VP, Information Technology Engineering

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 http://e-verify.gov. ABOUT THE TEAM 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; t's a core driver of how we compete, operate, and grow. This role leads the full technology infrastructure, business technology, and IT strategy for a fast-growing SaaS company, and the person who succeeds here will think about every IT challenge as an engineering problem first. . Our entire infrastructure is cloud-based, our predominantly remote workforce operates on Macs, and our core collaboration stack includes Google Workspace, Zoom, Slack, and Claude. You'll inherit a solid foundation and a capable team of 8. 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. WHAT YOU'LL DO - Define and execute a multi-year IT strategy aligned to company growth objectives, with a focus on scalability, security, and operational excellence. - 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. - Oversee all enterprise IT infrastructure including cloud environments, networks, endpoints, and SaaS platforms, ensuring systems availability, performance, and reliability meet or exceed SLAs. - Implement and operationalize cybersecurity policies and standards set by the CISO, covering identity and access management, threat detection, incident response, and data protection. - 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. - Lead, mentor, and grow a high-performing IT team of 8, fostering a culture of ownership, continuous improvement, and collaboration. - Own the IT budget, driving cost efficiency without sacrificing quality or reliability. Manage strategic vendor relationships and negotiate contracts to maximize value. WHO YOU ARE - 12+ years of progressive IT leadership experience, with at least 2 years in a VP-level or equivalent executive role at a SaaS or technology company. - Deep hands-on experience with cloud infrastructure (AWS or GCP), enterprise security frameworks, and modern ITSM practices in a cloud-native, predominantly remote, Mac-endpoint environment. - Experience owning enterprise business systems (CRM, telephony, ERP) and partnering with business stakeholders on system strategy and optimization. - 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. - Knowledge of the iPaaS and integration platform landscape (Workato, Boomi, MuleSoft, n8n, Zapier, Make) and when to use each. First-hand experience building on at least one platform, not just evaluating vendors. You can speak to the trade-offs between orchestration platforms and custom code. - Experience architecting or operating a data layer (ITSM, data lake, or analytics infrastructure) and a clear point of view on how ITSM, iPaaS, and data infrastructure work together as the core enablers of IT operations. - Demonstrated ability to build, lead, and inspire cross-functional technology teams with strong executive presence and the ability to communicate complex technical concepts clearly to non-technical stakeholders. - Strategic thinker who balances long-term vision with short-term execution, is comfortable operating in ambiguity, and sees routine manual work as a problem to be solved — not accepted. 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!