Head of AI Sales - Healthcare SaaS

Who We Are 

Paul Gough Media is a fast-growing marketing, education, and technology company helping private healthcare business owners grow more profitable and efficient businesses. 

PAULAI is our rapidly growing AI division, providing AI-powered solutions designed to help healthcare businesses improve lead conversion, communication, operational efficiency, and patient experience. 

We are looking for a Head of AI Sales who is first and foremost an exceptional salesperson and closer. 

This is not a traditional sales management role. 

You will not spend your days simply managing reports, reviewing numbers, and waiting for appointments to appear on your calendar. You will be expected to personally generate opportunities, book appointments, run sales calls, follow up relentlessly, and close business while also leading and developing our SDR function. 

If you are a proven closer who thrives on targets, competition, accountability, and building revenue, this could be an exceptional opportunity. 

The Role 

As Head of AI Sales, you will own the revenue number for PAULAI. 

You will personally prospect and generate a minimum of 4–5 qualified appointments on your own calendar every week, with a target of 20 self-generated appointments per month. 

You will personally run sales conversations and close a minimum of 5 new contracts per month. 

You will also lead and hold our SDR accountable for generating an additional 4–5 qualified appointments on your calendar each week, with a target of 20 SDR-generated appointments actually sat per month. 

Combined, you should have approximately 40 qualified sales appointments per month coming from your own prospecting efforts and SDR-generated opportunities. 

This is a hands-on sales leadership position. You are expected to lead from the front. 

Your Core Numbers 

Your performance will be measured against clear, objective targets: 

• 20+ self-generated qualified appointments per month 

• 20+ SDR-generated appointments sat per month 

• Minimum 5+ new contracts personally closed per month 

• 25%+ close rate 

• 80%+ appointment show rate 

• $1.2M+ in annualized contract value generated per month 

• Consistent month-over-month revenue growth 

• Accurate pipeline management and forecasting 

These are not aspirational numbers. They are the core expectations of the position. 

What You'll Be Responsible For 

Personally Generate & Close Business 

You will actively create your own opportunities rather than relying exclusively on inbound leads or SDR appointments. 

You will: 

• Prospect and build relationships with qualified potential clients. 

• Personally book 4–5 qualified appointments per week. 

• Run discovery calls, demos, presentations, and follow-up conversations. 

• Consistently move opportunities through the pipeline. 

• Handle objections confidently and effectively. 

• Maintain disciplined follow-up until opportunities are won or genuinely lost. 

• Personally close a minimum of 5 new contracts every month. 

Lead & Develop the SDR Function 

You will be responsible for ensuring the SDR consistently produces qualified opportunities for your calendar. 

You will: 

• Hold the SDR accountable for 4–5 qualified appointments per week. 

• Achieve a minimum of 20 SDR-generated appointments sat per month. 

• Conduct weekly coaching and development. 

• Review calls and outreach activity. 

• Role-play messaging, objection handling, and appointment setting. 

• Identify performance gaps quickly and address them. 

• Improve appointment quality, show rates, and SDR conversion. 

Own the AI Sales Pipeline 

You will own the sales number and have complete visibility over the pipeline required to achieve it. 

You will: 

• Maintain a minimum of 3X monthly revenue target in pipeline. 

• Track opportunities accurately through the CRM. 

• Maintain 95%+ CRM accuracy. 

• Provide reliable weekly and monthly forecasts. 

• Review pipeline and sales activity consistently. 

• Identify bottlenecks before they become revenue problems. 

Improve the Sales Engine 

We want someone who doesn't simply work the existing process — we want someone who makes it better. 

You will continuously improve: 

• Sales scripts 

• Prospecting strategies 

• Discovery 

• Demonstrations 

• Objection handling 

• Follow-up 

• Sales messaging 

• CRM workflows 

• Reporting 

• Conversion rates 

You will be expected to implement at least one meaningful sales process improvement each month. 

Who We're Looking For 

You are a proven high-ticket closer who enjoys being directly responsible for revenue. 

You understand that being Head of Sales does not mean stepping away from selling. You want to be in the conversations, working opportunities, overcoming objections, and closing deals. 

You should have: 

• A proven track record of personally closing high-ticket products or services. 

• Experience selling SaaS, AI, software, technology, recurring services, or another consultative high-ticket solution. 

• Strong prospecting and self-generation skills. 

• The ability and willingness to generate your own appointments. 

• Strong discovery, presentation, objection handling, negotiation, and closing skills. 

• Experience managing a sales pipeline and forecasting revenue. 

• Experience coaching or managing SDRs or sales professionals. 

• Strong understanding of sales metrics and conversion performance. 

• The ability to operate successfully in a fast-moving, entrepreneurial environment. 

• A high level of personal accountability and urgency. 

This Role Is NOT For You If... 

This position will not be a fit if: 

• You consider yourself primarily a sales manager rather than a salesperson. 

• You expect an SDR or marketing team to completely fill your calendar. 

• You are uncomfortable prospecting and generating your own opportunities. 

• You have moved away from personally running sales calls. 

• You don't want your performance measured against clear weekly and monthly numbers. 

• You struggle with consistent follow-up. 

• You prefer managing activity rather than being personally accountable for revenue. 

• You need a fully developed sales system before you can produce results. 

What Success Looks Like 

A successful Head of AI Sales creates a predictable rhythm of opportunity and revenue. 

Every week, you are generating your own qualified appointments while your SDR is generating additional opportunities for your calendar. You are consistently running sales conversations, following up with prospects, maintaining a healthy pipeline, and closing new contracts. 

Every month, the expectation is clear: 20+ self-generated qualified appointments, 20+ SDR-generated appointments sat, and a minimum of 5 new contracts personally closed. 

At the same time, you are developing the SDR, improving conversion rates, strengthening our sales process, maintaining accurate forecasts, and building systems that allow PAULAI revenue to scale predictably. 

Why This Role Matters 

PAULAI has established product-market fit and is entering its next stage of growth. 

We need a sales leader who can help take it there — not from behind a spreadsheet, but from the front lines. 

You will have the opportunity to personally drive significant revenue, build the sales engine around a rapidly growing AI product, develop a high-performing sales function, and play a major role in the growth of the business. 

If you are a proven closer who wants ownership, accountability, significant earning potential, and the opportunity to build something — we want to hear from you.

 

Location: Celebration, FL – In Office 
Compensation: $90-100k + Uncapped Performance-Based Commission