Vice President of Sales

Protect and Grow the Existing Revenue Base: Partner with Account Management and Operations on retention, renewals, service recovery, and expansion. Identify at-risk customers early, establish recovery plans, and assign executive sponsors to critical accounts. Improve the sales-to-onboarding handoff and strengthen coordination among Sales, Account Management, and service teams. Build systematic cross-sell and expansion strategies, managing acquisition, expansion, and retention as one integrated system. Define Where the Organization Can WinPartner with the CEO, Finance, Product, and Marketing to sharpen the ideal customer profile (ICP), priority segments, value proposition, and market priorities. Inform decisions through win/loss analysis, customer and broker feedback, segment economics, competitive intelligence, and pipeline data. Understand acquisition and retention economics by segment and channel, prioritizing growth opportunities with attractive long-term value. Establish clear investment priorities and make disciplined decisions about where the organization should compete and invest.

Strengthen Product Commercialization & Pricing: Partner with Product and Marketing to ensure products are commercially ready at launch. Incorporate customer, broker, and sales input into product strategy and prioritization, connecting product development to growth outcomes. Ensure launches include clear positioning, packaging, pricing, sales and broker readiness, and post-launch performance tracking. Establish disciplined pricing, discounting, and commercial terms that balance growth, competitiveness, and customer economics.

Build the Growth Operating System: Partner with Revenue Operations and Finance to establish a reliable commercial source of truth. Improve CRM discipline, pipeline stages, forecasting, reporting, account ownership, and analytics. Develop a concise growth scorecard for management and the Board. Use data to identify issues early, allocate resources effectively, and improve investment decisions.

Measures of Success: During the first six months, the Head of Growth will be expected to: Establish clear ownership and accountability across the growth organization. Stabilize and strengthen sales coverage across priority territories, brokers, and opportunities. Assess the organization and implement necessary talent and organizational changes. Install a rigorous weekly pipeline, forecasting, and performance-management cadence. Materially improve pipeline quality, CRM discipline, and forecast accuracy. Establish clear performance expectations and development plans for every seller. Improve seller productivity and develop a plan to address critical capacity gaps. Segment the broker base and establish actionable plans for the highest-priority relationships. Increase visibility into broker activation, production, pipeline, and conversion. Establish clear demand-generation priorities and measurement from marketing investment through qualified pipeline and revenue. Partner with Account Management to strengthen retention, service recovery, renewals, expansion, and sales-to-onboarding handoffs. Define priority customer segments, the ideal customer profile, differentiated value proposition, and market priorities. Implement an economically sound territory, coverage, compensation, and pricing model. Establish a growth scorecard and monthly business review. Demonstrate measurable improvement in the leading indicators of revenue growth. Build a fact-based plan for the next stage of profitable growth. Over time, success will be measured through sustained improvement in profitable revenue growth, gross revenue retention, qualified pipeline coverage, win rate, forecast accuracy, broker productivity, seller attainment and productivity, customer expansion, and growth operating discipline.

Requirements: We are seeking a growth leader who has demonstrated the ability to build, transform, and lead high-performing growth organizations. Experience in B2B services, employee benefits, HR technology, healthcare services, insurance-adjacent, or similar broker- and channel-influenced businesses is preferred. The successful candidate will have:

• Significant commercial or growth leadership experience and a track record of measurable, profitable revenue growth.
• Experience inheriting an underperforming or evolving organization and materially improving its performance.
• Experience building or upgrading sales coverage, territories, compensation structures, pipeline management, forecasting, talent, and operating cadence.
• A strong understanding of channel- and partner-led distribution. Experience working with brokers is highly desirable.
• Experience managing new-customer acquisition, demand generation, retention, and expansion as connected components of one growth engine.
• Strong analytical and financial capabilities, including the ability to translate market opportunity, customer economics, and unit economics into resource-allocation decisions.
• Experience partnering across Product, Marketing, Finance, Operations, and Account Management.
• A demonstrated ability to recruit, coach, evaluate, and develop commercial talent.
• Leadership Competencies
• The right leader for this position:
• Establishes a strong operating cadence, inspects the details, follows through, and makes accountability real.
• Understands customers, brokers, sellers, and markets, including what drives customers to buy, stay, grow, or leave.
• Grounds decisions in data and economics, using anecdotal feedback and intuition as additional inputs.
• Gets personally involved in important deals, broker relationships, talent decisions, pipeline reviews, and customer situations.
• Moves effectively between strategy and execution, from defining market opportunities to coaching sellers and redesigning growth coverage.
• Diagnoses issues quickly, makes difficult decisions, leads through significant change with urgency, and addresses persistent underperformance.
• Leads beyond direct reporting lines and aligns Product, Operations, Finance, Marketing, and Account Management around shared growth outcomes.
• Is energized by building a growth organization that is more disciplined, scalable, and effective than the one inherited.
• Demonstrates low ego and high accountability, focuses on outcomes, gives and receives direct feedback, and creates clarity for those around them.
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