Director of Sales

About Us 

Activated Insights is a SaaS leader in the post-acute and long-term care market, serving one of the fastest-growing sectors in healthcare. Our technology, surveys, and training solutions support over 7,000 customers across 23,000+ sites of care, impacting hundreds of thousands of seniors each year. 

We’re a team of 250+ mission-driven individuals who care deeply about the experience of employees, customers, and the people in their care. Backed by an experienced private investment firm and led by a high-performing executive team, we’re building a category-defining company in a space that matters. 

 

What Sets Activated Insights Apart:

1. We are at the heart of the healthcare industry's most dynamic sector, with an ever-growing demand for post-acute care and long- term care to address the fastest growing segment of the US population.

1. Our bond with healthcare providers draws compassionate, service-driven team members, fostering a spirited, collaborative culture aligned on our mission to deliver exceptional experiences for our employees, our customers and the people in their care.

1. A high performing executive leadership team with success in both public and PE companies, primarily in high-growth companies focused on the long term and post-acute care market.

1. Backed by a private investment firm with 40+ years of experience forging lasting partnerships across the healthcare industry. 

About the Role 

As the Director of Sales (Mid-Market & SMB), you will lead a team of 7–10 Account Executives responsible for driving revenue growth across our Mid-Market and SMB segments within the post-acute care industry. 

You will own team performance, pipeline health, and overall execution. This is a hands-on role where you’ll actively coach deals, develop talent, and help shape how we win in the market. 

Your team will be responsible for approximately $2.5M–$3M in annual revenue, with a mix of inbound and outbound opportunities and a wide range of deal sizes across SMB and Mid-Market customers. 

This role is ideal for a sales leader who knows how to create accountability, build strong teams, and drive consistent results in a fast-paced, growth-oriented environment.

What You’ll Do 

• Lead, coach, and develop a team of 7–10 Account Executives across SMB and Mid-Market segments

• Own and drive team quota of approximately $2.5M–$3M in ARR

• Manage a sales motion that includes roughly 40% inbound and 60% outbound pipeline generation

• Support a wide range of deal sizes from ~$2K to $75K, with the majority of volume in SMB (average deal size ~$6,500) and larger opportunities led by senior team members

• Own pipeline health, conversion rates, and forecast accuracy across the team

• Establish clear expectations, accountability, and performance standards across the team

• Recruit, hire, and onboard top talent, raising the bar with every hire

• Provide ongoing coaching through call reviews, deal strategy, and 1:1 development

• Step into key deals to support reps in complex or high-value opportunities

• Build and refine sales processes, metrics, and operating rhythms to improve efficiency and results

• Analyze performance data to identify trends, gaps, and opportunities for improvement

• Partner cross-functionally with Marketing, Sales Enablement, Product, and Implementation to improve conversion and customer experience

• Bring voice-of-customer insights to leadership to inform go-to-market strategy and product direction 

What You Bring 

• 5+ years of experience leading high-performing inside sales teams in a quota-driven environment

• Proven track record of driving revenue growth through team performance

• Experience leading teams across high-velocity SMB and Mid-Market sales motions, balancing inbound efficiency with outbound pipeline creation 

• Strong coaching skills with a history of developing Account Executives into top performers

• Ability to build structure, accountability, and consistency across a sales team

• Data-driven mindset with strong forecasting and pipeline management experience

• Experience in SaaS or technology sales strongly preferred

• Experience in post-acute, senior living, or healthcare markets is a strongly preferred 

What Great Looks Like in This Role 

• Your team consistently meets or exceeds quota

• Pipeline is healthy, predictable, and well-managed

• Forecasts are accurate and trusted by leadership

• Reps are developing, improving, and being promoted

• Sales processes are clear, repeatable, and continuously improving

• You are seen as a strong cross-functional partner across the business 

Compensation & Growth 

• Competitive base salary + performance-based bonus tied to team results

• Opportunity to influence go-to-market strategy and scale a high-growth sales organization

• Clear path for growth as the company continues to expand

Location 

• On-site in Tampa, FL 

Schedule 

• Full-time, 40 hours per week

• Monday through Friday, standard business hours with flexibility as needed