About the role

  • Director, Sales Operations role at Cobalt Benefits Group focused on sales execution in healthcare benefits. Leading sales operations, CRM management, and financial analytics in a hybrid work environment.

Responsibilities

  • Develop a deep understanding of Cobalt’s Financial performance and continuously refine Pricing Strategy to drive improved Profitability over time.
  • Lead weekly Deal Desk meetings to ensure optimal solution design and profitability for each new opportunity.
  • Design and maintain Cobalt’s long-term Sales Operations strategy.
  • Facilitate conversations around long-term client development, including product/revenue expansion via targeted upsells.
  • Lead development and execution of Sales Training and Enablement materials for new product initiatives.
  • Partner with leaders to optimize Sales Team structure and compensation.
  • Act as the primary System Administrator of Cobalt’s CRM.
  • Lead new user training and promote adoption of CRM technologies.
  • Identify opportunities to enhance the CRM and ensure complete and accurate data entry by the Sales Organization.
  • Evaluate, implement, and maintain technology solutions that support quoting and process improvement.
  • Develop and maintain sales dashboards for executive visibility into pipeline, conversion, sales cycle, onboarding timelines, and retention.
  • Provide data-driven recommendations to improve revenue generation and optimize solution design.
  • Own and continuously optimize Sales forecasts to inform investment and budgetary decisions.
  • Partner with Executive Leadership to identify and execute opportunities for margin expansion.
  • Liaise with the FP&A function to design, develop and inform KPIs to provide insight into Cobalt’s financial performance.
  • Oversee the end-to-end sales contract process, including drafting, review, approval, and repository management.
  • Maintain and update contract templates.
  • Lead technology evaluation and adoption to improve CLM across Cobalt.
  • Ensure timely contract renewals, amendment tracking, and compliance with regulatory and organizational standards.
  • Partner with Implementation and Account Management partners to optimize the operational handoff from sales to implementation, ensuring a smooth transition of new accounts into onboarding.
  • Collaborate with Implementation and Account Management partners to define and maintain SLAs and workflows.
  • In collaboration with the Customer Experience team, identify and resolve bottlenecks that delay go-live or disrupt alignment with the organization's broader customer experience strategy.

Requirements

  • Bachelor’s degree
  • Master’s Degree in related field is preferred but not required.
  • 5+ years of experience in Sales Operations with demonstrated ability to design, lead and execute cross-functional projects.
  • Demonstrated knowledge and experience with CRMs, particularly SalesForce.
  • Demonstrated ability to understand Financial Statements and business performance.
  • Experience developing and maintaining detailed Financial models and scenario planning tools.
  • Healthcare (specifically Health Insurance) Industry experience preferred but not required.
  • Self-starter, entrepreneurial mindset.
  • Strong communication skills.
  • Interest in working within a rapidly growing and evolving organization.
  • Demonstrated ability to lead and foster talent.

Benefits

  • Fantastic medical, dental, and vision insurance*
  • Twice annual employer HSA contributions, covering 50% of the HDHP plan’s annual deductible!
  • Company provided Basic Life and AD&D
  • Company paid Short-Term and Long-Term Disability**
  • Flexible Spending Accounts*
  • 401(k) Retirement Plan with up to a 6% employer-match** WOW! (100% fully vested after 3 years)
  • 10+ paid holidays
  • Generous paid vacation and sick time
  • Annual Volunteer Paid Day
  • Annual Tuition Reimbursement
  • Annual Health and Wellness Reimbursement
  • Lots of fun company events

Job title

Director, Sales Operations

Job type

Experience level

Lead

Salary

$95,000 - $115,000 per year

Degree requirement

Bachelor's Degree

Location requirements

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