Skyward Specialty and Sixfold extend partnership to scale AI-driven underwriting
Skyward Specialty Insurance Group has expanded its work with Sixfold to roll out AI-driven underwriting across U.S. P&C lines. Now in its second year, the program has moved well beyond pilot and is live across six business units and more than 10 product lines.
Deployments are moving in eight to ten-week sprints, signaling a practical cadence for teams that need quick wins without upending daily operations. The goal is straightforward: sharper insight, faster responses to brokers, and consistent decisions at scale-without removing underwriters from the loop.
What the platform actually does
- Pre-processes submissions to clean, structure, and centralize data
- Flags prioritization and appetite fit before an underwriter touches the file
- Summarizes risk drivers and pulls supporting context into one view
- Keeps underwriters in control with clear recommendations and audit trails
The intent is to cut cycle time, reduce leakage on appetite, and support faster, cleaner broker interactions. A feedback loop improves recommendations over time while keeping human judgment at the center of decisions.
Why this matters for underwriting teams
- Consistent triage: fewer missed opportunities and cleaner declinations
- Time back: less manual data hunting and email ping-pong
- Stronger broker service: quicker responses and more predictable SLAs
- Traceability: decision rationale and data lineage that stand up to audit
Leadership at Skyward Specialty frames this as disciplined innovation-give underwriters better inputs and more time for the hard calls. Sixfold underscores daily use across teams and the competitive edge that comes from consistency and speed heading into 2026.
Scope and rollout details
The collaboration spans multiple P&C lines and continues to expand. Typical implementation windows run eight to ten weeks per unit, which aligns with practical change management and measurable KPI tracking.
Company context
Skyward Specialty operates through nine underwriting divisions, including captives, professional lines, and surety. Its insurance subsidiaries include Great Midwest Insurance Company, Houston Specialty Insurance Company, Imperium Insurance Company, and Oklahoma Specialty Insurance Company.
These companies hold an 'A' (Excellent) Financial Strength Rating with a 'stable' outlook from AM Best. For reference on rating definitions, see AM Best.
If you're evaluating similar adoption
- Start with one or two product lines where submission volume and data quality support quick wins
- Translate appetite and referral rules into machine-readable guardrails before rollout
- Track before/after metrics: submission-to-quote time, hit ratio, bind ratio, and loss ratio for model-assisted vs. baseline cohorts
- Require explanation, versioning, and audit logs for all recommendations
- Pair the tech with training and change champions inside each underwriting team
For governance, align your internal controls with recognized frameworks such as the NIST AI Risk Management Framework: NIST AI RMF. If your team needs structured upskilling for underwriting, data, and operations roles, explore role-based programs here: AI courses by job.
Bottom line
AI is moving from proof-of-concept to everyday underwriting workflow. Skyward Specialty's approach shows what practical scale looks like: targeted deployments, underwriter-first design, measurable impact, and strong controls.
Expect more carriers and MGAs to follow this playbook-focused on speed, consistency, and better broker service, while keeping the decision maker where they belong: in the underwriting seat.
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