About The Position

The Director of Sales – Strategic develops sales opportunities in the strategic employer market, serving employers with populations under 8,000 lives. The role requires a broad understanding of employee benefits technology and services, and focuses on generating leads, building relationships, and closing deals. The Director presents products and services, coordinates sales-support resources, and works with channel partners and employers to develop qualified leads and a strong sales pipeline. The position is accountable for annual recurring revenue (ARR) goals and territory sales strategy. It executes a consultative sales process, including prospect discovery, demonstrations, presentations, deal strategy, and follow-up. The Director collaborates with sales leadership and teams across transition, sales support, marketing, product, and operations, while tracking sales activities and reporting progress. Travel may be up to 50%.

Requirements

  • Proven ability to develop and deliver presentations.
  • Proven ability to develop and maintain a business-development territory, including prospecting.
  • Proven ability to execute a thorough sales discovery process.
  • Proven negotiation and closing skills.
  • Strong interpersonal and communication skills.
  • At least 3 years of experience selling technology and services to strategic employers with populations under 8,000 lives.
  • Experience building and developing client relationships with brokers, consultants, and employers.
  • Up to 50% travel.

Nice To Haves

  • Bachelor’s degree preferred, but not required.
  • Channel sales experience preferred.
  • Experience selling HCM, payroll, health and welfare benefits, or benefits administration services.

Responsibilities

  • Achieve the annual recurring revenue (ARR) sales goal through sales strategy, new-customer sourcing, and productive long-term channel-partner relationships.
  • Develop a comprehensive understanding of company products and services and educate influencers and employers about them.
  • Engage brokers, consultants, advisers, carriers, and employers to build relationships that generate qualified leads.
  • Prepare action plans and schedules to identify targets and generate pipeline and qualified leads.
  • Maintain a valid, qualified sales pipeline and track activities and opportunities accurately using company tools and processes.
  • Develop and implement territory action plans based on data analysis, adjusting sales techniques based on field interactions and results.
  • Follow up on leads and referrals generated by marketing activity.
  • Execute a consultative sales strategy, develop client offers, and identify alternative paths to closing sales.
  • Deliver systems demonstrations, product demos, and presentations as part of the defined selling process.
  • Assess prospect needs and follow the sales process to achieve sales goals.
  • Develop and own deal strategy in partnership with the sales leader, transition team, and other sales-support resources.
  • Foster teamwork, collaboration, and trust with sales support, marketing, product, and operations.
  • Collaborate with prospect teams to establish a mutual understanding of opportunities and delivery capabilities.
  • Prepare status reports covering activity, closings, follow-up, and progress against goals.
  • Partner with sales leadership to identify marketing events, including seminars, trade shows, telemarketing events, and company-supported events.
  • Develop and manage marketing campaigns in partnership with marketing and sales leadership.
  • Perform other duties as assigned.
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