Most RevOps consulting engagements fail for one of three reasons: the firm sold strategy and delivered slides, the senior person who pitched was not the person who built, or the system was configured without anyone deciding what the business actually needed it to do. This guide is written for CROs, founders, and VPs of Sales in Chicago and the broader Midwest who want to avoid all three.
Revenue Systems Group is based in Chicago and is one of the options you will find. What follows is the evaluation we would want a prospect to run on us.
Start with the problem, not the vendor
Before you take a single call, write down the outcome in one sentence. "Our forecast is wrong every quarter." "Marketing and sales report different pipeline numbers." "Our HubSpot instance is three years of accumulated shortcuts." "We need to move off Salesforce before renewal." A firm that cannot restate your problem more precisely than you did after a 30-minute conversation is not going to fix it.
The two kinds of firms
- Marketing-first HubSpot agencies. Strong on campaigns, content, landing pages, and Marketing Hub. Often weak on CRM architecture, forecasting, and anything touching sales comp or CS handoffs. Fine if your problem is demand generation. Wrong if it is revenue systems.
- Systems-first RevOps consultancies. Built by former sales and revenue operators. Strong on data models, pipelines, lifecycle governance, forecasting, and cross-functional process. Usually less interested in your email templates.
Partner tier badges do not tell you which one you are talking to. Ask what percentage of their work is Sales Hub and CRM architecture versus Marketing Hub. Ask to see a data model they designed.
Questions that expose weak firms
- Who does the work? Get names. If the answer is "our delivery team," ask to meet them before signing.
- Walk me through your last three engagements. You want specifics: company size, the problem, what was built, what changed in the numbers. Vague answers usually mean junior staff or hiding behind NDAs.
- How would you define our lifecycle stages? A real answer involves questions about your sales motion, not a template.
- What would you tell us not to do? Good firms say no to scope. Firms that agree to everything will bill for everything.
- What happens when you leave? Documentation, training, admin handoff. If they cannot describe it, plan on dependency.
- Have you worked with companies like ours? For Chicago and Midwest companies that often means healthcare-adjacent, professional services, manufacturing, or member associations, not just venture-backed SaaS. Regulated data handling and multi-business-unit structures are where generalist firms stumble.
What to ask for in a proposal
- Fixed scope with named deliverables, not hours
- A regular cadence and a named client-side owner
- Clear separation between diagnostic, build, and ongoing support, priced separately
- Explicit statement of what is out of scope
Why local still matters
Remote delivery works for configuration. It works less well for the decisions that stall projects: getting the CRO, CFO, and VP of Marketing to agree on what a qualified lead is, or deciding which of 300 fields survives a migration. A Chicago-based firm can sit in that room. It also helps when the engagement ends and you need to hire a RevOps manager; a local firm knows the market and can help you screen.
Red flags
- A free "audit" that is actually a sales call with a large retainer fee for the audit at the end
- Pricing that is far below market
- Case studies that only cite marketing metrics for a RevOps engagement
- No opinion on your forecasting methodology
How we fit
Revenue Systems Group is a Chicago-based, operator-led RevOps and HubSpot consultancy. We work primarily with B2B SaaS and healthcare-adjacent companies between $5M and $50M ARR, and our work is systems-first: CRM architecture, pipeline and lifecycle design, forecasting, and the cross-functional process that makes the numbers agree. If that is the kind of partner you are looking for, start the conversation.
Quick answers
- What should I ask a RevOps consultant before hiring them?
- Ask who will actually do the work, what their last three engagements looked like, how they define lifecycle stages, what they would say no to, and what happens after they leave. Answers that stay at the strategy level are a warning sign.
- Are there RevOps consultants and HubSpot partners based in Chicago?
- Yes. Chicago has a growing group of independent RevOps consultancies and HubSpot solutions partners, including Revenue Systems Group, alongside larger agencies with local offices. Most serve B2B SaaS, healthcare, professional services, and manufacturing companies across the Midwest.
- Does it matter whether my RevOps consultant is local?
- Less than it used to for the build itself, but it matters for working sessions, executive alignment, and hiring support. A Chicago-based firm can be in the room for the decisions that stall remote engagements.