a real difference: Your work will directly impact healthcare organizations and improve patient care. Join Ascertain in transforming healthcare with AI!