Bestow

Title: VP, Information Technology Location: Dallas, TX Department: Engineering Compensation - $260K – $280K • Offers Equity Job Description: ABOUT BESTOW Life insurance is one of the world's most important products. It's also one of the hardest to build, distribute, and modernize. Bestow exists to change that. Bestow is a leading vertical technology platform serving some of the largest and most innovative life insurers. Our platform unifies the fragmented, legacy value chain, enabling carriers to launch products in weeks instead of years. Carriers choose us to scale and operate at unprecedented speed, powered by AI and automation. Bestow isn't selling policies. We're building the infrastructure that helps an entire industry move faster, reach more people, and deliver on its promise. Backed by leading investors (Goldman Sachs, Hedosophia, NEA, Valar, 8VC) and trusted by major carriers, Bestow is powered by a team that moves with precision, purpose, and heart. If you want to help reimagine a centuries-old industry with lasting impact, join us. Bestow offers flexible remote/hybrid work, meaningful benefits, equity, and substantial growth opportunities. Bestow uses E-Verify to confirm the employment eligibility of all newly hired employees. To learn more about E-Verify, including your rights and responsibilities, please visit E-Verify.gov. ABOUT THE ROLE We are at an exciting inflection point. As we scale our platform and deepen our footprint across the enterprise, technology is no longer just a support function. It's a core driver of how we compete, operate, and grow. We're looking for a Vice President of Information Technology to lead that charge. This is a rare opportunity to step into a high-visibility, high-impact executive role where you will own the full technology infrastructure, business technology, and IT strategy for a fast-growing SaaS company. You will sit at the intersection of business and technology, partnering directly with C-suite leaders and functional heads to ensure our systems, processes, and people are built to scale. Our Environment This is not a traditional IT operation. We run no on-premise servers. Our entire infrastructure is cloud-based, and our predominantly remote workforce operates on Macs. Our core collaboration stack includes Google Workspace, Zoom, Slack, and Claude. We are a technology-forward company that expects IT to operate the same way: modern, automated, and continuously improving. You'll inherit a solid foundation and a capable team of 8. Things work today, but we need to prepare for the next phase. Your job is to bring the executive leadership, process maturity, and strategic vision needed to evolve IT into a world-class function that grows alongside the business. If you thrive in environments where the problems are complex, the pace is fast, and the stakes are high, this role was built for you. WHAT YOU’LL DO Technology Strategy & Roadmap - Define and execute a multi-year IT strategy aligned to company growth objectives, with a focus on scalability, security, and operational excellence. - Serve as a key member of the senior leadership team, advising the CTO and functional leaders on technology investments, risks, and opportunities. - Build and maintain a forward-looking technology roadmap that anticipates business needs and keeps the organization ahead of the curve. Business Technology & Applications - Own the strategy, administration, and optimization of enterprise business systems including CRM (Salesforce), telephony and contact center platforms, productivity suites, and other business-critical SaaS applications. - Partner with functional leaders across Sales, Customer Success, Finance, and Operations to ensure business systems support their workflows, reporting needs, and growth objectives. - Lead the evaluation and selection of a next-generation telephony and contact center platform, with a focus on AI-native capabilities, automation, and modern customer engagement workflows. - Manage vendor strategy, contract negotiations, and lifecycle management for major third-party platforms. Infrastructure & Operations - Oversee all enterprise IT infrastructure including cloud environments, networks, endpoints, and SaaS platforms. - Ensure systems availability, performance, and reliability meet or exceed SLAs across the organization. - Lead IT operations including helpdesk, asset management, vendor relationships, and IT service management (ITSM) processes. Security & Compliance - Implement and operationalize cybersecurity policies and standards set by the CISO, covering identity and access management, threat detection, incident response, and data protection. - Partner with Legal, Compliance, and the CISO to ensure adherence to SOC 1, SOC 2, and other applicable frameworks. - Champion a culture of security awareness across the organization. AI, Automation & Innovation - Be an active daily user of AI tools to improve your own productivity and model AI-forward behavior for the organization. - Drive