Why Most Martech Consulting Engagements Fail
After working as a marketing technology consultant for the past several years — and hiring consultants myself when I was in-house — I've seen the same pattern repeat: companies hire for tool expertise and end up disappointed because the real problem was never about the tool.
Here are the 7 questions that actually matter when choosing a marketing technology consultant.
1. "Have You Been the In-House Person?"
This is the single most important question. A consultant who has only been a consultant doesn't understand the organizational dynamics that make or break implementations.
When I was at PatientIQ, I lived with the consequences of every CRM decision for 3 years. When I built HubSpot for AASM, I had to train 50+ people to actually use it. That's different from configuring a portal and handing over a documentation deck.
What to listen for: Specific stories about living with their own implementations. If they can't name a decision that came back to haunt them, they haven't been deep enough.
2. "What's Your Data Migration Philosophy?"
This question separates the strategic thinkers from the feature configurators. A good consultant will immediately talk about data quality, not timelines.
My answer: Never migrate dirty data. At AASM, we spent 3 weeks cleaning data before we moved a single record to HubSpot. The result was 100% data integrity post-migration. At companies that skip this step, I see 6-12 months of cleanup work that costs far more than the original project.
Red flag: "We can migrate everything in 2 weeks." Speed without a data quality plan is a recipe for expensive rework.
3. "How Do You Measure Success?"
If the answer is "on-time delivery" or "feature completion," that's a vendor, not a consultant. The right answer involves business outcomes.
When I implemented HubSpot at Ambience Healthcare, the measure wasn't "portal configured." It was $2.5M ARR in 30 days. When I rebuilt AASM's CRM, the measure was 1,200% webinar registration growth, not "workflows created."
What to listen for: Revenue impact, pipeline influence, adoption rates, time-to-value.
4. "What Will You Leave Behind?"
The best consultants work themselves out of a job. Ask explicitly: after this engagement ends, will my team be able to run and improve this system without you?
Every engagement I run includes documentation, team training, and a 30-day support window. The goal is self-sufficiency, not dependency. If a consultant's business model depends on you needing them forever, your incentives aren't aligned.
5. "How Do You Handle Scope Creep?"
Every martech project expands. The question is whether your consultant has a framework for managing it or just bills more hours.
Good answer: "We'll identify scope changes together, evaluate the trade-offs, and make a conscious decision about whether to include them now or phase them into a follow-up project."
Red flag: No mention of phasing or trade-offs. Everything is "yes, we can add that."
6. "Who Actually Does the Work?"
At larger consultancies, the person who sells the project is rarely the person who implements it. Ask directly: will you be the person in my HubSpot portal, or will I be handed off to a junior team member?
I'm a solo consultant specifically because I believe the person who designs the strategy should be the person who implements it. Every portal configuration, every workflow, every data migration — that's me.
7. "Can I Talk to a Previous Client?"
Not a testimonial on a website. An actual conversation with someone who has been through a full engagement.
Ask that reference: What went wrong? How did the consultant handle it? Would you hire them again? The answers to "what went wrong" tell you more than any success story.
The Bottom Line
The best marketing technology consultant isn't the one with the most certifications or the slickest proposal. It's the one who understands your business context, has lived with the consequences of their own decisions, and measures success by your outcomes — not their deliverables.
Looking for a marketing technology consultant? [Let's talk](/contact) about your specific challenges. Based in [Chicago](/chicago), available for consulting, fractional, and full-time engagements.