Vice President of Sales

Job Description

The organization is entering an important phase of its growth. It has meaningful customer relationships, an established broker ecosystem, a broad addressable market, and significant opportunity to expand its market position. The company is focused on building the commercial engine required to translate these assets into consistent, profitable growth.

We are seeking a VP of Sales, reporting directly to the Chief Executive Officer, to lead this effort. This individual will own the full growth strategy and execution, including sales, broker and channel development, marketing and demand generation, customer growth and retention, product commercialization, and revenue operations.

The immediate mandate is to stabilize and strengthen the existing business while building a more disciplined, scalable growth engine. The VP of Sales will shape the company's go-to-market strategy, growth organization, and operating model, with a significant opportunity to influence the trajectory of an established business.

Key Responsibilities

Lead the Growth Organization

• Own the growth agenda and accountability across the customer lifecycle, from market development through sales, onboarding, expansion, renewal, and retention.
• Establish and manage the operating cadence, including weekly pipeline and forecast reviews, seller performance management, monthly business reviews, and clear KPIs.
• Set priorities and focus resources on the opportunities that matter most.
• Build a culture of accountability, transparency, urgency, customer focus, and measurable performance.

Rebuild the Sales Engine

• Lead the sales organization and drive consistent execution across territories, sellers, and channels.
• Implement disciplined pipeline management, qualification, forecasting, territory management, and performance management.
• Evaluate talent, fill critical roles, strengthen onboarding and coaching, and establish clear goals for every seller.
• Build sales capacity and improve productivity and time-to-productivity.
• Partner with Finance and HR on territory and compensation structures aligned with market opportunity.
• Transition toward a segmented coverage model across field sales, inside sales, account management, and brokers.

Accelerate Broker & Channel Growth

• Make the organization easier and more compelling for brokers to work with.
• Segment brokers by production, potential, and relationship strength, with clear ownership and action plans for priority relationships.
• Grow the number and productivity of active producing brokers and improve opportunity creation and quote-to-close conversion.
• Build a systematic approach to broker activation, engagement, and relationship management.
• Develop the business case for national accounts, strategic partnerships, and additional channels as the growth engine matures.

Build a More Effective Demand Generation Engine

• Consistently generate qualified opportunities in the right markets.
• Partner with Marketing on target audiences, priorities, channel strategy, and investment levels.
• Track lead sources, funnel conversion, acquisition economics, and marketing effectiveness.
• Connect marketing investments to qualified pipeline, new customers, and revenue, reallocating resources toward the highest-return channels and programs.

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 Win

• Partner 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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