automation of routine IT tasks including ticket triage, provisioning, access management, and reporting, with the goal of eliminating manual overhead wherever possible. - Own AI cost governance including vendor relationship management, usage tracking, quota management, and reporting to budget owners across the organization. - Evaluate emerging technologies and pilot innovative solutions that provide competitive advantage or cost leverage. - Partner with product and engineering teams to align internal tooling with the company's broader technology vision. Team Leadership & Development - Lead, mentor, and grow a high-performing IT team of 8, fostering a culture of ownership, continuous improvement, and collaboration. - Attract and retain top technology talent, building organizational depth across infrastructure, business technology, security operations, and IT operations. - Establish clear goals, performance standards, and career development pathways for all direct and indirect reports. Budget & Vendor Management - Own the IT budget, driving cost efficiency without sacrificing quality or reliability. - Manage strategic vendor relationships and negotiate contracts to maximize value and minimize risk. - Report regularly to leadership on IT performance, spend, and strategic progress. WHO YOU ARE Experience - 12+ years of progressive IT leadership experience, with at least 2 years in a VP-level or equivalent executive role. - Proven track record leading IT at a SaaS or technology company, ideally through periods of rapid growth or organizational transformation. - Deep hands-on experience with cloud infrastructure (AWS or GCP), enterprise security frameworks, and modern ITSM practices. - Experience owning enterprise business systems (CRM, telephony, ERP) and partnering with business stakeholders on system strategy and optimization. - Experience managing a cloud-native, predominantly remote workforce on Mac endpoints. Leadership & Business Acumen - Demonstrated ability to build, lead, and inspire cross-functional technology teams. - Strong executive presence with the ability to communicate complex technical concepts clearly to non-technical stakeholders. - Strategic thinker who can balance long-term vision with short-term execution and operational demands. - Experience managing multi-million dollar IT budgets and vendor portfolios. Technical Depth - Fluency across enterprise IT domains including networking, cloud platforms, endpoint management, identity and access management, and cybersecurity. - Hands-on, daily experience with AI tools (e.g., Claude, ChatGPT, Copilot) and a strong point of view on how AI should transform IT operations. - Experience with automation platforms and a track record of applying them to reduce manual IT workload. - Experience with modern telephony and contact center platforms, including AI-native and automation-forward solutions. - Ability to evaluate build vs. buy decisions and architect scalable, cost-effective solutions. Mindset & Values - Bullish on AI and automation as a force multiplier for IT teams; sees routine manual work as a problem to be solved, not accepted. - Entrepreneurial and adaptable, comfortable operating in ambiguity and building process maturity where it's needed. - Collaborative and low-ego, with a genuine commitment to serving the business and its people. - Data-driven decision-maker who holds themselves and their team to high standards of accountability. - Passionate about building inclusive, people-first technology organizations. TOTAL REWARDS At Bestow, we’re proud to be awarded for our team members, innovative products, and culture. Our standard benefits include: - Competitive salary and equity based on role - Policies and managers that support work/life balance, like our flexible paid time off and parental leave programs - 100% paid-premium option for medical, dental, and vision insurance - Lifestyle stipend to support your physical, emotional, and financial wellbeing - Flexible work-from-home policy and open to remote - Remote and WFH options, as well as a beautiful, state-of-the-art office in Dallas’ Deep Ellum, for those who prefer an office setting - Employee-led diversity, equity, and inclusion initiatives Recent Employer Awards include: - Best Place for Working Parents 2023 + 2024 + 2025 - Great Place to Work Certified, 2022 + 2023 + 2024 + 2025 - Built In Best Places to Work, 2022 + 2023 + 2025 - Fortune’s Best Workplaces in Texas 2022 + 2023 - Fortune’s Best Workplaces in Financial Services and Insurance 2022 + 2023 + 2024 We value diversity at Bestow. The company will hire, recruit, and promote regardless of race, color, religion, sex, sexual orientation, gender identity or expression, national origin, pregnancy or maternity, veteran status, or any other status protected by applicable law. We understand the importance of creating a safe and comfortable work environment and encourage individualism and authenticity in every team member. Thanks for considering a job at Bestow!

