Account Executive (Healthcare SaaS)

Clickcase is hiring a high-performance Account Executive to help us continue scaling at a rapid pace.

This is not a passive, inbound-only sales role. This is a full-cycle sales position for someone who can create pipeline, run a disciplined sales process, and close deals. You will be expected to prospect, run discovery, deliver demos, handle objections, and win business.

We sell to private medical practices. Our platform helps practices get more of the right patients and operate more efficiently through AI-powered patient acquisition and front-end automation. We are building something far more advanced than a typical agency or software tool, and we need a salesperson who can understand that difference, communicate it clearly, and sell with conviction.

We are looking for a killer. Someone highly competitive. Someone who hates losing. Someone who can think, adapt, and execute at a high level. Someone AI-native who already uses modern tools to move faster, think better, and outperform.

If you are a clock puncher, need constant hand-holding, or want a cushy sales job where leads just show up on your calendar, this is not for you.

What You’ll Do

• Prospect and create your own pipeline through outbound activity
• Run sharp discovery calls with practice managers, administrators, and doctors
• Lead demos and sales conversations with confidence and control
• Manage opportunities from first touch through signed agreement
• Handle objections skillfully and move deals forward without getting emotionally thrown off
• Maintain consistent follow-up and keep momentum in every active deal
• Learn our product, positioning, and market deeply enough to sell with clarity and authority
• Understand basic marketing and patient acquisition language well enough to speak intelligently with prospects
• Use AI tools aggressively to increase output, improve research, prepare for calls, sharpen messaging, and operate faster
• Help us improve the sales process as we grow

What Winning Looks Like

• You generate pipeline, not just wait on it
• You consistently book qualified opportunities
• You run strong discovery instead of giving generic pitches
• You control the sales process rather than reacting to it
• You close business
• You raise the standard of the sales team through intensity, skill, and execution
• You become dangerous because you combine sales ability, speed, intelligence, and AI fluency

What We’re Looking For

• Proven sales ability in a closing role
• Comfortable owning both prospecting and closing
• Strong phone presence and real confidence in live conversations
• Able to sell to business owners, doctors, and practice leadership
• Sandler training or Sandler-style selling strongly preferred
• Highly competitive and internally driven
• Strong judgment, strong communication, strong follow-through
• AI-native is a must
• Understands basic marketing terminology and concepts
• Able to thrive in a fast-moving startup environment with high accountability
• Coachable, but not fragile
• Self-managed and hard to rattle
• The kind of person who naturally works harder than most because you are wired that way

Work Ethic Matters Here

We are not looking for balance-first people. We are looking for people who are obsessed with winning.

If you are the kind of person who thinks about deals after hours, who likes working, who gets energy from momentum, and who naturally puts in more reps than everyone else, that is a good thing here. We respect workaholics when that energy is paired with discipline, output, and results.

This role is for someone who genuinely wants to go hard.

You Must Be AI-Native

This is non-negotiable.

We do not want someone who is “open to learning AI.” We want someone who already lives in it. You should already be using AI tools to research accounts, prepare for calls, write better outreach, tighten messaging, organize information, and move faster than the average rep.

Clickcase is building in AI. Selling here without being AI-native is like showing up to a race on foot.

You’ll Probably Be a Strong Fit If You...

• Have real hunter energy
• Know how to open and control a sales conversation
• Ask direct questions and are not afraid of tension
• Can speak with both confidence and precision
• Care deeply about performance
• Like building inside an early-stage company
• Want upside tied to results
• Prefer high standards over comfort
• Understand enough marketing language to talk intelligently about lead flow, patient acquisition, conversion, follow-up, campaigns, funnels, and ROI
• Naturally work at a pace that most people would consider intense

You Will Not Be a Fit If You...

• Need constant oversight to stay productive
• Only know how to work inbound leads
• Get uncomfortable asking hard questions
• Avoid pressure
• Want a low-accountability environment
• Are more concerned with work-life balance than winning
• Are not naturally competitive
• Do not already use AI in your daily workflow
• Want a corporate sales environment with lots of structure and low personal ownership

About Clickcase

Clickcase is an AI-powered growth and patient acquisition company built for private medical practices. We help practices attract, engage, qualify, and manage prospective patients more effectively through software, automation, and AI. We are building the AI front end of the modern private practice.

We move fast. We expect a lot. We care about performance. We are not interested in average.

Compensation

• Base salary commission (OTE $120,000)
• Strong upside for the right closer
• Compensation will depend on experience and proven ability

How to Apply

Send your resume and a brief note explaining why you are a fit for this role.

Close us on choosing you.

In that note, include:

• your experience in full-cycle sales
• whether you have any Sandler background
• the AI tools you currently use in your workflow
• why you believe you would outperform other candidates in this role