Becoming a CFO Whisperer & Revenue Architect (Allison Metcalfe, CRO @ Zenoti)

The CRO as Therapist: How to Build Executive Relationships That Actually Work

It’s planning season, which means a lot of you are in the middle of disagreements you can’t seem to resolve.

CMO wants one thing. CFO wants another. CPO is chasing a different priority entirely. And you’re stuck in the middle, trying to get resources for a plan that feels increasingly like a fantasy.

Here’s what I’ve learned from watching dozens of these situations unfold: The revenue leaders who win aren’t the ones with the best spreadsheets (that helps though). They’re the ones who’ve built enough trust and credibility to actually influence decisions.

This week I sat down with Allison Metcalfe, CRO at Zenoti, to unpack this exact challenge. Allison has one of the more unconventional paths to the CRO seat; she spent her first decade in customer success before moving into revenue leadership at LiveRamp, Demandbase (CRO), and Cloudinary (CRO).

When I asked around about her superpowers, the same theme emerged repeatedly: she’s exceptional at managing executive relationships.

In an era where CROs are increasingly becoming systems architects rather than quota-crushers, this skill might be the most important one we’re not talking about.

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1. Everyone is already weighing in so you might as well let them

Early in her career, Allison attended a three-day workshop with Liz Wiseman, author of Multipliers, that fundamentally changed how she thinks about leadership.

Allison had just been promoted and was about to take over a distressed team at Jigsaw (Salesforce’s first acquisition). Her original plan was to fly to Spokane, present her vision, and tell everyone not to worry because she had a plan.

After the workshop, she ditched the entire presentation.

“I went up to Spokane and put everyone in a room with a whiteboard and a marker and facilitated a discussion. One of the biggest tenets of Multipliers is that everyone’s weighing in on what you’re doing as a leader, whether or not you’re inviting them to. They’re at the bar after your presentation, talking about your plan, what you don’t get, what they think is stupid. So you may as well give them the opportunity to weigh in and hear them out—because they’re doing it anyways.”

This isn’t just about being inclusive. There’s a psychological mechanism at work here called the endowment effect where people naturally value things more when they’ve invested time and effort into creating them.

When your team sees their language, their ideas, and their concerns reflected in your plan, they’re exponentially more likely to execute it with conviction. Our job isn’t to create pretty plans. It’s to drive behavior change. And behavior change starts with ownership.

There’s a 360-degree assessment in the Multipliers framework that asks a devastatingly simple question: On a scale of 1-10, how much of your intelligence do you use working for [your manager]? (I asked my People Business Partner to add this to our engagement survey structure immediately after I recorded with Allison).

If you work for what Wiseman calls a “diminisher,” you’re probably not using much of your brainpower because why bother thinking when someone’s just going to tell you what to do anyway? But if you work for a multiplier, you know you’ll be expected to bring answers, not just problems.

The question I’d challenge every leader to ask themselves: Are your people using 80% of their intelligence, or 40%?

2. Advocacy and inquiry: The two-part framework for productive disagreement

One of the most practical tools Allison shared is something her executive coach, Lesly Higgins, taught her: the framework of advocacy and inquiry.

Advocacy means showing your work. When you present a decision or recommendation, walk people through how you got there: “I started here, made this assumption, looked at this data, and ultimately landed here.”

Inquiry means asking others to do the same. Instead of assuming someone’s position is crazy, ask: “Can you help me understand how you got there?”

This sounds simple, but most executive teams are terrible at it. We jump to conclusions, build narratives about what our peers “really” think, and end up talking past each other for months.

The magic of this framework is that it creates space for productive disagreement without triggering defensive reactions. When you show your work, you give people specific points to push back on: “Actually, I don’t agree with assumption three—can we unpack that?”

That’s infinitely more useful than the vague objection you’d get otherwise.

A critical caveat: Allison was quick to point out that this doesn’t mean consensus-driven decision-making. That doesn’t scale.

“You have to be clear: this is not a democratic vote. I’m soliciting feedback, I’m curious, but ultimately it’s my decision. You’ve got to create space to hear people out without being beholden to the opinions of the entire group.”

3. The CFO relationship: Run toward the discomfort

If there’s one executive relationship that makes or breaks CROs, it’s the one with finance.

Allison’s approach is extremely powerful: lean in hard, even when it feels unnatural.

“I often find where I’ve been successful is by doing that which feels most unnatural. Run toward the discomfort and embrace it. I try to bring finance along with me wherever I go. I’ll invite my FP&A partner to leadership team meetings. I don’t want there to ever be a perception that I’m trying to hide anything.”

This goes beyond transparency. It’s building such deep partnership that your CFO could defend your plan to the board without you in the room. But here’s the part that many revenue leaders miss: this requires financial literacy on your side.

