Head of Sales Enablement

Activated Insights•Tampa, FL

1d•Onsite

About The Position

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: 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. 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. 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. 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.

Requirements

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 Haves

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

Responsibilities

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
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
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
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
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
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