VP, Information Technology

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 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!