Head of Sales Enablement

About Us 

Activated Insights is the leading experience management and workforce enablement platform for long-term and post-acute care, partnering with more than 16,000 care providers across North America. Backed by Cressey & Company, we are on a high-growth trajectory, unifying best-in-class solutions for recruitment, training, retention, and experience management to help organizations deliver better care and build stronger teams. 

We are scaling fast, adding products, expanding segments, and growing our sales organization. We need an enablement leader who can build the infrastructure, culture, and programs that allow our sellers to operate at peak performance every quarter. 

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. 

Why Is This Role So Special?  

This is not a traditional training role. As Head of Sales Enablement, you will own the strategy and execution of everything that makes our sales team more effective, from onboarding and ramp programs to playbooks, methodology, coaching frameworks, and competitive intelligence. 

You will sit at the intersection of Sales, Marketing, Product, and Revenue Operations, translating business strategy into field execution and ensuring our sellers are always equipped to articulate value, handle objections, and close with confidence. This is a high-visibility, high-impact role at a company that is growing aggressively and needs an enablement function that grows with it.

What You’ll Do: 

• Enablement Strategy and Program Ownership 

• Develop and own a comprehensive sales enablement strategy aligned to Activated Insights' GTM objectives, growth targets, and evolving sales motion across segments and products 

• Build and maintain a full enablement calendar covering onboarding, ongoing skill development, product launches, and methodology reinforcement 

• Define and track enablement KPIs including ramp time to quota, win rates, quota attainment, methodology adoption, and content usage, and report progress to senior leadership 

• Translate high-level sales strategy into concrete, actionable field execution 

• Sales Onboarding and Ramp 

• Design and continuously improve a structured onboarding program that accelerates new hire ramp time and ensures every seller deeply understands our products, customers, value proposition, and sales motion 

• Build role-specific onboarding tracks for AEs, SDRs, and Sales Managers that reflect the realities of selling into the LTPAC market 

• Establish clear ramp milestones and certification checkpoints in partnership with sales leadership 

• Sales Methodology 

• Champion and embed a layered sales methodology across the full team, built around three complementary frameworks: 

• SPICED Bowtie (Winning by Design) as the operating foundation, covering the full customer lifecycle from acquisition through expansion and renewal, with a shared language across Sales, Customer Success, and RevOps 

• Challenger Sale as the conversation layer for competitive, insight-led selling, particularly for new logos and complex upsell motions in the LTPAC market 

• SPIN Selling** as the discovery foundation for newer reps, building the questioning and diagnostic skills that make every other framework effective 

• Drive methodology adoption through training, reinforcement, and coaching, not just one-time rollouts 

• Codify the land-and-expand motion into clear playbooks that guide how AEs and CSMs coordinate on cross-sell and upsell opportunities across Activated Insights' product portfolio 

• Playbooks and Content 

• Develop and maintain a centralized library of sales resources in SharePoint: playbooks, battlecards, objection handling guides, discovery frameworks, competitive intelligence, talk tracks, and customer success stories 

• Partner with Product Marketing to ensure field-facing content reflects current positioning, messaging, and competitive differentiation 

• Ensure content is accessible, consistently maintained, and actively used by the team, not just created 

• Coaching and Field Enablement 

• Build a structured coaching framework that equips front-line managers with the skills and tools to coach effectively and consistently 

• Leverage Outreach engagement data and conversation intelligence to identify skill gaps, best practices, and coaching opportunities at the rep and team level 

• Deliver targeted skills training in response to real-time performance data 

• Cross-Functional Collaboration 

• Serve as the connective tissue between Sales, Marketing, Product, and Revenue Operations, ensuring enablement initiatives reinforce the company's broader GTM strategy 

• Collaborate with Marketing on lead quality, messaging, and handoff protocols between HubSpot-driven marketing and the sales team 

• Partner with the Sales Operations Analyst to use data and performance insights to prioritize enablement investment 

• Coordinate with the Deal Desk on pricing communication and objection handling for complex subscription deals 

• Work with Product to deliver launch enablement plans for new features and solution expansions before go-live 

Experience and Qualifications: 

• 7 to 10 or more years of progressive experience in sales enablement, sales training, or GTM leadership, with at least 3 years in a senior leadership role 

• Proven track record of building and scaling enablement programs in a high-growth B2B SaaS environment, ideally across multiple products and buyer segments 

• Deep knowledge of modern SaaS sales methodologies, specifically SPICED/Bowtie (Winning by Design), Challenger Sale, and SPIN Selling, with demonstrated ability to embed them into a sales culture 

• Strong hands-on experience with Salesforce and HubSpot; familiarity with Outreach or comparable sales engagement platforms 

• Data-driven mindset; you measure what matters, use performance data to prioritize enablement investment, and report outcomes in the language of revenue 

• Exceptional communicator and facilitator, equally comfortable presenting to the C-suite, running a workshop with AEs, or writing a crisp one-pager for the field 

• Strong executive presence with the ability to influence at all levels, from front-line reps to senior leadership 

• High-energy, collaborative, and low-ego; you build trust with sellers by being genuinely useful 

Nice to Have 

• Experience enabling sales teams selling into healthcare, senior care, or workforce management verticals 

• Familiarity with Zuora subscription structures and how they affect sales conversations and deal structuring 

• Experience in PE-backed, high-growth, acquisition-driven environments where integration and standardization are ongoing priorities 

Schedule: 

• Full time, 40 hours/week  

• Monday to Friday 

Work Location:  

• In-office, Tampa FL or Idaho Falls, ID