Michael Venman
Sales–Marketing Alignment
January 29th, 2026
7 min

The 5 most Common Challenges CRO's and CMO's Face when joining a new Company

Over the last several years, a large percentage of my work has been with newly hired CROs and CMOs.  Sometimes I’m brought in during their first month.  Sometimes a few months after they start.

Almost always after they’ve had the same realization.  Something like... “This is more complicated than I expected," or "I can't get the reporting that I was used to at my old company."

These leaders are brought in to create change and help organizations go from the "old way" to the "new way."  But... they don't have the time nor the expertise to diagnose what exactly needs to be ripped and replaced.

Different companies. Different tech stacks. Different stages.  

The same patterns show up again and again.  These are the five most common business system challenges I see when new CROs and CMOs walk into an organization — and what’s usually sitting underneath each one.

1. There Isn’t a Real, Shared Definition of the Funnel

Nearly every company I walk into can show me lifecycle stages and Contact Status values inside Salesforce or HubSpot.

Very few can show me a written, agreed-upon definition of:

  • What must be true for a lead to enter each stage?
  • Who has the responsibility of pushing it forward at each step?
  • What data is required and from which system?
  • What metrics we are looking at every day to adjust performance of our gtm plays?

Marketing describes the top of the funnel and attribution (how they get credit) because that's how they are measured

Sales focuses on the deal stages, territory alignment, and routing - but uses different language than Marketing (different cohorts, different qualification stages).

RevOps describes a field value and is into the Solution Design before understanding the "why" behind a project or how we will look at it in 3 months to figure out if something is going well or not.

Finance describes something tied to forecasting, Marketing ROI, Sales ROI, and revenue recognition.  Often again with different cohorts.

All reasonable. None aligned.

From the CRO or CMO’s perspective, this becomes an immediate blocker. You cannot diagnose funnel health if the funnel itself is undefined or leaders are talking past each other because the strategies aren't coordinated.

What most companies have are labels.

What they don’t have is an operational model.

Until that exists, every downstream metric is unstable.

2. Historical Data Looks Impressive but Isn’t Trustworthy

One of the first things new leaders try to do is analyze past performance.

Which channels worked?  Which segments converted?  Which motions produced the best deals?

What they quickly discover is that the data is technically present but logically inconsistent.

Fields changed names.  Stages were repurposed.  Required fields were optional for years.  Automation was partially implemented.  Sales bypassed steps.

Dashboards exist. Reports exist. Charts exist.

Confidence does not.

I routinely watch CROs and CMOs compare three dashboards that all claim to show “conversion rate” and all return different numbers.

At that point, data stops being an input to strategy and starts being a debate.

This is one of the most frustrating moments for new leaders, because they know what questions they want to answer — but they cannot get defensible answers.

If you can understand the historical changes within your systems, you can tell the story of the data.  If you aren't confident in the data, don't present it - fix it.

3. The Tech Stack Was Purchased, Not Architected

Most modern companies have a respectable looking stack:

  • CRM
  • Marketing Automation
  • Customer Service Software
  • Sales engagement Tools
  • Enrichment Services
  • Marketing Attribution visualization tools
  • BI tool (Tableau or Power BI)
  • AI (Clay, N8N, etc...)

On paper, it looks mature.  In reality, each tool was usually added to solve a narrow problem at a specific moment in time.  They were then stranded on an island and only looked at again if something went noticably wrong.  

Entropy... (it's a thing)

The result is a stack that functions, but does not operate as a system.  Status and Stage values (what conversion rates and therefor how a business understands what is working and what isn't) are based off a careful coordination with all these tools.

Especially as new CRO's or CMO's come into a new system environment - pulling apart the system so they can understand takes diligent work that they often don't have time to put together in earnest.  That's a big part that we help out with at The Sales Nerd.

4. Each Team Is Optimizing for Its Own Scoreboard

Marketing hits lead targets. Sales hits meeting or pipeline targets. Customer Success hits retention targets.

Everyone is doing what they are paid to do.

The problem is that those scoreboards were not designed together.

So I see situations where:

  • Marketing celebrates volume while Sales complains about quality
  • Sales celebrates activity while leadership complains about conversion
  • Customer Success retains customers while expansion stagnates

When a new CRO or CMO arrives, they inherit all of this.

They are expected to “create alignment,” but alignment is not a meeting.

Alignment is a system design problem - and not one that is easily solved within the business systems.

Until metrics, definitions, and data structures reinforce the same revenue story, teams will continue to optimize locally.  Only when they develop the revenue plan, have an accepted way of handling all the handoffs to that plan, and do a common plan review as a team (each week looking at the same dashboards to see performance to goal) will the system be aligned.  Anything short of that - there is still work to do.

5. The “Obvious Improvements” Run Into Hidden Constraints within the Business Systems or Operations team

Most new CROs and CMOs come in with clear ideas:

  • “We need better lead scoring.”
  • “We need better routing.”
  • “We need better attribution.”
  • “We need better segmentation.”

They are correct - but these are tactics.  Tactics do not come before defining the goals and the rules of the road.

Once leadership has defined those actions, they still get hung up due to the business system team, or their operations team, not having the system architecture expertise or not being staffed to do anything more than Keeping the Business Running.

What surprises them is how hard these are to implement.  Each tactic comes with a slew of pre-requisites (not unlike a 301 course in college).

  • Better lead scoring requires clean inputs.
  • Better routing requires accurate matching and a territory that is communicable.
  • Better attribution requires consistent stages and adherence to the process.

So improvement initiatives quickly turn into foundational repair projects.

This is often misinterpreted as resistance or slow execution.

In reality, the system simply cannot support the desired behavior yet and the CMO/CRO needs to stand up and make that clear.

The Pattern I See Across All Five

These are not five separate problems.

They are symptoms of one core issue:

The reason why a new CMO or CRO is brought in is to CHANGE the business and evolve it from an old system to a new system.

To this day I haven't heard a new Revenue team leader say - "I got in and everything worked as they said it would... I had the reports I needed to get started on day 1."  

How the Best Leaders I Work With Approach It

The strongest CROs and CMOs I partner with do not start with campaigns or dashboards.

They start with structure.

They insist on clarity around the following so that they can trust what lays underneath.

  • Funnel stages and definitions
  • Entry and exit criteria
  • Data ownership
  • System-of-record decisions
  • Core reporting questions

Only after that do they invest in scoring models, automation, attribution frameworks, and AI.

This sequencing feels slower.

In practice, it saves months and sometimes years.

Final Thought

When I see a new CRO or CMO struggling, it is almost never because they lack skill.

It is because they inherited a system that was built for an earlier version of the company.

Growth does not break because people forget how to do marketing or sales.

Growth breaks because systems lag behind reality.

Fix the system first.

Everything else becomes easier.