Senior Director of Sales

Century Support Services, LLC; Northern (KY); Hybrid; USD 180,000 - 260,000; Full time

Job summary

Century Support Services, LLC is seeking a Senior Director of Sales to lead enterprise sales strategy, operating model, and performance infrastructure, driving enrollment growth and client outcomes.

As a senior business partner to the executive team, you will translate growth objectives into scalable systems, disciplined execution, and measurable financial results.

Qualifications

• 10+ years of progressive sales leadership experience including senior-level ownership of strategy and performance infrastructure.
• Proven ability to build executive-level forecasting, capacity planning, and cross-functional decision-making.
• Experience in regulated, high-consideration environments preferred.

Responsibilities

• Define the enterprise sales operating model, including contact strategy, channel execution, sales technology, staffing, leadership cadence, and performance infrastructure.
• Own profitable growth strategy by managing CAC, contribution margin, sales productivity, lead quality, and channel-level economics.
• Lead quarterly and annual planning to identify forecast, capacity, margin, and execution risks early.
• Lead through Sales Managers by setting the leadership operating system for coaching, performance inspection, accountability, escalation management, and execution.

Skills

Enterprise sales strategy

Financial acumen

Sales technology & operations

Data-driven leadership

Leadership of leaders

Cross-functional governance

Ethical growth orientation

Executive communication

Education

10+ years of progressive sales leadership experience

Experience leading leaders and scalable sales management systems

Job description

The Senior Director of Sales is an enterprise-level sales leader responsible for Century’s sales strategy, operating model, and performance infrastructure. This role owns profitable enrollment growth across contact strategy, sales operations, technology enablement, enrollment quality, compliance alignment, and downstream client outcomes.

Serving as a senior business partner to the executive leadership team, this leader translates growth objectives into scalable systems, disciplined execution, accountable sales leadership, and measurable financial results.

DUTIES AND RESPONSIBILITIES

1. Contact Strategy & Sales Execution

• Define the enterprise sales operating model, including contact strategy, channel execution, sales technology, staffing, leadership cadence, and performance infrastructure.
• Set standards for speed-to-lead, channel mix, dialer strategy, workforce planning, sales playbooks, qualification frameworks, and compliant sales execution.
• Partner with Business Development and Marketing to align lead strategy, enrollment capacity, lead quality, CAC expectations, and company growthobjectives.
• Use executive-level reporting and cohort analysis toidentifytrends, improve execution, and guide decisions across rep, team, channel, and organization-level performance.
• Lead sales transformation initiatives that improve scalability, execution discipline, and organizational readiness for growth.
• Own the enterprise standard for enrollment quality and customer fit, ensuring growth is measured by volume, retention, client experience, compliance outcomes, and program performance.
• Create governance and feedback systems across Sales, Operations, Client Services, Quality Assurance, Compliance, and Finance to align sales strategy with downstream outcomes.
• Reduce fallout, early churn, rescissions, complaints, and quality issues through stronger qualification standards, disclosure practices, and leadership accountability.
• Connect sourcing, sales behavior, management practices, and incentive design to measurable post-enrollment business results.

3. Budgeting, Forecasting & Capacity Planning

• Own the sales budget, including headcount, compensation investment, technology spend, vendor partnerships, productivity assumptions, and return on sales investment.
• Build executive-ready forecasts and capacity models tied to lead supply, channel performance, staffing, productivity, service capacity, quality constraints, and margin expectations.
• Partner with Finance and executive leadership to evaluate growth scenarios, investment trade-offs, margin implications, and resource allocation decisions.
• Use sales, financial, workforce, and operational data to adjust staffing, spend, targets, incentives, and leadership priorities.
• Lead quarterly and annual planning toidentifyforecast, capacity, margin, and execution risks early.

4. CAC Management & Unit Economics

• Own profitable growth strategy by managing CAC, contribution margin, sales productivity, lead quality, and channel-level economics.
• Set guardrails for acceptable CAC, channel mix, lead quality, profitability thresholds, compliance risk, client fit, and operational capacity.
• Evaluate CAC payback, contribution margin, channel efficiency, and enrollment quality by source to guide sustainable scale.
• Partner with Marketing, Finance, Operations, and executive leadership to improve unit economics, ROI, enrollment quality, and revenue growth.

5. Team Leadership & Performance Management

• Lead through Sales Managers bysettingthe leadership operating system for coaching, performance inspection, accountability, escalation management, and execution.
• Build a high-accountability culture rooted in leadership ownership, transparency, ethical selling, disciplined performance management, and Century’s Core Values.
• Govern compensation and incentive structures to align behavior with enrollment quality, compliance retention, client outcomes, and sustainable unit economics.
• Strengthen leadership capability,successionreadiness, talent planning, onboarding, ramp expectations, and scalable team structure in partnership with HR.
• Oversee systemic resolution of QA failures, complaints, escalations, and compliance concerns through root-cause analysis and durable corrective action.

KNOWLEDGE AND ESSENTIAL SKILLS

• Enterprise sales strategy: defining scalable growth strategy, operating model, and performance infrastructure
• Financial acumen: managing budgets, forecasts, CAC, margin, and investment trade-offs
• Sales technology and operations:leveragingsystems, analytics, and process design to scale performance
• Data-driven leadership: using funnel, cohort, quality, and post-enrollment metrics to guide decisions
• Leadership of leaders: building manager capability, accountability, and succession readiness
• Cross-functional governance: aligning Sales, Marketing, Finance, Operations, QA, and Compliance
• Ethical growth orientation: embedding quality, compliance, customer fit, and sustainable unit economics
• Executive communication: presenting insights, risks, and recommendations to senior leadership

EDUCATION AND/OR WORK EXPERIENCE

• 10+ years of progressive sales leadership experience, including senior-level ownership of sales strategy, performance infrastructure, and revenue outcomes; experience in regulated, high-consideration environments preferred.
• Proven experience leading leaders, building scalable sales management systems, and developing a strong bench of sales leadership talent.
• Demonstrated ability to build executive-level forecasting, capacity planning, operating rhythms, and cross-functional decision-making processes that connect sales performance to companywide financial and service outcomes.

Any equivalent combination of experience, education, and training that provides the required knowledge, skills, and abilities.