Senior Director, Sales Operations & Analytics

Summary

Join Olo, a leading SaaS platform in the restaurant industry, as a Sr. Director, Sales Operations & Analytics. You will lead and optimize sales functions, overseeing operational efficiency and driving improvements in analytics, compensation, systems, and renewals. This hands-on role involves process optimization, collaboration with senior leadership and cross-functional teams, and strategic planning. You will report to the SVP, Sales and can work remotely from anywhere in the U.S. or at Olo’s NYC headquarters. The ideal candidate possesses extensive experience in sales operations, strong analytical skills, and proficiency with Salesforce and other sales tools. Olo offers a competitive salary and comprehensive benefits package.

Requirements

• 10+ years of progressive experience in sales operations, with at least 5 years in a hands-on leadership role
• Experience with Deal Desk, Renewals, Sales Compensation, and Sales Systems in a technology or high-growth environment, B2B SaaS experience strongly preferred
• Excellent analytical and quantitative skills used to translate data and trends, along with market and customer insight, into the execution of a clear selling strategy
• Demonstrated success operating in a cross-functional environment and delivering outcomes, with the ability to influence and work across departments
• Proficiency with Salesforce with excellent analytical, reporting, data manipulation, dashboard creation and business intelligence skills

Responsibilities

• Lead and develop a high-performing Sales Operations team
• Focus on optimizing current processes and systems to improve operational efficiency, sales effectiveness, and scalability by Identifying and implementing minor but meaningful improvements
• Work to reduce friction in the sales cycle and remove bottlenecks where possible, streamlining key operational workflows
• Collaborate with senior leadership to align sales operational strategies with overall business goals, ensuring the sales team is fully supported and equipped to succeed
• Work with Sales, Finance, Legal, and Customer Experience teams to ensure seamless execution of sales initiatives and cross-functional alignment
• Through collaboration with Sales Leadership, drive the strategy and execution of capacity planning, productivity review, market segmentation, territory carving, quota/incentive design, and headcount allocation
• Manage, develop & deliver sales performance reports, dashboards, and KPIs, and share key metrics & actionable insights for executive and board-level reporting to drive measurable improvements
• Ensure sales forecasts and performance metrics are accurate and aligned with business goals, working closely with the sales team to track results
• Drive the design and execution of sales compensation plans that align with business goals and drive motivation across the sales organization
• Oversee compensation processing, ensuring accurate and timely processing of commissions, incentives, and performance tracking
• Assess the effectiveness of compensation structures and make data-driven recommendations to optimize them for sales performance
• Oversee the Deal Desk function to ensure timely and effective deal structuring and approvals
• Oversee the Renewals process, ensuring smooth execution and effective customer retention strategies
• Work closely with sales and customer-facing teams to streamline deal and renewal workflows, focusing on impactful process optimizations
• Lead the development and optimization of CPQ (cost price quote) & sales systems and related sales tools, ensuring that they remain user-friendly and effective (including Salesforce, Clari and Copilot, Zoominfo, Linkedin SalesNav, and more)
• Focus on driving efficiencies through system improvements, integrating sales tools where needed, and enhancing data quality

Preferred Qualifications

• Strong knowledge of other sales and BI tools like Clari, Tableau, Domo, etc
• Strong problem-solving skills with a focus on execution, continuous improvement, and optimizing existing systems and processes

Benefits

• 20 days of paid time off
• 10 separate sick days
• 11 holidays, plus year-end closure
• Health, dental, and vision coverage for yourself and your family
• A 401k match
• Remote-office stipend
• Company equity
• A generous parental leave plan
• Volunteer time off
• Gift matching policy
• Remote work