Enterprise Sales Executive – Network Specialist

Explainable Artificial Intelligence is an approach to building AI systems that can provide clear explanations for their decisions and actions. It aims to increase transparency and trust in AI by enabling humans to understand how AI algorithms arrive at their choices. This is especially important in healthcare, where AI systems are increasingly used to support business decisions.

We are HealthWorksAI™; our mission is to develop and implement cutting-edge XAI solutions for designing health insurance products, specifically for Medicare Advantage. We aim to create cost-effective healthcare plans tailored to individual needs, ensuring optimal patient care at affordable prices. By identifying and mitigating bias in plan design, we are committed to promoting fairness and inclusivity, ultimately empowering insurers to make informed decisions that elevate the quality of care and benefit all stakeholders.

Job description

About HealthWorksAI

HealthWorksAI is a healthcare SaaS company focused on solving one of the most complex and financially critical challenges facing Medicare Advantage health plans: provider network performance, access, and compliance.

Our AI-driven platform helps MA organizations:

Optimize provider network design for overall performance
Improve access, quality, and member experience
Reduce administrative burden
Make faster, data-driven network decisions at scale

We sell into enterprise Medicare Advantage, Medicaid and ACA organizations, working directly with network strategy, operations, and business line leaders.

If you thrive in complex, consultative sales cycles where credibility, domain expertise, and value articulation matter, HealthWorksAI offers a meaningful opportunity to build category leadership.

The Role

We are hiring an Enterprise Sales Executive to lead new logo acquisition within the government sponsored health plan space with a focus on network performance solutions.

This role is ideal for a seller who:

Has sold complex healthcare SaaS into MA plans, payers, or adjacent regulated buyers
Is comfortable navigating long sales cycles, multi-stakeholder buying committees, and compliance-driven decisions
Can translate technical and analytic capabilities into executive-level business outcomes

The position offers some BDR support, however you will own the full sales cycle from prospecting to close, working closely with product leadership, Chief Growth Officer, and Chief Strategy Officer.

Key Responsibilities

Enterprise Sales Execution

Own and close high-value enterprise opportunities ($250K–$1M+ ACV) with Government Sponsored health plans
Sell a complex, AI-driven SaaS platform using a consultative, value-based approach
Navigate multi-threaded buying committees, including:
- Network strategy & contracting
- Provider operations
- Compliance & regulatory teams
- Finance and executive leadership

Discovery & Value Selling

Lead deep discovery focused on:

Provider network performance
Operational inefficiencies and cost drivers

Quantify ROI and business impact tied to:

Network performance improvements
Administrative and operational efficiency

Pipeline & Deal Management

Build and manage a disciplined enterprise pipeline
Accurately forecast deals and maintain strong CRM hygiene in HubSpot

Market & Product Feedback

Bring payer-level insights back to product and leadership teams
Help shape messaging, use cases, and sales playbooks as the company scales

What We’re Looking For

Required Experience

5+ years of B2B SaaS sales experience, with at least 3 years selling into healthcare payers or MA plans
Proven success closing enterprise deals with long sales cycles (6–12+ months)
Experience selling solutions related to one or more of the following:
- Provider networks / contracting
- Network adequacy & access
- Healthcare analytics or AI platforms
Strong understanding of Medicare Advantage dynamics, including CMS regulations and network requirements

Sales Skill Set

Consultative, insight-driven selling style (not feature-led)
Comfortable selling to director-level through executive stakeholders
Able to clearly articulate complex concepts in simple, outcome-focused language
Disciplined opportunity qualification and deal management
Background working with MA, Medicaid, or dual-eligible populations

Personal Attributes

Credible, confident, and highly professional with senior healthcare leaders
Curious and able to quickly develop deep domain expertise
Self-directed, accountable, and comfortable in a growth-stage environment
Motivated by building something meaningful in healthcare

Nice to Have

Experience selling network optimization, access, or compliance solutions
Prior experience at a healthcare SaaS startup or scale-up
Familiarity with CMS network adequacy standards

Why You will Love Working Here

Compensation & Benefits

Competitive base salary + uncapped commission
Defined contribution for medical benefits
Remote-first culture with flexible work environment
Opportunity to influence product direction and market strategy
Future equity opportunity

Why HealthWorksAI

Complex, high-value problems that reward strong enterprise sellers
Leadership team with deep healthcare and SaaS experience
A product buyers need—not just want—at a time when network optimization is a key profitability lever

Who Should Apply

If you are an experienced healthcare SaaS seller who:

Enjoys complex, strategic sales
Understands government-sponsored health plan network challenges
Wants to be part of a company building real category leadership

We’d love to talk!