How to sell to heads of operations at insurance companies

Cormac Repman
1 day ago
5 min read

Heads of operations at insurance companies are among the most rewarding targets in B2B sales. They control meaningful budgets, own the entire P&L for their operations, and they're genuinely motivated to optimize. But they're also deeply suspicious of vendors.

Here's what I've learned after hundreds of conversations with insurance ops leaders: they're not skeptical because they don't want to buy. They're skeptical because they've been burned by implementations that looked good on a demo but fell apart in production.

Who You're Actually Talking To

A Head of Operations at an insurance company typically owns:

Claims processing and automation

Underwriting workflow efficiency

Compliance and regulatory reporting

Vendor relationships and SLA management

Technology infrastructure and integrations

Cost control (this is critical)

They're 40-55 years old, have 15+ years in insurance, and have seen three generations of software fail. They're not impressed by pitch decks. They're impressed by people who understand their actual workflow.

The insurance ops leader sits between the C-suite and the claims floor. They get pressure from above on margins and from below on workload. They're literally the person responsible when something breaks.

Why Cold Outreach Actually Works Here

Insurance ops leaders don't get a lot of inbound. They get vendor calls from the same 20 vendors they already know. Most outbound is noise.

This is your advantage.

When you reach an ops leader with a specific observation about their operations, you land differently. You're not generic. You're not Fortune 500 sales spam.

I've tracked roughly 28% connection rates on first-call attempts to insurance ops leaders when you use the right angle. That's substantially higher than SaaS industry averages. But only if you know what angle to use.

Research Before You Call

This is where most reps fail. They call and immediately pitch.

Before you dial, find three specific things:

1. Their current tech stack

Look at their LinkedIn (who did they hire in the last 18 months?), check job postings (what skills are they hiring for?), and pull their annual report or 10-K if they're public. Insurance companies file detailed technology infrastructure data. You'll learn what vendors they use, which systems they're struggling to integrate, and sometimes even direct quotes about operational pain.

2. A recent company announcement that relates to your solution

This could be a new compliance regulation in their state, a product launch that expands their book of business, an acquisition, or a rate announcement. You need one recent fact, not old news.

3. A specific operational metric you can reference

If you're calling about claims processing, find their average claims cycle time (often reported in investor presentations). If you're calling about underwriting, find their new business conversion rate. This tells them you're not winging it.

The Opening Call: Sell the Conversation, Not the Solution

Insurance ops leaders will not book a demo. They will book a conversation if you've earned it.

Your first call should accomplish exactly one thing: get a 30-minute call scheduled with them in the next week.

Here's the structure that works:

1. Credibility in the first 10 seconds

"Hi [Name]. I'm with Nurturance, we work with insurers on claims operations. I know you're busy, so I'll be direct: I called because [specific fact about their company or recent announcement]. Do you have 60 seconds?"

2. One specific observation

"We've worked with 40+ carriers, and most are seeing roughly 8-12 days average on routine claims. I noticed [their company] filed a new product launch in Q2. When you're onboarding new business, claims volume spikes before your team is scaled to handle it. Is that showing up in your numbers?"

3. Earn the ask

"I'm not going to pitch you today. What I want to do is understand if this is something you're actually optimizing for right now. If it's not on your radar, I get it. But if claims velocity is a lever you're pulling, it might make sense to talk through what we've seen work. Does that seem worth 20 minutes?"

The goal is consent to have a real conversation, not a sales call.

In the Discovery Call

This is where you actually listen.

Ask about their current state:

"Walk me through your average claims process. Where does it start, and what's the first bottleneck?"

"What's your current cycle time? And what would success look like?"

"What's the gap between where you are and where you need to be?"

"Who would need to be involved if you decided to address this?"

Listen for the real problem, not the stated problem. An ops leader might say "we need faster processing," but the real problem is usually "we can't scale because our underwriters are a bottleneck and we can't hire fast enough." Different solution entirely.

Common Objections and How to Handle Them

"We already have a system in place."

"I get it. Most carriers do. What I find is the system handles routine cases fine, but the complex or manual workflows still drag. Is that showing up for you, or are you seeing pretty consistent throughput across all claim types?"

"We're not looking right now."

"That's fair. This isn't urgent. The reason I called is because most ops leaders we talk to don't realize how much of their time gets lost to [specific inefficiency]. When it matters to you, that's when this conversation becomes valuable. Would it make sense to check back in September when you're planning Q4?"

"You'd need to work with our vendor."

"Understood. And your vendor does a lot. What I've found is vendors optimize for their product, not for what you're trying to accomplish. The best conversations happen when you know exactly what outcome you need, and then you can direct your vendor or your tech team accordingly. That's really what this conversation is about."

"Send me something."

"I can do that, but honestly, it won't mean much until I understand what you're actually trying to solve. What if we spent 15 minutes on a call first, and then I can send you something that actually addresses your situation? Does Tuesday work?"

Why Heads of Operations Buy

They buy when:

They believe you understand their actual workflow

You've shown you work with similar operations

The ROI is clear and specific

Implementation won't blow up their current system

They trust that you'll be responsive if something breaks

You're not selling features. You're selling risk reduction and operational control.

Most insurance ops leaders want to optimize. They just want to work with people who actually understand what optimization looks like at their scale.

If you're selling to insurance operations, this is your lane. You're reaching the person with authority and budget, who genuinely needs what you're building.

At Nurturance, we've run this playbook with 40+ insurance teams. We handle the outreach, qualification, and call scheduling. You focus on the conversation.

If you're a fintech or insurtech founder who needs qualified conversations with heads of operations, let's talk. We work on a pay-per-meeting model through Glencoco, which means you only pay for actual booked calls.

Schedule time with us at cal.com/nurturance and we'll walk through what this looks like for your company.