The role involves leading and optimizing sales operations, enhancing efficiency, and improving processes in analytics, reporting, and sales systems.
Olo is a leading SaaS platform accelerating digital transformation in the restaurant industry, by helping customers deliver more personalized and profitable guest experiences. As a result, our digital ordering, payment, and guest engagement solutions enable brands to do more with less and make every guest feel like a regular.
We’re looking for a Sr. Director, Sales Operations & Analytics to lead and optimize our sales functions by overseeing and enhancing operational efficiency, and driving incremental improvements to key areas of the sales organization, including Analytics & Reporting, Compensation, Sales Systems, and Deal Desk. As Sr. Director, Sales Operations & Analytics, you will take a hands-on approach to optimizing key sales processes, systems, and operational functions.
You will report to the Chief Sales Officer and can work remotely from anywhere in the U.S. or at Olo’s headquarters in NYC.
What You'll Do
- 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.
- Own sales forecasting motion and hygiene to drive accurate pipeline, sales stages, progression, and bookings.
- 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.
- Partner with finance on 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.
- Work closely with sales and customer-facing teams to streamline 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.
Analytics & Reporting
Sales Compensation & Incentives
Deal Desk
Sales Systems & Tools Optimization
What We'll Expect From You
- 10+ years of progressive experience in sales operations, with at least 5 years in a hands-on leadership role.
- Experience with Deal Desk, creation of Sales Compensation plans, 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
- 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.
About Olo
Olo (NYSE: OLO) is a leading restaurant technology provider with ordering, payment, and guest engagement solutions that help brands increase orders, streamline operations, and improve the guest experience. Each day, Olo processes millions of orders on its open SaaS platform, gathering the right data from each touchpoint into a single source—so restaurants can better understand and better serve every guest on every channel, every time. Over 700 restaurant brands trust Olo and its network of more than 400 integration partners to innovate on behalf of the restaurant community, accelerating technology’s positive impact and creating a world where every restaurant guest feels like a regular. Learn more at olo.com.
We’re remote-friendly. Since 2015, we have been evolving our culture to continue to support a more distributed workforce and now over 75% of our team works remotely across the U.S. If you're in the New York City area, you can choose to work remotely or from Olo's headquarters, on the 82nd floor of One World Trade Center.
We offer great benefits, such as 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, and more!
Our best estimate of the compensation range for this opportunity is $153,000 - $209,000 annually, depending on the experience you bring and your location. This role is also eligible for incentive compensation. We look forward to discussing your salary expectations and our full total rewards offerings throughout the interview process.
We encourage you to apply!
At Olo, we believe bringing together people with varied experiences and viewpoints leads to better results. Don't check every box in the job description? Research shows many qualified candidates hold back from applying unless they meet all listed requirements. We're committed to creating a genuine workplace where everyone can contribute their best work—this improves our decision-making and helps us better serve our communities. So if you're enthusiastic about this role but your background doesn't align perfectly with every qualification, we encourage you to apply anyway. You might be exactly the right fit for this or other positions.
All applicants receive consideration for employment. We do not discriminate on the basis of race, religion, color, national origin, gender identity, sexual orientation, pregnancy, age, marital status, veteran status, or disability status.
California Residents: CCPA notice
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