Senior Director of Sales

Century Support Services• US,

About The Position

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.

Requirements

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: leveraging systems, 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
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.

Nice To Haves

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.
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 growth objectives.
Use executive-level reporting and cohort analysis to identify trends, 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.
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 to identify forecast, capacity, margin, and execution risks early.
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.
Lead through Sales Managers by setting the 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, succession readiness, 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.