• Own the technical architecture for IPC services, making design decisions that balance speed of delivery with long-term maintainability • Design, build, and operate backend services using Python + PostgreSQL, Go, and a Java-based Drools rules engine • Lead cross-team technical initiatives — coordinate with other Bestow engineering teams to plan and execute integration work across the platform • Drive platform capabilities that scale with Bestow's growing partner ecosystem — new carrier onboardings, product launches, and configuration flexibility • Mentor engineers on the team through code review, design review, and pairing — raise the technical bar without bottlenecking delivery • Ensure production reliability: define SLOs, improve observability, and share on-call responsibility for IPC workloads • Use agentic AI coding tools as a core part of your workflow and help the team adopt effective AI-assisted development practices • Communicate technical decisions, trade-offs, and status clearly in writing — the team is remote-first and async-heavy

• You will be developing core services primarily using Golang and PostgreSQL • We're a startup with a long product roadmap. You will help and accelerate foundational services to scale the output of our product teams. • Resolve issues with previously delivered features. • Write unit and integration tests for code you create. • Peer review code developed by others on your team. • Ensure software is secure, maintainable. • Work with designers, product managers, and other engineers • Encourage automation and continuous improvement.

• Work directly with other engineering teams, product, design, TPM, and external stakeholders to introduce new customer-facing platform features and support/evolve existing products. • Work with a distributed team of engineers–mentoring and driving engineering best practices. • Assist in setting the roadmap for team deliverables in a dynamic environment. • Drive delivery of high-quality product initiatives and engineering improvements. • Work with the team to identify, scope, and schedule improvements to the frontend platform. • Communicate effectively, excelling at explaining complex systems and requirements to non-technical cross-functional partners. • Be very technical and willing to participate in system design, code reviews, incident investigations, and directly contribute code towards team initiatives. • Be data-driven in their engineering management practices, fostering continuous improvement.

• Process Improvement and Automation. You will actively identify repetitive or error-prone workflows and drive automation across our tech stack. Your goal is to ensure our tools are properly integrated and operating as a reliable single source of truth. • Expenditure Ownership and AP Operations. You are the primary lead for all company spend. Every AP invoice, corporate card transaction, and employee reimbursement runs through your review. • Vendor & Internal Stakeholder Management. You are the point of contact for vendors and employees on all things payables. You will resolve billing discrepancies and partner with internal teams to help them understand our expense policies. • Month-End Close and GL Ownership. You own specific, material segments of the GL. You will produce audit-ready reconciliations and workpapers while hitting firm close deadlines. • Audit Support and Internal Controls. You will support the GL Accounting Manager during the annual audit by providing clear support for financial statement positions. • Technical Accounting and Policy Development. You should have the technical foundation to read a standard, apply guidance, and document a position.

• Drive operational excellence across call center operations • Manage and develop Team Leads; establish clear expectations • Analyze call center data to identify trends and gaps • Monitor and improve workflows to enhance efficiency • Own end-to-end onboarding process for new hires • Collaborate with Workforce Management on real-time management and forecasting

ABOUT BESTOWLife insurance is one of the world's most important products. It's also one of the hardest to build, distribute, and modernize. Bestow exists to change that. Bestow is a leading vertical technology platform serving some of the largest and most innovative life insurers. Our platform unifies the fragmented, legacy value chain, enabling carriers to launch products in weeks instead of years. Carriers choose us to scale and operate at unprecedented speed, powered by AI and automation. Bestow isn't selling policies. We're building the infrastructure that helps an entire industry move faster, reach more people, and deliver on its promise. Backed by leading investors (Goldman Sachs, Hedosophia, NEA, Valar, 8VC) and trusted by major carriers, Bestow is powered by a team that moves with precision, purpose, and heart. If you want to help reimagine a centuries-old industry with lasting impact, join us. Bestow offers flexible remote/hybrid work, meaningful benefits, equity, and substantial growth opportunities. Bestow uses E-Verify to confirm the employment eligibility of all newly hired employees. To learn more about E-Verify, including your rights and responsibilities, please visit E-Verify.gov. ABOUT THE TEAMThe Bestow Data Engineering team plays a significant role within the organization, working across the entire company to provide scalable data solutions