Questions You Should Be Asking
Internal recruiters and external headhunters are in full force.
They reach out non-stop offering up the moon: “send me your resume, we’ll skip the process you can speak with the CRO directly”. I get 20 inbounds like this… every month.
There are REAL questions you should ask, aside from “how much?” and “which tools do we have?”.
Eventually I ask questions about the condition of the revenue engine but first I think about things like:
the role and my responsibilities
the company and its culture
the current state of the department
how hiring works in the Org
Let’s get specific.
Here are 20 questions any Head of RevOps should ask before joining a firm.
About the Role & Responsibilities
What are the specific goals and objectives for the RevOps team in the first year?
What are the key performance indicators I'll be measured against?
What is the current state of the RevOps tech stack and what are the plans for future investment?
What is the size and structure of the RevOps team, and what are their individual roles and responsibilities?
How does the company define success for the RevOps function and the Head of RevOps role?
About the Company & Culture
What is the company's overall growth strategy and how does RevOps contribute to it?
What is the company's approach to data-driven decision-making?
What is the level of executive sponsorship for RevOps initiatives?
How is cross-functional collaboration between RevOps, Sales, Marketing, and Customer Success fostered?
What is the company's approach to employee development and career growth?
About the Current State of RevOps
What are the biggest challenges currently facing the RevOps team?
What are the areas of opportunity for improvement within the RevOps function?
What is the current state of data quality and integrity within the organization?
What are the existing processes for lead management, opportunity management, and forecasting?
What is the level of automation currently in place across the revenue operations process?
About the Hiring Process & Compensation
What is the timeline for the hiring process and when can I expect a decision?
What is the compensation and benefits package for the role?
What are the opportunities for professional development and training?
What is the company's approach to work-life balance?
What are the next steps in the interview process and who will I be meeting with?
By asking these questions you gain a comprehensive understanding of the role, the company, and the current state of the RevOps function, enabling you to make an informed decision about whether the opportunity is the right fit.
But I have more questions. Specifically, about the revenue engine. I could ask questions like these all day:
What are the biggest bottlenecks in the sales process?
What are the biggest challenges facing the marketing team?
What are the biggest challenges facing the customer success team?
What are the biggest challenges facing the RevOps team?
What are the biggest opportunities for improvement in the revenue engine?
What are the key performance indicators that are used to measure the success of the revenue engine?
How is the revenue engine currently performing against its KPIs?
What are the biggest risks to the revenue engine?
What are the biggest threats to the revenue engine?
What are the biggest opportunities for growth in the revenue engine?
Ask how the last big “revops project” went… did it receive support from on-high, was all the work ripped out and replaced for some reason, etc…
Before you commit to joining an org, ask to speak with the previous admin. I like to speak to the last 3, especially if there is a high turnover rate (tenure 2 yrs or less).
I’ve heard:
“that’s confidential”
“we can’t reach them”
“goes against our policy”
If THEY can ask YOU for references… you can check their references.
You can go on LNKD and search for the company’s name in the Prior slot, go find ex-employees with your title or the org’s CRM in their description (all SF people mention SF, same thing with HS) and reach out directly.
Ask those same questions from above again.
If the answers are very different 🚩
If they are under a hefty do-not-disclose agreement 🚩
Revenue engineers, revenue operations leaders, go-to-market technologists and specialists… these are the most valuable skillsets and responsibilities in 2025 and beyond. Be selective about who you work with.
You have earned that right.
Know what you are stepping into before you suit up.
You can use these questions as you move into new situations. Now you have your eyes open. You are fully armed with a high-quality 3D picture of the department, the revenue engine and the broader org.
All from asking the right questions.
👋 Thank you for reading Mastering Revenue Operations.
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I started this in November 2023 because revenue technology and revenue operations methodologies started evolving so rapidly I needed a focal point to coalesce ideas, outline revenue system blueprints, discuss go-to-market strategy amplified by operational alignment and logistical support, and all topics related to revenue operations.
Mastering Revenue Operations is a central hub for the intersection of strategy, technology and revenue operations. Our audience includes Fortune 500 Executives, RevOps Leaders, Venture Capitalists and Entrepreneurs.