Head of Consulting & Brokerage

Benbase•Bartlett, IL

15h•Remote

About The Position

Benbase is seeking a Head of Consulting & Brokerage to lead and scale the consulting and brokerage operations of the company. This senior leadership role reports directly to the President and Co-Founder and is responsible for the strategy, performance, and execution of client consulting, brokerage services, and carrier/vendor relationships. The ideal candidate will provide day-to-day leadership to ensure Benbase's continued growth with operational rigor, market credibility, and an exceptional client experience. This role involves setting the direction for client advisory, carrier negotiations, and building a scalable service model that integrates human expertise with AI tools. The Head of Consulting & Brokerage will act as a strategic partner to the Co-Founders, a coach to consultants and account leaders, and the senior voice on complex client relationships. This is an opportunity to build the kind of brokerage the candidate has always wished to work for.

Requirements

10+ years of progressive experience in employee benefits, brokerage, consulting, or agency leadership
Senior leadership experience within a brokerage, consulting firm, or benefits practice
Active life and health insurance license
Bachelor's degree in a business-related field
Deep knowledge of employee benefits consulting and brokerage — plan design, funding approaches, renewals, underwriting, carrier strategy, and client advisory work
Proven track record building, scaling, or running a book of business, practice area, or brokerage operation
Strong commercial judgment across client, financial, and relationship dynamics
Executive presence and exceptional written and verbal communication that build credibility internally and externally
Proven success leading high-performing teams and developing strong leaders in a fast-paced, growth-oriented environment
Ability to build structure, improve processes, and drive accountability without creating unnecessary complexity
Fluent use of technology, automation, and AI to improve operations and service delivery
Self-motivated, dependable, and committed to the highest ethical standards

Nice To Haves

Candidates will be based in San Francisco or the surrounding area (preferred for a remote position)

Responsibilities

Own the overall direction, performance, and success of Benbase's consulting and brokerage business, aligning the practice with company strategy, growth goals, and service standards.
Translate company priorities into clear initiatives, decisions, and expectations for the team, serving as a trusted strategic partner to the Co-Founders and senior leadership.
Provide executive-level oversight on client strategy, plan design, renewals, funding approaches, carrier negotiations, and complex benefits issues.
Serve as the senior advisor on high-impact client relationships, shaping recommendations that balance client needs, market realities, and long-term value.
Act as the senior escalation point on complex client, carrier, and service matters, sustaining retention, deepening strategic relationships, and identifying opportunities for account growth.
Lead Benbase's approach to brokerage strategy, including carrier relationships, vendor partnerships, underwriting philosophy, market positioning, and solution design.
Build and sustain strong partnerships with carriers and key vendors, staying ahead of market, legislative, and compliance developments.
Guide renewal and market review strategies to ensure recommendations are competitive, credible, and aligned with client goals.
Lead, mentor, and develop the consulting and brokerage team, setting clear performance expectations and fostering a culture of ownership, sound judgment, collaboration, and excellence.
Coach team members to strengthen strategic thinking, client leadership, and decision-making.
Partner with senior leadership and HR on organizational design, hiring, succession planning, and capability building.
Partner with leadership across the business to align consulting and brokerage work with broader company priorities.
Collaborate closely with account management and operations to ensure a seamless client experience.
Contribute to company strategy with insights on market direction, client needs, growth opportunities, and organizational readiness.
Help shape how Benbase differentiates itself as a modern, high-value employee benefits partner.
Design and strengthen workflows, standards, and operating rhythms for consistency, quality, and scalability.
Ensure strong execution across client deliverables, renewals, financial reviews, carrier negotiations, and internal coordination.
Leverage technology, automation, and AI-enabled tools to improve efficiency, insight, and the client experience.
Establish performance indicators to track the performance of the team, clients, and the business.