within the platform and toward integrations with external partners. The data engineering team works closely with internal analytics and data science team members in order to improve data architecture, rapidly prototype, and serve data science predictions. In addition, data engineers work closely with stakeholders, members from product, and engineering to design and launch new systems for extracting, transforming and storing data. You’ll be called upon to improve Bestow’s data reliability, efficiency and quality and will be expected to scale your solutions to the cloud environment of a SaaS company, iterate quickly, and make pragmatic choices around what tools and technologies to adopt. WHAT YOU’LL DOAs a Staff Data Engineer, you will serve as a technical leader and strategic advisor for Bestow's data infrastructure and architecture. You will drive the long-term vision for our data platform while mentoring engineers and influencing technical decisions across the organization. Technical Leadership & Strategy - Define and drive the technical roadmap for data infrastructure, establishing architectural patterns and standards that scale across the organization - Lead the design and implementation of complex, multi-system data architectures that support business-critical operations and enable innovation (data ingestion + export and delivery) - Evaluate and champion adoption of emerging technologies and best practices in data engineering, MLOps, and GenAI - Establish data governance frameworks, quality standards, and operational excellence practices across all data workloads - Drive cross-functional initiatives that require coordination between data, product, engineering, and business teams Architecture & Systems Design - Architect enterprise-scale data solutions for transferring data from first and third-party applications to and from our data warehouse - Design and oversee the development of robust, scalable APIs (REST, GraphQL, gRPC) that enable data access for internal teams and external partners - Lead the evolution of event-driven and API-first data architectures that support real-time data sharing and integration - Leverage Google Cloud (GCP) tools (Cloud Run, Cloud Functions, Vertex AI, App Engine, Cloud Storage, IAM, etc.) and services (Astronomer - Apache Airflow) to architect and bring enterprise data workloads to production - Design resilient, self-healing data systems with comprehensive monitoring, alerting, and automated remediation - and participating as part of an on-call rotation. - Lead the evolution of our data platform on Google Cloud (GCP), leveraging advanced services and optimizing for cost, performance, and reliability - Define patterns for streaming and batch data architectures that serve diverse use cases - Establish best practices for data contracts, API versioning, CI/CD, documentation, and partner integrations MLOps & AI Leadership - Lead MLOps strategy and implementation, establishing patterns for model deployment, monitoring, and governance at scale - Architect and oversee Generative AI infrastructure, enabling rapid prototyping while ensuring enterprise-grade security, compliance, and cost management - Partner with Data Science leadership to translate research initiatives into production-ready solutions - Drive innovation in AI/ML tooling and infrastructure, staying ahead of industry trends Mentorship & Team Development - Mentor and guide Data Engineers at all levels, conducting design reviews and providing technical feedback - Establish engineering standards, documentation practices, and knowledge-sharing processes - Participate in hiring and onboarding processes, helping to build a world-class data engineering team - Foster a culture of engineering excellence, experimentation, and continuous improvement Collaboration & Influence - Partner with product, engineering, and business leaders to align data strategy with organizational goals - Making decisions as a team. The things you build will be maintained and improved upon by others; there is a shared responsibility to make defensible design considerations and high collaboration. - Communicate complex technical concepts to non-technical stakeholders, building alignment and driving informed decision-making - Represent data engineering in cross-functional planning and architecture forums - Build strong relationships with external partners and vendors WHO YOU ARE - 10+ years working in a data engineering role that supports incoming/outgoing feeds as well as analytics and data science teams - 5+ years of advanced Airflow and Python experience writing production-grade, efficient, testable, and maintainable code - 3+ years of experience designing, building, and maintaining production APIs (REST, GraphQL, gRPC) for data access and integration, including API gateway management, rate limiting, authentication/authorization, and versioning strategies - 3+ years leading ML/MLOps initiatives, including model deployment, monitoring, and governance at scale - 3+ years of hands-on experience with Google Cloud Platform (GCP) including Cloud Run, Cloud Functions, Vertex AI, Cloud Storage, IAM, and other core services. - Deep expertise with columnar databases (BigQuery, Snowflake, Redshift) and advanced SQL optimization techniques. - Demonstrated experience with AI Coding assistants – AI tools are heavily engrained in Bestow culture. - Proven track record designing an end-to-end data