Questions to ask before you hire a RevOps agency

Most buyers walk into a RevOps agency sales call planning to listen to their pitch instead of asking questions. They let the agency run the meeting, nod along, and ask far fewer questions than they should. But that kind of passivity is exactly how the wrong agency gets hired. Businesses that end up with a mismatched partner rarely choose from bad options. They just don't know how to spot the right ones because they aren't asking the right questions. We’ve sat on the other side of these conversations for years, watching prospects focus on surface-level details while the questions that actually matter go completely unasked. That's why we created this guide: to arm you with the exact questions you need to take control of the conversation and find the right partner.

Who will actually be doing the work?

Ask to meet the team who'll work on your account, before you sign anything.

Get this settled before you sign, because it's usually where the trouble starts. What happens too often is a prospect meets with the founder or owner of an agency, someone who clearly knows RevOps inside and out, and walks away feeling confident enough to sign. Then the ink dries and the client gets handed off to someone junior, often overseas, with weak project management skills and a communication style that leaves them re-explaining their own business every week. It happens more than you'd expect. Before you sign anything, ask to meet the actual team who will be doing the work, not just the person who closed the deal. If an agency won't arrange that, treat it as an answer in itself.

Have they done this exact project before?

Ask for a project just like yours, and get the name of the person who ran it.

Take your actual project list into the call and go through it with them, one item at a time. Don't accept a general "yes, we can do that." Ask specifically whether they've handled this exact type of project, ask to talk to the person who led it, and ask them to walk through how it was solved step by step, including what went well and what didn't. If a CPQ implementation is on your list, say so directly and press for specifics. Agencies get vague when they haven't actually done the thing being asked about, and without that pressure, the gap usually doesn't surface until you're the one funding their first attempt at it.

What does success look like, and what does failure look like?

Ask them to name their own top three reasons this could fail.

Every agency can tell you what winning looks like. Fewer can describe, honestly, what a bad one looks like, and that gap is where the useful information sits. This approach borrows from Charlie Munger, who worked alongside Warren Buffett for decades and made a habit of thinking backward from failure instead of only forward from success. Ask what a successful 90-day engagement looks like (a strong answer sounds like becoming a raving fan, leaving a five-star review, referring the agency to others), then ask them to name the top three reasons the engagement could fail. A thoughtful agency will point to real risks: the client going dark, a merger disrupting the relationship, a new VP of Sales coming in and changing priorities. An agency that brushes the question off or insists nothing could go wrong hasn't examined its own failure modes, which means those failures will surface on your project instead.

What does their communication cadence actually look like?

Get their exact communication cadence in writing before you sign.

Every agency says they communicate well, right up until they don't. Push for the specifics behind that claim. A solid standard looks like a weekly call at minimum, a dedicated Slack or Teams channel with daily back-and-forth, a daily update posted in that channel, and a weekly recap email that reaches both the key stakeholders and the people doing the day-to-day work. Ask a prospective agency to lay out their cadence in that level of detail. If the answer is vague, something like "we hop on calls whenever you need" or "we mostly work over email," that tells you something important about whether their working style fits your team.

What do they need from you as the client?

Ask exactly what they need from you, in hours and access, before day one.

Agencies rarely bring this up on their own. It's easier to say "don't worry, we'll take care of everything" than to ask you for time up front. Every engagement needs something from the client side: a certain number of hours from your team each week, access to specific tools, introductions to the right people internally. If that isn't clearly laid out before the contract is signed, it tends to surface mid-project, usually at the worst possible moment. Push the agency to name what they need from you, not just what they'll deliver in return.

Who are their best clients, and who are their worst?

Ask what their best clients have in common, and their worst.

Watch how they answer this one as closely as what they say. Ask what their most successful clients have in common, then ask the same about the ones that didn't go well. If the best clients all turn out to be car dealerships and the company asking is B2B SaaS, that's a sign of a mismatch, no matter how many five-star testimonials get shown along the way. And if an agency claims nothing has ever gone wrong, that's not honesty, that's a dodge. A candid answer sounds specific: engagements tend to struggle, for example, when a client is under five million in revenue, hasn't found product-market fit yet, and isn't ready to run a CRM the way RevOps requires. That's not a knock on the client, just a mismatch that no amount of good execution changes. A prospect already well past that threshold knows immediately the concern doesn't apply to them. Listen for that kind of specific, honest answer, and treat a vague one as a signal.

Are they strategic or technical, and which do you need?

Ask them to call themselves strategic or technical.

Every agency leans one way or the other, and both are fine, as long as it's the one you actually need. A technical agency executes well when the client already knows precisely what to build, down to the workflow and field level. A strategic agency is the better fit when something is clearly broken but the fix isn't obvious yet: redesigning a commission structure from scratch, planning territory assignments, preparing an executive team for a board meeting, or figuring out where the company actually stands on RevOps maturity in the first place. Ask directly where an agency's strengths lie. An agency built for technical execution will struggle if what's actually needed is help figuring out the plan before anyone touches a workflow.

Have they worked with a company like yours?

Ask how many clients your size, stage, and ownership they've actually worked with.

Every agency ends up with a niche, whether they planned for one or not. One might be excellent with legal tech companies, another with edtech, logistics, or healthcare, and it's worth finding out where a given company fits inside that specialty. Ask how many similar clients an agency has worked with, and press for specifics: employee count, revenue, ownership structure. This question carries extra weight for private equity backed companies. A portfolio company has more riding on getting RevOps right than most, since the numbers feed directly into board reporting, valuation conversations, and eventually a due diligence process where messy data becomes somebody else's problem to untangle. That calls for a partner who has actually worked with an Operating Partner before, not one guessing at what that relationship requires. The same logic holds for VC-backed companies scaling fast, or public companies with reporting obligations most agencies have never had to work inside of. Ask the question plainly, and ask how those specific engagements went.

Are their certifications and partnerships real?

Ask for certifications by name, not a logo on their website.

Here's a pattern worth watching for: an agency lists both HubSpot and Salesforce on its website, implying equal depth in each. Meet the team, though, and they're often excellent at HubSpot with one person in the back who touched a Salesforce project five years ago, at a different company. The fix is simple: ask specifically whether the team holds current certifications in the CRM being used, not whether the agency broadly claims familiarity with it. Extend the same question to the rest of the stack. For tools like Chili Piper, Gong, Clay, Marketo, Webflow, Claude, or Incycle, ask whether the team is certified or holds an official partnership, not whether one person on staff has used it before. There's a real difference between a team that's built workflows in a tool dozens of times and one where somebody once poked around in it.

How do you spot a bad agency before you sign?

Ask to talk to a current client in your industry, no exceptions.

The fastest tell is how quickly they hand you a name. A confident agency hands over a name without hesitation and says to ask them anything. One that hesitates or gets defensive about a reference request is communicating something, whether it means to or not. Check reviews on the HubSpot partner portal, the Salesforce partner portal, and G2Crowd, and ask specifically to speak with a current client in a similar industry or situation. A genuinely good agency won't find any of that hard to arrange.

Bring this list into the next conversation with a RevOps agency and watch which questions get welcomed and which ones cause hesitation. You'll know which kind of agency you're dealing with before they finish answering.

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