VP of Business and Digital Transformation

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Orange, CT, US

7 days ago Requisition

Salary Range: $ To $ Annually

The Family Security Plan (FSP) is a leading supplemental insurance distributor in the credit union channel, delivering life, accident, and health protection to members of 60+ credit unions across the United States. Our products are excellent, our members truly need and value them, and we are transforming how we connect, educate and sell across every channel to serve them better.

FSP is transforming to a digital-first operating model, and this role owns that transformation end-to-end. Any business process where digital tooling and AI can materially change how FSP operates is in bounds — sales, marketing, member engagement, HR, recruiting, training, scheduling, payments, back-office, and how we work with our credit union partners. You will redesign how the work actually gets done, built on modern cloud platforms, AI-enabled tooling, and tight integration with our carrier partner, our CRM, and our credit union customers' digital ecosystems.

This is a hands-on role. You will do the work, not just direct it.

• Own the digital and AI transformation of FSP's business processes end-to-end —across sales, marketing, member engagement, HR, recruiting, training, scheduling, payments, and back-office operations. Scope evolves as new priorities surface.
• Put real-time member and prospect data in front of every seller
  and pre-sale connector, seamlessly across all seven of FSP's engagement channels.
• Design and build short-term CRM and payment workarounds
  inside FSP's existing technology stack, resolving current friction while long-term platform work runs in parallel with our carrier partner.
• Own marketing technology adoption and its integration
  with FSP's sales channels and CRM, including TCPA-compliant texting and outreach on behalf of and with credit union partners.
• Lead the transformation of FSP's Member Engagement channel
  — AI-enabled targeting, better inbound demand generation, materially restructured economics.
• Modernize FSP's internal operating tooling
  — HR/recruiting/training systems, sales and BD scheduling, payment follow-up — replacing manual processes with automated, AI-supported workflows.
• Define and deliver the integration path
  between FSP's products and services and credit union banking apps and digital platforms.
• Lead and grow FSP's internal development capability,starting with a Senior Full-Stack Developer hired to your specification.

• 8–10 years leading business systems adoption, marketing technology, and digital innovation — with direct hands-on responsibility for redesigning end-to-end business processes.
• Strong grounding in sales, marketing, or distribution operations — you understand what technology must do at the point of human interaction with a customer or member.
• Financial services, insurance, fintech, or credit union background strongly preferred. Familiarity with CU digital platforms or core banking integration is a plus.
• Demonstrable experience integrating marketing technology with CRM and sales channels, and comfort with modern cloud platforms (Microsoft Azure/365, AWS, or comparable).
• Daily fluency with AI tools — AI coding assistants, AI-powered prototyping, LLM-based workflow tools — as your own working practice and as a strategic lens for what FSP should build, adopt, or automate.
• Technical depth sufficient to assess architecture, write specifications, evaluate developer work, and make credible build-vs-buy decisions independently.
• Communication and presence to represent FSP credibly in credit union executive conversations and partner working sessions.

• Direct experience with credit union banking platforms, digital-banking integration, or supplemental benefits distribution.
• Track record delivering TCPA-compliant messaging programs at scale.
• Prior experience as the senior-most digital or transformation voice in a company of $50M–$150M scale.