Senior Director of Sales Operations

About Us: Medical Guardian and MobileHelp, a Medical Guardian brand, are leading consumer healthcare service brands, providing connected health and safety solutions for aging-in-place. With high-performing inside sales teams across two brands, we are scaling our ability to acquire, serve, and retain members through innovative technology, a strong performance culture, and a relentless focus on the customer. We are seeking a Sr. Director of Sales Operations to partner with our Chief Sales Officer in building the next generation of our sales engine. This leader will own sales technology, process design, analytics, reporting, enablement, and compensation administration. The role is critical to ensuring that our 100+ sales reps and managers are enabled, supported, and equipped to achieve their goals. --- Role Overview: The Sr. Director of Sales Operations will be responsible for designing, implementing, and managing the infrastructure that powers sales performance. This includes oversight of CRM systems, reporting dashboards, workflow processes, and training and enablement programs. This role requires both a strategic mindset and hands-on execution, ensuring sales leadership and frontline managers have the insights, tools, and support to maximize productivity and deliver predictable results. --- Key Responsibilities: Sales Technology & Systems Management: Serve as the business owner for the sales technology stack, including CRM (Salesforce or equivalent), dialers, call analytics/QA platforms, workforce management tools, and reporting dashboards. Evaluate, recommend, and implement new tools such as AI-powered coaching, call scoring, or automation platforms to increase rep productivity and improve conversion rates. Ensure system adoption across all sales teams through training, support, and process reinforcement. Partner with IT and vendors to manage integrations, data flows, and troubleshooting. Sales Process Design & Optimization: Map and document all inside sales workflows from lead intake through member onboarding. Identify bottlenecks and inefficiencies, and lead process improvement initiatives. Standardize lead distribution, call flows, objection handling, and escalation paths. Design and maintain sales playbooks that outline best practices for reps and managers. Partner with Marketing, Retention, and Member Services to align lead management and ensure a seamless customer journey. Reporting, Analytics & Forecasting: Develop and maintain executive dashboards that provide visibility into KPIs such as cost per sale (CPS), lead-to-close conversion, rep productivity, and revenue performance. Deliver weekly and monthly reporting packages for the Chief Sales Officer, Finance, and senior leadership. Support the Sales team with team-level insights to drive accountability and coaching. Own forecasting processes to ensure accurate projections of sales performance. Conduct deep-dive analyses on lead sources, call outcomes, and win/loss patterns, and translate findings into actionable recommendations. Training, Coaching & Sales Enablement: Design and oversee onboarding programs for new reps, including system training, product knowledge, call flow certification, and shadowing programs. Partner with the CSO to identify skill gaps among reps and managers, and develop targeted training programs to close those gaps. Create ongoing learning content such as playbooks, best practice guides, and call scoring rubrics. Implement QA processes and monitor call recordings to ensure consistent execution and identify coaching opportunities. Introduce role-specific training for Sales Managers to elevate their ability to coach and develop their teams. Strategic Projects & Cross-Functional Alignment: Lead cross-functional projects that impact sales, such as new product launches, pricing adjustments, or new channel development (e.g., healthcare partnerships). Serve as a liaison between Sales, Marketing, Operations, and Finance to ensure alignment on goals, performance tracking, and execution. Partner with Marketing to evaluate lead quality and optimize lead routing and nurturing strategies. Provide data-driven support for executive decision-making on investments in new markets or sales models. Team Leadership & Administration: Ensure reporting, comp tracking, and administrative tasks are completed efficiently. Build and mentor a small but high-impact operations team as the function grows. Foster a culture of continuous improvement and accountability. Ensure clear communication and collaboration to balance people management with operational excellence. --- Qualifications: 7+ years of experience in Sales Operations, Revenue Operations, or Sales Enablement, with leadership responsibility in high-volume inside sales environments. Strong knowledge of CRM systems (Salesforce preferred) and related sales technology tools. Proven ability to design and optimize sales processes that scale. Deep analytical skills; able to interpret complex data and present actionable insights. Experience managing sales compensation plans and incentive programs. Excellent collaboration and communication skills, with the ability to influence senior leaders and partner cross-functionally. Demonstrated success in building onboarding and training programs that improve rep performance. Hands-on leadership style; comfortable managing both strategic initiatives and tactical execution. Must be legally authorized to work in the United States without the need for employer sponsorship now or in the future.  --- Why Join Us Opportunity to shape and scale the sales infrastructure behind two nationally recognized healthcare brands. High-visibility role reporting directly to the Chief Sales Officer. Mission-driven culture focused on improving lives and empowering older adults to live independently. Collaborative, entrepreneurial environment where great ideas are valued and implemented quickly. Benefits Health Care Plan (Medical, Dental & Vision) Paid Time Off (Vacation, Sick Time Off & Holidays) Company Paid Short Term Disability and Life Insurance Retirement Plan (401k) with Company Match