How to sell to IT Directors at Insurance companies
IT Directors in the insurance industry are primarily measured on system uptime and security compliance. They respond positively to outreach that clearly addresses how a solution can enhance operational efficiency or reduce downtime. Demonstrating an understanding of their current technology stack and specific pain points, like integration challenges with legacy systems, will prompt them to engage with you.
Written and maintained by the SoloRiff team, who build outbound software and run outbound with it. The figures below are our own: we measured 562 insurance company domains over public DNS on 2026-09-03. Last updated 2026-09-03.
What actually hurts
- system downtime
- legacy system integration
- regulatory compliance pressure
- data security concerns
The playbook
- 01
Identify recent system outages
Use industry news sites and social media platforms to pinpoint insurance companies that have recently experienced system outages or security breaches. Focus on those that are likely seeking immediate solutions to prevent future incidents, as they will be more open to discussions about improvements.
- 02
Target companies adopting cloud solutions
Filter your list for insurance firms that have announced transitions to cloud technologies. These companies are often looking for tools that can integrate seamlessly with their new systems, making them more receptive to solutions that promise improved compatibility and efficiency.
- 03
Highlight regulatory compliance challenges
Craft your messaging around the regulatory pressures faced by insurance IT Directors, particularly in relation to data security and compliance. This specificity will resonate more than generic benefits, as they deal with compliance audits and data protection regulations regularly.
- 04
Address integration with legacy systems
Acknowledge the difficulties insurance IT Directors face when integrating new technologies with legacy systems. Offer insights or case studies that demonstrate how your solution has successfully navigated similar challenges in the past, which can help ease their concerns.
- 05
Follow up after industry conferences
Monitor industry conferences and webinars that focus on insurtech advancements. Send a follow-up email to attendees, referencing specific talks or discussions that align with your solution, as they will likely be in a mindset to explore new technologies after such events.
Can insurance companies even receive your mail?
We measured the DNS of 562 insurance companies, sampled evenly across company sizes, to see how many authenticate their own email. It matters in both directions: a domain that does not authenticate is a domain whose team is used to mail going missing — and if your own domain is in the gap, yours is the mail going missing.
Publishes a DMARC policy of quarantine or reject — the domain actually asks receivers to act on failures.
The gap is the finding: 16.3% of 1–10-person companies against 88.4% of the largest — 72 points apart. Small companies are where the unauthenticated domains are, and small companies are who most cold outreach is aimed at.
Where does your domain sit?
Same three lookups, run live against your domain. Nothing is stored and nothing is emailed to you.
How this was measured
Company domains were sampled within employee-count bands, then queried over public DNS for SPF (TXT at the apex), DMARC (TXT at _dmarc.) and MX. One domain per company, deduplicated. Anyone can reproduce any single row of this with dig.
DKIM is deliberately absent. A DKIM key lives under a selector that cannot be enumerated from outside the domain, so a company with flawless DKIM under a name we did not guess would be counted as having none. That would measure our guess list, not the industry.
Domains with no MX record are excluded rather than counted as failures — parked and redirect-only domains would otherwise drag every figure down and make the result an artefact of the sample.
Sampled within bands, so this describes the population of companies, not of employees: a 10-person company counts once, as does a 10,000-person one. Each band is at least 60 domains; bands below that are not published. Figures are percentages of the sample, not of the whole industry, and we publish no company names — only counts.
Measured 2026-09-03. Re-measured monthly.
The full census across every industry — sortable, with sample sizes, free to reuse under CC BY 4.0.
Subject lines that fit
- Improving system uptime
- Navigating compliance challenges
- Streamlining legacy integrations
Questions
- Why do IT Directors in insurance ignore outreach about new technologies?
- Many IT Directors in insurance are overwhelmed with the constant influx of new technology pitches, especially when they are focusing on urgent issues like system stability and compliance. If the outreach does not directly address these pressing concerns, it often gets overlooked.
- What compliance issues are IT Directors most concerned about?
- IT Directors in the insurance sector are primarily focused on data protection regulations, such as GDPR and HIPAA. They are also concerned with maintaining compliance during technology transitions, as any lapse can lead to significant penalties and damage to their reputation.
- How can I demonstrate value to insurance IT Directors?
- To effectively demonstrate value, tailor your messaging to show how your solution can enhance security, reduce downtime, or streamline processes. Providing concrete examples of past success in similar organizations will help build credibility and trust.
- What triggers an IT Director to consider new technology?
- An IT Director is likely to consider new technology when faced with significant system outages, regulatory changes, or when their current systems cannot support new business objectives. They are also influenced by peer recommendations and industry trends.
Or have it run itself
SoloRiff does every step above on its own — finds the companies, finds the people, writes each of them individually, and handles the replies. Drop your URL and watch it work before you sign up for anything.
Try it on your site