I’m often surprised when revenue leaders reach out for advice because their CFO is pushing back on something, and when I ask basic questions ”What’s the LTV:CAC of this channel?” they don’t know. How can you have credibility in that conversation if you don’t understand the financial language?

Allison framed trust using a formula I hadn’t heard before: Trust = Competence + Caring.

The caring part is about demonstrating that you genuinely care about the financial health of the business, not just your sales number and comp plan. The competence part is about being able to have substantive financial conversations through unpacking cells, explaining the numbers behind the numbers.

One more insight that’s worth noting: different CFOs care about different things. At one company, it was all about EBITDA. At another, sales and marketing as a percentage of revenue. At the next place? ARR per employee.

“I want to know what you care about, and I’ll optimize for that.”

4. How to navigate planning season logjams

With 2026 planning in full swing, a lot of leaders are stuck in exactly the kind of disagreement Allison and I discussed. Her framework for working through these impasses is practical and immediately applicable.

Guard Rails and Conditions for Ignition

When proposing new investments (which are always scary, especially if it’s something new), Allison structures the conversation around three zones:

• Green Zone: We’re comfortable. The investment is working as expected.

• Red Zone: Something’s off. We need to pause, pivot, and reevaluate.

• Ignition Conditions: It’s exceeding expectations. Time to double down.

This framing does two things. First, it shows you’re not being a cowboy—you’ve thought about what happens if this doesn’t work. Second, it creates shared ownership of the decision. You’re asking the CEO, CFO, and CPO to agree upfront: “If it hits this threshold, we keep going. If it hits this threshold, I’ll stop.”

Present Trade-offs, Not Ultimatums

The other critical move is articulating what doesn’t happen if you don’t get the investment.

“I do think we as CROs don’t have that conversation as well as we should. We’re talking a lot about ‘I need this to do this.’ But you also need to say: ‘If this is not here, this can’t happen. This is what’s at risk.’”

This isn’t about creating fear or manipulation. It’s about presenting complete options rather than demands.

And here’s the key: you can’t be attached to a specific outcome. The moment you’re pushing “my way or the highway,” you trigger psychological reactance—that automatic resistance people feel when their freedom of choice is threatened. Instead, come in with genuine options and let the trade-offs speak for themselves.

5. The Sasha Fierce Principle: Developing your Alter Ego

Toward the end of our conversation, Allison shared something unexpected on how she handles the emotional weight of executive feedback using what she calls the “Sasha Fierce principle.”

“When I first got more senior and was getting into tough conversations... the feedback gets harder and harder the more senior you get. No one really says ‘great job’ anymore. I read this thing about Beyoncé—someone asked, ‘You always say you’re so shy, but then you’re on stage.’ And she said, ‘That’s not Beyoncé. That’s Sasha Fierce.’ When she reads things about herself, she’s not reading about herself—she’s reading about this other alter ego.”

This resonated deeply with me. I’m actually reading Todd Herman’s book The Alter Ego Effect right now (he’s coming on the podcast soon). Herman built the Black Mamba alter ego with Kobe Bryant and has worked with athletes like Roger Federer and Cristiano Ronaldo on the same concept.

The idea is simple but powerful: develop a professional persona that is you but not you. It creates psychological distance from criticism and allows you to perform at a higher level in high-stakes situations.

Allison has fully embraced this—even naming her car Sasha Fierce.

“Develop a persona that’s the professional version of you. It helps you be a little bit tougher.”

What Separates Good CROs from Great Ones

I asked Allison what she thinks separates a good CRO from a truly great one. Her answer was deceptively simple:

“A great CRO really cares about the customer. A good CRO really only cares about sales efficiency. A great CRO cares just as much about CSAT as they do about win rate.”

This tracks with something I’ve been thinking about a lot lately. The best revenue leaders think holistically about enterprise value, not just their number and comp plan. When you only optimize for your own metrics, everything eventually falls apart.

The other piece of advice that stuck with me was about horizontal growth versus vertical growth—something Allison learned from, of all people, Sherry Redstone:

“If you’re ambitious and want to grow, too many people are focused on climbing up. But the great people really focus on going wide. The higher up you get, the more valuable it is to have a broader perspective on the business and not just your thing.”

This is the opposite of what most ambitious people do. We’re taught to specialize, to go deep, to become the expert in our domain. But at the executive level, that myopia becomes a liability.

The Bigger Picture

What I took from this conversation is that the CRO role is evolving. Personal sales acumen matters less than systems thinking, architectural capability, and—critically—the ability to build trust across the executive team.

Allison put it bluntly: “I don’t think I’m the best salesperson at Zenoti by far. My skills are in my architectural way of thinking and the fact that I always think about the entire customer journey.”

As AI continues to transform how revenue gets acquired, this shift is only going to accelerate. The CROs who win will be the ones who can think like revenue architects, collaborate genuinely with their peers, and navigate the complex human dynamics of executive leadership.

That’s less about closing deals and more about opening relationships.

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