pipeline in cloud frameworks (such as GCP, AWS, Azure) with requirements from multiple stakeholders - Experience with upstream data coordination through data contracts. - Experience building CICD pipelines for data processing using tools such as Docker, CircleCI, dbt, git, etc - Extensive experience with infrastructure as code (Terraform, Pulumi) and GitOps practices - Expert level knowledge of data orchestration frameworks such as Apache Airflow (or similar) to manage SLOs and processing dependencies - Experience in building streaming / real-time ingestion pipelines - Experience with creating alerts and monitoring pipelines which contribute to overall data governance. - Experience with containerization and container orchestration technologies with cloud architecture and implementation features (single- and multi-tenancy, orchestration, elastic scalability) - Deep understanding of standard IT security practices such as identity and access management (IAM), data protection, encryption, certificate, and key management. - Adaptability to learn new technologies and products as the job demands. - Proven ability to mentor engineers and lead technical initiatives across teams - Nice to have: Familiarity with building tools that draw upon Generative AI (GenAI) integrations (Enterprise-grade, not simply vibe-coded). TOTAL REWARDSAt Bestow, we’re proud to be awarded for our team members, innovative products, and culture. Our standard benefits include: - Competitive salary and equity based on role - Policies and managers that support work/life balance, like our flexible paid time off and parental leave programs - 100% paid-premium option for medical, dental, and vision insurance - Lifestyle stipend to support your physical, emotional, and financial wellbeing - Flexible work-from-home policy and open to remote - Remote and WFH options, as well as a beautiful, state-of-the-art office in Dallas’ Deep Ellum, for those who prefer an office setting - Employee-led diversity, equity, and inclusion initiatives Recent Employer Awards include: - Best Place for Working Parents 2023 + 2024 + 2025 - Great Place to Work Certified, 2022 + 2023 + 2024 + 2025 - Built In Best Places to Work, 2022 + 2023 + 2025 - Fortune’s Best Workplaces in Texas 2022 + 2023 - Fortune’s Best Workplaces in Financial Services and Insurance 2022 + 2023 + 2024 We value diversity at Bestow. The company will hire, recruit, and promote regardless of race, color, religion, sex, sexual orientation, gender identity or expression, national origin, pregnancy or maternity, veteran status, or any other status protected by applicable law. We understand the importance of creating a safe and comfortable work environment and encourage individualism and authenticity in every team member. Thanks for considering a job at Bestow!

• Own Bestow's platform messaging and positioning — using AI-assisted research and synthesis to develop narratives that resonate with enterprise insurance carriers at every stage of the buying journey, and iterate them faster as the market evolves. • Lead go-to-market for product launches, coordinating across Product, Sales, and Marketing — leveraging AI tools to accelerate content production, personalize messaging by segment, and ensure every release lands with clarity, confidence, and market impact. • Build and maintain a high-quality sales enablement library — pitch decks, one-pagers, battle cards, and objection-handling guides — using AI workflows to produce and update materials faster without sacrificing quality. • Develop and maintain competitive intelligence using AI-powered monitoring tools to track competitor moves, surface insights continuously, and keep Sales sharp and positioning refined in real time. • Partner with Communications to ensure product narratives show up in analyst conversations and earned media moments — using AI tools to help draft, adapt, and tailor content across formats and audiences. • Conduct customer and market research using a mix of traditional methods and AI tools to synthesize buyer language, needs, and decision criteria at greater depth and speed than either approach alone. • Establish a measurement framework to track how product marketing is contributing to pipeline and win rates — using AI-assisted analysis to surface patterns and make the case for what's working.

• Collaborates with the CSO Team to support the development, maintenance, and implementation of security standards. • Partner with IT to support the secure implementation of access controls and identity management • Participate in and contribute to initiatives for operating system, Docker images, Kubernetes/GKE and configuration hardening in the public cloud • Support the execution of vulnerability and patch management programs, including tracking remediation efforts. • Work with engineering teams to communicate remediation steps required for vulnerabilities identified through scans or penetration tests. • Support IT, Legal, Finance, Insurance Operations, External Examiners, and business areas during compliance exams. • Assist with the day-to-day operations of security scanning and web penetration testing tools • Support the implementation of security monitoring measures to secure the production environment • Contribute to regular metrics and reporting on the state of the environment • Identify and surface opportunities to improve security tooling, processes, and best practices.

