Director of Sales Operations

About This Role

Overview

The Director of Sales Operations will lead and optimize the sales operational strategy for our Managed Services business. This role ensures alignment across Sales, Marketing, Finance, and Service Delivery to enable scalability, performance visibility, and predictable revenue growth. The ideal candidate brings a data-driven mindset, process excellence, and experience in recurring-revenue business models within the IT/MSP ecosystem.

Salary: $115,000-$155,000

Key Responsibilities

Sales Strategy & Planning

Develop and implement a unified sales operations strategy that aligns with corporate growth objectives. Partner with the Chief Growth Officer (CGO) and sales leadership to design coverage models, territory plans, and quota frameworks for both “Velocity” (new logo) and “Core” (existing client) teams. Manage forecasting, pipeline analytics, and KPI dashboards to ensure visibility into bookings, renewals, and multi-year managed services growth. Drive pricing standardization, including GM%, TCV, and MRR-based incentive alignment.

Process Optimization

Standardize and document the Lead-to-Cash process; from marketing-qualified lead through renewal. Enhance cross-functional coordination between Sales, Marketing, RevOps, Finance, and Service Delivery. Oversee proposal automation, quoting tools, and approval workflows to improve turnaround times. Create and maintain sales playbooks, templates, and compliance documentation (e.g., E-Rate, SLED bid frameworks).

Systems & Data Integrity

Own the CRM environment (HubSpot, NetSuite, or ConnectWise) and ensure accurate pipeline hygiene, forecast reporting, and stage management. Integrate RevOps intelligence leveraging automation and analytics tools (e.g., Gong, ZoomInfo, LinkedIn Navigator, HubSpot Sequences). Develop dashboards to track activity metrics (calls, demos, meetings, pipeline velocity, conversion rates, etc.). Ensure sales data integrity, audit compliance, and consistent process adoption.

Revenue Operations Alignment

Partner with the Director of Revenue Operations to synchronize sales forecasting with finance and delivery capacity. Support compensation plan modeling, quota assignment, and attainment tracking. Evaluate the success of spiffs, accelerators, and incentive programs through ROI-based analysis. Deliver executive-ready reports for Board and ELT review on sales efficiency and profitability.

Leadership & Enablement

Lead a small team of analysts or coordinators to support reporting, analytics, and system administration. Partner with Sales Enablement to design training, onboarding, and certification programs for Account Executives and Inside Sales. Act as a strategic advisor to leadership, ensuring accountability, transparency, and continuous improvement across the sales engine.

Qualifications

8–12+ years of experience in Sales Operations, Revenue Operations, or Sales Strategy, ideally within a Managed Services Provider, VAR, or IT Services organization. Proven track record of driving forecast accuracy, pipeline hygiene, and operational scalability in a high-growth recurring revenue model. Proficiency with CRM and BI platforms (HubSpot, NetSuite, Salesforce, Power BI, Tableau). Strong understanding of MSP metrics including GM$, MRR, churn, TCV, and sales productivity ratios. Exceptional analytical, financial modeling, and executive communication skills. Demonstrated ability to work cross-functionally with Finance, Marketing, Delivery, and HR. Bachelor’s degree required; MBA or advanced degree preferred.

About Custom Computer Specialists

CCS is a leading technology consulting firm providing best in class solutions to our clients for over 45 years. Expressed simply in our tagline – Right People, Right Results, Right Careers! Our philosophy is, in fact, an obsession that drives our behavior, our culture and our work. It’s why we put tremendous emphasis on hiring individuals that embody the principles that align with our obsession. We continue to successfully provide network integration, support services, products solutions, and applications services to our valued clients in the northeast. Our focus is simple...our goal is to make technology easy and to help our clients use it as effectively as possible.