In the last six months, we've all watched hundreds of businesses try to adopt AI, and what I've learned is simple: we're living through the Oregon Trail of modern business. AI is the new frontier, and most teams are preparing for the journey with the wrong map, the wrong wagon, and no guide.
Everyone wants the opportunity on the other side, but the path between here and there is uneven, unpredictable, and not at all what the sales brochures promised. Nowhere is the confusion more intense than in sales operations, where the pressure to move faster collides with uncertainty about tools, data, risk, integrations, and impact.
Recently, I reviewed over 250 questions submitted during a broad audience AI webinar. The questions painted a vivid picture — not of curiosity, but of real operational pain:
"How can we automate follow-ups in Pipedrive?"
"Can AI summarise our sales calls and update the CRM?"
"What's the safest way to connect GPT to HubSpot or Dynamics?"
"How do we prevent AI from hallucinating and damaging customer trust?"
"Can AI read a PDF purchase order and create a sales order in NetSuite?"
"What do we need to get right before we even start?"
These aren't marketing questions. They're operations questions from leaders who know AI has value, but also know it can break things if implemented badly.
Why AI in Sales Ops Feels Like the Wild West
In the mid-1800s, thousands of settlers stood on the edge of the frontier with the same problem businesses face today. They wanted the opportunity, were told it was easy, packed wagons full of tools, and believed they could "figure it out on the way." Most of the danger wasn't visible until they were already in trouble.
AI adoption follows the same pattern. Bad data is like dysentery. Poor workflow design? That's your broken axles. Wrong tools mean lost oxen. Shadow IT is the bandits. Rushed implementation is crossing rivers at flood stage, no governance means waking up to a ruined wagon, fragmented systems are the mountains blocking your path, and lack of readiness is winter arriving too early.
The pioneers who crossed successfully did one thing differently: they didn't travel alone. They hired guides who knew the terrain—guides who didn't promise a fancy wagon or the latest equipment, but promised safe arrival.
Modern AI Needs the Same Thing: Guidance, Not Guesswork
Every company today is experimenting with AI, but very few are operationalising it. Why? Because AI isn't just a tool—it's a system-level capability that depends on clean data, a coherent sales workflow, well-defined handovers, CRM hygiene, documented customer processes, consistent follow-up rhythms, clear risk and compliance boundaries, and team buy-in.
Most businesses don't have these foundations nailed, which means adding AI on top simply magnifies the chaos. That's why the most valuable questions from real sales teams right now aren't "Which AI model is best?" or "Should we use ChatGPT or Claude?" The real questions are:
These are the questions of pioneers deciding whether to cross the frontier — and looking for someone who has travelled the ground before.
The Four River Crossings Every Sales Team Must Navigate
After working with mid-sized NZ and Australian companies, I keep seeing the same four AI "river crossings." These are the strategic choke points that determine whether AI becomes a breakthrough or a breakdown.
1. Follow-Up Automation — Most revenue isn't lost at the top of the funnel, it's lost in the middle. AI can turn inconsistent follow-up into a reliable, automated, documented system.
2. Call Summaries → CRM Updates — Salespeople hate typing notes. Leaders hate that reps don't type notes. AI bridges the gap, if the underlying process is sound.
3. Document Understanding & Sales Order Creation — Every company wants PDF in, validated data out, sales order created. It's achievable, but only with data readiness and guardrails in place.
4. CRM Hygiene & Workflow Integrity — AI cannot fix a broken process. CRMs with missing fields, outdated data, or inconsistent usage will choke every advanced capability.
These four areas are where businesses need guidance, not tools.
The Right Question Isn't "Should We Use AI?" It's "Are We Ready?"
Before you build workflows or connect models or automate anything, you need an honest assessment. Is your sales workflow clearly defined? Is your CRM populated consistently? Do reps follow a predictable process? Are your tools integrated or siloed? Is your data accurate enough to trust? Do you have policy and governance in place? Are your leaders aligned on what good looks like? Do your salespeople understand how AI fits responsibly into their day?
This is the single biggest blind spot in the market right now: companies adopt AI before they evaluate their readiness, and the implementation fails because the foundation is shaky.
That's why I've created a readiness survey specifically focused on AI in sales operations, not generic "AI maturity." It's based directly on the questions real businesses are asking today and gives you a clear picture of where you're strong, where you're exposed, which workflow to automate first, which risks to mitigate, and whether now is the right time to move.
Take the AI Sales Operations Readiness Survey
Before you automate anything, understand where you stand. This short diagnostic will help you assess workflow readiness, CRM/ERP integration maturity, data quality, team capability and adoption barriers, compliance/safety risks, and your fastest wins.
👉 Take the AI Sales Ops Readiness Survey --> Take the Survey
Final Word
We're in the early days of a new frontier. The opportunity is huge, but so is the risk of choosing the wrong path. You don't need another AI tool, another hype-filled workshop, or another wagon salesman. You need a guide who understands the terrain, the dangers, the timing, and the systems that must work together for AI to deliver real value in sales operations.
That's what Fractional Direct does. And if you're ready to explore what's on the other side, it starts with readiness.