ABOUT BESTOW Life insurance is one of the world's most important products. It's also one of the hardest to build, distribute, and modernize. Bestow exists to change that. Bestow is a leading vertical technology platform serving some of the largest and most innovative life insurers. Our platform unifies the fragmented, legacy value chain, enabling carriers to launch products in weeks instead of years. Carriers choose us to scale and operate at unprecedented speed, powered by AI and automation. Bestow isn't selling policies. We're building the infrastructure that helps an entire industry move faster, reach more people, and deliver on its promise. Backed by leading investors (Goldman Sachs, Hedosophia, NEA, Valar, 8VC) and trusted by major carriers, Bestow is powered by a team that moves with precision, purpose, and heart. If you want to help reimagine a centuries-old industry with lasting impact, join us. Bestow offers flexible remote/hybrid work, meaningful benefits, equity, and substantial growth opportunities. Bestow participates in the E-Verify Program. The Underwriter I serves as a technical anchor for Third-Party Administrator (TPA) operations. You will balance high-volume transactional underwriting with specialized risk analysis, ensuring that policy issuance aligns with carrier guidelines and regulatory standards. This role is a mix of active risk assessment, compliance auditing, and strategic partnership management. WHAT YOU'll DO - Underwriting & Appeals: Execute transactional tasks, manage complex appeals, draft decline letters, and resolve application discrepancies or medical impairment inquiries. - Compliance & Audit: Lead Post Issue Audits (PIA), manage MIB (Medical Information Bureau) reporting, and conduct partner reviews to ensure adherence to carrier and regulatory guidelines. - Claims & Data Integrity: Review applications for accuracy prior to FNOL (First Notice of Loss) submission, manage claim status changes in the Admin Portal, and maintain consolidated claims reporting. - Carrier & Partner Relations: Act as the primary technical point of contact for carrier inquiries, facilitate reinsurance meetings, and manage data vendor audits (e.g., Milliman). - Process Improvement: Manage the general underwriting mailbox to improve response times and collaborate with the CX team on "Future Feature" requests and Gen-AI tool testing. - Operational Support: Maintain travel advisories, monitor OFAC watchlists, and provide backup for general operations and reporting. WHO YOU ARE - Experience: 2+ years in underwriting (Insurance/Financial Services) with a focus on claims or technical underwriting. - Technical Knowledge: Deep understanding of FCRA, OFAC, MIB coding, and medical impairment risk evaluation. - Software Proficiency: Advanced Microsoft Excel skills; experience with underwriting workbooks, Admin Portals, and Milliman reports. - Analytical Skills: Strong ability to investigate disputed data, audit complex files, and interpret evolving carrier guidelines. - Communication: Proven ability to draft legally compliant correspondence and manage high-level relationships with external carriers and reinsurers. TOTAL REWARDS At Bestow, we’re proud to be awarded for our team members, innovative products, and culture. Our standard benefits include: - Competitive salary and equity based on role - Policies and managers that support work/life balance, like our flexible paid time off and parental leave programs - 100% paid-premium option for medical, dental, and vision insurance - Lifestyle stipend to support your physical, emotional, and financial wellbeing - Flexible work-from-home policy and open to remote - Remote and WFH options, as well as a beautiful, state-of-the-art office in Dallas’ Deep Ellum, for those who prefer an office setting - Employee-led diversity, equity, and inclusion initiatives Recent Employer Awards include: - Best Place for Working Parents 2023 + 2024 + 2025 - Great Place to Work Certified, 2022 + 2023 + 2024 + 2025 - Built In Best Places to Work, 2022 + 2023 + 2025 - Fortune’s Best Workplaces in Texas 2022 + 2023 - Fortune’s Best Workplaces in Financial Services and Insurance 2022 + 2023 + 2024 We value diversity at Bestow. The company will hire, recruit, and promote regardless of race, color, religion, sex, sexual orientation, gender identity or expression, national origin, pregnancy or maternity, veteran status, or any other status protected by applicable law. We understand the importance of creating a safe and comfortable work environment and encourage individualism and authenticity in every team member. Thanks for considering a job at Bestow!