Senior Health & Welfare External Consulting Leader

Senior Health & Welfare External Consulting Leader
Optimatum Solutions is seeking a Senior Health & Welfare External Consulting Leader to lead client engagements at the intersection of benefits strategy, vendor management, and operational performance. This role is built for experienced professionals with external consulting backgrounds from Big Four, national benefits, or management advisory firms who want to apply their skills in a setting where they own the work from scoping through delivery, and where their impact on clients and on the firm is direct and visible.
If you've built your career advising employers on Health & Welfare and Retirement programs inside a large external consulting practice, you already know the playbook: structured problem solving, rigorous analysis, executive-ready deliverables, and trusted client relationships. At Optimatum, you'll bring that same discipline to a growing, entrepreneurial firm without the layers, utilization pressure, or narrow scope that can come with a large practice. You'll lead engagements end to end, shape how our solutions are delivered, and help build the practice as we grow.
Our Story
Optimatum is a leading vendor management firm, delivering savings for the HR supply chain since 2007. We are the first company in the market to bring best practices in vendor management to HR Supply Chain operations: Employer-Sponsored Healthcare, Retirement, HR Systems, and M&A/Transitional Services. Our turnkey solutions improve the financial and operational performance of health care plans for our clients located nationwide through our unique multidisciplinary approach, which includes forensic analysis and the maintenance of existing vendor relationships, while at the same time increasing HR vendor transparency and accountability.
We're a high-performing, entrepreneurial organization built on a foundation of client focus and innovation. Our culture celebrates individuality, inclusion, and collaborative growth. At Optimatum, you'll find an environment that encourages continuous learning and personal development—without the constraints of corporate bureaucracy. Every team member plays a meaningful role in driving our success and is recognized for their unique strengths and contributions.
The Opportunity
The Senior Health & Welfare External Consulting Leader is a client-facing advisory role responsible for leading engagements that deliver operational optimization, cost containment, compliance improvement, and process streamlining across clients' HR and benefits programs. You'll serve as the primary point of contact and trusted advisor to HR, Benefits, and Finance leaders, owning the engagement from diagnostic through implementation.
Key Responsibilities
• Engagement Leadership: Lead client external consulting engagements across the full array of Health & Welfare, Retirement, and HR programs, from scoping and diagnostic through recommendations and implementation. Own engagement quality, economics, and client outcomes.
• Strategic Advisory: Serve as a trusted advisor to senior client stakeholders, including CHROs, Benefits leaders, and CFOs, translating complex analysis into clear, actionable recommendations that drive measurable financial and operational results.
• Project and Workstream Management: Apply the project management discipline of external consulting, including work plans, status reporting, risk and issue tracking, and steering committee updates, to deliver engagements on scope, on time, and on budget.
• Vendor Management: Apply the tenets of vendor management to the HR supply chain, including carriers, TPAs, PBMs, retirement recordkeepers, and HR systems providers. Lead vendor performance reviews, contract and fee assessments, RFPs, and renewal strategies.
• Plan, Program, and System Advisory: Partner with client stakeholders on the design and management of complex Health & Welfare plans, including the annual benefit plan lifecycle, HRIS, and financial and clinical analysis.
• Forensic and Diagnostic Analysis: Lead hypothesis-driven analysis of HR and benefits documents, claims and financial data, contracts, and processes to identify savings and optimization opportunities, and guide clients through implementation.
• Implementation and Transition Support: Provide project and vendor management during periods of change, such as new vendor implementations, M&A integrations, and carve-outs. Serve as the subject matter expert ensuring all HR and benefits transition elements are completed.
• Compliance Advisory: Advise on compliance matters including plan documents, annual notices, and applicable regulations (e.g., ERISA, ACA, COBRA, HIPAA, and transparency requirements).
• Executive Communication: Develop and present polished, executive-ready deliverables, including findings, business cases, and roadmaps, and support client communication efforts.
• Issue Resolution: Proactively prevent and expedite issue resolution through effective management and escalation.
• Client Relationship Development: Build and deepen long-term client relationships, manage stakeholders across the client organization, and identify opportunities to expand the scope of work and value delivered.
• Practice Development: Contribute to the growth of Optimatum's external consulting practice by shaping methodologies, tools, and service offerings, and by supporting proposals and business development efforts.
• Team Leadership: Manage, coach, and develop analysts and consultants, fostering a high-performance external consulting culture and ensuring quality across deliverables.

Qualifications
• Bachelor's degree required; MBA or other advanced degree a plus
• 7+ years of relevant professional experience with demonstrated expertise in HR and Employee Benefits plans, programs, and vendors, including employer-sponsored healthcare and retirement programs (required)
• Significant external consulting experience, ideally within a Big Four, national benefits, actuarial, or management advisory firm (required)
• Proven track record leading client engagements and workstreams, including managing scope, timelines, budgets, and deliverables (required)
• Prior people management and mentorship experience, including leading engagement teams (required)
• Experience serving as a trusted advisor to senior HR, Benefits, and Finance executives (required)
• Strong structured problem-solving skills and the ability to develop fact-based recommendations from complex data
• Advanced proficiency in Microsoft Excel and PowerPoint, including building financial analyses and executive-level presentations
• Advanced data analysis skills, including experience with claims, financial, and vendor performance data
• Knowledge of project management tools, methodologies, and governance practices
• Ability to communicate clearly, confidently, and persuasively at all levels, both internally and externally
• Proven ability to manage multiple engagements and priorities simultaneously, often on condensed timelines
• Highly detail-oriented with a strong commitment to accuracy and quality, while maintaining a strategic, big-picture perspective
• Executive presence and personal credibility to quickly establish trust with clients
• Experience supporting proposals, business development, or account growth preferred
• Demonstrated integrity and professionalism in all aspects of work
• CEBS designation or pursuit of CEBS preferred

Why External Consultants Join Optimatum
• Lead engagements end to end, with real ownership over client outcomes
• Direct access to firm leadership and a voice in shaping the practice
• Broader scope across Health & Welfare, Retirement, HR Systems, and M&A work
• The rigor of external consulting, with the agility of a growing, entrepreneurial firm

What We Offer
We offer competitive compensation and a generous employee benefits package, including:
• Salary and bonus
• Comprehensive Benefits Program: Medical, Dental, Vision, Life Insurance, STD & LTD
• 401(k) with employer match
• Flexible time off policy, including vacation, personal days, and holidays

Join the Optimatum team in our New York City office in Midtown Manhattan.  This is a hybrid role.
We look forward to discussing this opportunity with you. Please complete the application to start the process.
* The expected base annual salary ranges from $150,000 - $225,000 plus incentive and bonus. Base salary offers are based on a wide range of factors including, but not limited to, relevant skills, training, experience, education, geographic location, performance, travel requirements, revenue-based metrics, any contractual agreements, and, where applicable, certifications and licenses obtained. Market and organizational factors are also considered. In addition to salary and a generous employee benefits package, successful candidates are eligible to receive a discretionary bonus.