Land and Expand

⏰ Today in 5 minutes or less:

• Fractional CROs are a high-ROI investment that are 100% focused on revenue generation.

• Leading with service, not persuasion, builds trust during the sales process.

• An assessment that looks for common problems in your niche is often a successful way to get in the door with new clients.

How Kristi Gaudioso Diagnoses Revenue Problems in One Hour 

Yes, you can land clients without immediately selling something.  

How? Kristi Gaudioso does it by offering insights first. 

After years of working in Microsoft and other tech companies, she went solo as a fractional CRO. Today, she runs Luminate Consulting – a growing firm that wins clients with a one-hour pipeline analysis and a pilot-in-a-box model. 

In this interview, she breaks down how she got early traction, what makes her entry offer perfect for any business size, and why going from one to two people was the hardest (and most important) jump. 

Watch the full interview here:

A lot of people still think a Chief Revenue Officer has to be full-time and in the office. What does being a fractional CRO look like, and how did you get into it? 

Kristi: People assume CROs need to be fully immersed, leading the team every day. But when you're a fractional CRO, you're not there for everything else – you’re there to execute. 

You come in with a specific mandate: identify what’s broken in the revenue engine and fix it. Since you’re not pulled into all the internal noise, you’re incredibly focused and efficient. 

I didn’t always know this was a career path. My early background was in outbound sales, like most of us. I worked across industries over time until I landed in tech – and that’s where I found my niche. 

I joined Microsoft through an acquisition and stayed for over a decade.

That’s where I built a lot of my capability – working in stretch roles, managing large sales teams, and leading regional sales strategy. It also taught me a lot about go-to-market, positioning, and educating the market – especially when you're launching something entirely new. 

After Microsoft, I worked with several startups and found myself repeatedly drawn to the same kind of challenge: something isn’t working, something is about to scale, or the company needs to figure out how to grow revenue in a way that’s smart and sustainable. 

When I left my last startup, I asked myself: when have I been happiest in my career? 

And the answer was always tied to those moments of building and transformation. That’s when I knew going fractional was the right move. 

You didn’t stay solo for long, because now Luminate Consulting is a team. How did you go from being an independent consultant to building a firm with other salespeople? 

Kristi: It started with the realization that there was a better way to pilot sales strategy. I was embedded with startups and SMBs, and I kept seeing this pattern: leadership would tweak the strategy, and the entire sales team would have to pivot. 

That causes burnout, frustration, and confusion. I thought – what if I could bring in my own sales team to test a new approach before rolling it out? 

And then, the “pilot in a box” model was born. 

Instead of asking a founder to completely rebuild their sales team to try a new idea, I can offer a fractional version of that team: me as the sales manager, plus an AE and a BDR. We test the motion, collect KPIs, and if it works, we pass it to the internal team with real evidence. 

It’s collaborative, not competitive. The goal is never to replace their people – it’s to de-risk the change and speed up the learning.  

As for building my team, the first person was the hardest jump because I had to consider “what takes a lot of my time that I can delegate?” 

I did hire an admin agency at first, but I didn’t have enough to delegate to them. Eventually, the first person I brought on was someone I worked with before. 

He was in between jobs, but I knew he had the right mindset: comfortable with cold calls, coachable, and collaborative. It worked so well that I brought on two more people I’d worked with in the past.  

Everyone I hire has that same DNA: a strong foundation in sales, deep experience, and the ability to adapt quickly. We’re now a team of four, and we’re growing. 

My team has experience in sales, customer success, and marketing, which makes us really flexible. 

One of the things I love about your model is your pipeline analysis – it’s such a smart, no-pressure entry point for clients. Can you walk us through how that works? 

Kristi: The pipeline analysis is a one-hour working session. I sit down with the client – a rep or their CRO – and we walk through their live pipeline. I ask questions about each deal: where it came from, why it’s in that stage, what’s been done so far. And through that conversation, I can usually spot what’s not working. 

What’s wild is that the same types of issues come up again and again. I’ve built a kind of internal playbook because there are maybe 20 common problems that show up in different forms. 

Maybe deals are stalling at the same stage. Maybe reps are chasing the wrong personas. Maybe the qualification process is weak. Whatever it is, it’s usually clear within that hour. 

Clients love it because it gives them immediate insight – and it builds trust. We’re not locking into a six-month engagement right out of the gate. It’s low commitment, but high value. 

And because of that, it often leads to more. 

Once they see how quickly we can diagnose and recommend, they’re a lot more comfortable bringing us in for deeper work. 

What We Can Learn from Kristi Gaudioso: 

1. Productize your way in. A one-hour pipeline analysis has become Kristi’s go-to entry point. By diagnosing issues live and offering immediate insight, she builds trust fast and turns small starts into long-term engagements. 

2. Evolve your offers as you go. Kristi didn’t have a fixed offer set on day one. She let client needs and engagement patterns guide the development of assessments, advisory, and project-based roles. 

3. Sales is service, not persuasion. Kristi succeeds in sales because she leads with curiosity, not pressure. She sees herself as a connector and treats each conversation as a chance to help – not pitch – and pairs that mindset with structured processes she’s refined over time. 

Chart Crimes: A Concentric Nightmare

🚨 Chart crimes! 

If you think pie charts are awful, this concentric ring chart about Australian rules football is bonkers. 

Are they running routes? I don’t know. 

And look at the end points...they don’t even line up.  

Remember, the path to success is paved with continuous learning and embracing fresh perspectives.

Let's stay connected, share ideas, and elevate your consulting business.

Stay curious, friends.

The 2×2 is brought to you by Keenan Reid Strategies

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