Chief Information Security Officer (CISO)

At Swyfft were reshaping the way home insurance and commercial package products are priced and bound. Weve created an insurance experience thats smart instant and designed to deliver unparalleled customer service.

Joining Swyfft means becoming part of a dynamic team of forward-thinkers who thrive on moving fast and delivering exceptional products. We pride ourselves on fostering an environment where creativity and positive energy thrive.

As we continue to grow and expand were on the lookout for experienced professionals like you to join us in transforming the insurance landscape. If youre passionate about leveraging technology to provide the best customer service experience and are ready to be a part of our journey we welcome you to explore opportunities at Swyfft!

About the Position:

Were looking for a CISO who can do two things exceptionally well: build and run a robust security compliance program AND do hands-on technical security work. This isnt a role where youll spend 100% of your time on PowerPoint and vendor questionnaires (though there will be some of that). Youll be reviewing architecture working with our development team on secure design and making real technical decisions.

The immediate challenge: Were transitioning from a limited exemption to full NYDFS (23 NYCRR 500) compliance with our first full certification due April 2026. Youll be building our compliance program while also establishing long-term security practices that actually make us more secure not just check regulatory boxes.

The Reality of Year 1

We want to be transparent: The first year will be challenging. Youll be:

• Building the TPSP governance program from scratch (we have a lot of vendors)
• Getting us ready for our first full NYDFS certification (April 2026)
• Overseeing MFA implementation across thousands of users
• Documenting and formalizing security practices were already doing

Its going to be a mix of rewarding technical work and necessary compliance grinding. After Year 1 the job shifts more toward proactive security work architecture reviews and continuous improvement.

If you want a CISO role where you only do compliance paperwork this isnt it. If you want a role where you only do technical security with zero regulatory work this also isnt it. But if you want to build a security program thats both compliant AND actually makes the company more secure - and you want to stay technical while doing it - this might be perfect.

*This position is a 100% remote U.S. based opportunity that can be based in one of the following states only: AL AZ FL GA KY LA MA MO NC NJ NY OH OR PA SC TX UT VA WA WI.

Some travel for day-to-day work team meetings and training will be required.

Key Responsibilities: (What youll be asked to do)

• Security Program & Compliance (40-50% in Year 1 30% ongoing)
  • Own Swyffts cybersecurity program end-to-end including NYDFS compliance
  • Build and manage our Third-Party Service Provider (TPSP) security governance program (vendor inventory risk assessments security questionnaires ongoing monitoring)
  • Conduct annual risk assessments and coordinate penetration testing
  • Create and maintain security policies incident response plans and business continuity documentation
  • Prepare annual board reporting and regulatory certifications
  • Manage security awareness training program
  • Coordinate incident reporting to NYDFS when required (72-hour notification window)
• Technical Security Work (50-60% in Year 1 70% ongoing)
  • Oversee implementation of multi-factor authentication (MFA) across our web platform (currently in planning phase)
  • Review and improve security architecture for our C#/.NET applications and infrastructure
  • Work directly with engineering teams on secure development practices and code review for security issues
  • Manage vulnerability assessments and coordinate remediation with engineering
  • Design and implement security controls and monitoring capabilities
  • Evaluate and implement security tooling (SIEM vulnerability scanning etc.)
  • Respond to security incidents and conduct post-incident analysis
  • Review API security authentication/authorization patterns and data protection controls

The Successful Candidate: (What were looking for)

• Pragmatic security mindset: You understand the balance between security and business needs
• Self-starter: You can build a program from the ground up with limited hand-holding
• Technical credibility: Engineers respect your technical opinions and will listen to your guidance
• Efficient with compliance work: You can motor through vendor questionnaires and policy documentation without it consuming your life
• Clear communicator: You can explain security risks and recommendations to non-security people without drowning them in jargon
• Comfortable with ambiguity: Were building this program - you wont have a playbook to follow
• Strongly Preferred
• Specific experience with NYDFS 23 NYCRR 500 compliance
• Background in financial services or insurance industry
• Experience implementing authentication systems (OAuth SAML MFA)
• CISSP CISM or similar security certification
• Experience with cloud infrastructure security (AWS Azure or GCP)
  

Some Requirements:

• 7-10 years in information security with a mix of technical and compliance work
• Experience with regulatory compliance programs (NYDFS SOC 2 PCI-DSS HIPAA or similar frameworks)
• Strong technical background - you should be comfortable reviewing C# code understanding web application architecture and discussing database security
• Proven track record building security programs not just maintaining existing ones
• Experience working with remote/distributed engineering teams
• Excellent written and verbal communication skills (youll be explaining security decisions to both engineers and executives)
  

Education:

• A Bachelors degree in Computer Science Computer Engineering or equivalent work experience is required.

Computer Skills:

• You dont need to be a full-stack developer but you should be able to:
• Read and understand C# and Typescript code well enough to spot security issues
• Review system architecture diagrams and identify security concerns
• Understand web application security (OWASP Top 10 authentication flows API security)
• Work with SQL databases and understand data protection requirements
• Evaluate security tools and integrate them into development workflows
• Were a MS Office environment (Outlook Word Excel Powerpoint)
• Experience using video and chat technology (MSTeams & Slack)
  

Other:

• Reliable high-speed internet connectivity required.
• Designated quiet work from home space.

The typical base pay range for this role across the U.S. is: $200000.00 - $220000.00 per year benefits.

There is a different range applicable to specific work locations. This salary range is a good-faith estimate of what Swyfft may pay for this position at the time of posting. Actual compensation may vary based on skills qualifications and experience. The range reflects annual compensation (as applicable) and does not include bonuses or other incentives that the company may choose to pay at its sole discretion.

In addition to base compensation Swyfft offers a comprehensive benefit package.

We Have a Great Benefits Package!

• Medical Dental and Vision
• Short- and Long-Term Disability (Company Paid)
• Voluntary Long-Term Disability
• Employee Life & AD&D (Company Paid)
• Voluntary Employee Spouse and Child Life & AD&D
• Healthcare Dependent Care and Transit FSA and Healthcare Savings Account (HSA)
• 401K with a generous matching contribution and no vesting schedule
• 20 days of PTO annually (prorated based on hire date)
• Company Paid Holidays and 2 Choose Your Own Holidays

It is the policy of Swyfft to provide equal employment opportunities to all employees and applicants for employment without regard to race religion color ethnic origin gender gender identity age marital status veteran status sexual orientation disability or any other basis prohibited by applicable federal state or local law. EOE/AA/M/D/V/F.

If you require accommodations during the application or interview please contact Human Resources at and we will make every effort to accommodate your needs.

Please Note: Swyfft is not accepting 3rd party agency resumes for this position please do not forward resumes to our careers email address or Swyfft employees. Swyfft will not be responsible for any fees related to unsolicited resumes.

Required Experience:

Chief