Head of Sales

DSD Recruitment Logo
DSD Recruitment
United States, US
  • Production
  • FullTime
  • Applications have closed

We are conducting a confidential executive search on behalf of a forward-thinking insurance organization. This company is investing heavily in its distribution channels and seeking to empower its sales force through modern enablement strategies, technology, and training programs.

The Role

As the Vice President of Sales Enablement, you will report to the Chief Revenue Officer and act as a strategic partner to the sales leadership team. You will lead the development and execution of initiatives that increase sales productivity, improve onboarding, and support a consistent and scalable sales process across the organization.

Key Responsibilities

  • Build and execute a sales enablement strategy aligned with business goals and sales objectives

  • Lead programs for onboarding, training, certification, and continuous learning for all sales and distribution roles

  • Collaborate with sales, marketing, product, and compliance teams to build sales content, playbooks, and learning paths

  • Develop KPIs and reporting structures to measure enablement impact, including ramp time, quota attainment, and win rates

  • Manage a remote team of enablement professionals and oversee vendor relationships for training tools and platforms

  • Drive adoption of CRM and enablement tools across the sales organization

  • Ensure all enablement programs align with industry regulations and internal compliance standards

What We’re Looking For

  • 10 or more years of experience in sales enablement, sales training, or revenue operations, including at least 3 years in a senior leadership role

  • Prior experience in the insurance or financial services industry is preferred

  • Strong understanding of complex sales environments, channel partnerships, and field sales structures

  • Proven ability to design enablement programs that drive measurable business outcomes

  • Skilled in tools such as Salesforce, Seismic, Highspot, LMS platforms, and other enablement tech

  • Strong communicator with a strategic mindset and experience working across distributed teams

Who This Is For

You are a senior enablement leader who thrives in high-growth, results-driven environments. You are passionate about building programs that make sales teams more effective, and you are confident leading remote teams and cross-functional initiatives. You bring structure, creativity, and focus to the sales organization and enjoy seeing your programs directly impact revenue.

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