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Senior Sales Operations Analyst

Direct Supply · Milwaukee, WI · Full time

Posted Sep 8, 2026 · We last checked this listing on Oct 6, 2026

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Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

Tell me about an analysis you did that led leadership to change a sales program. How did you show ROI?

What they are checking: Whether their work drives measurable decisions, which the posting stresses with ROI.

How do you present findings differently to senior sales leaders versus frontline sellers?

What they are checking: Communication range across audiences, a skill the posting calls out.

Tell me about a time you took on leadership within a team without having formal authority.

What they are checking: Readiness for the leadership responsibilities the role may add.

What would you do

A top seller says the new comp plan is unfair to their territory. How do you respond?

What they are checking: Ability to take field concerns seriously and test them with data while staying neutral.

You notice seller activity is up but revenue is flat. How do you dig in?

What they are checking: Analytical curiosity that looks past activity metrics to what actually drives results.

About the work

Walk me through how you would design or review a sales compensation plan so it drives the behavior leadership actually wants.

What they are checking: Understanding that comp plans shape seller behavior and can produce unintended results.

How would you approach territory planning for a sales team covering senior living communities?

What they are checking: Ability to balance workload, opportunity and fairness when drawing territories.

What CRM administration have you done, and how did you keep data quality high enough to trust the reports?

What they are checking: Hands-on CRM ownership and awareness that insights are only as good as the data sellers enter.

Where have you used AI or automation to make sales operations work faster or more accurate?

What they are checking: Practical application of technology to reduce manual reporting and analysis.

How would you build the sales budget for next year, and who would you involve?

What they are checking: Understanding of budgeting inputs and the need to align finance, sales leaders and operations.

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The full job description

As published by Direct Supply.

Position Summary: Direct Supply is building the future of healthcare technology with industry-leading products, solutions and platforms to help improve the lives of millions of seniors and those who care for them. In the Senior Sales Operations Analyst position, you’ll drive efficiency and effectiveness across core sales operations, including budgeting, sales compensation, territory planning, and CRM administration. You’ll analyze key sales programs, providing leadership with data-driven insights to enhance seller performance and activity. Collaborating closely with the Team Manager and Senior Sales Leadership, you’ll proactively identify challenges within the sales organization and recommend high-impact solutions with measurable ROI. Additionally, you may take on leadership responsibilities within the team to support strategic initiatives and operational excellence. Skills Needed: • Applies AI and Technology - Identifies opportunities to boost efficiency and add value using AI and tech. Embraces and applies digital innovations and tech solutions to build business. Eagerly learns and integrates new technologies where they matter most. • Communicates Effectively – Develops and delivers impactful communications for diverse audiences across channels. Excels in both small and large group interactions. Captures attention, actively listens, and guides discussions towards targeted goals. • Provides Customer Value - Delivers cutting-edge , tech-driven solutions paired with outrageous customer service with an eye to profitability. Seizes opportunities that reward both the customer and DS, fostering robust customer relationships. • Solves Problems - Uses technology and sharp logic to craft inventive solutions to complex issues, digging deep to tackle root causes. Conducts impartial analysis, leaving no stone unturned for comprehensive insights. • Experience using ChatGPT, CoPilot, or other Generative AI tools What You’ll Do and Impact: • Administer and optimize sales processes and systems, including CRM, by leveraging AI and technology to improve sales effectiveness. • Collaborate with senior sales leaders and sales operations partners to define and calculate variable seller compensation on a monthly and quarterly basis. • Utilize data analytics to support sales leadership in designing and optimizing sales territories for maximum impact. • Lead the annual sales budgeting process for designated sales groups. • Leverage AI tools and customer insights to identify opportunities for conversion, retention, and market growth. • Partner with sales leadership and sales operations teams to execute projects that drive revenue, productivity, and profitability. • Translate complex data into clear, actionable insights, presenting recommendations to sales leadership. • Serve as the go-to expert for sales reporting and analytics, providing support on key sales operations initiatives. • Engage in cross-functional collaboration, routinely working with senior management and executive leadership. • Mentor and develop Sales Operations team members, providing training and guidance. • Assist the team manager in prioritizing workload, ensuring efficient execution of key initiatives. Experience: • Bachelor’s degree in Business , Mathematics, IT, Engineering, or a related STEM field. • 4-6 years of experience in sales operations or a related analytical role. Additional Items of Interest: • External certification in related field or advanced degree. • Prior experience in a customer-facing sale s role. • Familiarity with Microsoft Dynamics CRM Software. • Knowledge of Python, R, or other statistical programming languages. Job to be performed in the location listed. Generous benefit package available. © 2013 to 2026 Direct Supply, Inc. All rights reserved.

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