Director, Sales Operations

Cobalt Benefits Group LLC•Boston, MA

1d•Remote

About The Position

Join our team at Cobalt Benefits Group and start an exciting new career in employee benefits solutions. This Director, Sales Operations role is open to candidates based onsite in Burlington, VT or Exeter, NH, as well as remote candidates located within the Central or Eastern U.S. time zones. In this role, you’ll play a critical part in enabling effective sales execution and helping us deliver customized, self-funded insurance solutions to our clients and members. This position is eligible to participate in Cobalt Benefits Group’s annual bonus program, subject to individual and company performance and plan terms. Job Summary: The Director, Sales Operations at Cobalt Benefits Group will play a transformational role in enabling effective sales execution in a fast-paced self-funded insurance environment. This position will oversee Sales Operations, Pricing Strategy, Technology (e.g. CRM, RFP & Contract Management tools), Financial Analytics & Contract Management. Additionally, the role will focus on optimizing the end-to-end client experience as it relates to the sales process and transition from Implementation to Account Management, in alignment with the company’s broader Customer Experience vision. The ideal candidate combines proven experience leading Sales Operations processes, financial modeling, technology fluency, and a passion for Healthcare and customer experience.

Requirements

Ability to remain in a stationary position (seated or standing) for extended periods while working at a computer and participating in meetings.
Ability to operate a computer, keyboard, mouse, and other standard office equipment on a regular basis.
Ability to communicate effectively primarily via video conferencing platforms, phone calls, an in-person meetings, Ability to review, analyze and interest data on a commuter scree with sustained visual focus.
Ability occasionally moves about within an ovine environment to attend meetings or access equipment.
Must be comfortable using and being on camera during meetings
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.

Nice To Haves

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.

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.

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